That may be the right path for you but I want to convince you that there might be another path.

I want to share my version of how I’m playing something Packy McCormick calls the “great online game.” A version that focuses on building a life where I can work in different ways to pay the bills, have plenty of time for creative pursuits, and don’t have to be tied to a full-time job.

What follows are five principles that have emerged that have guided my path. They have emerged slowly and organically. Only now do some of them seem obvious. I fully expect that they may morph over time. These principles serve as a compass for me as I navigate the infinite possibilities of the internet.

I think that nearly everyone, including people on the default path, should develop their own principles. This is because the stories of how we think about our work and lives are outdated, one based on a 1950s reality. This story worked in a time in which people worked for one company in their life when growth rates of 5% were normal, and most women didn’t work.

The trap of this story is that it actually works in the first few years of anyone’s career. Many companies still believe in this story and this is why the first five years of your career are still filled with promotions and a clear career path. Anyone that’s made it past that point, however, knows the truth. That there aren’t many clear career paths left and because of slowing growth rates, competition and politics are more central to getting ahead than some may think.

Developing your own principles and strategy is the only choice left if you don’t want to play those games. For the self-employed, developing your own game and set of principles is not a choice but a necessity. It is the only way to survive over the long term.

Here are five principles that help guide my path.

Principle #1: Coming Alive Over Getting Ahead

In April of 2020, my strategy consulting skills course started taking off. This was a weird moment because it took off at the same time I started dealing with extreme fatigue following complications from a tooth extraction. My course was selling like hotcakes and I was either wandering around the Canary Islands talking to doctors or sleeping in bed. This is one of the weird things about being a self-employed creator. Your financial reality can shift dramatically in a short period of time and often due to things outside of your control.

I had spent hundreds of hours to get it to that point but it was never my intention to hit a monthly revenue goal. I genuinely thought it would be fun to figure out how to create an online course (If you want to go much deeper, the full story is here). If you had talked to me in January of 2019 you might have thought my principles of keep doing stuff I like, give generously, and don’t work too much were pretty stupid because I had made less than $3,000 doing so in a year. Two years later I’ve somehow made a decent American salary for two straight years.

After a strong year of sales, I reflected on my success with StrategyU. My inner consultant knew that the obvious solution was to double down, add more courses, level up the marketing, create more content, and see where it goes. I was even invited to an accelerator program for proven course creators to make this happen. I could see the path and had a reasonable level of confidence that I could 4-5x my course sales if I wanted to.

But then I challenged myself, “what would you do once you had that money?” I realized I would write. I then reflected upon the fact that I could simply do that now. I was already making enough to support myself and still save a little money each year.

With this in mind, I decided to make a commitment. In 2021 I would write a book. This would be a way to commit to what I claimed to care about and also be a way of testing out this principle of “coming alive over getting ahead.”

My course has remained steady but has not grown much more than the previous year. However, the act of committing to writing a book has been one of the most thrilling commitments of my life. I’ve never felt so alive, challenged, and excited about anything I’ve worked on.

If a choice emerges between spending more time on making money but means I’ll have to cut back on some of the things I like doing like learning, writing, and connecting with people, I plan to walk away from that choice.

Principle #2: Don’t Be Attached

While my online course continued to succeed, I realized that I had come to expect that income.

With a few hours of maintenance per week, I was able to keep a profitable business running while writing my book and studying Chinese full-time for a three-month stretch. In one of those months, I even worked with a client to run a four-week consulting skills bootcamp which led to my best month since being self-employed. Then in May, the sales of my course tanked, likely driven by a change in the google search algorithm, people returning to the office after covid restrictions, and travel for the summer.

These kinds of ups and downs would be terrifying if I had a high fixed-cost lifestyle or if I had not experienced them before. To anyone that’s been self-employed for a long period of time, they learn to deal with these shifts. Here is an example of some various swings in different income sources I’ve experienced over the past five years.

With this in mind, I try to make sure that I’m not assuming that any of these income sources are permanent. I’ve embraced a visualization exercise where I go through an exercise of visualizing all my digital properties and revenue streams evaporating and then asking “am I okay?”

When my consulting course struggled for a couple of months after doing so well for more than a year, I was able to reflect on the fact that I’ve started from scratch in the past and I could do it again.

Principle #3: Build An Income Floor & Optimize For Income Streams

About a year into self-employment I realized I really want to stay on my path longer than my initial plans for a one-year experiment. I realized that if I wanted to commit to this path, I needed a better strategy for earning money than only freelancing.

Freelancing is one of the best ways to get started with self-employment. It enables you to leverage your existing skills while giving you more flexibility with time to spend on other things you want to work on or to simply work less. This worked well for me. I had much more time to work on creative projects but realized that following that path was a lower-income and precarious version of my previous path.

I wanted to embrace an antifragile approach, one in which I would not be as susceptible to stretches without income or to shocks in the broader economy. Freelancing is one of the best ways to make money in a strong economy, but it’s also one of the quickest things to disappear when companies are cutting costs.

With that in mind I set out to focus on two goals:

• Earn money in as many different ways as possible
• Build a portolio of income streams that act as a high probability “floor” of income

This lowered my income in the short term but boosted my confidence and resilience. Knowing how to make money in a number of different ways gave me practical skills and an expanded imagination about what I could do to make money.

While I had a hard time realizing it at the time, my overall income also steadily increased over time with this approach. I now have had at least three sources of income generate over $200 for more than a year and have had at least six income sources for longer than that.

In my first year of self-employment, I had high earnings but it was inconsistent. I had six months with less than $2,000 income and three months with more than $10,000 per month. The second year I shifted away from consulting and had seven months with less than $2k income. The last two years? I’ve made at least $2k every month.

This is much more valuable for the game I’m playing as it dramatically lowers the odds that I will run out of money and gives me more freedom to walk away from any type of work I don’t want to do without feeling like I might go broke

Principle #4: Start Slow & Keep Trying Things

I like trying a bunch of different things for a few reasons. First, I genuinely like creating new things and experimenting. I find the process of turning ideas into my head into things that can be helpful for others to be fun. This is a unique advantage in the world that is emerging and I’m fully aware of this.

Second, it keeps things interesting and also exposes me to a number of different ways of engaging in the world such that I can help others do the same.

Finally, it helps me build a portfolio of “small bets” as Dan Vassallo shared in this conversation with me – any one of which could have unexpected payoffs.

With my newsletter and podcast, both started as ways of sharing what I was up to and without any intentions of turning them into businesses. I didn’t promote them or share them widely because I wanted to be able to quit without people noticing. Tim Ferriss took this strategy with his podcast. He told himself that he would do six-episode and if he was having fun and didn’t hate it, he would keep going.

Conventional wisdom says to grow fast, to take advantage of every launch. However, that increases the odds that you end up doing something you don’t want to do. My approach has been to take a slower path. Five years into this journey, almost everything I’m doing I want to be doing and this has been from a series of incremental “yeses.”

I recently launched a freelance consulting skills course. This course was the result of helping a couple of freelancers that were doing work for me level up my skills. I realized I was having a lot of fun helping them be better and they were finding the information and feedback useful. I had validated both the idea and the feeling. That second part is often ignored. Too many people don’t think about the fact that once they build something that makes money, they have to spend a lot of time doing that thing. I only built the course because I enjoyed helping people become freelancers. Right now it’s still a small bet but when the opportunity emerges to take it somewhere else, I will consider it and if it feels right, I’ll say “yes.”

Principle #5 Make Friends. Be Helpful

This is the most important principle and the one that makes everything else more fun. Yet, it is also the one where I struggle the most.

I’ve always been the person that likes helping other people. In college, I proactively volunteered to help fix people’s computers and help with resumes, job searches, and interviewing. After I graduated I helped people make career changes and write essays for grad school. At my jobs I always took on extra roles to help with training and coaching.

It was fun. But the world tells you that these are silly things. People tell you, don’t get taken advantage of. Adam Grant writes books showing how to avoid being a pathological altruist and to make sure you balance yours gives with your takes. Others ask “why you don’t charge?” You spend your time at work helping your struggling colleague while you watch the skilled politician land another raise.

I was cynical about this for a while. I wanted the working world to change. I wished there were paths for people to progress and get raises while remaining a front-line manager. My first blog was called “better working world project.” Eventually, I realized it was better to create my own game rather than try to swim upstream.

So I experimented. I started a career coaching business on the side. I started writing. I eventually went out on my own and was able to be the kind of freelancer I wanted to be. I had more time to spend helping people for fun without feeling like an idiot (though sometimes it still feels silly to do things for free).

As I continued to do this and built an audience through my writing, people starting sending me thank you notes. I received one note from someone that I had a conversation with a few years earlier. She told me that her conversation with me completely changed her mind on what she wanted to do. Now she was doing something she loved and wanted to thank me for the inspiration. I’d be lying if I said that these moments are fucking awesome.

I did an exercise in which I had to rank my “yearnings” or the things we really crave. My top two were appreciation and freedom. Appreciation was something that surprised me but it felt true. Leaning into that and realizing that it is something I need but can also be fuel is a powerful thing to know.

A couple of years ago I did another exercise in which I had to write down my “purpose.” The person that created it said to keep writing versions until you cry. I thought it was silly but I’m always open to trying new things. It worked and this is what I landed on.

Connect as a real friend to people to give them the courage to create, help simplify the world to enable people to imagine new possibilities, and continuously be more brave in discovering the people and things that matter in my own life

I know that my desire to help others might be a little pathological and after reading Adam Grant’s Give and Take it seems that I’ll probably succeed financially a little less. But I don’t buy his argument that this is something to fix. I have realized that I want to design a life around making this weird quirk a great part of my life. I know that it undermines my ability to be financially successful sometimes and that’s okay.

I’ve just decided that it matters.

The Bottom Line

I don’t know what will be paying the bills next year but the longer I play this game the more confident I become. It could all blow up at any second, but the whole point of the game is to enjoy the journey.

I spent ten years on a path where I was always focused on the next project or the next step.

This is way more fun and I hope I’ve convinced you to find your own game worth playing.

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 Designing Your Own Infinite Game In The Creator Economy appeared first on Boundless by Paul Millerd.

People are often surprised at two things that emerge from a deeper exploration of this topic:

1. How little they’ve really analyzed their own relationship to money
2. How deeply I have thought about it

One of the surprising things of self-employment is that it forces you to face your money fears immediately and because of the unpredictable nature of income flows over time, forces you to develop a working mental model of how to think about money. This is in contrast to many full-time employees who because of steady income flows can put off ever having a coherent framework for thinking about money as long as they stay employed.

What follows are some of the principles I have adopted for how I think about money. Remember this works well for me and might not work for you.

Belief #1: Financial insecurity can’t be “cured” by making more money

Financial insecurity seems to be a proxy for all sorts of insecurities including a general fear of death, the general anxiety of rising costs of the modern world and feeling like you’ll run out of money, and not feeling like you are good enough.

Financial insecurity appears in different forms and has varying level of costs. For some it is a hacking of their brain in the form of a daily refresh of a Mint.com or personal capital profile. For others it is the explicit cost of hiring a financial advisor and paying them 1% of annual assets. For others it can be a desperation to take and stay at any job that will take them regardless if it makes your life better. This insecurity led to me becoming desperate when looking for consulting work a few times when income streams had dried up which led to underpricing or taking project that were not a great fit.

Most people try to quiet these insecurities by making more money, getting another gig, or sometimes, investing in riskier things. It never gets rid of those voices, it only quiets them. I made good money while I was employed but was surprised at how potent some of my hidden insecurities were when I quit my job.

This is why taking a break for employment or earning less money is often one of the most counterintuitive and effective ways to grapple with financial insecurity.

When I first moved to Taiwan my consulting work dried up and I made about $500 over a stretch of 4-5 months. In response I cut my spending dramatically and I learned two things: I didn’t need much to be happy and I could radically re-arrange my cost of living pretty in less time than I thought.

This did not cure my financial insecurity completely but it just made me more comfortable with the feeling and instead of letting it hack my decision making processes I could practice sitting with the discomfort.

Another thing people do when they think about quitting their job is frame it as an all-or-nothing leap. It’s either go into the risky path of self-employment or stay in full-time work forever.

Going “back” to salaried employment is often much easier than people imagine and what people really fear is that people will not accept them anymore. If I decided to go back to full-time employment I am much more confident I’d be able to find work and an arrangement that would work for me because of what I’ve learned over the past few years.

The reality is that most self-employed people like it and don’t want to go “back.”

Belief #2: People will spend years avoiding discomfort

People go to enormous lengths to avoid having to face these emotions directly and this is what makes quitting full-time employment so terrifying. It is not the prospect of going broke or earning less that scares people but having to be uncomfortable for long stretches of time.

Have you ever seen someone that was a bit older and had made really good money for a while lose their job? You probably thought, “wow they have worked hard, maybe they will take some time off and regroup.” What likely happened instead was that they were aggressively job searching the next day.

What you are seeing is someone that has used full-time employment and a steady income as a way to masks deeper insecurities and discomfort.

I was lucky because a two-year health crisis threw me out of the working world. I literally had to sit with discomfort. Sitting in my bed each day I dealt with the physical discomfort of Lyme disease and also the psychological discomfort of being out of work without a paycheck and unsure of who I was.

This is something people don’t see when they look at my current path. I’ve been through some shit and gotten to the other side. I could do it again.

When I decided to quit my job I confused when people would tell me how brave I was or that they could never do such a thing because “they couldn’t pay rent.”

These statements are rarely the result of a financial analysis but instead of the paycheck mindset of one-month, one-paycheck. To imagine life without a paycheck each month is uncomfortable for people and they’d do almost anything to avoid it.

Having a steady flow of income keeps you blind to the fact that when you remove this cash flow your mind will naturally start coming up with ways to make money.

In 1944 worries about food shortages from the War started to emerge. At the University of Minnesota they recruited 36 participants to take part in a starvation study. After extended periods without food, they starting becoming obsessed with food. It was all they thought about and talked about. They planned to open restaurants, to become restaurateurs, memorized recipes, and compared food prices of different newspapers for fun.

The first few months after quitting my job I didn’t make any money. I became increasingly proactive and imaginative about ways of making money. I ended up making a lot of money over the next six months. My worries about making money receded quicker than I imagine but my deeper discomfort with how I would navigate this up and down emerged as the real issue. This is something that never goes completely away but if you start to see the potential scarcity of income as a feature that helps you grapple with this discomfort you can start to see how not leaving your job might be the risky thing to do.

Belief #3: People don’t define “enough”

Many people refuse to commit to a number or salary that is “enough” and even when they do they will often change it once they have reached that number. It is amazing how much wealth people will accumulate without ever realizing this fact. In addition, most people’s expectations of what they need are built on their current lifestyle and if you have head steadily increasing salaries and expenses you will assume it is only possible to live and be happy in such an arrangement

I’ve talked to people with millions of dollars who are convinced they are struggling. I’ve talked to people making $500,000 a year who think that they won’t be able to afford college for their kids, let alone retirement. People who say they need $1 million to retire and then when they hit it they change the number to $1.5 million.

For these people, it is impossible to ever have enough because enough is just always more than they have now. This is the result of refusing to grapple with the underlying insecurities that making more money hides.

Instead of defaulting to “more is better” I’ve tried to calculate what I have, what my ideal lifestyle cost, and try to imagine a range of possibilities and whether or not I’ll be able to make it work.

One thing I did early on in self-employment was to login to the Social Security site which gives you information about the government’s pension scheme. I was curious how much retirement I might get from something like this. I was surprised to find that I had already “fully qualified” after working for 40 quarters in my life. I had not maximized my potential payouts but I could start collecting a payment at about age 62 in the US.

I was also surprised to find that under a worst-case scenario of needing to take money at age 62 and only making $30,000 a year until retirement (and not counting my spouse who isn’t a US resident yet), that I would received $1312 a month until I did.

That’s not bad! Especially considering that we have enjoyed living in different countries, our worst case scenario is probably a nice cushion on top of our existing retirement savings.

I’ve always invested for the future. Perhaps I knew that I’d want to leave the world of knowledge work. As soon as I started working I invested about 15-25% of all paychecks into retirement. The stock market is 4x what it was in 2009. This seems to have paid off even though I never made a crazy high income.

Right now if I project even a very conservative 4% annualized market return for the next 30 years, invested no additional money, and then took out the money and put it in cash and paid myself an annual salary for 25 years this would be an additional $3,423 per month (if you are ambitious you can figure out the details).

This puts me at a “retirement” of nearly $5,000 a month starting at age 65 based on no additional investments and that I can break even for the next 30 years.

Barring any health issues that prevent me from working I would guess that 95% of future life paths will end up better than this. Pretty cool.

To those of you that are saying that $5,000 is not enough this article is not for you. I write for the people who might want to opt for more time rather than more stuff and people who don’t want to design their lives around work.

This analysis helped me shift from a generalized worry about the future to a very clear understanding of what kind of risk I was dealing with. My risk of ruin is quite low which means I can spend a lot more time making small bets on interesting opportunities or even using my time for non-work and spending time with people I love.

I know how to make more money and one day I might change my mind and try to earn more but for not figuring out how to be happy on less money is a way more interesting game to play than trying to keep a steady income or even earn as much as possible.

I think that we can have a pretty good life in most parts of the world, even with kids, making $40,000-$50,000 per year. The biggest challenge will likely be judgement from other people if we decide not to opt-in to the default high-priced success path of high-income knowledge workers. I don’t have kids yet so I am also happy to revisit this admit that I am wrong when that time comes.

Other people see my life as extremely risky but I see the possibility of ruin as almost zero. Defining a “worst-case” scenario enables me to leave space for opportunities to emerge or for extended periods of non-work without anxiety.

I don’t buy into the default retirement story

A lot of thinking about money and retirement comes with a default picture of work and life that says you work 40 years and then retire and live a life of leisure. This does not appeal to me. I want to be actively engaged with the world, even when older.

The current paradigm of work seems to suggest that one should suffer for a long stretch of time working full-time and then at a certain age let out a deep breath and head somewhere warm to retire and spend time with other retired people.

I am quite sure I don’t want this because I am not interested in a life of leisure, at least how people think about it now. I’m much more interested in the historical definition of leisure, one that centered around contemplation and active engagement with the world.

We’ve lost a connection to this idea of leisure because our obsession with work has drained it from our souls. The most interesting thing that has emerged for me in exploring self-employment is the shock at how much energy and enthusiasm for life has reappeared after a decade in the corporate world.

This showed up because I was actively engaging in the world in many different modes. I’ve worked in many different types of gigs and volunteered and spent extended time with important people in my life. My imagination for the possibilities for my life and work have expanded exponentially. When I think about the latter stages of my life I think about how I can continue to do the things that matter to me, writing, teaching, and mentoring in various capacities.

The modern idea of retirement is tied to the idea that work is suffering and that retirement is a relief. While I don’t see work as the most important thing in my life, I also don’t see it as the worst. Thus I likely see it playing some role in my life. Whether I try to make money from those modes of being or not will depend on my needs but I hope it will be the latter.

The other major fear that drives people to follow this script is healthcare. I come from the only first world third world country when it comes to healthcare. I’ll write a bit more about this below but my country is one of the few that regularly bankrupts its citizens who have health issues that are out of their control.

However, we’ve already talked about how making more money is never going to solve the fear of not having enough money. Combine this with a real health crisis I faced in my twenties and I know that compromising parts of your life for future potential worries is just not worth it. I’ve heard too many horror stories of people facing health crisis right after retiring and never getting to live out their dreams.

This is why I think much more about “pre-retirement” experiences like extended vacations with family members and friends now rather than in 30 years wen my health, energy levels and ability to deal with discomfort (and cheap hotels) will be much resilient. Since I plan to always do different types of work I don’t think I’ll be resentful if I have to do work later if I need money.

I rather steal minutes from today and lose money in the future. If I run out of money I know that I can figure it out.

I had a weird experience in Mexico last year when I found myself in a tropical location, watching beautiful sunsets every night with my wife, working a few hours a day and being quite happy. I thought to myself, “this is the goal of retirement people aim towards, huh.”

The bigger challenge with this in mind is what I aim towards instead of a traditional retirement? The simple answer is that I’m not aiming towards anything. I’m trying to be fully alive today.

The Largest Uncertainty: “What about healthcare??”

Healthcare in the US is an absolute dumpster fire and probably is the most valid reason for worrying about the future.

I do worry about the future of healthcare and my ability to afford it but I also don’t see it as a good enough reason to re-orient my life around making as much money as possible through full-time employment.

After dealing with complicated dental issues, nerve damage, getting bit by a dog, an intestinal parasite, and an ear infection while traveling around the world it has eased some of my worries of being able to pay for healthcare.

The best argument for getting super rich is so that you can get access to the best doctors and pay for expensive treatments. However, this is a very American issue. Since my wife is from another country and I am comfortable getting healthcare in other countries, I’d be okay with living outside of the US even when old (or for our generation, maybe especially when old!)

If the US healthcare system is not fixed in the next 30 years we will have much worse problems. Many people are holding off on their dreams because of this and it kills me. I’m not willing to let a broken system shape the course of my life.

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 I Think About Money & Retirement While Self Employed appeared first on Boundless by Paul Millerd.

A review of the first 30 years of the data in 1996 highlighted a fascinating shift in values.

Especially notable are changes in two contrasting value statements: The importance of “developing a meaningful philosophy of life” and of “being very well off financially” In the late 1960s developing a meaningful philosophy of life was the top value, being endorsed as an “essential” or “very important” goal by more than 80 percent of the entering freshmen. Being very well off financially, on the other hand, lagged far behind in the late 1960s, ranking fifth or sixth on the list with less than 45 percent of the freshmen endorsing it as a very important or essential goal in life. Since that time these two values have basically traded places, with being very well off financially now the top value (at 73.6 percent endorsement) and developing a meaningful philosophy of life now occupying sixth place at only 43.1 percent endorsement

You can see a visual representation of this swap in the following graph.

While “developing a meaningful philosophy of life” seemed to drop steadily from survey launch, the goal of being well off financially didn’t seem to take off until the early 1970s.

The other interested thing from this long-term data is how consistent the other values have been. I looked at the top 4 values from 1970 – 2015 and found that despite the two above mentioned values changing place, the other three values remained remarkably consistent.

Those three things?

1. Raising a family
2. Helping others who are in difficulty
3. Becoming an authority in my field

Essentially, take care of the people in your life, try to help others and be good at what you do.

These seem like a good recipe for like and aligns with the wisdom and research on what leads to a meaningful life.

But still, why did college students become so obsessed with money and why has it remained so central?

Could it be due to how school has become about test scores and grades?

A Harvard study from 2014 highlighted the gap between what parents claim to care about and what children thought their parents cared about.

According to a 2012 study, 96% of parents surveyed viewed developing moral character in children as “very important, if not essential” and highly valued their children “being honest, loving, and reliable”(Bowman et al., 2012). Research suggests that most parents across race/ethnic groups value caring or “benevolence” more than achievement and are far more likely to value “benevolence” over “power” (Suizzo, 2007).

When you ask parents what they care about they say that they want their kinds to be kind people with integrity.

But what happens when you ask their kids? Here is the results of a survey of 10,000 students asked to rank what their parents value:

Hmmm. Who you going to trust, the parents or the kids?

I was lucky not to have parents that cared a lot about grades but it was still clear that getting good grades was the best thing you could do in school. If you were not getting good grades, parents often were quite concerned about that person’s future. The social pressure to achieve was clear at an early age.

Its easy to see children raised into this environment looking for the next metric they can optimize for after college. There may not be any grades in life but your compensation is is the next best thing.

But What Does Society Want?

Almost everyone seems to have an opinion of what “society” wants and this seem to be very different about what people report about what they really want.

Partly because of my own experiences earning less money and partly because of a fascinating survey from Gallup called the Success Index. In their survey they ask people two questions:

1. How do you personally define success?
2. How do you think others define success?

Take a look at the main section of this on status:

Almost everyone thinks success is about being good at something you care about while at they same time they think that almost everybody else only cares about being rich and famous.

How can this be?

Either most people are lying about how they define success or people have a terrible understanding of the motives of other people.

My guess would be that it is a bit of both. It’s very easy to delude ourselves into thinking we are doing things for the right reasons while assuming that others are in it for the wrong reasons.

What I think this survey tells us is that even if people do have good motivations for doing whatever they are doing, they feel that they will be judged by a different societal standard.

A different section of the survey shows this in an even more dramatic way. It asked people to rank 76 different elements that are part of their personal definition of success. Similar to the survey with college freshman we see that having a family is an important part of people’s lives.

However, when you ask the same people about their perception of broad societal definitions of success we see the lowest ranked value from above jump all the way to #1 and to a dramatic degree.

It seems that most people assume there is a broad societal benchmark of “success” that mostly has to do with how much money, status and fame one has. Despite this, most people also seem to proclaim very different definitions of success.

What does this all mean?

Could it be that people still care about what it means to live a philosophically meaningful life and that they are too ashamed to share that?

Or have money and fame overtaken everything else as the de facto aim of life for most people?

It’s worth looking back at the start of the original data set. Who were the people answering the survey in 1966?

William Whyte’s book titled “The Organization Man,” which detailed the new trend of young people moving to suburbs and large corporations, gives us a glimpse into the mindset of a college student in that time.

While they talk little about money, they talk a great deal about the good life. This life is, first of all, calm and ordered. Many a senior confesses that he’s thought of a career in teaching, but as he talks it appears that it is not so much that he likes teaching itself as the sort of life he associates with it—there is a touch of elms and quiet streets in the picture. For the good life is equable; it is a nice place out in the suburbs, a wife and three children, one, maybe two cars (you know, a little knock-about for the wife to run down to the station in), and a summer place up at the lake or out on the Cape, and, later, a good college education for the children. It is not, seniors explain, the money that counts.

William Whyte, The Organization Man

In the book he shares how it was genuinely shocking how little risk young people wanted to take compared to previous generations. They saw the chaos of the war and did not want to repeat those days. With this backdrop it might make sense that developing a meaningful philosophy of life might become a central goal of one’s life.

Over time, however, young people started to care more about money until it became the most important metric in their life. This was furthered by the common knowledge that everyone knew that everyone else thought getting rich was the prime aim of life.

Revisiting the American Freshman data, the #1 goal of students was has remained “being very well off financially” for almost 50 years and throughout that time has only become more important. In 2019 it reached one of the highest levels on record with 84% of students said that being well off financially was essential or very important.

Despite this, all of these surveys share some very consistent themes over the past 55+ years. People still see having a family, being helpful to others and being good at what you do as things that are centrally important to a life well lived.

It doesn’t appear that money is losing its grip on our imagination but it might be a relief to consider the fact that many people only conform to these goals because they think everyone else thinks this way.

I for one don’t have wealth as my #1 metric of success and I officially give you permission to abandon that as a central aim of your life as well.

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 Why Did People Stop Caring About Developing a Meaningful Philosophy of Life in the 1970s? appeared first on Boundless by Paul Millerd.

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Why is talking about money so hard? Diania puts it bluntly:

When were talking about money, were talking about what we value

This conversation covers Diana’s journey over the past several years reinventing her path and learning about new modes of living life. She shifted from someone who graduated college assuming she “would be the highest paid CEO in the world” to someone who wanted more ownership over her time, creativity and money.

Asking for time off from work

A few years ago she had just finished another year at work and was likely going to get a big raise. However, she didn’t actually want more money.

She wanted more time.

She decided to go into her manager’s office and ask instead for two months off so that she could walk the Camino de Santiago, a famous walking pilgrimage in Spain.

On the first day of that trip she had a profound experience of being able to help others in a powerful way that was the start of a shift of how she wanted to orient herself in the world.

Launching the EconoMe conference

Experiments with the FIRE movement, minimalism and seeing how resourceful she could be in her life taught her a lot and led her to want to create a space where people could build bonds and share their experiences for a “new American dream”

She was a brave early tester of my Reinvent course in summer 2018 and prototyped the origin story for the conference, which will happen March 7th, 2020 in Cincinnati, Ohio:

I love what Diania is doing so I am sponsoring one free ticket to the EconoMe conference. All I require is that you share this podcast via twitter or another social app. Use the hashtag #reimaginework and I’ll shoot you a message if you win!

The conference will explore “The American Dream” which Diania believes originated as an ideal where “every person has the right to pursue his or her own idea of happiness.”

EconoMe is a one day conference about reclaiming this right!

Join them.

Links Mentioned:

• Mr. Money Mustache
• Econome conference
• All the Money in the World

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 Diania Merriam on Imagining The New American Dream appeared first on Boundless by Paul Millerd.

• Unpaid internships to get experience
• Going into debt for credentials to get access to certain jobs or industries
• Opening up your network to help people so you’ll be helped in the future
• Taking a certification course for credibility (see MBTI, coaching, Yoga, Six Sigma)
• Doing favors for “successful” people to earn social capital for favors to be named later

All of this behavior operates on the assumptions of what many have called a “prestige economy.” Kevin Simler gives us a good working definition of this kind of system (or hierarchy):

If dominance is the kind of status we get from intimidating others, prestige is the kind of status we get from doing impressive things or having impressive traits or skills.

When you start to understand these dynamics, I believe they can explain a lot of behavior. I would also argue that the assumptions behind our prestige economy has also come to dictate the conventional wisdom on the best way to live a life – at least in the western world.

Put simply: pursue prestigious things…keep doing it…eventually you’ll be respected and rewarded (financially, but not always)

The Prestige Economy Is Undermining Itself

At the extreme ends, the payoffs to prestige-seeking are still very high. I would be crazy to recommend against anyone attending Harvard.

However, many other examples are less clear cut.

While writing this article, I went over to LinkedIn and searched “MBA MS BS” and in the first result found something that highlights the logical outcome of this system. Someone with four degrees, yet still searching for the payoff to their investment in the prestige economy.

Journalist Sarah Kendzior’s thoughts on the prestige economy are a good example of a growing school of thought about the modern economy:

Success does not matter because, in a prestige economy, success has nothing to do with employability. Achievements are irrelevant in a system that rewards money over merit, brand over skill.

Put more simply….the game is rigged!

When I tell people that I still think I would have learned more by staying at my job and not attending MIT for grad school, they look at me like I am slightly insane.

Skills aren’t the ultimate arbiter of success in a prestige economy. The appearance of skills is good enough.

Kendzior’s argument is that the prestige economy is undermining itself. By taking the appearance of competence as a proxy for competence and using money as a way to gain access to these prestigious institutions, people will eventually lose faith in the whole thing:

Institutions that use unpaid labor are hastening their own demise. They are sinking in quality and destroying their own reputations, which is what they bank on to hire unpaid labor in the first place.

Another word for the prestige economy is the meritocracy, which David Brooks calls out as one of the fundamental lies of our current culture:

The myth of the meritocracy is you can earn dignity by attaching yourself to prestigious brands. The emotion of the meritocracy is conditional love, you can “earn” your way to love. The anthropology of the meritocracy is you’re not a soul to be purified, you’re a set of skills to be maximized. And the evil of the meritocracy is that people who’ve achieved a little more than others are actually worth a little more than others.

People have started to lose faith in the traditional recipe of prestige. But that does not mean it was even the recipe that everyone wants.

Some People Are Opting Out Of Traditional Prestige Economics

If we are not aware of the nuances of prestige economics, it would be easy to assume that prestige is universal and translates to different domains. People will often say things to me like “you can travel the world because you worked at X.”

While my past experience has helped me create new things, I’ve entered these new communities having very low status. Luckily, many of these communities trade prestige for things other than money or things that can be bought:

• Maker communities: technical competence, sharing your journey & lessons
• Digital nomad communities: generosity with connections, & technical know-how
• Online content creators: # of followers, originality of ideas, ability to bring people together
• Gift communities: Time bank communities, coliving communities operating on what you are uniquely suited to offer

These are examples of still relatively new communities and I think that is important. Eventually some of the status within these communities will be standardized and eventually sold (will Lambda school be the Harvard of maker communities?), but they are all founded on new stories.

Enabled by digital communities, people are coming together from around the world and aligning around new values – things like competence, generosity, care, citizenship – and granting prestige to the people that embody these values.

Money still matters, but it isn’t central.

Who We Admire Determines Who Gets Status

If I think about my family, I think instantly about my grandmother. She is turning 90 this week and has a tremendous amount of status. This status is not a result of dominance, fear and control. Instead because she is respected and admired. Simler makes this same point in his essay:

So  admiration, rather than prestige-seeking, is the lynchpin of the prestige system.

It doesn’t matter is someone seeking prestige has good or bad intentions. All that is required for them to reap the rewards of prestige is that people admire them.

But outside of a closed system like a family, how do you figure out who you admire? Scott Alexander makes the simple but powerful point that there isn’t really much thinking behind this other than accepting the wisdom of our peers:

…since it’s hard to figure out who’s good at things (can a non-musician who wants to start learning music tell the difference between a merely good performer and one of the world’s best?)  most people use the heuristic of respecting the people who other people respect.

This is a sensitive topic for me. Since leaving my consulting job, many people seem to be confused about why I would give up all the prestige that I had earned.

When we get past the BS, they ask me directly: how could you give up the money?

It doesn’t make any sense and is a hard conversation to have until you understand that we have different definitions of prestige.

For me, I want to shift to a groups where generosity is a bigger factor than my title and where helping teach others is more important than how much I earn.

We are obsessed with money as the sole indicator of people’s success. Economic growth has given us many good things, but many people are craving a different story.

Next time someone is talking about how much money someone is earning, perhaps we inject a story of an amazing person that has contributed to the world in a different way.

Aren’t those the kind of communities we want to live in anyway?

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 Future Of The Prestige Economy: Who Gets Status? appeared first on Boundless by Paul Millerd.

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John Zeratsky was a designer in the tech industry has worked with hundreds of startups in his time at Google Ventures.  He’s also obsessed with redesigning time and thinking about what matters in life. Earlier this year he just got back from 18 months living on his boat sailing around Central America, which he wrote about in an article titled “What quitting my job to sail around central america taught me about fulfillment.”

John describes himself as “risk averse” but after being influenced by different perspectives on risk (including thoughts from the incredibly thoughtful Brian Koppelman) he realized that he could take smaller steps to test out a bigger leap.  So in advance of taking the trip, him and his wife avoided the trappings of lifestyle creep by saving 50% of their salaries and avoiding the urge to upgrade their apartment.  As a way to test whether they would like a longer sailing trip or not, they took smaller trips, going for a two week trip and a two month trip before heading out. This helped them learn about how they would feel and practice some of the skills they would need while living on the boat.

In this conversation we talk about:

• Growing up in a small lake community
• His love of sailing growing up
• Why him and his wife change their mind on taking the trip in 2015
• Rethinking convenience and comfort
• What comforts are worth paying for
• Belonging and community
• How his relationship with money has changed
• How him and his wife are structuring their life to work how they want
• The one change that helps people be less addicted to their phones

Links Mentioned:

• Designing Your Life
• Sprint: How To Solve Big Problems and Test New Ideas In Just Five Days
• Make Time: How To Focus On What Matters Every Day
• Twitter: @jazer

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 John Zeratsky on what living on a boat for 18 months taught him about work, belonging, comfort & money appeared first on Boundless by Paul Millerd.

The Money-Empathy Gap

That’s all.

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 post The money empathy gap appeared first on Boundless by Paul Millerd.