It’s about his internal struggle between competing interests: money or life enjoyment.

Spoiler: he’s actively embracing an approach with his business and life that chooses to leave money on the table.

I found it fascinating to watch. At many moments you see him twitch and scratch his head as if his rational brain inside him is trying to stop him from what he is doing.

I’ve consciously chosen the “leave money on the table option” over and over again and I’ve tried to do this from the beginning. My biggest reason was that I wanted to see what happened. True fuck around and find out energy.

Most of the time? It felt silly. Like I was wasting my talent, lighting the ten years of intense consulting and business school training on fire. But also over the last 6-7 years, it’s sort of worked. My days are nice. I’ve spent 98% of my days on my terms and I’ve felt better about the person I’ve become.

But if I laid out my decision to people in my shoes now it would be an active choice to give up $1M of incremental income that I easily would have earned if I had stayed on my former path. While I think I still could have turned it down, I realize its damn hard for most people.

I am lucky. I found work I like doing, writing, and want to keep doing for another 10+ years. It always seems like there are things I can improve and my curiosity never seems to fade. On top of that, I’ve slowly built solid relationships by taking advantage of not having to ask people for help.

Ali talks about being uncomfortable asking podcasters to help him promote his book even though almost everyone would likely be happy to do it. I get this. I sense the discomfort comes from the acknowledgment that we are turning a potentially meaningful relationship with another human into something that starts as a transaction. I sense this is what’s been behind my interest in leaning against the obvious financial opportunities. I don’t feel like I’m wired for a business battle. I genuinely want to hang out with people that inspire me.

I was at an event this week with some VERY successful creators and there was a part where we had to ask for help. I asked people for help getting on some BIG podcasts and while doing it my voice cracked. It’s still weird. I know my book is pretty good now and I’m a lot more confident about saying that it’s a banger but I still have some latent insecurity, work scripts, and a genuine desire not to mix work with connection that holds me back.

Over the years I’ve left money on the table in many ways:

• Not doubling down on my StrategyU business which has much more potential because it doesn’t feel like I can do it for 20 years
• Never tried to make money from writing for five years and even with the book didn’t see it as a money-making thing (which has made the money a delightful surprise). I tried getting into a proper publication once and then didn’t again because I didn’t feel good
• I didn’t do a book launch or tour because I just don’t feel good thinking about it
• I didn’t sell my book to Penguin because the conversations didn’t feel good

In the video, Ali similarly says, “I don’t want to do stuff that feels bad.” He continues, “I don’t want to do things that I don’t want to do. That probably means I’ll have a smaller business than other people.”

This must be hard for him to say.

As many of you know, I’ve gotten to know Ali over the past few years. He’s generously shared his audience with me despite me never asking. Maybe he senses that I don’t feel good asking either?

The interesting thing is that you can leave money on the table and there is an interesting opportunity to share with people about what it feels like to do that.

That’s a lot of what you all are interested in and as I’ve found out there’s been a hidden audience of people that want to hear about unconventional approaches to life.

Right now, there’s an open portal to experiment with your life and pair it with creativity. Sharing videos like Ali, or writing like me. EVERYONE knows how to google the ultimate best practices and I think this is great for some people but drives a bunch of other people crazy. We are long on tactics but short on sharing ideas around the inner game of how to carve a path that is true to your own nature. This is a great thing. We need more “experiments in living” as John Stuart Mill once wrote.

In a podcast I did with Tim Malnick, he detailed two paths: the money path and the life path. The money path is the belief that “one day when I sort this out I’ll get to do what I want.” Suffer now for a future payoff. The alternative is something he calls the “life path.” This is the idea that you can “do what you love and the more you follow it you will have your needs met with and without money.”

And the key thing here is the second path: your needs met with and without money.

And this is what I’ve experienced. I’ve left tons of money on the table but I’ve been compensated richly with time with my wife, with my family, with my daughter, space to think and grow as a person, new friends who are willing to spend time with me, and an overall psychological richness that I would never give up.

Ali shared an email he received from April Perry that’s amazing and puts it far better than me:

Hey Ali,

People always talk about leaving money not the table like it’s a terrible thing. Why don’t you sell another digital product? Why don’t you do a mastermind? What don’t you sell physical products?

But no one ever speaks of the mental and emotional costs associated with managing all of that.

I think we need to shift our perspectives. Why are you leaving peace of mind on the table? Why are you leaving family time on the table? How about mental health and being enough with what you already have and do? How’s your connection with god? What’s the quality of your marriage? Can you just sit and just sit be? Can you laugh and sing and truly relax with loved ones? Can you look at your relationships and nature and all that God has given you and sit in awe for a moment?

It doesn’t have to be either/or but all that if I have my family’s financial needs covered, the first thing I’ll leave on the table is money.

I’ve embraced a lot of this because I read many books about people’s regrets at the end of their lives or regrets after “making it” and decided to take them seriously. I thought, “What if I skip the aiming at success thing?” and tried to aim directly at what those people said mattered.

41k+ Sold! (Top 1% Book) The Pathless Path is Paul's book about walking away from a "perfect" job with a promising future and starting over again. Through painstaking experiments, living in different countries, and a deep dive into the history of our work beliefs, Paul pieces together a set of ideas and principles that guide him from unfulfilled and burned out to what he calls "the pathless path" - a new story for thinking about work in our lives. Learn More & Buy The Book Here

The post How Do You Leave Money On The Table? appeared first on Boundless by Paul Millerd.

Die With Zero is an entertaining, persuasive, and useful book that argues that far too many people, “save tend to save too much for far too late in their lives.”

This is a hard topic to talk about, but Perkins does it well. Money is a topic where many people are better at saving than spending, including me. Our relationships to work and money are tightly linked and the more I think and read about these two things, the more I think that our money beliefs are foundational to our relationship to work. I don’t think you can have a good relationship with work without first interrogating and grappling with your money beliefs. 

While I’ve questioned a lot of my beliefs around money, such as how I think about generosity, retirement, and fear, this book still challenged me in interesting ways. Most notably, it’s pushed me to dream a little bigger about how I’m spending my time right now and in the near future. It also nudged me to consider questions like

• Am I saving too much?
• What experiences might I not be able to take in ten years?
• What experiences might I enjoy a lot less in twenty years?
• How can I think about giving my children money earlier in their life when they have more time but not money?

If these questions excite you, the book will likely be a fun read.

Here are some other reflections from the book:

Takeaway #1: It reframes life away from purely a money problem to a life force problem

Many people look at life in clear, linear stages: youth, adulthood, and then retirement. This is less about any sort of life stage and more about how one fits in an economic system. It’s useful to know the world works like this but if we take the system’s economic goals for our own, we forget that we have a life to live.

Perkins pushes back against this tendency in the book, reframing life as a problem of life energy: “What’s the best way to allocate our life energy before we die?”

This is a push against the default or what he calls “autopilot.” Most people look at life and retirement as a money problem because, well, that is what everyone else is doing. By looking at life as a life energy allocation problem you might make different choices like giving money to your children while they are still alive, deprioritizing work and buying back time before you are “supposed” to retire, and spending lavishly on experiences that might pay “memory dividends” to you and people in your life.

His idea of a “personal interest rate” was useful for thinking through the tradeoffs you might make between life and money.  This is just a way to “discount” future time and force you to think about the value of the present moment. It also means that the older you are, you should be way less willing to trade your time for money. This is because your life energy is becoming scarcer and thus, more valuable. Taking a full-time job with no vacation when you are 80 would be a tragic circumstance for most people. But what about 68? 60? When does the cost of the time you must give up become too high? These are the tricky calculations you must figure out yourself.

Many of Perkins’s friends tell him, “Well, I don’t like anything else,” or “I like work!” To which he replies, “How do you know what your tastes are if you haven’t done anything besides work or raise kids.” The message: dream a little bigger, you only have one life!

“You Takeaway #2: Retire on Your Memories”

As we get older, we spend more time reflecting on our lives. This is why Perkins argues that more people should think about old age as a combination of savings AND memories. Through this lens, having memorable experiences earlier in life, especially before retirement, can be valuable because they will pay memory dividends. And there’s good evidence that this is what makes people happy. I’ve written before about how the Nobel prize winner Daniel Kahneman abandoned studying happiness after realizing that “people don’t want to be happy the way I’ve defined the term – what I experience here and now.”  Instead, he thought that people want to be satisfied by the “story they tell about their lives.”

For several years before my grandfather passed away, I increased the amount of time I spent with my Nana. This was a conscious decision. After I lost my grandfather suddenly in 2010, I knew that I wouldn’t have much time left with her. I also really enjoyed her company. She seemed to really understand me and always was excited to hear about my life. In 2018 before I moved to Taiwan, I set a goal of spending fifty days with her over the summer.

I was only one year into self-employment and was barely covering my cost of living at the time, but I had the sense that time with my grandmother was far more valuable than any money I might earn. I was buying time with money (or at least potential money). It’s easy to see the logic in Perkins’s argument to make these kinds of decisions because there is literally no amount of money you could pay me to erase these memories from my life.

Takeaway #3: Periods of our lives are finite

I recently became a father. I’ve entered the period that Khe Hy calls the “magic window” – the period of 10-12 years where your children think you are the greatest thing on earth.  There are experiences I can have with my family right now that I will not be able to have when they are older. But this is also true no matter what phase of life we are at. I can’t live my twenties again (where I wish I had quit working full-time a lot earlier). And I won’t get a do-over on my 30s (which I’m a little happier with how I spent my time).

An exercise he proposes to help people become more aware of these expiring periods is doing a “time bucket” reflection. Here is Bill’s own reflection from the book:

I like this for two reasons. First, it’s a generative exploration of possibility. Angie and I often do exercises like 5-Year “dream life” plans and others where it nudges us to imagine things we aren’t thinking about already. It’s always fascinating how easy it is to come up with ideas outside of our current imagination and realize how few people ever spend 15 minutes trying such things.

The second I like about this exercise is it might help you realize experiences that are worth waiting on – like in Bill’s case an Alaskan cruise in his 70s. I feel similar! A cruise now? Eh. But in my 70s? Maybe!

In my travel around the world, I saw so many elderly people traveling who struggled to walk and more. I’ve increasingly thought that at that age maybe it’s time to retire to a reading nook and give up travel. Which makes me want to travel and live abroad in the coming decades with my children, during the years I’ll never be able to relive.

Many of us see travel as part of the deferred life plan. We will travel when we retire. That’s just what you do. Die With Zero offers many helpful reframes, but this quote stuck with me the most: “How much do you think you’ll enjoy climbing Rome’s Spanish Steps when you’re in your nineties?

Takeaway #4: Don’t Trade Years of Your Life for A Hospital Bill at The End of Life

“But healthcare!!”

In the US this is a common reason people have for saving as much as possible for retirement. But I think what is really happening is that they are picking the most convenient excuse to not have to deal with their underlying money insecurities.  Saying you are worried about healthcare costs sounds smarter than saying you fear dying and running out of money (or at least is more accepted at a dinner party).

The thing is you can pull data on all of this.  There are tons of it.  A few I found quickly:

• “In the U.S., only 1 percent of hospital care at the end of life is paid for out of pocket” (Richmond Federal Reserve)
• Only around 30% of people die in hospitals (Reuters)
• If you do save you can buy long-term health insurance with predictable costs
• Increasing numbers of people are choosing to die in hospice
• Most Americans (and people in other countries) are not only covered by government healthcare but also have steady income via things like social security

But even without the data, someone might be able to point to an extreme example where someone’s family went bankrupt from medical issues. But Perkins is not saying that healthcare costs are never high – he’s saying that people should think about what they are trading off to save as much as possible for when they are old. Is it worth working several more years of your life, withholding life-changing gifts from people, or giving up meaningful life experiences all for having to potentially extend your life another month at the tail end of your life? Probably not and it’s likely not going to cost as much as you think.

And there are clear data that people do save too much in the US. Nick Maggiuli’s book Just Keep Buying pointed out that in any given year, “58 percent of retirees withdraw less than their investments earn.” The result? He writes, “The average retired adult who dies in their 6os leaves behind $296k in net wealth, $313k in their 70s, $315k in their 8os, and $238k in their 90s.”

The biggest problem with claiming to care about healthcare expenses is that it implies you are prioritizing your health. However, Perkins would just say: if you really cared, why not spend it on a personal trainer right now?

Takeaway #5: Inheritance is wasted on the elderly because they have enough money but not enough time or health

“But I want to leave an inheritance for my kids!”

Perkins gets pretty fired up about this. He often tells his friends they are hypocrites. They “aren’t putting their children first but instead are treating their kids as an afterthought.”  The reason is simple: “A person’s ability to extract real enjoyment out of the gift declines with age.”

In the US, 80-90% of wealth transfers are inheritances and the most likely time this occurs for people is sometime in their 60s. What also happens in our sixties? People tend to read their highest point of wealth. We can see this clearly by looking at median net worth data from the Federal Reserve in the US.

Perkins writes about giving his grandmother $10,000 when he had “made it” in his career. She was in her 70s and had little use for it. She had a simple life and didn’t end up spending any of the money. This taught him that it was probably better to try to create memorable experiences for the people in his life, or at minimum give gifts to people earlier in their lives.

And this is the other side of an inheritance. He argues that thinking only about money is a cop-out. Parents should think about the inheritance of memories that they wish future generations to have. What are the life-changing gifts one could make during someone’s life? What are the experiences that might seem extravagant, but people would talk about for years? The odds are if you see your relationship with your kids as something that is “solved” through a transfer of money, it’s already on shaky ground. You’d be better off trying to turn at least some of that money into memories.

Because we tend to spend less as we age and the upsides of being able to spend money intentionally earlier in life are higher, Perkins believes the ideal age to give children an “inheritance” is sometime between 25-35 years old. This is because they are money-poor but time and health rich. They can create experiences or take risks that they would not be able to otherwise take when older. Of course, this is hard. As I’ve written about with work, we have DEEPLY embedded scripts that people need to learn how to struggle their way through their work lives. I suspect this is more of a cope from an industrial era where you really did need to put your time in. My parent’s generation had to work twenty years to get 4 weeks of vacation. Success really was downstream of time. This is no longer true and the suffer=good script is holding us back in how we think about work AND money.

Angie and I received a small gift when we had our daughters from Angie’s parents, and it was not at all something I was expecting. It was a profound gesture and really made us think more deeply about how we can proactively use that money to spend more time in Taiwan, help her parents travel, and create amazing experiences for our daughter. 

But if you don’t want to give to your kids? Fine. The point still stands – spend the money now. Give it to a charity. Create life-changing experiences. Because if you’re leaving it behind you’re already elderly children? They probably won’t do anything with it except put it in a retirement account. Life satisfaction upgrade = 0.

How I’m Thinking About This

I’m fascinated with people’s relationship with money because it is often so deeply linked to people’s relationship with work. Show me your insecurities around money and I’ll show you your potential for thriving.

Most of us learned some lesson about money from childhood that has stuck with us. We will never have enough. People with money are bad. Money is the most important thing in life. You will never make money. Money makes people do evil things. Money is deserved. You can go on forever.

But one of the most powerful scripts with money is around when and how you should spend your money during your life. Almost everyone has the same strategy. Save as much as possible for retirement.

Perkins’s book has persuaded me that I might be making this mistake and saving too aggressively for retirement – a time in which my health will be worse, my spending habits will be tamer, and my desires to travel will likely be less enthusiastic.

The book was inspiring and it’s pushed me to think deeply about how I can spend more intentionally on creating life experiences with my family that might pay memory dividends for decades, how I can gift my children “pre-inheritance” that might enable them to live more boldly while young, and how we should move up some of our plans to integrate living abroad and travel into the next few years.

As always, you can follow along here, as I’ll be sharing what I learn along the way.

41k+ Sold! (Top 1% Book) The Pathless Path is Paul's book about walking away from a "perfect" job with a promising future and starting over again. Through painstaking experiments, living in different countries, and a deep dive into the history of our work beliefs, Paul pieces together a set of ideas and principles that guide him from unfulfilled and burned out to what he calls "the pathless path" - a new story for thinking about work in our lives. Learn More & Buy The Book Here

The post Die With Zero: Why Too Many Save Too Much for Too Late In Their Lives (Book Review) appeared first on Boundless by Paul Millerd.

The ultimate way you and I get lucky is if you have some success early in life, you get to find out early it doesn’t mean anything.

– David Foster Wallace

I had no master plan to quit my job. Even now, several years after doing so, when people ask about my journey, I’m more confused than you might expect. Choosing to leave full‑time work was not a single bold decision but a slow and steady awakening that the path I was on was not my path.

It’s tempting to tell a simpler story. People want to hear about bold acts of courage, not years of feeling lost. On my way toward leaving my job, I never had a clear picture of my next step. Experiencing this makes it easy to spot these kinds of phases in other people’s stories and I’ve done my best to highlight them in my writing and podcast.

My conclusion from this is simple: beyond the headlines of dramatic life changes are almost always longer, slower, and more interesting journeys.

Pebble in My Shoe

As I recovered from my health challenges, I entered a phase of restlessness typical of anyone that eventually makes a life change.

A friend, Khe Hy, provides a perfect description of this phase. Fifteen years into a successful career in finance, he walked away to find a new path. However, it took him a long time to make that decision. He reflected, “It definitely wasn’t a sudden realization. It’s a little bit like having a pebble in your shoe, where you’re walking and something is off, and it’s mildly uncomfortable.”

When he got raises or promotions the discomfort would subside but never disappear. Slowly, he became more curious about that feeling and realized that despite his external success, he had become a “passive participant” in his life. Eventually, this convinced him to embark on his own pathless path.

When I returned to work after regaining my health, I had discomfort that could only be described the way Khe put it, as a pebble in my shoe. It wasn’t enough of a feeling to make me do anything dramatic, but it threw me off just enough that I was forced to pay attention to my life in a different way.

As I started to pay attention, I slowly came to realize the reality that I had been living in was an invisible bubble, one of my own creation. I started to push the edges of that reality and wasn’t sure what would happen.

A Daily Reminder

If there are clear boundaries to behavior within a given field of endeavor, then there is also great freedom to adapt and imagine within those lines. These boundaries, however, should always be tested to see if they are actually still real. It takes conscious acts by individuals to test these edges.

– David Whyte

After returning to work, I felt like I had gone through a major transformation, but to my colleagues, I appeared back to normal. I was physically present but detached. Rather than participating in meetings as a good team member, I observed them as a visiting anthropologist. I saw my colleagues with new eyes. Are they happy? What kind of pain or challenges are they dealing with? Is this how they want to be spending their time?

Once you ask these questions there is no going back. Not because of the contradictions in other people’s lives, but because it makes it difficult to live in contradiction in your own life.

This inspired me to act. I wanted to design a career that worked for me and decided to start with a simple commitment, one inspired by a talk from Earl Jones, an MIT alumnus who had shared his leadership principles with my class in grad school. I remembered how he had a list of words that reminded him of what he values, something that popped up on his calendar every morning.

I followed his example and created a daily calendar entry of priorities for my life. First on my list was health. After recovering from my health challenges, I would do anything to stay healthy. Next, my head told me to list “career,” but my heart told me to list it last. This simple decision was my first conscious commitment to exploring the possibility of a life not centered around work. My final list included four items: health, relationships, fun & creativity, and career. Since 2013, this list pops up on my phone at 8:30 a.m. each morning.

Staring at those four items, in that order, was scary. Without knowing it, I had embraced a question that would shape my decisions: “How do you design a life that doesn’t put work first?”

The answer, my dear reader, is simple. You start underachieving at work.

You stop setting an alarm and you cancel morning meetings because the energy gained is worth fighting for. You start working remotely on Fridays without asking because the extra 24 hours with your grandmother is worth it. You start taking naps at the office because there’s a nap room and someone has to use it, right?

I felt like a rebel, like I was doing something wrong. At the same time, I had the sense that taking ownership of my life in this way, especially to prioritize my health, was something worth doing.

Instead of being consumed with thoughts about work and my next step, I had time to continue to experiment, and in the space that emerged, a creative energy entered which started to become a central force in my life.

Want to keep reading?

You can purchase the book on Amazon, Barnes & Noble, iBooks, Audible (Audio), Itunes (Audio), or Gumroad

41k+ Sold! (Top 1% Book) The Pathless Path is Paul's book about walking away from a "perfect" job with a promising future and starting over again. Through painstaking experiments, living in different countries, and a deep dive into the history of our work beliefs, Paul pieces together a set of ideas and principles that guide him from unfulfilled and burned out to what he calls "the pathless path" - a new story for thinking about work in our lives. Learn More & Buy The Book Here

The post A Pebble In My Shoe (Excerpt From The Pathless Path) appeared first on Boundless by Paul Millerd.

Over and over again, when people take a step away from such an existence, they report that they were duped.  Things were not as scary as they were led to believe and the upside of having more space and time in their lives was far greater than they could imagine.  Many people even gladly return to their former paths with a better understanding of the hidden costs they were paying and a stronger set of principles to guide them.

Almost every week, I talk to someone who has solved the financial aspects of life but is impoverished when it comes to the things that matter in life.  Over time, and seemingly without them being aware of it, they have lost their sense of joy, their creative impulses, and even more shockingly, any passion for the things they are doing – the ones that they used to be so excited about. They were led to believe, like me, that if we just put our heads down and worked and made a regular paycheck, life would figure itself out. 

What we bought into was a silent conspiracy. One where as long as we remained employed, we could pretend that we had it figured out. The only thing that enabled people to keep existing in this state was our own silence. As the pandemic forced us to let our colleagues into our homes, we could no longer pretend.

The pandemic and the reshuffling of work have thrown a once stable equilibrium into flux. It is now common knowledge that many people have doubts about their relationship to work and are starting to wonder if putting their heads down and working most weeks of every year of their adulthood is the best use of their time on earth.  And despite media organizations trying to quickly label things as a “great resignation,” “antiwork,” or “quiet quitting,” the truth is that we really don’t know where we are headed. 

At the heart of this shift, many people, like me, are realizing that they priced and sold their time at way too low a rate and for far too long. Leaving my job in 2017, I did not expect that my relationship with time would change as much as it did. Before I quit my conception of “working on my own” was merely doing what I had been doing but with a little more freedom and flexibility.

What I didn’t realize was that for almost all of my adult life, including six years of higher education and eight years of full-time work, I was rarely present. I choreographed every step of my life, living in the future. 

In the first year of being self-employed, I got a taste of something completely different. It was a state of being that was not tied to external metrics of achievement or even any sort of work identity at all. It was a state where I was simply existing, one step at a time, one breath at a time. For the first time, I had taken a deep breath and decided to look around. 

It was experiencing this that convinced me that I had been insane to spend as long as I did on my previous path and when people ask if I have any regrets I tell them I wish I had left earlier! The opportunity to connect to yourself, others, and the world is one that should never have a price, and on my previous path, I had slowly been trading it away at somewhere around $50-75 an hour.

After working on my own for more than five years I’ve realized that the way I had oriented my life previously was completely unnatural. And I sense this is the case for many people.  Structuring our lives working for a company most days of the week almost all of the weeks of the year is a crazy way to spend your time on Earth. Yet it is the default path and so we go along with it.

I like to tell people that I price my time now at a million dollars an hour. Of course, I’m only half joking. I’m not living a monastic existence and need some money to make my current life work. But it’s also not a lie either. Those moments where you’ve had enough space and time to connect to yourself and remind yourself that you only have infinite time on this Earth? They are priceless.

In the movie Up In The Air, there is a powerful scene where the senior consultant character, played by George Clooney, asks a guy he is firing a direct question, “How much did they first pay you to give up on your dreams?” The guy answers, “27 grand a year.”  Clooney then responds, “…and when were you going to stop and come back and do what makes you happy?”  The guy answers softly, “good question.” 

I was once like Clooney, a consultant. And for the most part, I enjoyed working in the industry. Yet at some point, the upsides of learning faded away. I kept chasing the energy and excitement of the first few years of my career, jumping from job to job, and never quite found it. While doing this my salary steadily inched up, igniting the dopamine receptors in my brain every time. The crazy thing about my path is that if a few things worked out differently I might still be on that path. But I’m not and now I know that the costs of trading most of my weekdays for almost every week of the year was a terrible trade and I did it for far too long at too low of a price.  

Unlike the guy in the clip, however, I didn’t have any dreams or an alternative path I wanted to chase. Which is why it took me so long to leave. If I had to plant a piece of wisdom in the brain of my younger self it would simply be to tell him that the state of existence, that of a worker who works most of his adult life, is unnatural. I would tell him that a different state of being is possible, and until you experience it, you haven’t quite lived. 

41k+ Sold! (Top 1% Book) The Pathless Path is Paul's book about walking away from a "perfect" job with a promising future and starting over again. Through painstaking experiments, living in different countries, and a deep dive into the history of our work beliefs, Paul pieces together a set of ideas and principles that guide him from unfulfilled and burned out to what he calls "the pathless path" - a new story for thinking about work in our lives. Learn More & Buy The Book Here

The post Selling My Time Too Cheap: How Full-Time Year-Round Work Blinds Us To The Joys of Life appeared first on Boundless by Paul Millerd.

This is something I call a hustle trap – trying to play someone else’s game as a way to avoid figuring out what really makes you tick.

While I don’t have great advice other than finding something you want to do and do it consistently, I have thought a lot about my “creative process” and it might be worth sharing what’s enabled me to consistently show up, keep writing, and continue to have fun along the way.

The secret is really something I call my “creative engine.”

The “Creative Engine”

At the time of writing, I’ve published more than 170 issues 200+ issues in my newsletter. Some people have asked me, “how did you keep going to write that many issues?”

At a high level, I’ve found work I like doing and have focused more on the conditions that enable me to keep doing it rather than embracing any writing tip or productivity hack. Let’s dive in:

Step 1: Filter Content Input for High-Quality Content

Here’s a high-level belief: if you are serious about generating interesting ideas, you will not be able to generate them if you are mostly following what other people are following. You will need to block default sources of information and start curating your own. By blocking, I don’t mean “I try to avoid watching too much CNN” or “I check out Fox News to balance my viewpoint” but a total blockade.

One easy way to do this is with Feed blockers. Here are what my Twitter and Facebook feed looks like:

I installed the Facebook newsfeed eradicator several years ago and now barely check Facebook. Part of this is because it’s not all that interesting and I’ve shifted to Twitter where I can control the information a lot better. Regardless, I also run a feed blocker on Twitter and actively add words to a “mute list” (see privacy settings) of anything that is generating high levels of outrage (most political names and divisive issues are a good starting point). In addition, I highly recommend unfollowing large media company sites like CNN, Fox, MSNBC, and so on. They are not in the business of informing people – they are in the business of turning your attention into dollars.

If you need to check the news I recommend Ground News. It’s a good place that shows you the range of sources of the stories and isn’t geared toward hacking your brain.

Once you’ve blocked the main sources of outrage, you can start actively seeking out people, sources, and ideas that interest you. Subscribe to interesting newsletters, follow interesting people, and keep adjusting over time.

Suggestions: Here is list of 28 interesting people I like following (Dec 2021)

Another source of interesting ideas and writing for me is the conversations I have with people. We’ll get to this part in a little but it’s hard to understate how valuable it is to be known as someone interested in a certain topic. Given that I’ve written so much about our relationship to work, each week I get 3-4 “have you seen this?” e-mails, DMs, or messages and I appreciate every single one of them.

Another thing I’ve found is that the more I read, the better my ability to put ideas into context among a vast web of information that I’ve been exposed to. I like what Tyler Cowen says about how he reads so much:

The best way to read quickly is to read lots.  And lots.  And to have started a long time ago.  Then maybe you know what is coming in the current book.  Reading quickly is often, in a margin-relevant way, close to not reading much at all. 

Unfortunately, I didn’t reach much beyond school until the age of 21 but ever since I’ve been reading probably 20-50 books per year for almost 15 years and every year I get more value from books.

At a high level my information diet looks like this:

• 35% books: I am typically reading a few books at once and read about 3-4 books a month. I get most of my book recommendations from friends, podcasts, and sources in many of the things I read. If I don’t like the book I stop reading and move on.
• 25% longform: There is a lot of good writing on the internet, you just need to have a good eye for it and know where to look. I generally get great recommendations from newsletters like The Browser, Longform, Sunday Long Reads, Rad Reads, and many others writing great newsletters. Anytime I stumble upon something worth reading, I tag it to Instapaper or matter and then end up reading it at some later point. I love reading so there is no planned reading time in my life. It just happens.
• 20% Zeitgeist / Shortform / Twitter: I tend to scan a lot of stuff and try to get a feel for things happening in the digital / creator/internet world. I shifted my life in this direction a few years ago and its been fascinating to see the world shift in my direction. It still seems like the digital worlds are a few years ahead of the rest of the “mainstream” world but I expect that gap to more or less close over the next decade. I’ll keep watching until it stops being interesting.
• 20% Conversations: This is my personal secret sauce. Not because there is anything special about conversations but because I get so inspired by other people. When I’m sharing ideas, answering questions, engaged in e-mail replies or doing podcasts, I always tend to come up with new ways of thinking about things I write about and come up with new ways of talking about something.

Step 2: Filter Ideas Through a “Second Brain”

Until 2018, I didn’t take notes or store anything I was thinking about. I had always managed everything in my head and that seemed to work just fine for most of my jobs. However, this changed when my friend Jonny shared Tiago Forte’s initial essays about using a “second brain” approach to take notes in Evernote. I hacked together an 80/20 approach in a couple of hours and it seems to be the missing piece to my process.

From the beginning, I’ve never had a complicated system. I more or less only created some structure (and then was able to abandon that when I shifted to roam) and just synced up highlights from various reading apps which I was already using.

Here are some apps I use:

• I pay for Instapaper premium at about $30 per year which lets me save all my highlights and search all the articles I save.
• I use Matter, which is an amazing app for finding, sharing, taking notes, and even listening to articles. It also syncs to Readwise.
• I use Readwise which collects notes from kindle, e-books, Instapaper, and Matter and then sends them directly to Roam. This app is magic.

Then each week when I go to write my newsletter, I check:

• Articles I read or bookmarked in Matter
• Articles I read, marked or highlighted in Instapaper
• Any notes I automatically synced to Roam
• Bookmarks I marked on Twitter
• Notes from conversations about topics to write about I keep in Roam

At a high level, I don’t spend any time structuring most of my notes, especially around my writing around work. I have a belief that “nothing good gets away” and I’ve tried to embrace this spirit in my work.

The ideas that I get excited by, I keep coming back to, and this means I’ll search past things I’ve marked. Do I lose track of stuff? Sure. But over time, most of the ideas I’m excited about gets written.

I think this is probably true for most people and spending more time on creating and output would probably be a better use of time than improving a note-taking system.

Step 3: The Doing Mode – Where The Magic Happens

The doing mode is simply having time to think and create. Sounds simple but is harder than you might think.

People underestimate how much time creative work takes. Not just the time to actually work through ideas and then turn them into something but also the time to contemplate, ponder, and think about the ideas. Dave Perell does a good job of highlighting these two modes:

Beer mode is often ignored by people especially those who have spent most of their time in a structured work environment. It took me a while to realize that the best way to be “productive” is often to spend extended periods of time not working. Instead, I’m taking long walks, biking around the city where I live, or just leaving open space to live in the moment.

Creating the space in your life for ideas to blossom is a non-obvious thing to do and is often only learned through experience. Some people need more of “beer mode” and other people need less.

I tend to work in bursts followed by indefinite rest. I will write intensively for a few days and then literally do nothing “productive” for the next few days. When I was writing my book, I was feeling really stuck after working on it for a few weeks. I knew that the only way forward was to stop writing entirely until the next steps became obvious.

The way to notice if you have a good balance is to pay attention to your energy. When I am energized and can maintain a good level of energy over a long period of time but when I am going too hard without rest, I lose energy and the ideas stop flowing. This might undermine the whole system.

Another underappreciated thing about creating in written or visual form is that you need a bottom-up process for researching and working through details AND a top-down “sensemaking algorithm” for how you structure, combine, remix, and synthesize those details.

Most knowledge economy jobs will help you learn this skill (or you can take something like Building a Second Brain). Some of the best training grounds for research, analysis, and sensemaking are Banking, Consulting, Advertising, or other client service jobs. Those jobs are underrated as launchpads for more creative or entrepreneurial paths in the future. A great example of this is John Legend. Where did he start his career? Boston Consulting Group.

For me, the brute force of 1000s of iterations in consulting gave me a mode I can drop into to dissect, understand and explain most topics. At the most basic level, it involves shifting back and forth between two modes of thinking – bottom-up and top-down.

In top-down mode, I’m structuring and thinking about the flow of ideas, outlines, and the overall message. In bottom-up mode, I’m not worried about the overall flow of ideas and I’m just letting myself wander into curiosity rabbit holes.

From consulting, I gained a lot of comfort from hundreds of iterations through this kind of process and it’s helped me see the inherent uncertainty of creation as part of the process rather than a problem to be solved.

Short Aside: Tiago Forte’s Building A Second Brain Approach

I recorded a short reflection on what I learned from Tiago Forte’s book, Building A Second Brain

Step 4: Output – It’s Very Hard To Sustain Creation Without Completion

I think there are two phases of creation:

• Phase 1: Developing a basic creation muscle and overcoming resistance
• Phase 2: Playing an “infinite game” – tweaking your environment to enable sustainable creation

The whole point of phase 1 is just to get to phase two. This is also why advice like “find your niche” is not always helpful for newbies. More important is overcoming resistance and finding a way of creating and sharing that is enjoyable and allows you to continue to explore, grow, and evolve.

Our schools and workplaces tell us that we need credentials or a level in a company to have permission to speak. Phase 1 is about questioning that assumption and finding ways to force ourselves through the insecurity, self-sabotage, and impostor syndrome that conspire to keep us from doing things we want to do.

My secret to breaking beyond phase one started with challenging myself to post daily on Quora for three months every day before work in 2016. Every day, I would come into work and answer questions about things I knew about like getting an MBA, breaking into consulting, how consultants think, how to deal with health challenges, UConn basketball, and so on. There was no goal and it was easy to keep going because no one I knew in real life used Quora and I was finding it increasingly fun. It was exciting to see some of my responses get a lot of positive feedback.

Dickie Bush’s #ship30for30 is something I’ve seen people use to break phase 1 – it’s a similar thing to my Quora experiment – a 30-day challenge where you have to write a mini-essay each day..

Despite feeling more comfortable sharing in public, I didn’t graduate to phase two until 2018. This was when I arrived in Taipei with time and space to let my mind wander and the thing I kept coming back to was writing. I decided I wanted to commit to writing, indefinitely. So I started committing to a weekly newsletter and to “write, most days.” As a priority in my life, I’ve spent a lot of time creating the conditions such that I could keep this creative spark alive.

Step 5: Results & Feedback

The real thing that guaranteed I was going to keep writing and sharing my ideas publicly was building an audience. As more people started replying my newsletters, scheduling curiosity conversations, and sharing my ideas I was motivated to keep going.

People are often ashamed to admit that they like attention. I don’t think all attention is bad. We tend to have negative reactions towards people that blindly pursue wealth, status, or fame. It’s good to be skeptical, but when thinking about our own lives, its important not to undermine our desires. If you desire status, just make sure you’re doing it in a way that aligns with how you want to live.

For me, I was ashamed to share at first and also afraid to admit to myself that I liked the attention. After some reflection, I realized that I desired appreciation from others. This is normal – anyone on a creative path is often doing something that others don’t understand. I realized that if I could seek out appreciation from people I liked, respected and doing similar things, it could unlock a virtuous cycle in my life.

The important thing is not to be ashamed of what we really want – this typically only leads to self-sabotage in the creative process. We all have different motivators. Here are some of mine:

• Friends: I love the people I end up connecting with here and the conversations that emerge from what I put out into the world
• Money: With subscribers and patrons, I am making about $300-400 per month from small donations and while this isn’t going to change my life, it is a huge boost of confidence that 60 people are like “hell yeah, I’ll support this!”
• Likes: I do like when people share my stuff and get a kick when something I write gets shared and read by a lot of people.
• Opportunities: It’s pretty exciting that writing publicly is one of the best paths to career stability. My current path has a very uncertain salary but by writing about topics I care about I have a proof-of-work that gives me access to opportunities in the future if I might want them

For me, this is the loop you see at the bottom here and it’s what’s transformed creative action from a linear process into something that sort of happens as a product of my life.

Finding an “audience” for your writing can be a tricky thing, especially at first. I highly recommend starting out in places like Quora, LinkedIn, or Medium where there is a built-in distribution. It’s also smart just to learn about the different algorithms. You don’t want to create for the algorithms, but it’s also not smart to be naive either. If you can tweak something 10% without losing the spirit of what you’re creating then do it!

The biggest mistake people I see people make is that they pay far too much attention to what “works” on social media platforms. This might help you build followers but it will not lead to an engaged group of supporters. Over the long term too, it’s just much harder to sustain interest in topics that aren’t aligned with your natural curiosity.

If you really care about building an audience around something you care about there is one thing you can do that will help you more than anything else: write or create something longform that is interesting, thought-provoking, and original. It’s surprising how few people take this approach but when I think about the pieces, ideas, or things people connected with most, it’s almost always the longest thing I’ve written.

Far fewer people may read the longer posts, but the people that do are likely very excited about your topics.

Another thing to do once you’ve written high-quality stuff is to share it with people writing and exploring similar ideas.

The Iron Law of The Internet: Nerdy people who go deep on topic X want to befriend other nerdy people going deep on topic X.

The easiest way to get me excited is to write deeply and thoughtfully about something I’m curious about. I was surprised to find after sharing my own work how willing many writers, thought leaders, and authors were willing to talk to me to talk about their writing. I was blown away when Alex Pang gave me a quick yes to talk about his book Rest on my podcast. Yet during the conversation, I realized: he loves this too!

Protecting My Creativity & Non-Attachment

When I look back on my life, I see evidence everywhere of my interest in writing. Yet it only became apparent about a year and a half after quitting my job that it was something I wanted to commit to.

When I came to this realization, I had a deep sense that this was a gift. One that I needed to protect. This is why for most of the past few years I’ve ruthlessly protected my time and energy such that I could continue to write. Over time, I stumbled into a set of conditions that not only enabled me to keep writing but started to make my life better. Unlocking my “creative engine” enable me to flourish and led to to the most meaningful project of my life, writing a book.

Yet you may be surprised that even with some success, I don’t have any goals or aims with my writing. I like creating for the sake of itself and this is something you can only understand if you’ve experienced it yourself. As Seth Godin says, I’ve embraced my inner artist:

The last element that makes it art is that it’s a gift. You cannot create a piece of art merely for money. Doing it as part of commerce so denudes art of wonder that it ceases to be art. There’s always a gift intent on the part of the artist.

I’ve tried to embrace this more and more over time. So while I do get some value from the appreciation, I don’t do it for any specific outcome. When I hit publish, it’s as if the work I’ve created disappears. I’m much more interested in diving into the next piece.

So with that, I shall hit publish here 🙂

41k+ Sold! (Top 1% Book) The Pathless Path is Paul's book about walking away from a "perfect" job with a promising future and starting over again. Through painstaking experiments, living in different countries, and a deep dive into the history of our work beliefs, Paul pieces together a set of ideas and principles that guide him from unfulfilled and burned out to what he calls "the pathless path" - a new story for thinking about work in our lives. Learn More & Buy The Book Here

The post My “Creative Engine”: A Curiosity-First Second Brain Approach For Creating Online appeared first on Boundless by Paul Millerd.

This is the first time I’ve sat down to write an in-depth review of my year.  In the past, I’ve only done a quick scan of questions and a surface-level review of my business.  

However, inspired by other people who have shared their reviews, I thought I’d do my own.

In this review I’ll cover a few things:

• Three things to celebrate
• Three lifestyle experiments & lessons
• My five favorite places
• Overall Financial Results from 2021
• Business experiments & learnings from 2021
• Pivoting from freelance to “creator” – five year reflection
• Questions and themes I’m thinking about 2022

Before we dive in, some stats:

• Countries Lived In: US, Taiwan, & Mexico
• # Of Accomodations >1 Week: 14 places Puerto Escondido, Mexico City, Taichung, Taipei, Hualien x3, Taitung, Green Island, Orchid Island, Kenting, Taichung, Connecticut, New York City
• Total Accommodation Expenses For 2021: ~$8,500
• Total Estimated Rent for 2022: Much Higher
• # Of Hours Spent on The Book: ~1,500
• # of Vaccines Gotten In Taiwan: 1
• # of vaccines in the US: 1 (15 weeks after the one in Taiwan)
• Published words in a book: 57,500
• # of Green Cards Acquired for the Wang/Millerd Family: 1

Three Things Worth Celebrating

Inspired by Chris Spark’s own beautiful reflection where he details “five celebrations” I decided it would make sense to do the same.  With the recent release of my book, I realized that I don’t spend much time celebrating myself.  This is partly a good thing – I’ve created a path that isn’t tied to outcomes, status, identities, or things like promotions.  

However, as I’ve become comfortable detaching what I’m doing from any sort of extrinsic reward, I think I’ve become a bit too shy about being excited when good things do happen or even stopping to celebrate just because it’s something worth doing.

So here are three things that I’m really happy about with 2021:

1. Angie getting the green card!
2. Moving to the US and being able to do it with an optimistic and excited attitude
3. Finishing and shipping my book and in the process pushing myself beyond what I thought I was capable

#1 Angie getting the green card!

Although we haven’t got the physical card yet, we went through a 13-month process of endless paperwork and Angie was given a green card to be a permanent resident of the US. It’s so great to see this journey through her eyes. She said something a couple of months ago: “I don’t think you know how lucky I am to have this opportunity.” Despite many people being negative about this country, many people abroad still want the chance to live and work here.

I’m excited to see the US through her eyes as we continue to spend more time with my family, make new friends, and travel the country.

#2 Moving to the US and being able to do it with an optimistic and excited attitude

When I left the US in 2018, I was searching for a new way forward in life.  I was also a bit lost – I had become disconnected from myself and didn’t know who I wanted to be.

A few years later I can say with a lot of confidence that I’ve found myself – as cliche as it sounds.  I’m married to an incredible woman, spend almost every day doing things I am 10/10 excited about and have a great foundation of friends and family across the world to support me.

Yet I was really scared about moving back to the US for most of the year.  Angie and I applied for her green card in late 2020 and our plan was to spend most of 2021 in Taiwan waiting for the completion of the process.  Due to the incredibly slow speed of the immigration process, this meant I had a year to prepare.  

I decided to “practice” optimism.

The first step was remembering.  Remembering who I was when I was younger and figuring out how to inject the joy, enthusiasm, and humor that were once such vital and natural parts of how I showed up in the world back into my life.  This was hard.  I did a number of things like talking to some of my optimistic friends more, writing about my fears and doing things I loved as a kid like Tennis, Basketball, Yo-Yoing.  Through all these things, I realized how rigid I had become as an adult and it made it even more clear how important it is to continue to look for ways to inject a playful attitude into my life.

In our first couple of months back in the US we lived with my cousin Brian in New York.  This was a great decision because he’s someone that I’d describe as fully alive and engaged with the world.  Loves his job, has plenty of things he’s excited about and is constantly getting pumped about what other people are doing.  In only a couple of months, I realized that I really had changed a lot in a few years abroad and was able to channel completely different energy than in the past.

Another thing was concerns about money.  I realized early on in the year that worries about the skyrocketing cost of living in the US were beside the point.  I knew how to make money if I needed it and we have some savings to let us still invest in our life without needing to earn a lot in the next six months.  So I decided to commit to not complaining about money whatsoever and instead start with the life, locations, and things we want to do and then worry about making the money for it later.

Put more simply, I found out who I am and now I have a lot of confidence I can show up in the world as I want to, less impacted by the criticism and pessimism of others than I have been in the past.

Feels awesome!

#3 Finishing and shipping my book and in the process pushing myself beyond what I thought I was capable

In my book, I write about the “real work of your life” as finding the things worth doing and then committing to them.  The book was the biggest project I’ve committed to on the pathless path and it has been by far and away the most rewarding.  

In addition to pushing me well beyond what I thought I was capable of in terms of writing, it also was a learning experience.  I had worked on complex projects, but nothing like a book.  At almost every stage of the process, I overestimated how quickly things would take and underestimated how much work I would have to do.

I had complete confidence the entire year that I’d be able to write the book I wanted to but I didn’t know how I’d get to the finish line.  This is where my experience in consulting, to trust the process amid ambiguity, really helped.  I would write for an extended period, take a step back (time off), then restructure and write again. I went through this process four or five times and each time I felt like I was getting a little closer.

It wasn’t until a couple of weeks before leaving Taiwan that I figured out what the book was about. It came to me after being frustrated with writing and Angie suggested I go for a scooter ride around the town.  Less than 30 seconds into the ride, everything came to me and I started crying.  

A voice in my head was telling me: “these ideas matter and you don’t need to be scared to say that.”

I knew that in order to write a book I needed to unleash the bold side of me that I had kept back in my writing and in my life. 

These ideas fucking matter.

I also was able to connect it to seeing my parents struggle and knowing how much more capable they were than what the world was telling them they were allowed to do because they didn’t have degrees.

It was a book for them and the hundreds of people I’ve talked to over the past few years but also the world.  And from there, the rest of the book seemed to pour out of me like it had been there the entire time.  By mid-December I knew I had the book I was proud of and from there it was just editing and getting the details right.  

If you haven’t bought it yet, check it out here.

Lifestyle Experiments & Learnings

I’m living a life far beyond what I thought possible five years ago.  Most days I wake up and work on whatever I want to do and have the freedom to go wander, exercise, meet up with friends, or go for a bike ride most days if the opportunity presents itself.  At the same time, I’ve found work I love doing – writing, curiosity conversations, mentoring, creating digital products & teaching online.

Despite this optimal existence, I am still fascinated with how motivation shifts based on where I’m living, who I’m surrounded by, and what I’m curious about.  This means I’ve continued to experiment and learn about how I like working.  

Three key themes stand out from 2021:

#1 Improving my Chinese skills during an intensive class that also aligned with a three-month period of living my “ideal life”

In March, I took an on-campus class in Taipei studying Chinese.  I found it incredibly enjoyable.  In addition to the 30+ hours of in-class instruction and studying, I was also spending time biking around in the afternoons, writing my book, and still running my StrategyU business.

It made me remember how much I loved learning and that if I can build in similar blocks of intensive learning throughout my life, I will likely be a very happy and engaged person. 

Each day, I had class from 9:00-12:00 and then would ride my bike around campus and the city.  From there, I might grab lunch with a friend, wander a bit, or do some writing.  During this time, I also hosted my first corporate workshop, which helped me develop a corporate offering for my course, which already has its first client in 2022.

I was “working” a lot and there was no clear separation between night, morning, weekday, or weekend, but it was a period of absolute perfection. Everything I was working on was by my own creation and on my own terms.  I couldn’t have been happier.

This was also when I started to realize that this is why people struggle to talk about work.  They tend to only be talking about “jobs” rather than the work they want to be doing.  Most people want to work, we just accept that some or a lot of it are supposed to be a grind.  Most of my path has been about running away from that and along the way, I essentially realized what I was doing was “designing for liking work” (h/t Venkatesh Rao for pointing this out to me.)

#2 Inspired by Sean McCabe, I tested, implemented and have committed to a “every 7th week off, no matter what” model for at least 2022. 

Inspired by a conversation on our podcast and looking for better ways to structure my work, I implemented Sean’s “take every seventh week off” sabbatical approach.

In our conversation, we both had opposing reasons for doing the experiment.  Sean originally did it because of overwork and I wanted to try it because I felt like I had a lovely life, but wasn’t quite going all-in on the projects I was excited about.  

Now in each six-week block, I plan on picking one or two priorities work-wise and trying to focus on those.  During the past year, it was vital in helping me power through different phases of the book before taking a week off to wander and reflect.

#3 People over work

Coming back to the US I was excited to see some of my friends again!  In New York, I decided that I would prioritize meeting up with anyone who asked over any work I might be doing.

This was great at first but I was a bit too ambitious in terms of how much socializing I wanted to be doing after a year of relative solitude in Taiwan.

In Austin, I’m finding a good balance again and am also excited to have a home base for at least five months where I can get back into a solid routine.

Five Favorite Places of the Year

Mirador de Tortugas: An amazing sunset spot Angie and I found in our last month in Puerto Escondido.  After finding it, we proceeded to design our day around making it there for sunset each night

Dulan in Taitung, Taiwan: If there is any place that has more of a hippie nomad energy in Taiwan, this is it.  Situated right on the cliffs on the southeastern shore of Taiwan, this is a much quieter place in Taiwan that attracts a lot of young and international people.

Fuli District In Hualien, Taiwan: Between an epic bike ride through the greenest rice fields I’ve ever seen and the beautiful golden needle flowers, this place was magical

Green Island and Orchid Island, Taiwan: We spent a week on each of these islands in September and both were unique experiences.  Orchid island feels like a completely different country than Taiwan while on Green Island, I found another place filled with beautiful views.

Austin, Texas: I’ve only been here for three weeks but I am blown away by how much we’ve enjoyed the energy of the city, how relaxed and friendly everyone seems to be, and how nice the weather is (half of each week at least)

Business Results, Experiments & Learnings

Overall this was my best year since becoming self-employed.  I say this from a completely holistic perspective.  It was both my best year financially and my best year personally.  In addition, the amount of work I did that was based on me needing to join specific meetings or be available at certain times of the day was less than 20 hours for the entire year.  

A win for async work!

Overall Financial Results

Overall here’s where I ended up according to my accounting software

• Revenue: $102, 567
• Net Profit: $72,257
• Self-Employed Taxes: $16,195
• Net Income after Self-Employed Taxes: $56,062

Of course, these are only estimates – actual US taxes paid and potential rebates are yet to be determined.  

Here are breakdowns of earnings and costs by source (costs are assigned on a % basis according to revenue).  All earnings are after transaction fees.

Results By Business Focus

StrategyU: $87,510

Developed a clear advertising strategy. Created, piloted, and won first client for $15k corporate virtual workshop program. Ran for BFCM deal using Brennan Dunn’s playbook => $13k in Black Friday sales

• Think Like a Strategy Consultant: $74,531
• Corporate Workshops / Training: $10,897
• Digital Products: $2,082

Costs: ~$24,209 (majority contract labor + advertising spend)

Profit Margin (pre-tax): 72%

Boundless: $8,905

Focused on writing consistently (newsletter & book) – 72 subs for Boundless.  Launched Freelance Skills Course (~3k in Sales) – an opportunity for marketing in 2022. Does not include $5k investment in Book

• Newsletter: $3,906
• Courses + Digital Products: $3,787
• Book Pre-Sales: $1,212

Profit Margin (pre-tax): 90-93% (estimated)

“Passive” Income: $8,905:

 YouTube revenue saw some decline throughout the year, but peaks in Aug-Sep

• YouTube: $2,148
• Other: $2,713 (includes bounties from AppSumo, affiliate deals from Teachable, Podia, Convertkit, courses and payments from Skillshare, Amazon, and Medium)

Profit Margin (pre-tax): 90-93% (estimated)

Coaching: $4,025

This is from 1-on-1 coaching earlier in the year and group coaching kicking off in December.

Profit Margin (pre-tax): 90-93% (estimated)

Five Biggest Experiments & Lessons

#1 – Think Like a Strategy Consultant had its best year – Traffic continued to increase on my website and Youtube with very little effort to add additional content.  I hired two ads people in Croatia who have helped me implement an effective advertising program.  It hasn’t gone as well as I would have hoped, but I definitely see more potent

#2 – Prototyping, launching & selling a Corporate Virtual Workshop – Last spring, a data analytics company in the US wanted to train their team with my self-paced online course.  I decided I would develop a corporate workshop for them and sold it to them at a discount to help me prototype it.  It went far better than I expected and I ended up developing a clear “signature offer” for my course to pitch to companies.

#3 Productizing other stuff on StrategyU  – Inspired by this post on Austin Church’s site, I decided I needed to take some of my own advice and develop “packages” for some of the work I liked doing.  One reason was to make it simpler for the increasing number of corporate types who were stumbling upon my page and also to create easy on-ramps to working with me.  

Here’s an example on the coaching front.  I make it cheap and easy (but still have a cost) to talk with me but also signal that I do higher-end work (with high price signaling).  Using this I’m already working with two senior executives in 2022 to help them with Board presentations (which I love doing!)

Here’s an example of the corporate workshop.  It clearly signals that I am only working with serious companies that are willing to pay my fee.  If they aren’t they can self-select out and I save the time I might spend on a phone call.

#4 Shipped my freelance course – In June after being locked down in Taiwan after a local outbreak, I decided to create a freelance course that had been existing in my head as a future potential creation for more than a year.  

I think it’s a pretty badass course on helping people become strategic partners to senior-level business leaders.  It walks through the nitty-gritty of everything from proposals, to documents, to pricing, to what to say in conversations.  I am still not sure if I should integrate this with StrategyU or keep it separate but I’m guessing the answer will emerge this year as I plan to put a bit more effort behind this in 2022.

#5 Group Coaching – Throughout 2022, I had more people asking questions about finding other people following similar paths.  Inspired by Tim Ferriss’ question, “what if this were easy?” I decided to create a survey gauging interest in group coaching.  I got 30 responses and from this, I created a landing page, some stripe payment links, and sent out an announcement about doing cohorts starting in December.  I’m currently running an “early career” one and a “mid-career” one and both are going really well!  I think group settings are much better for the work stuff than 1-on-1 because I only have so much experience.  I’m not sure what I’ll do next with these but I’ll likely scale up to something more interesting 

Reflecting on the past five years

On the business front, I seem to be nearing successful completion of a pivot I originally made about 9 months into self-employment when I realized I didn’t want to spend the rest of my life as a freelancer.  At that time, I was also realizing I wanted to optimize for non-work time over almost everything else.  This led to a dramatic decrease in earnings (2017 was only 7 months!) and a shift to a different way of thinking about work.  You can see the transformation here in these two charts:

In this first one, we see that for 2018 and 2019 I wasn’t making much money (which was fine at the time, I wasn’t too focused on making money)

What I was focused on instead was developing skills, experimenting with creating online (which I found I really loved), and finding new income streams beyond freelancing. For most of 2021, I had >10 income streams with 3-5 earning me more than $200 a month:

The biggest driver behind this shift was the slow but steady growth of my course Think Like a Strategy Consultant.  The course has generated more than $172,000 in revenue over the last three years, far exceeding anything I could have ever imagined.  

Through the course, I’ve had a ton of inbound requests to work with me and because I only wanted to work on things I liked doing, I’ve purposely only accepted things I want to test and then potentially turn into an offering.

Over the past two years, I’ve now developed a pretty robust corporate offering, a coaching offering and am even turning this experience into freelance strategy work with corporate strategy groups and boutique consulting firms.  I’m pretty excited about most of this because it’s work I like doing, am good at, and it doesn’t take too much time.

You can see this shift in the following chart:

Luckily, this has given me a lot of time and space to continue to write and explore my curiosity around work.  While the course has provided most of the income, most of my time has been devoted to writing for more than three years.

For 2022, here are five questions and themes themes I’m thinking about for both work and life:

#1 How do I use my happiness, optimism & energy to support others?

I’ve found my footing as a self-employed creator/solopreneur/whatever you want to call me.  I’ve also reclaimed some of my childhood excitement towards life.  The question I’m asking this year: how do I broaden the sphere and support others with this energy?

#2 How do I level up the ambition in ways that are exciting and sustainable?

My fear five years ago: creating a job for myself.  I now am quite confident that’s not going to happen.  I know what drives me, how to fire up my curiosity, and I know when to say no.  With this, I’m thinking about ways to be a little more ambitious with what I’m doing.  I’ve been comfortable tweaking and making 1% improvements over time.  I don’t have any interest in 10x-ing anything but am interested in potentially doubling the scale of the things I’m doing and looking for other ways to help people beyond my comfort zone.

#3 How do I help Angie succeed?

My wife is amazing – smart, curious, and creative.  How do I continue to make sure she is able to do the things that bring her alive while also having the resources to take chances and risks in order to grow.  I think about this a lot but it’s worth writing down here as a gentle reminder.

#4 What are the business or personal things I’m not thinking about (yet)?

Angie and I are always asking some form of this question.  It’s an easy way to keep dreaming and imagining new possibilities.  It’s very easy to know what the default next steps are, especially in the US.  Everyone in my age cohort seems obsessed with owning a home.  It all seems a bit too frenzied for me right now not to mention it’s just not my goal.  However, that means we often need something to aim for.  Right now seems incredibly open after finishing my book.  I don’t need to have an answer but I’m listening for clues.

#5 What are the experiments I can do to continue to grow?

This year is all about play, experimenting, having fun, joy, and trying to remain optimistic.  To do this I plan to continue to do things like play sports, Yo-Yo, hosting events, and then try new things.  Some things on my list: tap dancing, DJ lessons, and hosting a party using Nick Gray’s new book.  In addition, I want to write more essays, create more YouTube videos, do some deeper writing for StrategyU, potentially do a meditation retreat, and much more. 

41k+ Sold! (Top 1% Book) The Pathless Path is Paul's book about walking away from a "perfect" job with a promising future and starting over again. Through painstaking experiments, living in different countries, and a deep dive into the history of our work beliefs, Paul pieces together a set of ideas and principles that guide him from unfulfilled and burned out to what he calls "the pathless path" - a new story for thinking about work in our lives. Learn More & Buy The Book Here

The post Paul’s 2021 Annual Review – From Mexico to Taiwan to the US appeared first on Boundless by Paul Millerd.

Despite Kahneman’s view, when you poll people about life goals, the response of many, especially in Western countries, is “to be happy.” Unfortunately, happiness is what artificial intelligence researcher Marvin Minsky calls a “suitcase word.”  It has a different meaning to everyone.  

The word “happiness” traces its roots to the Greek term “eudaimonia,” which translates more closely to “human flourishing.”  For the ancient Greeks, experiencing eudaimonia meant devoting one’s life to the pursuit of wisdom or virtue. To be happy was to be wise. Yet even in ancient Greece, people had their own definitions of happiness.  This frustrated Socrates.  He chastised his fellow Athenians, asking, “are you not ashamed of your eagerness to possess as much wealth, reputation, and honors as possible?”  He wanted them to embrace his version of happiness, which meant reflecting on “wisdom or truth or the best possible state of your soul.”^[2]

We could conclude that Socrates was right and there is one correct way to live and experience happiness.  I reject this stance.  On the pathless path, we assume that humans are complicated, and we should be wary of simple models, such as Socrates’ definition of happiness, to describe what everyone wants from life. 

Another simple model is Abraham Maslow’s “hierarchy of needs,” which is typically represented in pyramid form.  While loosely based on Maslow’s research, the pyramid was invented by a business journalist in 1960, arguing that meeting people’s non-monetary needs was a way to pay them less money.  Maslow’s actual research, however, offers a more interesting model, one that fits with the pathless path.

Maslow first proposed his “hierarchy of needs” in a 1943 paper that explains his perspective on human motivation.  He thought people are motivated by five needs: physiological needs, safety needs, love needs, esteem needs, and the need for self‑actualization.  He hypothesized that “the appearance of one need usually rests on the prior satisfaction of another,” but the rest of the paper questions this theory.^[3] 

He found exceptions to the hierarchy in his work with patients.  For example, Maslow noticed that sometimes a creative person’s desire to create overrides all other needs.  Moreover, some people are willing to give up meeting their needs in order to fulfill societal expectations.  Others pursue esteem needs instead of love needs because love is missing in their lives. Finally, some people reach a level of satisfaction and have no desire to meet other “higher” needs like self‑actualization. Maslow’s conclusion is complex: people are “partially satisfied in all their basic needs and partially unsatisfied…at the same time.”^[4]

He spent the next twenty years exploring this tension. He thought the field of psychology was too focused on fixing “broken” people.  He sought to counter this by exploring how people grow and evolve throughout their lives and by developing a new theory of human motivation based on two different perspectives of human behavior.  These were Being-Psychology and Deficit-Psychology, or more simply “B‑Psychology” and “D-Psychology.”   Maslow wanted to emphasize the B‑Values, or Being‑Values such as wholeness, perfection, aliveness, richness, simplicity, beauty, effortlessness, and playfulness.

To Maslow, no one is climbing up through a hierarchy; instead, people are always dealing with a confusing range of needs and desires at the same time.  For example, a lot of research shows that long commutes lead to a permanent decline in happiness.  However, this conclusion ignores a person’s need to feel important, responsible, and loved, not to mention many other needs and desires which may be hard to understand.  While happiness researchers might be confused by a person’s willingness to stick with a long commute, to Maslow it would make sense.[1] 

On the default path, I told myself stories about what I wanted and needed without testing those beliefs.  In contrast, the pathless path enables you to move beyond what you think you should want and get to know what really matters, what really makes you happy.  Unfortunately, we can’t design perfect lives.

On the pathless path we are not progressing up a simple pyramid, but balancing a confusing mix of deficits, desires, and needs.  Indefinitely.

[1] Mandel, Amir. “Why Nobel Prize Winner Daniel Kahneman Gave up on Happiness.” Haaretz.Com, 11 Oct. 2018, www.haaretz.com/israel-news/.premium.MAGAZINE-why-nobel-prize-winner-daniel-kahneman-gave-up-on-happiness-1.6528513.

[2] Plato. Apology. Independently published, 2020.

[3] Maslow, A. H. “A Theory of Human Motivation.” Psychological Review, vol. 50, no. 4, 1943, pp. 370–96. Crossref, doi:10.1037/h0054346.

[4]  Maslow, A. H. “A Theory of Human Motivation.” Psychological Review, vol. 50, no. 4, 1943, pp. 370–96. Crossref, doi:10.1037/h0054346.

41k+ Sold! (Top 1% Book) The Pathless Path is Paul's book about walking away from a "perfect" job with a promising future and starting over again. Through painstaking experiments, living in different countries, and a deep dive into the history of our work beliefs, Paul pieces together a set of ideas and principles that guide him from unfulfilled and burned out to what he calls "the pathless path" - a new story for thinking about work in our lives. Learn More & Buy The Book Here

The post Do We Really Want Happiness? Lessons from Socrates, Kahneman & Maslow appeared first on Boundless by Paul Millerd.

Instead of sharing more about my story, I want to share the stories of the many people I’ve talked to over the last few years. This includes millionaires and people that are broke and the unique Americans who are in massive amounts of debt before they start their careers. People spanning from the US to Malaysia to India to Nigeria and Pakistan. Across all these people I’ve discovered one consistent intervention that consistently enables people to improve their relationship with work and has a 100% approval rating.

That thing? Taking an extended break from work.

A Quick History: Sabbaticals In Universities

Harvard University was one of the first universities in the world to offer a sabbatical to professors in 1880. In predictable fashion, other universities followed suit and by the early 1900s, many universities had their own program.

Here is a statement from Columbia University in 1907 describing the thinking behind their own policy (bolding mine):

The practice now prevalent in Colleges and Universities of this country of granting periodical leaves of absence to their professors was established not in the interests of the professors themselves but for the good of university education. University teaching must be progressive; it requires on the part of the teaching body, as it were, a periodical refurbishing of its equipment. It is not merely national, it is international; contact with other institutions, with specialists of other countries, with methods of acquiring and imparting knowledge in vogue elsewhere, which cannot be obtained during the summer vacation, as this is a period of rest practically everywhere, is for the real University teacher an intellectual and practical necessity.

Here is a similar statement from Dartmouth University in 1922:

The purpose of the sabbatical leave is to render the recipient more useful to the college as a teacher, as an investigator, or as an administrator. Leaves of absence are in nowise to be regarded as increased vacation periods, as primarily opportunities for increased financial advantage to the instructor, or as due him upon the ground solely of the length of service. They are an investment of college funds designed to increase the efficiency of the teaching force

While Dartmouth framed the sabbatical in the interests of the university, they are acknowledging that they are also attached to the idea of a teacher as someone that should have a broader range of knowledge and wisdom. The mindset of both of these schools was that there was something valuable in existing outside of the domain of their primary work that was of value to both the University and professor as well as the society at large (schools were not seen primarily as job-training at this time).

In the early 1900s, the kind of “knowledge work” that professors engaged in was the exception rather than the rule but now almost all readers of this newsletter are engaged in a similar sort of intellectual, knowledge-based work.

Why then, do we still accept a factory schedule for our lives?

Taking A Break Is Scary & Not Broadly Accepted

One of the hurdles that stop people from taking a break is the idea that life transitions are all-or-nothing leaps. Work is either something you do indefinitely until retirement or something you quit and then go live on a beach.

David Vaucher wrote a viral post on LinkedIn a few years ago about “ending his career” a few years ago. He decided to take a break from work to spend time at his father’s home in France, one he didn’t get to enjoy because he passed away before he retired from work. David felt that he needed to shake things up but admitted at the time “Who knows how this really all turns out.” I reached out to him last year to see where he was on his journey and was surprised to learn that not only had he returned to work full-time he was also really happy with his choice:

I now see the foolishness in feeling life is only about work, and that more hours lead to more and better output. I have near- complete professional autonomy, as well as the time to pursue things outside the office and it’s been fantastic. I’m in the most creative period of my life, my clients are happy, the product line I manage has improved by leaps and bounds and the team I helped build is phenomenal.

Finally, the bigger shift is I don’t feel the need to chase the next promotion or raise. I am grateful for all the things I do have right now, and I trust that if I do my best when I am in the office, things will work out.

For many people, like David, a sabbatical is not the start of a crazy adventure but a pause to ask questions that might add to the wisdom needed to live the life we want to live. This kind of break is not for the “what about…” people but for the people who have the fear of“living a life that was not true to themselves” as Bronnie Ware wrote in her book Five Regrets of the Dying.

And when people take these breaks they tend to experience many of the same things:

#1 People Are Surprised At How Burned Out They Were

The day after I quit my job I woke up and started to write. I wrote about being burned out, something I would have denied a day earlier. I felt broken and it shocked me that I had spent the previous six months in a numbed state, going through the motions, and pretending everything was okay. A German report on burnout described my state:

They may start being cynical about their working conditions and their colleagues. At the same time, they may increasingly distance themselves emotionally, and start feeling numb about their work.

One of the weird benefits of self-employment is you become hyper-aware when you are becoming cynical, exhausted, or burned out. Without managers and the other sort of emotional pressures to do your work, you have to face the fact that you created the conditions you claimed you didn’t want. In full-time work, you can go years doing work you don’t really like all because it’s the normal thing to do in today’s world.

A friend who recently took a sabbatical shared his surprise at how things had gotten out of alignment without him noticing:

#2 Curiosity Re-Emerges

One thing that seems to consistently happen is that people re-discover hobbies, relationships, and ideas they were once drawn to.

Here is Edward, who took a break from medicine:

I’ve been lucky enough to take a few extended vacations, of one month or more, but even after a couple of weeks, I notice that my brain starts to change, starts to alight upon new topics or rediscover old subjects of interest. I find myself writing a lot of notes on a whole host of different topics and wanting to explore them further. This is my creative process, liberated by the neocortex now that my mind isn’t wholly occupied by the strain of everyday sustenance, the rat race, and the grind.

For some people, it’s curiosity about a different way of life. Gabe, writing about an unexpected sabbatical after getting laid off shares: “A month ago, I was newly unemployed and unchained in the panhandle of Florida. Now I live in an eco-village on a volcano, in the middle of a lake in Nicaragua.”

#3 It’s Uncomfortable But Often The First Step In A Longer Journey

Jacqueline Jensen planned a “structured sabbatical” for herself centered around a question: “What if I took work…working for a paycheck, what if I took that out of the center of my life, what would my life look like?

She found it much harder than expected, “It was hard. It was not a four-month vacation. It was a lot of work to untangle myself from all the things I get from work – the validation, the excitement.” However. at the end of the sabbatical, she found a new spark for life, ended up deciding to write a book, and reprioritizing what she was willing to compromise for success in her career and has found a stable remote job that has enabled her to live in Portugal while still doing work she enjoys.

Diania Merriam had worked up the courage for months to ask her boss for unpaid leave to walk the Camino de Santiago. She walked in and to her surprise, her boss said “sure” instantly. What she didn’t expect was how scared she would feel before she took her trip:

I planned as much as I could on the material side and the physical side but what I could never plan for was the emotional side of being without work for two months, completely disconnecting, and dealing with the uncertainty of where I would be every night, where would I get food? I just had to trust that I was going to walk and find it. Battling the uncertainty of all of it on the way there and while I was in it.

She went back to work for a couple years, but her curiosity led her to a number of side projects, including launching her own conference to explore a “new American dream” and a part-time podcast host gig on personal finance. Eventually, she decided to take the full leap to self-employment.

Another friend shared how she took multiple sabbaticals with her partner and kids as part of a larger transition to become self-employed.

So for some it may be a one-off thing but for others, it is the first step of many.

#4 Lots of People Start Writing

I’m not sure which direction the causality goes here, but many people who take an extended break end up finding writing as something that they want to keep doing. Like Jacqueline, Lenny comments on how his sabbatical led directly to him deciding to launch a paid newsletter and to continue writing

After leaving, I planned to take 6 months to explore and tinker. That turned into a year, and that turned into the newsletter that you’re now reading. There is a 0% chance this newsletter would have emerged if not for the space that this time off created—the space to tinker, to research, and to write.

Alex Pang’s own sabbatical inspired led him to live what he described as a “leisurely” life and while on his, reading a book by Virginia Woolf inspired him to go down a rabbit hole which has led him to write several books about our relationship with work7.

I had been reading Virginia Woolf’s book A Room Of One’s Own that makes the argument that for in order for women to be creative, but really for anyone to be creative, they needed a certain kind of space and independence that had long been denied to women. That got me thinking about all these issues and their interconnection.

I had been writing before I took a break from work but it definitely exploded when I moved to Taiwan and had no paid work to do. I think the reason writing is such a draw for people is that to take a sabbatical in today’s world is to split away from the default reality of today’s world. This can be disorienting and writing is a way of figuring out what you actually think.

#5 Forces You To Look At Your Life From A Distance

Sean Blanda has written one of the best posts on sabbaticals. If you follow any of the links I mention, it should be Sean’s. He offers eight insights that people typically have from taking a sabbatical. Here are the eight:

1. You are creating a new map.
2. Be ready for “the thrash”
3. Release your “curiosity constipation”
4. You may have the instinct to plan this like a vacation. Don’t do that.
5. You won’t do this alone. Much of your progress will come through people.
6. The distance from your “normal life” will make you realize what you miss and what you don’t.
7. When you come back, you’ll need a narrative.
8. Lastly, every single person I spoke to would do it again:

A lot of them resonate with what I’m sharing here but I thought the most interesting was his idea of the “thrash” which is the moment when you “peel away layers of your identity” and start to realize that you are more than what you do:

The fact that you are able to take a sabbatical means you have enough money and are good enough at something to give you a bit of an ego. But for this trip, that person who is “good at something” is no longer you. It’s just part of you. And you’ll have to let that part go (for now). And it will feel like starting from scratch. And it will feel like you’re giving up all the “progress” you’ve made.

One day you are going through the motions of your life and the next month you are suddenly disconnected from that former identity and seeing everything you were doing much more clearly. A friend, James, noticed how a break helped him get back on track with what he really wanted:

I started to realize how, on a personal level, my job was excluding me from so many opportunities. It offered some opportunities as well, but they could be taken away by office politics, the election cycle, or the company deciding I was more valuable to them in a role I didn’t enjoy.

The sabbatical let me think more objectively about my career because it removed me from that environment long enough for me to figure how to pay attention to myself, rather than all the external demands that came with the job.

#6 Travel Often Amplifies The Effects Of A Sabbatical

Our modern conception is limited to vacations. Josef Pieper was writing in the 1940s that people had started to lose connection with a definition of leisure that prioritized contemplation and active engagement with the world before work became so central. He noted that the vacation was “part and parcel of daily working life” and that it is “there for the sake of work. It is supposed to provide ”new strength” for ”new work.”

Contrast this with how travel writer Pico Iyer talks about travel, “We travel, initially, to lose ourselves; and we travel, next, to find ourselves.” Iyer came to realize that the real power of travel was that it enables one to “become young fools again—to slow time down and get taken in, and fall in love once more.”

In the last four years, I think one of the interesting things to see that my body language has softened. You can kind of see it in this how it started, how it’s going comparison from a month after my leap to another from last month:

The biggest shift happened when I moved to Taiwan and didn’t have any sort of script to guide me for how I was supposed to feel:

Walking around in Taipei was the first time I experienced this feeling. When I was living in New York or Boston in the previous ten years I might be wandering around the city doing very little but it was always in tension with the predominant culture that I should be doing something, that I might have forgotten something, or I might not have done enough.

In Taipei, that feeling evaporated. I didn’t yet know the cultural scripts or expectations around me. I was both in a state of not-knowing and non-doing. 

Edward, from above, feels that “You don’t have to necessarily travel during these times but I believe it is optimal” There is something about travel that enables you to get distance and to start to ask the questions that matter.

Michelle And Cecile Reflect on Taking A Sabbatical

On my podcast, I interviewed Michelle Varghoose and Cecile Marion who both had taken sabbaticals in the prior year. Michelle decided to extend her indefinitely while Cecile returned to work.

I originally reached out to both of them after reading their thoughtful reflections. Here is Michelle in her essay, “Sabbatical Mindset“

A sabbatical was a blessing because I had the opportunity to step away from the rat race and learn to build a life that was centered around what brought me meaning.

Two years in, I’m now naturally busier as my creative projects have compounded. The word sabbatical is starting to feel like an old sweater that doesn’t fit quite the same way anymore.

I don’t define myself by whether or not I’m working. Instead, I’ve found a new way to engage with life and work that works better for the person I am now. Having that freedom to move away from the corporate world allowed me to develop this new life.

Similarly, Cecile had many thoughtful reflections she had shared on Twitter:

Both are passionate supporters of taking breaks from work as both were able to reconnect with themselves, reignite “forgotten hobbies,” and find things they enjoyed doing.

Cecile is now helping people plan their own sabbaticals and is offering calls to support people.

Sabbaticals Are Essential For The Way We Work

Sabbaticals are shifting from a rare thing to something that a much broader range of people will consider. A big part of this is the changing nature of work. As I covered last week, the types of jobs that people often need breaks from demand much more lifelong learning, decision-making, and “management” work than before. In addition, it’s also creating much more gig work driven by the explosion of technology, platforms, and disappearing middle-class jobs. Gig workers will likely be the ones that pave the way in taking sabbaticals and normalizing them in our culture and corporations and full-time employees will eventually fall in line.

The idea that one should have a straight, linear path of work throughout their life is still alive in many people’s minds but not a great strategy for a career. The industrial labor economy leaned on people’s ability to do repeatable tasks while also aiming for incremental improvement. The digital economy is oriented much more around creative work, complex decision-making, and information abundance.

This new economy will favor those who work as Naval Ravikant described:

We are moving from what Seth Godin has argued is a competition of “being more ordinary, more standard, and cheaper” to “being faster, more remarkable, and more human.” Many jobs operate like this but we are stuck with the 40-hour workweek mostly because all the people that used to argue for shorter workweeks have already passed away.

I’ve noticed increasing numbers of people taking breaks from work earlier in their lives, like Maria who decided to cash out $4,500 from her retirement account to explore for four months. Here was her reflection and call to action:

After 4 months and 4500 spent, I feel more self-aware, confident, and energized than ever. I feel more mellow, grounded, and more in control of my future. I grew so much that I had now made it a rule to have a big break in between gigs fully devoted on play.

I keep highly highly recommending to any and every of my friends to do this. Put some money aside and just live your life. The money will be plentiful in your 30s but your time and independence will be scarce – at least that is my belief; take it or leave it-.

Another model might look like what Sean McCabe embraced in his life after realizing he literally had no life beyond work. He was simply working all day every day including weekends. He decided to try an experiment where he would “work six weeks and take off every seventh week” and has said that it changed his life9. After six years of doing this, he decided he would take it to the next level and take every seventh year off.

Taking a break is scary but from what I’ve seen it’s probably one of the simplest ways to grapple with one of people’s biggest fears: that they didn’t live a life that they were capable of. Taking a break is a way to take a different perspective of your life, remember the things that mattered to you, and sometimes simply rest and be with the ones that matter to you.

As Alex Pang concluded in his book: “If you want rest, you have to take it. You have to resist the lure of busyness, make time for rest, take it seriously, and protect it from a world that is intent on stealing it.”

41k+ Sold! (Top 1% Book) The Pathless Path is Paul's book about walking away from a "perfect" job with a promising future and starting over again. Through painstaking experiments, living in different countries, and a deep dive into the history of our work beliefs, Paul pieces together a set of ideas and principles that guide him from unfulfilled and burned out to what he calls "the pathless path" - a new story for thinking about work in our lives. Learn More & Buy The Book Here

The post The Ultimate Guide & Reasons To Take A Sabbatical appeared first on Boundless by Paul Millerd.

Prior to that I lived a pretty normal life, working full-time and signing year-long leases.  At the age of 32, driven by dissatisfaction and curiosity, I decided to take steps towards a different kind of life.

Many people have this yearning but it is quieted by an offsetting fear of the unknown. Exploring this unknown has become a central theme of my writing. I want to help people make sense of life off the default path.

With a global pandemic forcing many people to work from home, lives like mine have become a lot less weird and many people are re-assessing their priorities and dreaming up new possibilities for their life. 

I’ve received more questions in the last nine months about my life and how to work remotely than expected so I decided to write about many of these questions I received. I’ll publish this on my blog and keep it updated and make edits as appropriate, but I’ll dive into some of the following questions:

• How do you think about travel?
• How much should you work?
• How do you bank and get access to money abroad?
• How do you make friends and deal with loneliness?
• What should you bring with you?
• How do you handle visas, healthcare & taxes?
• How do you pick where to live?
• What do things cost?

Without further ado:

How to think about long-term travel?

When you are living nomadically, travel shifts from something that can be consumed to something that you are living every day.  The preferences you think you have will shift because you are no longer traveling within tight time constraints or in an attempt to escape from work.  Travel is your life.

This can be a pretty wild mindset shift at first and can leave you feeling a bit detached from reality, not to mention disconnected from your friends “back home.”  One of the best things I did to deal with this was to journal and write about the experience.

In addition, I also recommend reading books about travel. Reading about what you might expect before and during the initial travel can help you make sense of the experience. Here are some books and writing that were useful for me along the way:

• The Field Guide To Getting Lost: Her quote “That thing the nature of which is totally unknown to you is usually what you need to find, and finding it is a matter of getting lost” helped me make sense of wandering into the unknown when I arrive in Taiwan in 2018.
• Vagabonding: This book by Rolf Potts is a must-read for anyone embarking on long-term travel.  In his terms, “Vagabonding is about looking for adventure in normal life, and normal life within adventure. Vagabonding is an attitude—a friendly interest in people, places, and things that makes a person an explorer in the truest, most vivid sense of the word .”
• The Four-Hour Workweek: This book is a bit outdated with its resources but still valuable in how Tim thinks about the relationship between time, work and money. The title often confuses people as an attack on work but really this book helps spur the imagination for the possibilities of one’s life in powerful ways.
• Being an Illegible Person: This older post from @vgr on Ribbon Farm is still very relevant to someone not following the default path of work:“nomadism has almost nothing to do with the rooted-living behavior it nominally resembles, travel.”

How does one actually make the shift and how do I tell my loved ones what I’m planning?

As you simplify your life and look forward to spending your new wealth of time, you’re likely to get a curious reaction from your friends and family. On one level, they will express enthusiasm for your impending adventures. But on another level, they might take your growing freedom as a subtle criticism of their own way of life. Because your fresh worldview might appear to call their own values into question (or, at least, force them to consider those values in a new light), they will tend to write you off as irresponsible and self-indulgent. Let them. As I’ve said before, vagabonding is not an ideology, a balm for societal ills, or a token of social status. Vagabonding is, was, and always will be a private undertaking—and its goal is to improve your life not in relation to your neighbors but in relation to yourself. – Rolf Potts, Vagabonding

The aspiration to live abroad or test out remote working often emerges slowly.  For me it emerged over a period of six months period while working on a remote project in the US and during a month of travel in Asia.

I didn’t have a reason other than a general curiosity pulling me towards living abroad but as I shared it with others I realized this was not good enough for others. When you are starting to tell others what you are thinking you need to think about their process of becoming comfortable with your move. They may see it as dramatic and it can be useful to give them the same space that you needed in the first place.

Thus it can be practical to start with “I’m thinking of doing this, what do you think?” before progressing to “I’m doing this…” Similarly, if you are trying to get your employer to let you work abroad frame it as a one or two month experiment before asking to make the move permanently. The norms are changing fast but living and working abroad is still quite new and strange to most.

In my own case, despite a hunch that my own experiment might be longer than a few months, I framed it as a three-month “trip.” While others saw this as a bit crazy and a risk to my success as a freelancer, I knew I had to go. At the end of the day making people uncomfortable is an inevitable part of live beyond the default path.

How much does it cost to live abroad?

“The more we associate experience with cash value, the more we think that money is what we need to live. And the more we associate money with life, the more we convince ourselves that we’re too poor to buy our freedom” –Rolf Potts

People that live in expensive cities around the world like London, NYC, San Francisco, Sydney, and Hong Kong often assume that apartments cost thousands of dollars, meals cost at least $15 and for Americans, healthcare requires insurance and must be expensive.

Depending on the country you decide to go to (and even parts of your own country) these facts need not be true.  My biggest costs when living abroad tend to be housing, food, and transportation. Here is a sample of some of the costs:

Housing:  The more often you move the more you pay.  If you can stay at least a month in a place prices start to drop dramatically.  At 3-months you can start talking to local brokers about signing a lease and saving even more money.

• Taiwan: I spent no more than $800 a month staying in shared AirBnBs with local hosts and when I signed a lease with my wife in a 1BR we paid about $533 per month.
• Bali: I stayed in a 1BR without a kitchen at a hotel with a common area and restaurant for about $700  a month
• Thailand: We spent a month in Chiang Mai and Pai in December 2018 and spent $20-25 a night on lodging.
• Spain: We spent about $800-1000 per night living on the canary islands in coliving houses and AirBnBs
• Mexico: We are spending $800-1200 per month living in shared houses with kitchens
• US: I lived in shared apartments in Boston for $850 and $800 per month in 2017-2018.  One of these apartments was with 4 other people and 1 shared bathroom 🙂

One note on AirBnBs. They can be a great on-ramp to getting local housing but are often 30-100% higher than a rate you may pay for local apartments. I recommend using AirBnB (or Agoda or Booking) for your first couple of weeks but if you plan to stay you can often find brokers through local facebook groups that are offering monthly rentals.

Food:  The higher the price of food the more valuable it is to have your own kitchen which should factor into your housing decisions.  Eating out in many countries is much more common and lower cost outside the US and especially so in Asia.  In Taiwan, Bali, and Mexico, meals ranged from $2-10 per person per meal.  A few examples:

• Cheap Meals: In most countries there is a local go-to meal.  Taiwan you can walk out to find bounties of street vendors and get a selection of 3-5 items to share with two people at a cost of about $5-7 a person.  In Mexico you can find great street tacos for $1.  In Thailand you can find a kick-ass Khao Soi for $2-3 and in Bali you can find a great Mie Goreng or Nasi Goreng for $1-3.  In many parts of Europe you can find a local item that is cheap such as the Crepe in France.
• Nicer Meals: In Taiwan, Thailand, Bali and Mexico you can get a pretty good “western” meal (think instagram friendly with lots of colors) for $5-10.  
• Fancy Meals: In cities like Taipei that serve as international hubs you have meals that are just as expensive as you might find in Hong Kong or New York City.  In smaller places like Puerto Escondido in Mexico, you can get a filet mignon at the fanciest restaurant in town for $15.

Transportation: One of the biggest costs of travel, especially if you plan on going to many places can be air travel.  This has not been a major expense for us mostly because we have decided to stay in places for 2+ months at a time.  

In terms of local transformation. the most common way of getting around is a scooter or motorcycle.  Some countries require an international driver’s license (or at least the cops will try to extort you if you don’t have one in Thailand and Bali) while others do not (you should be okay with a US license in Mexico)

• Scooter Rentals: For $75-200 a month you can usually easily rent a scooter in Taiwan, Mexico, Thailand and Bali
• Bike Shares: Many locations are starting to roll out bike share programs.  This made living in Las Palmas, Gran Canaria about 100 times better as it made the whole city bike-able in less than 20 minutes.
• Car rentals: I rarely rent cars and this can range in price dramatically but think anywhere between $10-$30 per day

What about healthcare?

Healthcare is often a major concern for Americans because our healthcare system is in the early stages of collapse. It was a surprise to learn for me that confusing layers of insurers and unexpected high fees are not a common thing in other places.  I haven’t gotten healthcare everywhere, but here are some things I’ve learned:

• Insurance:  There are many providers that offer global health insurance.  Last year I had a plan with Cigna that covered catastrophe care helping me to limit the downside if I had to deal with anything serious.  I had about $3 million in coverage for $90 a month and this covered me for up to 3 months in the US.  This didn’t cover normal doctor’s visits but that was not something I needed given the low costs of care in the places I went.  I have used SafetyWing in a couple of places and haven’t had to submit a claim but they have solid customer service and its not too expensive (affiliate link).
• Paying Direct for Doctor’s Visits: Taiwan’s healthcare system is one of the best in the world and seeing a doctor is pretty easy.  You can see a doctor and get a prescription for $10-15.  In Spain, I had to see several doctors to deal with a health challenge after a tooth removal and paid about $60-$80 per doctor’s visit.  Prescriptions from pharmacies in Spain were about $2-10 per medication.

Special section on US healthcare

The US is a pain in the ass and this becomes apparent when you start looking at international plans and realize that the only country in the world that raises your premium substantially is the US (really).

If you do need insurance and are planning on going back into the US I suggest that you start the process early. You can access state exchange plans at any time of the year because moving back into the country is a qualifying event. You should start the process before you arrive so that the insurance will start by the time you arrive. Otherwise you will have to fight with them to backdate your start date (which is possible in some states).

I’ve done three stints in the US without insurance and have learned that there are ways of accessing healthcare without insurance (sometimes its even better than if you had insurance)

1. Most pharmacies have special codes for people without insurance.  This can lower the price of the prescription to even lower than many copays.   You can check sites like GoodRx to get a sense of what these costs might be.
2. If you don’t use insurance you can also get your full prescription.  I was able to get a full year of my thyroid medication at once because I was using an uninsured coupon code and not going through insurance.
3. Ask for the price ahead of time always! Many doctors and services have “cash prices” if you pay up front, but it can take a bit of calling around to find them.  These are often lower than the post-insurance price you’ll pay (crazy, I know)
4. You can often negotiate the price after your care or ask for forgiveness programs.  This is still pretty hard and if you really want to go to battle over the costs, there are probably better resources to find on the web.
5. In many medium or large cities there are services that offer free care and regular services like bloodwork or basic doctor’s appointments without insurance. Some googling around will usually dig up something. Just be prepared to fill out a bunch of paperwork.

Taxes?

Taxes are a tricky subject and I recommend reaching out to an accountant. I scheduled a paid consultation with Grace from Gracefully Expat who helped me answer 10-15 questions I had in less than an hour. While there are some ways to avoid US taxes, the US is the most aggressive country in terms of collecting taxes from citizens living abroad. I know other countries are much more lenient, but you shouldn’t be taking tax advice from me…

I have a pretty simple business and keep track of all my business spending and income through Quickbooks Self-Employed and use a Chase Business Ink card which has no international exchange fees abroad.

Visas

In many countries you can go work remotely as a “tourist.” Depending on your country this means you can show up and spend 30, 60 or 90 days without a formal visa. While this can technically be a legal grey area because you are “working”, countries like Indonesia and Thailand have softened their enforcement of this and have realized that these workers often stay and invest in local businesses and communities.

Countries are increasingly competing to attract these kind of workers with new kinds of Visas. Fellow remote worker Leandro has a great article from September on the entrepreneur and nomad visas that are being offered around the world.

If you are on a tourist visa you will likely have to do a “visa run” which means you have to leave the country and come back. In Bali, people often do a weekend trip to Singapore before coming back but sometimes people will fly out and back in the same day. It all depends on how strict the enforcement is at the country you are entering.

How to pick where to live?

I recommend three ways:

1. Follow your curiosity: Is there a place you can’t get out of your mind after visiting or reading about?  There’s probably a reason why.  Go and see!
2. Use Nomadlist: This site by Pieter Levels was created to help nomads figure out where to live and where others might be living and working remotely.  I’ve met many people around the world through their slack community.  This is also how we ended up in the Canary Islands.  We used the platform to screen places with >20 degrees Celsius in February in Europe and were left with two options: Tenerife and Las Palmas.
3. Follow one friend: This algorithm has worked pretty well because if you have a friend in one place, they can help you get settled, solve problems and introduce you to friends they’ve already made.  This is what brought me to Taiwan, Mexico and Bali.

Using things like Nomadlist and reading travel blogs will help you find more popular destinations.  I recommend starting with those “mainstream” places and then once you arrive you’ll often find other villages and communities nearby that might be a better fit after you’ve adapted to the local environment.  For example, in Bali, Canggu and Ubud are the go-to nomad locations, but once you’ve familiarized yourself you can check out living in other parts of the island.

How do you make sure nothing bad happens?

For people that are used to short vacations you are likely used to paying much more for luxury accommodations and services such that nothing goes wrong. This makes sense. Who wants to waste 3 days of a 10 day trip trying to solve various issues?

With long-term travel you should expect things to happen that make you uncomfortable unless you are willing to pay vacation prices (this likely only works if you are making $100k+).

Anytime we arrive in a new location we plan not to get much work done and to spend the first few days solving issues, for example:

• Lack of pillows and sheets
• A shower that had an electric current running through the water
• Lost ATM card and no other way to get money
• Ant infestations in our clothes and bags
• Internet that doesn’t work
• Broken A/C in 95% humidity weather
• Shared AirBnbs with people we were not comfortable living with
• A scam hotel booking that was actually an empty parking lot
• Lots of noise nearby (busy street or partying)

Growing up we had a phrase when I would go camping with my aunt and uncle that helped us to deal with issues as they arose, “it’s all part of camping!” Now my wife and I say “It’s all part of travel!” and try to laught about the experiences we face.

Once you have enough experience solving these issues you tend to worry less about your accommodations and where you sleep. This has been a game changer because its also enabled us to spent less money on lodging because we have more wiggle room for discomfort.

How Do You Bank Abroad?

The two things you should investigate before leaving your country: a no-fee international credit card and a no-fee ATM card.

For Americans, I highly recommend the Charles Schwab International ATM.  It refunds you ATM fees so all you pay is the transaction fee.  This is vital in the many countries where cash is the only way to pay for many things.

I also recommend signing up for Transferwise.com which is a great way of sending money internationally.  It often has a delay but you can use this to pay for housing or other high-ticket items.

How much do you want to work?

For remote workers with full-time jobs you won’t have as much flexibility as nomads, but probably still have freedom to design your day.  Think about the key elements that give you energy such as eating, socializing, exercise and sleep.  See if you can design your day around those things.  If your work day controls everything about how you’re spending your time, you’ll probably be frustrated with remote work.  I have more tips here (that you shouldn’t show your boss).

For others who are either taking a sabbatical or are self-employed, getting the balance between work, life and adventure can take a while to figure out and my ability to get in any sort of rhythm depends more on the environment and people I’m around more than I expected.

I tend to think about my work in terms of projects.  Recently I’ve been focused on my writing and my goal is to have 4-5 days a week when I spend at least 2 hours writing.  This is the kind of work that brings me alive and it’s the answer to Derek Sivers’ question “What do you hate not doing?”

Working for myself has given me an unbelievable amount of freedom.  Once I realized that my ideal life cost much much less than I imagined, I no longer start with the idea that I need to work every day or for a certain number of hours a week or month.  This can be disorienting as you struggle to spend time around people that still design their life around work and it can be incredibly rewarding.

I was able to spend more than eight weeks in full-travel mode with my now-wife in the first six months of dating and later traveling with my Aunt, Uncle and mother during their first visit to Asia.  I imagine in 25 years, these are going to be the memories that matter.

Similarly, I also spent two separate months developing two online courses one of which has taken off in unexpected ways. I wrote about one of these “sprints” and how I shared my progress in public along the way.

Living and traveling abroad while working shifts the imagination in unexpected ways.  There is no “right” way to balance this but it’s important to experiment as much as possible with these without getting locked into the same routing from back home.

How to meet people & make friends?

As I mentioned, I try to pick places where at least one friend is already living there.  However, here are the general approaches we use to make friends:

• Couchsurfing: Though this has waned as a popular traveler app you can still find interesting events and people in various places.  They have a great meetup tool where you can find others looking to do something right now
• Nomadlist: Nomadlist has an active slack group with channels by location and country that makes it easy to find others
• Coworking Spaces: These spaces often have events and other friendly travelers that also want to make friends
• Facebook: In Asia, facebook is much bigger than in other countries and in nomad hubs, there are often 2-3 groups where locals, expats and nomads share housing, meetups and ask and answer different questions.  Search “location name ” + some combination of “foreigners” “expats” or “nomad” and you should find an active local group,
• Language Exchange: Many people want to learn English and if you are interested, you can find local language teachers and locals who want to make friends and learn each other’s languages.  
• Twitter: Increasingly I meet and engage with people on Twitter in different countries.  If you don’t have a big following send me a message and I’ll retweet your request to find people in a specific location to see if anyone can connect you. 

How do you deal with loneliness?

The other side of making friends while traveling is that you often have a number of short, fleeting and shallow relationships with people that you may never meet again.  Sometimes these relationships lead to great memories like when a few locals picked me up in Koh Samui and brought me to a private beach for sunset or when I spent the day with some travelers from the Philippines biking around Seoul. 

While I’m lucky now to travel with my wife, sometimes we do get a bit down after feeling like we haven’t built many lasting relationships.  The benefits of travel still outweigh the costs for now but I do wonder how long I’ll want to keep living this life.  

Over the past three years I talk to many friends and family much less because I often spent a lot of time with those people in-person.  Time zones and living in a different country add enough friction that this is just hard to avoid.  Video calls are fantastic, but in-person connection is just so much better as many of us have realized in 2020  I’ve missed out on holidays and birthdays and get-togethers and am not around to see my brother’s newborn start laughing, crawling and talking.  Part of this is because my wife is applying for the green card and she can’t enter the US until she’s approved and part of it is because we’ve decided this crazy life on this pathless path is worth it.

It’s hard to write about these things because I have moments where I feel like I’ve abandoned my friends and family but I also know that I feel bad because these people would do anything for me.  This gives me the courage to keep going and keep listening to this deep drive within me to keep wandering and seeing where life takes me.

I’m also lucky to have found a partner that shares my curiosity and helps me make sense of navigating this amazing, confusing and beautiful life we are living. 

It’s hard to be too lonely when you have that.

How to decide what to travel with?

I’m a pragmatic minimalist.  I’m not against owning a bunch of stuff, but owning a bunch of stuff while traveling makes it a lot more stressful.  The more you have the more complex moving around, flights, packing and fear of losing your stuff becomes.

The most important things to bring with you is not high-tech backpacking gear but things that you will use every day. Things like coffee, tech equipment, equipment to exercise and sleep gear.

Since we try to stay in warm weather locations year round my wife and I don’t bring a lot of clothes. Instead we find things we like wearing a lot and make sure our apartment has a washer in the apartment. Instead of clothes we pack things that make our lives better.

My wife tends to use a lot of space for art equipment and fitness equipment as those are two things she loves doing. I tend to have more space for tech equipment like mics, cameras and recorders because I enjoy continuing to create digital content (you can see my full packing list here).

While it can feel like an accomplishment to travel with very little, it also can be easy to travel with slightly more if you plan on staying in location for a month or longer.

When I first started traveling I tried to get everything down to two carry ons. Since we now try to stay in locations for 2-3 months and rent monthly this is less of a concern. Still we don’t travel with that much. When we arrive in a new place we often take the first few days to take a few runs to the local superstore (e.g. Carrefour, Chedraui) to upgrade our pillows, blankets and home goods as necessary.

How do you travel with kids?

I don’t have kids so I’m not going to chime in here with an uninformed opinion but I have met many parents with kids who are either living abroad permanently or traveling with kids and I can offer their reflections.

Often people who pose this question do it from a perspective of missing out on education or “falling behind.” Most of the parents I’ve met traveling with kids reframe things in terms of the experiences or lessons their family and kids will learn while experiencing a different mode of life. It’s certainly not for everyone, but parents seem to take three aproaches to thinking about education while traveling:

• Homeschooling / self-teaching: Parents teach the kids and keep up to date with any requirements from the state or governments in terms of reporting. I know several parents who have taken this path.
• Formal homeschool programs: There are many online services such as Kahn Academy which enable people to do remote learning from many places across the world. I met a 14-year old in Mexico last week that does all his school through Kahn Academy.
• Enrolling in local international schools: Depending on where you are there are often international schools that you an enroll your kids in. This is what Christine Bader did with her kids in Bali and what Ben Keene did with his kids when he moved to Koh Lanta with three little ones.

It seems there will be a lot more possibilities that emerge with homeschooling an virtual learning over the next decade and I expect to see many more parents take sabbaticals or years abroad with their kids once they no longer have to commute to an office every day.

41k+ Sold! (Top 1% Book) The Pathless Path is Paul's book about walking away from a "perfect" job with a promising future and starting over again. Through painstaking experiments, living in different countries, and a deep dive into the history of our work beliefs, Paul pieces together a set of ideas and principles that guide him from unfulfilled and burned out to what he calls "the pathless path" - a new story for thinking about work in our lives. Learn More & Buy The Book Here

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The biggest losers, we suggest, have been management students

This was the takeaway of three researchers who dug into the history of the invention of Maslow’s pyramid. We’ll get to that story but first let’s take a look at what has become one of the most sacred ideas in the management world, Maslow’s pyramid:

The conventional way of thinking about the pyramid is a series of steps that you progress through with the goal of eventually spending more time focusing on self-actualizing. It is often used when thinking about what motivates people at work and thinking about how to improve culture to drive more productive employees.

The problem? The pyramid is an interpretation of Maslow’s research from the 1940s which he spent the next thirty years second-guessing and adding more nuance. By the end of his life, his investigations were well beyond any sort of neat and tidy pyramid that I had trouble trying to even describe and understand what Maslow thought about human motivation at all.

Let’s dive in.

A hierarchy, but not a pyramid

Maslow’s early research, presented in A Theory of Human Motivation (1943) presents something that feels familiar to someone who has seen the pyramid:

• The ‘physiological’ needs: The bodily drives for homeostasis included warmth, coolness, and hunger
• Safety Needs: Protection from danger and harm such as crime, violence, wars, etc… Some experience this as a lack of money as well.
• Love Needs: People have the desire to belong and be part of something
• Esteem Needs: The desire to be respected by others and by yourself
• Self-Actualization Needs: People that have satisfied their other needs and can spend time fulfilling their “potential”

In writing about self-actualization, this is where he says that being self-actualization is about meeting the other basic needs first but then goes on to share that he doesn’t really know much about how this is done:

The clear emergence of these needs rests upon prior satisfaction of the physiological, safety, love and esteem needs. We shall call people who are satisfied in these needs, basically satisfied people, and it is from these that we may expect the fullest (and healthiest) creativeness. Since, in our society, basically satisfied people are the exception, we do not know much about self-actualization, either experimentally or clinically. It remains a challenging problem for research.

This is the question that would shape his future research.

Maslow’s research quickly evolved beyond the basic “hierarchy of needs”

He moved even further away from a clear upward trajectory and embraced more nuance around human needs. He thought that for most people, the natural state was that many people were satisfied and dissatisfied at the same time:

In actual fact, most members of our society, who are normal, are partially satisfied in all their basic needs and partially unsatisfied in all their basic needs at the same time. 

Kyle Kowalski has a great deep dive on all of this and details what an updated pyramid of Maslow’s pyramid should actually look like:

In Motivation and Personality, he outlines his research on the people who are actually thriving in life. He called “Peakers”

Peakers seem also to live in the realm of Being, of poetry; esthetics; symbols; transcendence; “religion” of the mystical, personal noninstitutional sort and of end-experiences.

He differentiated these peakers from non-peaking self-actualizers, which seemed to be what we might call a highly effective “normie” today. He described these people as tending “to be practical, effective people, mesomorphs living in the world and doing very well in it.”

Here is his prediction in 1954:

My prediction is that this will turn out to be one of the crucial characterological “class differences,” crucial especially for social life because it looks as though the “merely healthy” non-peaking self- actualizers seem likely to be the social world improvers, the politicians, the workers in society, the reformers, the crusaders, whereas the transcending peakers are more apt to write the poetry, the music, the philosophies, and the religions.

Perhaps this is why so many people who seem to be so successful still feel like something is missing?

D-Psychology & B-Psychology

In the late 1950’s he started to see that certain kinds of people (the peakers) were living in a different reality from everyone else. He became obsessed with people who were able to spend a lot of time achieving what he came to call “full-humanness” or more simply, people that were in states of being unmotivated by their deficiencies.

He started to see the field of psychology as two domains – b-psychology and d-psychology. One with a focus on being and a focus on deficiency. He felt that psychology, especially as it increased its use of data, was too focused on what people lacked and wished the field would embrace more of the mystical and unknown side of life.

I think Maslow would be pleased to see how broadly those terms like “being” have been embraced and more awareness of eastern practices that emphasize states of being but likely a bit disappointed by the field of psychology and its continued obsessions with experimental data.

By the time Maslow wrote Towards a Psychology of Being in 1968, Maslow had all but abandoned the rigid hierarchy of his basic needs from 20+ years earlier and started to add dashes to almost everything using the b- and d- to signify that he was talking about two different perspectives of psychology – being and deficiency.

This is also when his ideas become a bit hard to follow. We’ll get to that but first…

Wait, So Where Did The Pyramid Come From and What Did Maslow Think?

Todd Bridgman, Stephen Cummings, and John Ballard wrote a fascinating paper trying to find out where the pyramid came from.

What they found was that the pyramid emerged in a number of steps of other people’s interpretations of the pyramid. The first was Douglas McGregor of Theory X and Y fame who found Maslow’s ideas useful for his writings on human relations.

This was the jump from the psychology world in Waltham, MA to the business world down the road in Cambridge, MA. However, the first use of anything resembling a pyramid was in Keith Davis’ writing on human management. Here is the first time the hierarchy was visualized:

From there it showed up three years later in an article titled How Money Motivates Men by a “consulting psychologist” named Charles McDermid writing in Business Horizons:

What was the takeaway of the article? That you could use this pyramid and the theories of Maslow to meet employee’s needs through means other than money:

For management the important conclusion to be drawn from the whole theory is that no one incentive is the only answer to motivating men on the job. Money is powerful, but its power is limited. Aiding group activities, creating opportunities, recognizing worth, encouraging growth, and fostering individual expression can also promote employee effort, in some cases more effectively than money.

All of you underpaid startup employees have this guy to thank!

Maslow’s Big Question & Meandering Ideas

It’s worth pausing here before going deeper into Maslow’s ideas to reflect on Maslow the person.

In his later writing, I have the dual sense of thinking he is a genius and a bit off his rocker. He shifts between the deep truth of a poet and a more tenuous grip on reality reminiscent of a new age seeker who just watched The Secret.

This starts to make sense if you read his writing on how he was thinking about the stakes of the day. This is from 1968, two years before his death:

We are now in the middle of such a change in the conception of man’s capacities, potentialities and goals. A new vision is emerging of the possibilities of man and of his destiny, and its implications are many, not only for our conceptions of education, but also for science, politics, literature, economics, religion, and even our conceptions of the non-human world.

There’s no question that Maslow found something to work on that mattered to him but it seems he may have been frustrated by the rest of his profession not approaching it with the same sense of urgency and you can see in his writings later in life that he had a flurry of ideas that never quite connected.

Yet as his orientation shifted toward thinking about being and transcendence, why was he so willing to go along with an older 1943 version of his thinking?

It seems that his own love and belonging needs were lacking.

As Bridgeman writes:

By the time the (hierarchy of needs) was beginning to be celebrated by McGregor, Davis, McDermid and others aspects of Maslow’s professional life were unraveling. He felt underappreciated in psychology, whose journals had been taken over by experimental studies, which depressed Maslow for their lack of creativity and insight. He also had more pragmatic concerns, suffering periods of ill health and financial difficulties. Maslow found personal and professional redemption in his acceptance in the management community and financial gain through speaking engagements and consulting. He welcomed the new field showing an interest in his ideas and offering the potential for personal benefit.

The rest of the exploration is quite harsh on the pyramid and attempts to understand how a theory that Maslow didn’t fully accept came to be adopted almost completely in the business world. They argue it is one of the most viral memes in the business world:

But Maslow’s (hierachy of needs) may be the only management theory that has “gone viral” and become a meme, and it is doubtful that this would have happened if it did not comepackaged in a pyramid with five clear categorical levels.

The lesson for the business world? Make it pretty, worry about facts later.

Later Research: D-Needs and The B-Realm

Despite the emergent popularity of the pyramid in management thinking, Maslow’s remained dedicated to the evolution of his thinking.

His later research still referenced needs but in a much more complex way than his simple hierarchy published in 1943. He defined them as d-needs or deficiency-needs. These are the things we are motivated to solve so we do not feel lacking – lack of safety, lack of love, lack of food, and so on. These are the closest things to his early hierarchy.

The other side of that was b-needs which are about our desire to grow, to become, or to embody certain human values. He called these b-values or being values:

B-Values: wholeness, perfection, completion, justice, aliveness, richness, simplicity, beauty, goodness, uniqueness, effortlessness playfulness, truth, self-sufficiency

This list likely gives us a glimpse of why he was so frustrated with his field of psychology. All of these concepts are so deeply human that it requires a much different orientation towards life to appreciate and accept them and what I mean is a mostly non-academic, non-scientific orientation towards life.

It seems he had more in common in his day with his contemporaries Ram Dass and Alan Watts and his description of what he called the b-realm might have had more uptake in the emerging “turn-on, tune-in, drop-out” late 60s crowd:

“Deals with ends; with end-states, end-experiences (intrinsic satisfactions and en­joyments); with persons insofar as they are ends-in-themselves (sacred, unique, non-comparable, equally valuable with every other person rather than as instruments or means to ends)”

It’s sad then, that Maslow passed in 1970. You can imagine the excitement he may have found trying to make sense of the human potential movement and having a bit more time to come up with something as coherent as the pyramid.

Despite his writings being a bit all over the place, I got the sense in revisiting his major works this week that Maslow really just wanted people to see how beautiful life was, despite his own struggles with that own journey.

So I might propose a simple framework for his later ideas. Not as catchy as the pyramid, but simply two bubbles of two different worlds:

Maslow doesn’t give a lot of prescriptions for how to move from the d-realm to the b-realm but talked a lot about having an attitude that the b-realm was possible.

That’s what I try to show above. That despite most of us spending almost all our time trying to satisfy our d-needs – acquiring more things, attention, approval, or money – we are missing the fact that there is a b-realm close by that offers a different and more interesting lens on life.

A world where we can just “B”

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