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by
Paul Millerd
it was clear that the longer people stay at a company, the higher odds that they would become what the company wanted.
Sounds familiar... Mga nakakain ng sistema?
I had been following a formula for life that was supposed to guarantee happiness. It didn’t. Confusion kept me on a path that wasn’t mine for more than ten years. Along the way, I learned how to play the game of success and achievement, but never paused to find out what I really wanted. I found myself in rooms surrounded by business leaders and didn’t quite fit in.
With so many options it can be tempting to pick a path that offers certainty rather than doing the harder work of figuring out what we really want.
Certainty - medicine is such a traditional job... you'll never go hungry...
A friend, Ranjit Saimbi, who has since left law to pursue software development, shared that he was attracted to the law profession because “the steps are laid out for you.” A career in the law signaled to others that he “was a serious and intelligent person.” But the longer he spent on the path, he realized that the real promise had been that “life’s existential fears are traded for certainty.”11
This is the trap of prestigious career paths. Instead of thinking about what you want to do with your life, you default to the options most admired by your peers.
That experience sent me down the “way of loss,” opening me up to the questions I had ignored by orienting my life around my work. What was I living for? What did I really want? How did I want to look back on my life when it was my time to go? Difficult questions but ones that I was finally ready to contemplate.
I had contemplated the question, “what would people think if I couldn’t work again?” and had been surprised by my answer. I would be okay. So much of my identity had been connected with being a high achiever. Straight A’s. Dean’s List. McKinsey. MIT. When I was sick, I would have traded every last credential for a single day of feeling okay.
Being okay is way better than achieving stuff!
Some people inherit values and practices as a house they inhabit; some of us have to burn down that house, find our own ground, build from scratch, even as a psychological metamorphosis. – Rebecca Solnit
“How are you complicit in creating the conditions you say you don’t want?
the right way to think about burnout was to focus on the disconnect between an individual and the culture of the company in which they worked.53
A German report on burnout found that when burned out, people “may start being cynical about their working conditions and their colleagues…” and may “…distance themselves emotionally and start feeling numb about their work.”54
The author Gretchen Rubin decided to override her “ought to” self when she said, “I’ve come to a point where I’d rather fail as a writer than succeed as a lawyer, and I need to try and fail or try and succeed, but I need to do it.”68
Opening yourself up to the possibilities for your life can help you decide to make a life shift, but it will not help you deal with the uncertainty of being on a path that others don’t fully understand. In the months leading up to leaving my job and the year or two after quitting, I struggled to make sense of my journey. When others asked how I was doing, I felt compelled to give them proof that I had a plan and knew what I was doing. It was not until I found the philosopher Agnes Callard’s idea of an aspirational journey that I started to be more comfortable not knowing where I was headed.
Callard defines aspiration as the slow process of “trying on the values that we hope one day to possess.”69 This is in contrast to an ambitious journey where we already know what we value. For example, someone who wants to make a lot of money already values money. They don’t need to learn why they want it along the way. An aspirational journey is more ambiguous, and it is harder to predict what sort of values we will adopt along the way.
Aspirational pursuits go hand in hand with the pathless path because they can appear incomprehensible to others and even yourself, sometimes for years. Callard argues that the aspirant’s understanding of the value of their pursuits “is characterized by a distinctive kind of vagueness, one she experiences as defective and in need of remedy.”71 Learning to exist with this vagueness is vital, especially at the earliest stages of making a change. It’s worth it though, because as Callard says, what is really at stake is you are “learning to see the world in a new way.”
The most common regret? Not staying “true to themselves” in their lives and focusing too much on what others expected of them.
Unfortunately, the pathless path is an aspirational path and can never be fully explained, as Callard tells us, so attempts to convince people that you are moving in the right direction can be futile. People who value comfort and security often cannot understand why anyone would willingly pursue a path that increases discomfort and uncertainty.
I reached out to people who had taken such breaks and found that most people credited these breaks from work as one of the most important things in helping them see the possibilities in their life. I also started to notice that many of the shifts that people experienced were somewhat predictable. Four stand out:
First, people become aware of their own suffering.
“I used to think ‘this job isn’t so bad, I make enough money to make it worth it.’ Then you get a breath of freedom and realize, no, it may have been worth it at one point, but not anymore.”82
Second, curiosity re‑emerges. When people have time, they try new activities, revisit old hobbies, explore childhood curiosities, and start volunteering and connecting with people in their community. Edward, a friend and a doctor who has taken several sabbaticals, reflected that “new ideas often pop up and old topics of interest float back into my consciousness. I find myself writing notes and thinking more freely. This is the creative process, liberated by the neocortex now that the mind isn’t wholly occupied by the strain of everyday sustenance, the rat race, and the grind.”84
Third, people often desire to continue their “non‑work” journey.
by the end of the break, it was crystal clear to me that I was ready to move on to a new adventure.” Several weeks into his sabbatical, he stopped checking his email: “My heart was no longer in the work. I didn’t yet know what I wanted to do next, but I knew it was time to shake things up.”85
Fourth, people write.
I try to think about time in blocks of one to three months and within each block, I pick one or two things I want to prioritize and test. It might be living in a different type of place, working on new projects, traveling, or learning something new. My goal is to test my beliefs to get a better understanding of what really makes my life better.
This kind of variability is hard to design into your life on the default path. On the pathless path not only is it possible, but it can be one of the most rewarding benefits.
The secret to doing good research is always to be a little underemployed. You waste years by not being able to waste hours. — Amos Tversky
When I quit, this kind of spending stopped immediately, and I was surprised at how little I missed it. I’ve since found guidance to reframe how I think about money from Ramit Sethi, an entrepreneur who helps people with personal finances. He asks a great question: “What is your rich life?” The purpose of this question is to stop you from looking at money as an accountant and looking at it as something that might help you live your ideal life. Over time, I’ve found a clear answer: having ownership of my time enriches my life.
If I wasn’t working for money, why was I working? When we work full‑time, employers are paying for our dedication and commitment to the job as a central part of our life. When I became self‑employed, I was disoriented because the people paying me for the projects didn’t care when and how much I worked. They just wanted their problems solved.
No amount of money can buy the peace of mind that comes with finding a path that you want to stay on.
In response to the question, “How do you personally define success?”, 97% agreed with the following statement: A person is successful if they have followed their own interests and talents to become the best they can be at what they care about most. In response to the question, “How do you think others define success?”, only 8% gave the same answer. Instead, 92% felt that other people defined success as follows: A person is successful if they are rich, have a high-profile career, or are well‑known.100
In the first couple years, it felt silly to tell people how I defined success: feeling alive, helping people, and meeting my needs. Over time, I realized that the real benefit of this orientation towards success was that I wasn’t competing with anyone.
This means embracing the pathless path requires grappling with the feeling of being a “bad egg.” This often drives people who leave the default path to eagerly embrace new identities that are still recognizable as legible to the “traditional” economy. They gravitate to titles like a startup founder, entrepreneur, freelance consultant, or even the newly emerging “creator.”
The pathless path is about ignoring the pull of needing to be a “good egg” and learning what truly enables you to thrive.
Part of the promise of being a “good egg” is that we will not feel lost. But the “bad eggs’’ on the pathless path eventually realize there is wisdom in being lost. This doesn’t mean it will be easy. Like Billups, you will sense that you are doing something wrong, or at minimum, don’t know what you are doing. Simple questions from others like “what do you do?” will expose your own uncertainty and can feel like a death blow to the soul.
We can weaken the impact of these kinds of questions by knowing that there is no way to avoid being seen as a “bad egg.” The only way forward is to eventually get to a point when you realize that, in fact, there are no good eggs or bad eggs at all. The pathless path is about releasing yourself from this way of seeing the world and realizing that the number of career paths worth following is infinite.
Enough is seeing a clear opportunity that will increase my earnings in the short‑term, but knowing that saying “no” will open me up to things that might be even more valuable in ways that are hard to understand.
These readers thought that my criticism of the default path was too harsh. Their disapproval stayed in my head and my writing became too safe. But eventually, I realized I wasn’t writing for them. I was writing for people like me: those struggling on the default path who want to dream bigger.
You care. You want to do things in good faith. You want to help people, to listen, and connect with others who share your passions. This doesn’t mean you need to build an audience or a business, but what might emerge if you dare to share your writing, painting, dancing, crafts, or other acts of creativity with others? What friends might you meet? What opportunities could you pursue? What communities could you join?
I am successful on my own terms. Because if your success is not on your own terms, if it looks good to the world but does not feel good in your heart, it is not success at all.
I never realized how much I was constraining my imagination when I was only considering paths or jobs that already existed.
I encourage everyone to write a description of the person you don’t want to be, then brainstorm actions that might create that outcome. This exercise may be uncomfortable because undoubtedly you will see traces of the person you imagine in your present life. These traces are clues about what to change in your life right now.
“whether a carpenter makes a table, or a goldsmith a piece of jewelry, whether the peasant grows his corn or the painter paints a picture, in all types of creative work the worker and his object become one, man unites himself with the world in the process of creation.” As he said, in a world where we are pushed to “regard our personal qualities and the result of our efforts as commodities that can be sold for money, prestige, and power,” engaging in a creative endeavor allows us to find value in the act itself.157
In other words, only by taking action do we learn and only by learning do we discover what we want. Without this, we will struggle to take advantage of the freedom that the pathless path offers.
getting lost was simply the understanding that “the world has become larger than your knowledge of it.”177
