Things they don't tell you in the "real world" — the pathless path to indie hacking

In 2016, I was burned out. I didn't know it at the time but was struggling to get through each day, resentful at my boss, my company, and myself.

I was also trying to get promoted.

I tell you that last part because if there's one thing I've learned about taking a dramatic leap it's that the path ahead of us is often not obvious until we have a chance to look back many years later. This fact, one often lost in the rush to tell simpler and more impressive stories, has fascinated me for the past five years.

In 2017, I decided to quit my job and shift from a full-time strategy consultant to a freelance consultant. Creative, right? Nope. The truth is that I had no imagination for any other possible way of life other than doing what I had been doing with slightly more freedom and flexibility.

In the first six months of freelance mode, I was able to land clients and make some money but I also experienced a jolt of reality from the extra time and space in my life. I realized that I had been following a very narrow path - something I now call the "default path" - that kept me from figuring out what I really wanted or exploring further possibilities for my life.

This inspired me to embark on several years of experiments, following my curiosity and creativity rather obvious paths to success and money.

Earlier this year, I just published a book about all of this called The Pathless Path: Imagining a New Story for Work & Life.

Here are some of the lessons I learned and share in more depth in the book:

#1 Our default stories of work are outdated

Our beliefs about work originate in religious ideas like the "calling" of the Protestant Reformation from 500 years ago and in cultures that evolved dynamically with capitalism. These beliefs have evolved over time but have solidified in the post-World War II era. Ideas like having a "steady career trajectory," working continuously throughout adulthood, and suffering in the present to "earn" retirement became the norm. These ideas have become so strong and prevalent that we have a hard time realizing that for most of history, these ideas were not the norm. The problem? We don't really have any good alternatives - so its often comforting to continue to exist with these ideas.

#2 No one asks "why are you doing this?" if you work like everyone else

When we are firmly on the "default path" - of the socially-accepted path of your culture, we have a hard time seeing that there is any other way to live. This was made clear when I quit my job. Immediately, people started asking me, "why are you doing this?" I realized for the ten years prior no one had ever asked me that question. Nor had I dated to ask it myself.

#3 We often don't realize we crave a different path until we have a crisis

Two things led to an existential opening for me: losing my grandfather, and dealing with a health crisis for two years. Both made it clear that work can only exist as the center of life if at the cost of other things and if we are healthy. When sick, I faced an extended stretch of time when I was not able to work and I had to grapple with the fact that I saw myself first and foremost as a worker. As I recovered, I tried to deprioritize work as the primary vector of my identity.

#4 Most people don't just want to chill on the beach

When I first left my job I wanted to escape. I thought I didn't want to work. Chilling on the beach without a worry in the world sounded great. It turns out that almost no one, including me, wants this - even when it's an option. I know this because I've been to places like Bali, Puerto Escondido, and Thailand where I met people who both had the financial resources to never work again and also just lounge on the beach. The reality: it gets old after a couple of weeks.

#5 Most people want to be useful

Usefulness, whatever form it may take, is the price we should pay for the air we breathe and the food we eat and the privilege of being alive. And it is its own reward, as well, for it is the beginning of happiness. -Eleanor Roosevelt

What do people want instead? I believe that most people want to be useful. People want to contribute to the world, experience a connectedness to the others and themselves through work, and do things that they think matter. This was hard to see when I had so much of my time and work dictated by what other people wanted. When I had space and time to explore, I was pulled towards work that I wanted to keep doing. Eleanor Roosevelt has a great quote about this:

#6 There are many traps on unconventional paths that are hard to avoid

They have $100k MRR, so of course, that's what you want too. It's possible to copy-paste someone else's approach but in my experience, it's rarely sustainable and typically ends in burnout. On an indie path, the only sustainable way to do it over the long-term is to start with your own unique psychology, motivators, and desires and then determine what path and "game" make sense for you.

#7 You may be thriving on your path but one comment from your parents or a friend may still crush you

When you take an unconventional path, you immediately realize that a large number of people design their life around fitting into conventional paths. Your continued existence will incite cognitive dissonance in people around you and you may experience unprompted anger or skepticism from others. Be patient. Trying to convince them that your path makes sense is a fools' errand. If you can, share the inevitable vulnerability you are dealing with that may help others understand and make sense of your path. However, in my experience, some people may never understand and always be uncomfortable with your path - especially your parents. But if you're like me - you are drawn towards the uncertain, towards adventure, and experimentation. You know you have to take this path. You'll have to figure out some way to live with that tension and be okay that it may never be resolved.

#8 The best way to find sanity is to "find the others"

Seth Godin tells people to "find the others." This likely doesn't make sense until you are on an indie path. The "others" are not only important, they are an essential part of staying on an unconventional path. They will inevitably become your friends and people you go to when you don't know what you are doing. This is also a great reason to share what you learn. Sharing on the internet is a generous act - it is an invitation to others to join you on the journey. Do that long enough and you might end up changing your life. Or even writing a book. :-)

Happy to answer questions you have or share more about my experiences with non-work, de-centering work in my life, and finding a positive sustainable path with work!

Your friend on the journey,