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by
Paul Millerd
Read between
February 19 - March 5, 2023
I turned down the offer and started to ask harder questions. Why was I trying to get a raise when I knew I was not in a good environment? What was I seeking? Why did I keep changing jobs every two years? What was that pebble in my shoe really telling me?
In it, I defined a leader broadly as someone that could be a “role model in all aspects of their life.”
Some examples included a desire to lead with empathy, to embrace humility, to inject humor wherever possible, to avoid becoming too serious, to prioritize learning, to think independently, and to create memorable experiences for others through my work.
First, my curiosity and passion for learning at work were nonexistent.
Jerry Colonna, an investor turned executive coach, asks his clients this question, “How are you complicit in creating the conditions you say you don’t want?” After the reflection, I knew that I was complicit. I also knew that if I wanted things to change, it was solely up to me.
Burnout. I couldn’t be burnt out. I was too smart! Burnout is for investment bankers and lawyers working every weekend and logging 80‑hour weeks.
The word burnout was coined in the 1970s by Herbert Freudenberger, an American psychologist who studied workers in free health clinics. He found that the prime candidates for burnout were those who were “dedicated and committed,” trying to balance their need to give, to please others, and to work hard. He noticed that when there was added pressure from superiors, people often hit a breaking point.52
He was intrigued by Professor Cary Cherniss’ definition of burnout as “the bureaucratic infringement on a professional’s autonomy”
What if the value system of the institution is diametrically opposed to the values, ethics, and competencies of the individual professional? What if the individual professional seeks to live up to the external, organizationally imposed criteria of what constitutes success and achievement, but is unable to do so?
Unfortunately, success for the company does not always align with what is best for the person, and over time, a disconnect can emerge. This is what happened to me.
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 This is the tricky thing about burnout. If you are suffering from burnout, you are likely not thriving at work, and over time it’s easy to see yourself as the cause.
The philosopher Erich Fromm has argued that “creative union,” or when “man unites himself with the world in the process of creation,” is a way to experience love.
Our tendency to glorify and simplify stories of people quitting their jobs convinces far too many people that this move is only possible for uniquely courageous people. My story is not one of courage, but of pragmatic and safe experiments, experiences, and questioning over several years.
This kind of approach, focused not on being brave, but instead on eliminating risk, is common for people who take unconventional paths.
discovered the financially independent, retire early (FIRE) community.
For most people, life is not based on all‑or‑nothing leaps of faith. That’s a lie we tell ourselves so that we can remain comfortable in our current state. We simplify life transitions down to single moments because the real stories are more complex, harder to tell and attract less attention.
We can explain this strategy with a simple equation: Uncertain Discomfort < Certain Discomfort + Coping Mechanism
In other words, given sufficient coping strategies, people will be willing to tolerate consistent levels of misery for long stretches of time. Is there anything that can override this? In my conversations with people who have made changes in their life, one thing seems to work reliably: wonder.
Uncertain Discomfort + Wonder > Certain Discomfort
In thoughts about the future, worry is traded for wonder. People stop thinking about worst‑case scenarios and begin to imagine the benefits of following an uncertain path. They get curious about who they might become if they embrace discomfort and are filled with a sense of urgency that says, “if I don’t do this now, I might regret it.”
One challenge to embracing possibility is knowing when to override what psychology professors Gilovich and Davidai call our “‘ought to’ self.” This is the voice that helps us follow through on commitments but can also keep us from making changes in our lives.
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.
Find the Others According to Callard, people on aspirational journeys, or what I call the pathless path, are “characteristically needy people.” Because their worldviews are incomplete and evolving, they are dependent on the support of other people.
had to find inspiration from podcasts and social media where people like Seth Godin, Derek Sivers, and Tim Ferriss exposed me to a broader set of ideas of how to live and work.
Whyte saw this as a dramatic shift from the past because these organizations offered something that previous generations did not have, a safe haven from the real world, noting that “come graduation, they do not go outside to a hostile world; they transfer.”95 Because I belong to the third generation of this tradition, I didn’t have people around me to tell me how life without a paycheck would feel.
used Mint.com to audit my spending and was shocked that I had been spending nearly $6,000 per month living in New York City.
I started to believe that my spending was the reason I was working.
Ramit Sethi,
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?
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. It was up to me to figure out how to spend my time.
Belief clings, but faith lets go. – Alan Watts
Having faith is admitting that you don’t have all the answers for what comes next. Another phrase I’ve found useful to describe this state of mind is what the spiritual teacher Tara Brach calls “radical acceptance,” which she says “is the willingness to experience ourselves and our lives as it is.”
Many people I talk to are convinced that the formula for living on their own terms is saving up enough money. I wish they knew what I know: the longer we spend on a path that isn’t ours, the longer it takes to move towards a path that is. Money might help pay for therapy, time off, and healing retreats, but it won’t help you come to a place where you really trust and know that everything will be okay.
Having faith does not mean being worry‑free. I still worry about money, success, belonging, and whether I can keep this journey going. However, I’m able to recognize that the right response is not to restructure my life to make these worries disappear.
People have the notion of saving the world by shifting things around, changing the rules, and who’s on top, and so forth. No, no! Any world is a valid world if it’s alive. The thing to do is to bring life to it, and the only way to do that is to find in your own case where the life is and become alive yourself. – Joseph Campbell
Just as when we talk about taking leaps and picking life paths, we simplify the messiness of human nature down to simple stories. When we talk about our goals, we disguise our intentions, especially if we think they demonstrate greed, envy, or pride.
I’ve realized that my case is closer to the norm and the people that are on the path they are meant to be on are more the exception than the rule.
As author Ryan Holiday wrote, “You know deep down that accomplishing things won’t make you happy, but I think I always fantasized that it would at least feel really good. I was so wrong. Hitting #1 for the first time as an author felt like…nothing. Being a ‘millionaire’…nothing. It’s a trick of evolution that drives us, and no one is immune from making this mistake.”103 This is what Harvard professor Dr. Ben‑Shahar calls the arrival fallacy, the idea that when we reach a certain milestone we will reach a state of lasting happiness.104
Eleanor Roosevelt once argued that “when you adopt the standards and the values of someone else or a community… you surrender your own integrity. You become, to the extent of your surrender, less of a human being.”
The better way is what I call the “second chapter of success” in which you shift your mindset from what you lack to what you have to offer, from ambition to aspiration, and from hoping that joy will result from a specific outcome to experiencing it as a byproduct of your journey.
Author Kevin Simler defines prestige as “the kind of status we get from doing impressive things or having impressive traits or skills.”108 In some domains, like sports, this works well. Those we pay the most attention to, like Tom Brady or Lebron James, are also the most skilled. In the business world, however, talent is harder to assess and we tend to use proxies like credentials to determine quality and prestige.
This can be a good way for a company to make talent decisions at scale, but it also motivates many people to seek credentials rather than finding work they enjoy.
was being granted special status in a “prestige economy” that, as the writer Sarah Kendzior argues, places “money over merit, brand over skill.”109
With freelancing, I was competing on the quality of my ideas and my ability to do good work for clients. A lot of former consultants who become freelancers are surprised at how much less time it takes to do the same work. This is not because it’s any easier. In fact, it’s a lot harder without the support of an entire firm’s resources. It’s just that there are no longer hundreds of different people you need to impress.
With more possibilities to work independently and become an entrepreneur, I’m here to tell you to take your own doubts seriously and demand better!
Junger reflected, “humans don’t mind hardship, in fact, they thrive on it; what they mind is not feeling necessary.”140 Junger argues that “modern society has perfected the art of making people not feel necessary.”
The need to feel useful is a powerful one. This is the hidden upside of the pathless path and a reason why finding work that aligns with what matters to you and makes you feel useful is so important.
My friend Jonny Miller argues that “human existence is an infinitely unfolding process of remembering, forgetting, and remembering again.”141
To thrive on the pathless path, we must ignore the shiny objects and distractions and strip away the stories that are not our own to remember who we are. One of the biggest concerns people have when they talk to me about quitting their job is how to make money.
