Early in his career, Ben had a lot of passion. However, he had picked a career that had a very set path. The “typical” path was to put in about nine years of steady, hard work, and then at that point, he was free to operate with a little more freedom. Deep down, he knew this was a bit too long, but for the sake of doing what his elders told him, he obliged for several years.
Like many young people, he had an inflated sense of his capabilities. He thought he was capable of more, yet his boss demanded that he put in his time and wait his turn. His boss could be cruel, even abusive. Ben could think of nothing more than overthrowing his boss and replacing him.
He got a small taste of this when his boss was forced to take a leave of absence and for a short period of time, Ben had autonomy and loved the freedom. This gave him a sense that it was something he needed to have in the future.
As soon as his boss returned, the old ways resumed. Resentful, Ben took matters into his own hand. He first tried to secretly obtain work with competitors in the city, but most people knew his boss and didn’t want to get on the wrong side of him. Even though they saw Ben’s talent, they didn’t dare make an enemy in the process.
Ben realized that he would have to leave the city he lived his whole life and start fresh. At the age of 17 years old and after six years working for his brother as an apprentice, Benjamin Franklin set out for Philadelphia.
The urge for freedom, adventure and to carve our own path is timeless. Most college students tell me that one day they “hope to run their own business.” Most people in the corporate world harbor some fantasy to do something more entrepreneurial even if they are afraid. Even those inching towards the end of their careers are not immune. I talk to baby boomers who see retirement as a way to engage in those things they always wished to pursue when younger.
In Franklin’s time, a journey from Boston to Philadelphia was not an easy drive down Interstate 95. He had to take a boat. Here is how he describes his journey in his autobiography
In the evening I found myself very feverish, and went in to bed; but, having read somewhere that cold water drank plentifully was good for a fever, I follow’d the prescription, sweat plentifully most of the night, my fever left me, and in the morning, crossing the ferry, I proceeded on my journey on foot, having fifty miles to Burlington, where I was told I should find boats that would carry me the rest of the way to Philadelphia.
It rained very hard all the day; I was thoroughly soak’d, and by noon a good deal tired; so I stopt at a poor inn, where I staid all night, beginning now to wish that I had never left home
Most people’s capacity for discomfort is less than Franklin’s. Yet we still have the same urge for carving our own paths. To reinvent. To step into the unknown.
What we lack is not courage, but a deeper set of mindsets, tools, and models for navigating the modern world and making sense of what the journey might look like. We don’t need another article telling us that pursuing our passion is going to make us happier. We don’t need to be told that our boss doesn’t know how to manage.
We need an updated map of reality and better approaches for thinking about stepping into the unknown. Here are six ways that work and carving your own path in the world are different than we think.
🧠 We need to update our expectations of what work actually provides
Less than a third of people work in full-time jobs. Even less have jobs with great healthcare, benefits and a path for personal and income growth. Yet our assumptions about the working world are based on a myth of the “organization man” from the 1950s:
As Seth Godin says:
The educated, hardworking masses are still doing what they’re told, but they’re no longer getting what they deserve.
Follow the path and be taken care of.
I get e-mails and have conversations with people on a weekly basis who “played by the rules.” They got the degrees, credentials and jobs that were supposed to guarantee them everlasting fulfillment. Yet they face misery, anxiety or unexpected failures in their jobs.
Here is a friend who had followed the default path of success and had experience at a top consulting firm and had a top-tier MBA:
As an amazing example of big corporate bullshit, the new position I was going to accept was then re-orged into oblivion as part of an unrelated org change that wasn’t coordinated with the first one – effectively laying me off for a second time in six weeks. From there, the guy who would have been my boss kept putting me in touch with internal people who had open positions, which I felt I might as well explore.
Half of those conversations were about mind-numbingly boring jobs or resulted in the hiring manager saying “I’ve heard great things about you, we had a great conversation and you seemed great to work with, but I need to hire someone with more specific experience here”. Those reactions highlighted that whatever cachet I had as a high-potential general manager was evaporating before my eyes as part of this acquisition of my business unit.
This story is all too common. However, our conventional beliefs about the working world is that it is working just fine so they don’t tell anyone. It is surprising how many people I talk to in these situations that have not told anyone in their life. There”s probably a deeper question about why they are telling me, a stranger on the internet, but that’s not worth exploring here. Career stagnation and finding yourself lost on the journey still brings enormous shame because we are operating with broken assumptions.
For many, they do get what they deserve. At least in the beginning of their careers. For many college graduates, there is a somewhat straightforward path that looks something like this:
…but then things get wacky. Many companies still promote a clear career path but struggle to fulfill their promises because of slow growth rates. Many people expect some sort of easy path to a senior Director or executive role. The reality is a bit messier. This means that people’s careers start to look a little more like this:
Navigating a career and more importantly, a life, in the modern world is hard. You used to be able to bank on steady income rises to cover a 3-year mortgage, but how do you bank on that now?
I wish this wasn’t the truth, but as I’ve talked to hundreds of people over the past few years, I’ve realized that the people who have mastered reinvention – dealing with uncertainty, keeping flexible financial obligations and experimenting with new work identities – seem most excited about the future.
So while that senior executive tells you “work hard buddy and you’ll be taken care of one day” look at him and smile, not because you’ll be taken care of but you know something he doesn’t know. That there are no guarantees and that counting on that kind of path is a bit crazy.
Quick quiz: What do the following items have in common?
- Data scientist
- SEO Manager
- Substack Paid Writer
- Chief Happiness Officer
- Blockchain Developer
- Remote Fitness Instructor
- Online Course Designer
These are all jobs that barely existed when I graduated in 2007. Now, there are literally hundreds of thousands of people doing these jobs around the world.
How would I have planned for that? In one of my consulting gigs last year I had to rely on my website building skills which I first taught myself for fun when I was about 10 years old. I certainly didn’t plan that – I was just lucky I could help.
🏆 Unreasonable ideas of success prevent us from taking action
Everyone has seen an article like this. It exists (and works) because it taps into our deepest insecurities about money, status and power. This is great for clicks, but this line of thinking convinces us that being successful means making a lot of money and convinces many that its not even worth getting started.
Over the past 2+ years I’ve fielded countless questions about my plans for hiring employees and growing. The assumption is that everyone is an entrepreneur and that everyone must always want more. This assumption is so strong that it convinces countless people to invent plans for scale even though deep down they know they have enough.
Paul Jarvis, who wrote a book called Company of One, once wrote about a new business venture he joined with two other people:
‘If this company needs business growth beyond the three of us, I’m out.’
…Not because I’m afraid of success, but because “success” to me means being able to get what needs done, done without having to hire a team
When I was thinking about launching a podcast, someone asked me how I was going to monetize it. I told him that wasn’t my goal. I just wanted to try something new and see if I had fun doing it. My gut told me that it was a forcing mechanism to be creative and push my thinking to the next level. It only cost me about $75 for a microphone to get started.
I talk to many people who have been stuck for years. They would love to try out working on their own or some creative project but have a deeply embedded fear of failure. Part of this comes from our ideas of what success looks like.
We don’t see stories of the solopreneur like Jarvis who is more focused on “having enough” than getting rich. We think instead in terms of the brands and personalities that capture our attention. If you are thinking about becoming a freelance consultant you worry about competing with Mckinsey and BCG. If you are thinking about starting your own thing, you think about Gary Vaynerchuk and Tim Ferriss. If you are thinking about starting a podcast, you are competing with Gimlet and NPR.
It’s easy to fall into this trap. Here is a screenshot of my podcast in Apple’s mediocre podcast app:
When we look at this, it seems like we are in direct competition with each other.
Except This American Life operates like a Fortune 500 business unit instead of a fledgling startup and this is only one of NPR’s many podcasts. Let’s take a look at their team compared to mine and the number of listeners.
If I’m comparing to NPR, I’m an absolute failure. Yet those 200+ people that listen to my episodes? Some of them include you and I think you are some of my favorite people in the world.
I’ll take my people any day of the week.
When people think about carving their own path, they immediately think about whether or not they will be successful and by successful, they mean money and what other people think of them. While this can keep people working and hustling for years, its not a path to building a sustainable life.
The real challenge of carving your own path is finding the work that you want to keep on doing. This will create a feedback loop that gives you energy, enables you to meet people that are excited in similar ways and keep coming up with ideas to experiment with.
When people think about the internet, they assume that everyone is engaged in some form of molotov cocktail verbal warfare. What I’ve found is that most people on the web aren’t actively engaging in negativity and instead are just looking for interesting ideas or interesting people to connect with.
As of this year, Mary Meeker tells us there are 3.8 billion people connected to the internet. What this means is if you are looking for the people that might resonate with something you are creating, working towards or sharing, your search might be easier than you think.
You just need to find your relevant speck of the universe. If you are working as a freelance consultant, you likely need no more than 5-10 steady clients to support your life for the next 5-10 years. If you are selling a course for $200 and want to earn $100,000 a year, you only need to worry about finding 500 people who are excited about what you are creating.
You’re also probably not thinking weird enough.
For Marielle Chartier Hénault. In 2015 she started a Mermaid School and now has 10 schools across Canada and the US. She supports her life with this:
She likely started the business to find out if there were other people that shared the same interests. The same driving force led me to start my podcast, keep my newsletter going, and to keep experimenting and trying new things. She found a bunch of people that wanted to go on a journey with her and I’ve found a bunch of people that keep e-mailing me or having curiosity conversations with that say “keep going.”
Maximizing wealth and size are only two options for orienting your behavior. The internet has enabled even more options for sustaining your life than ever before.
🎨 We need to stop ignoring our craving to create and express ourselves
What would you do if money didn’t matter and you couldn’t tell anyone about it?
I like this question because it helps remove prestige and status from the equation. However, when thinking about getting started, people stumble in two areas:
First, most of us think about creativity as something we need permission to do. We need to get accepted into a job before we can create something. We need to be formally part of certain organizations.
While there are still some gatekeepers, you don’t need permission to publish your own book, publish your own music, share your writing or thoughts, sell your crafts or even offer your services. You can even become a cab driver via Uber or Lyft.
Second, people are terrified of putting something out there. There is that internal voice that says “what will people say?”
I can’t cure this for you. In fact, I still feel like a fool every time I hit publish or share. This is from George Leonard in Mastery:
The early stages of any significant new learning invoke the spirit of the fool. It’s almost inevitable that you’ll feel clumsy, that you’ll take literal or figurative pratfalls. There’s no way around it. The beginner who stands on his or her dignity becomes rigid, armored…
The only way to overcome this is to get started. This is what I did when a career coach challenged me to e-mail 100 people I knew in 2015 and tell them I was taking the leap to become a career coach. That small step was one filled with terror and a feeling I can’ only describe as peak feeling like a fool.
I still feel silly, but I’ve done a number of experiments over the last five years as you can see by some of my below-average logos:
All of these experiments started simply – typically with a conversation where someone was excited about the same thing or asked me “why haven’t you done this?” My rule is that if three people ask me to do something, I probably should. Despite a number of experiments under my belt, launching my podcast in December 2017 was was still a nauseating thing to do.
Each of the experiments has been valuable. Some have turned into things that help support my life. Others have helped me realize what I didn’t want to do.
We’ve already talked about our unreasonable mindset of success, but what is a good model for thinking about creation. Shouldn’t we have a goal? For me, my model is simple. It’s all about finding out what’s in the unknown:
People write about the hacks for getting started, but overcoming your own insecurities is just not that easy. This is why the most “successful” often tend to rub us the wrong way. Let’s just say that their inner voice saying “you are a loser” is just not as powerful as yours.
What does work is finding people that believe in you. I get a bit too excited when others share their creative ideas with me. I tend to turn into an instant cheerleader and supporter, asking them “why not?!”
Earlier this year, while spending some time in Bali, I put a post in a coworking community that I would help anyone launch a podcast in less than an hour. A brave group of three people volunteered and 70 minutes later, we had a podcast launched.
I’ve turned this into a sort of personal mission, helping anyone and everyone launch new creative ventures. There are plenty of people that will tell you how your idea sucks, how it won’t work, how you haven’t thought through the business model or that it already exists. Get away from them. Find a crazy weirdo like me who thinks you have something worth sharing.
Overcoming friction to getting started is hard. We need to embrace tools My personal favorite tool for doing this is called the Most Dangerous Writing App. In fact, it’s how I ended up writing the introduction for this article. Set the timer and write. If you stop typing, everything disappears. Try it out for 5 minutes and let me know what you think.
While you may be thinking you have nothing to share, nothing to create I bet that deep down there is something there. If you are subscribing to this newsletter, you probably have a small drop of creativity waiting to be released. David Whyte offers some powerful questions about where to look:
- What is the work that brings you alive?
- What are the places that bring you alive?
- What are the conversations that vitalize you?
- In who’s presence simply by being in their presence do you find becoming your best self?
🦘 Life is (incorrectly) framed as all-or-nothing leaps
We glorify the leap. The person that takes a bold leap into something new. We wish we could be them, but shit that looks scary.
We tend to judge people’s actions by an external interpretation of what’s happening. One day they’re working full-time and the next day they are not. One day someone is working as a glorified telemarketer at a startup and the next day they are in nursing school. I’m sure many people saw my personal leap without any clients as madness.
What people didn’t see in my own journey were the years of small experiments, the new connections I made through my writing, the growing courage through stepping into uncertain opportunities and my dreams about carving a new path. Leaving the corporate world was inevitable. Many small experiments got me to a tipping point where I had enough courage to leave. I just had to pick a day.
Some of you may have listened to the podcast I did with John Zeratsky. He wrote a viral article titled, “I Quit My Job to Sail Around Central America for 18 Months.” While the title of the article makes sense to get people interested, the truth was a bit more nuanced. He and his wife had dreamt up the plan five years prior and had already delayed the trip once by two years. Prior to taking the big leap, they tested their plan:
“Before we left…we would take small sailing trips, we would go somewhere for one night…later that year we would do that for a long weekend, then for a week and then for two weeks. A couple years before we left on the “big trip” we went for two months.”
Instead of taking a leap, they “prototyped” their life seeing how smaller trips felt, what skills they needed to learn and to see if they wanted to keep going.
I’ve been living in Asia for the last year, living as a “digital nomad” in Taipei, Bali and Chiang Mai. Four years ago I never would have imagined living in such a way. As I started my self-employment journey, I found myself having more flexibility than before and found I could often design my work around my life. I took two one-month trips and on the second trip ended up doing some work while traveling. Only on that trip did it dawn on me that I could reinvent the way I was living. I decided to prototype a longer “trip” of three months in Asia. That trip has turned into a year and who knows what’s next.
Alastair Humphreys once traveled the world for four years straight and has gone on some incredible adventures. However, as he has started the next chapter of his life and is raising a family, he has found a way to embrace that adventure that was core to his life. He works with people and challenges them to think smaller and embrace “micro-adventures.” He describes them as:
an adventure that is short, simple, local, cheap – yet still fun, exciting, challenging, refreshing and rewarding…for normal people with real lives.
You don’t have to pack up your life and become a nomad, but you also don’t have to be scared of shifting in a new direction.
What is the dream you have that you might be able to prototype?
🏆 Our craving for security is real, but the pursuit of money & traditional metrics will not solve that
In 2015, Kevin Durant left his team of nine years to join the best basketball team in the world. In the NBA, great players like Durant are judged based on whether or not they win championships and this undoubtedly factored into his decision to dramatically increase his odds at a title.
Except when he ended up winning a title, he was disappointed. In the off-season, his friend Steve Kerr could tell that winning the title had only made him realize there is more to life than achieving other people’s goals.
Many people face this same realization after landing their dream job, making $100,000 for the first time, getting promoted to Partner or getting accepted into their dream school. They realize that they need to pick another more challenging goal or come up with some deeper perspective for how they want to live their life.
Daniel Kahneman won the nobel prize for his work on how the brain works. Earlier in his career, he started studying happiness, but ultimately decided to abandon it and work on something else. Here is what he found:
“People don’t want to be happy the way I’ve defined the term – what I experience here and now…it’s much more important for them to be satisfied, to experience life satisfaction, from the perspective of ‘What I remember,’ of the story they tell about their lives.”
People want a story about their lives that they can be proud of. When we chase easily defined metrics they leave us inevitably empty. People in their early twenties can more easily come up with new goals to chase (think about the cliche of the 27 year old deciding to run a marathon) because they have accomplished so little in terms of traditional metrics.
At some point people reach a “wtf” moment, where they start to reflect on their life in a certain way and realize that there is a deeper game worth playing. While money can lead to happiness and life satisfaction, there are limits. Research has shown that in terms of day to day well-being:
health, care giving, loneliness, and smoking are relatively stronger predictors of daily emotions
This makes intuitive sense to most of us and even more sense to people that have faced a health crisis. Such a crisis is often a “WTF” moment for people. For others it is getting fired, losing a loved one, an end of a relationship or even just a moment of desperation after years of a slow, creeping sense of dread.
Andrew Luck was at the top of his game when he decided to step away from being the Quarterback of the Indianapolis Colts. Yet his “WTF?!” moment probably happened four years prior to that decision. He was injured and for the first time in his life, he didn’t dedicate every waking moment to football. Here he is talking about the experience:
“I’ll say it right now—I think it was a blessing in disguise,” Luck said. “Absolutely. It forced me to reevaluate many, many things in my life. And the result has been … yeah, really positive. And I shudder to think of not having that. I don’t think I’m married if that had not happened. I think I eff that up. I truly do. I truly do.”
He had found that the “easy metrics” of a first chapter weren’t enough for him:
“I’d put way too much of my self-worth directly into how I was performing on the football field,” Luck said. “And then I wasn’t on the football field and I felt quite empty. It was very unhealthy, first for me, second for the relationship with my now-wife, and my other relationships.
While the circumstances of Luck’s decision, namely the fact that he’s walking away from one of the most desirable and high-paying jobs in the world, make his decision seem crazy – the same type of decision is being made around the world every day.
We need to embrace the deeper game of the second chapter.
Don’t Be Afraid To Start Your Next Chapter
Benjamin Franklin’s accomplished an enormous amount in his life. He can lay claim to inventing the lightning rod, political cartoons and bifocal lenses, played a pivotal role in the declaration of independence, became the first postmaster general and helped start the University of Pennsylvania.
However, many of these accomplishments happened in the second half of his life, only after he decided to walk away from a successful printing press and other appointments at the age of 42:
When I disengaged myself, as above mentioned, from private business, I flatter’d myself that, by the sufficient tho’ moderate fortune I had acquir’d, I had secured leisure during the rest of my life for philosophical studies and amusements.
One of the biggest challenges people face in modern times is walking away from a life that makes sense as Sophie Kleeman says:
It made perfect sense in my mind, but it felt as though most of the people around me were baffled.
We confuse “making a living” with living the life we want to live. We also confuse leisure with “idleness.” In Franklin’s time, leisure still met both reflective contemplation and active engagement in the world.
Over the next 42 years, he lived a life of adventure, experimentation, and creativity all because he had the courage to reinvent.
If you find yourself saying “hell yeah!” at the end of the post, I offer a self-paced course that will help you go through some of these activities and lay the groundwork for your own reinvention.
33k+ 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