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by
Paul Millerd
On my previous path, I was more than on my way to a magical retirement number but was also making great progress in undermining the spontaneity, creativity, and energy that would enable me to enjoy life once I got there.
For me, testing out different ways of structuring my life now is a win‑win proposition. I’m lowering the odds that I’ll be unhappy in the future all while crafting a life I’m more and more excited to keep living.
Right now, I’m orienting my work around taking every seventh week off from work no matter what. This was inspired by tech entrepreneur Sean McCabe, who adopted the policy for himself and eventually, his entire company.
The fixed points along the default path are not inherently bad, but they do tend to push people towards doing what others do. This can be a good starting point, but if you lean into your own unique psychology, interests, and sense of humor, your journey will be a little more fun and much more meaningful.
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
William Whyte, wrote about this shift in his book The Organization Man, published in 1956. He shared a snippet of writing from a young man typical of the era: “What distinguishes the comfortable young men of today from the uncomfortable young men of the last hundred years…is that for once the younger generation is not in revolt against anything…We don’t want to rebel against our elders.94
No underlying logic justified my spending and a lot of it could be classified under what writer Thomas J. Bevan calls a “misery tax.” This is the spending an unhappy worker allocates to things that “keep you going and keep you functioning in the job.”96 For me, it was a mixture of alcohol, expensive food, and vacations, and as the amount inched up during my career, I started to believe that my spending was the reason I was working.
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.
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. It was up to me to figure out how to spend my time.
Opting out of work and opting in to other aspects of your life can create questions about who you used to be. It feels weird at first, but over time, you start to change what you value. As I unlocked more time for creative projects, travel with my family, time with my grandmother, and time for learning, I was finally doing the things I claimed to care about.
No amount of money can buy the peace of mind that comes with finding a path that you want to stay on. Once we know, as Vicky Robin argues in her book Your Money or Your Life, that “money is something we choose to trade our life energy for,” it is nearly impossible to give up your time for money without thinking deeply about the trade-offs.
Belief clings, but faith lets go. – Alan Watts
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. It’s to develop a capacity to sit with tho...
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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
In 2019, Gallup surveyed Americans about success. 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.
In today’s world, he says, the most attention and respect goes to people with money, fame, degrees, and power.
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
I once asked a partner at my consulting firm about his dream job. He told me he wanted his boss’s position. “At the same company?” I asked. “Then what?” He shrugged and moved on to something else. Something tells me that when the partner achieves his goal, he’s not going to feel satisfied.
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.”
For years I believed that once I had achieved an imaginary future leadership position, I would then finally be able to be myself. This is an obvious delusion, but one many people tell themselves.
The pathless path is a define-your-own-success adventure. 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 meant that the odds of success were incredibly high and the benefits of staying on the pathless path would only compound and increase over time.
Economist Adam Smith once wrote that people desire “not only to be loved, but to be lovely.”
Author Kevin Simler defines prestige as “the kind of status we get from doing impressive things or having impressive traits or skills.”
How does one get lots of users? They had all kinds of ideas about that. They needed to do a big launch that would get them ’exposure.’ They needed influential people to talk about them. They even knew they needed to launch on a Tuesday, because that’s when one gets the most attention. No, I would explain, that is not how to get lots of users. The way you get lots of users is to make the product really great.
While I was at MIT, I read William Deresiewicz’s essay, “The Disadvantages of An Elite Education.’’ His argument that elite schools often incentivize behaviors that undermine living a meaningful life excited me, but I had no idea what to do about it.
This is why I’m fond of the advice angel investor Naval Ravikant offers, “play long‑term games with long‑term people.”
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.
Are you helping people? Are they happy? Are you happy? Are you profitable? Isn’t that enough? – Derek Sivers
it is easier to accept the economic logic of profit‑seeking organizations, that “more is better,” and apply it to our own lives.
She calls this her “busyness breakdown.” After work she had no energy left to invest in relationships, health, and other things that mattered to her.
Enough is knowing that no amount in my bank account will ever satisfy my deepest fears. It’s knowing that I have enough friends that would gladly open their door and share a meal if I was ever in need. It’s the feeling that I’ve been able to spend my time over an extended stretch of time working on projects that are meaningful to me, helping people with a spirit of generosity, and having enough space and time in my life to stay energized to keep doing this over the long‑term. Enough is seeing a clear opportunity that will increase my earnings in the short‑term, but knowing that saying “no”
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If we don’t define “enough,” we default to more, which makes it impossible to understand when to say no.
I’ve discovered in conversations is that no matter how much money people have, they will go to enormous lengths to avoid any discomfort related to their financial situation. This is what makes quitting full‑time employment seem terrifying and a steady paycheck so addictive.
The researchers concluded that when we feel we lack something, we tend to obsess over it.
American anthropologist Ernest Becker was convinced that most of our actions in life are driven by a fear of death.
There’s so much more to who you are than you know right now. You are, indeed, something mysterious and someone magnificent. You hold within you – secreted for safekeeping in your heart – a great gift for this world. Although you might sometimes feel like a cog in a huge machine, that you don’t really matter in the great scheme of things, the truth is that you are fully eligible for a meaningful life, a mystical life, a life of the greatest fulfillment and service. – Bill Plotkin
It’s an acknowledgment that there are deeper forces at play in the world and we are a tiny little part of all that magic. It’s about existing within that magic and still daring to ask questions about what matters or where you fit in.
In my favorite essay, “Solitude and Leadership,” William Deresiewicz highlights the importance of searching for wisdom in real conversations with close friends: Introspection means talking to yourself, and one of the best ways of talking to yourself is by talking to another person. One other person you can trust, one other person to whom you can unfold your soul. One other person you feel safe enough with to allow you to acknowledge things—to acknowledge things to yourself—that you otherwise can’t. Doubts you aren’t supposed to have, questions you aren’t supposed to ask. Feelings or opinions
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We are always falling in love or quarreling, looking for jobs or fearing to lose them, getting ill and recovering, following public affairs. If we let ourselves, we shall always be waiting for some distraction or other to end before we can really get down to our work. The only people who achieve much are those who want knowledge so badly that they seek it while the conditions are still unfavorable. Favorable conditions never come. – C.S. Lewis
John reflected, “As soon as I let go of this notion of huge success, that’s when success started coming to me.”
What does make sense is experimenting with different kinds of work, and once you find something worth doing, working backward to build a life around being able to keep doing it. It’s a shift from the mindset that work sucks towards the idea that you can design a life around liking work.
Finding work you want to keep doing, says author Stephen Cope, is “the great work of your life.” Cope’s biggest fear is that he might “die without having lived fully.”
His exploration was inspired by a passage he read in the Gospel of Thomas: If you bring forth what is within you, what you bring forth will save you. If you do not bring forth what is within you, what you do not bring forth will destroy you.135
The assumption is that making money or finding a way to turn a passion into a job is one of the most important things. While money is important on the pathless path, using it as a filter for finding the work worth doing, especially at first, is a mistake.
More important is the realization that finding something worth doing indefinitely is more powerful and exciting than any type of security, comfort, stability, or respect a job might offer.
Professor and author Brene Brown’s clarification of shame and guilt helped me understand what’s really going on when we struggle to pay attention to our intuitions and desires. She defines shame as “the intensely painful feeling or experience of believing that we are flawed and therefore unworthy of love and belonging.” She believes that most people give too much power to this emotion when making life choices.”
Author Sebastian Junger, in his book about soldiers who had returned from war, found a similar thing. Despite dealing with post‑traumatic stress disorder, many of the soldiers wanted to return to dangerous warzones. Why? Because at war, they felt part of something, deeply connected to the men and women they were serving with. 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.”
My friend Jonny Miller argues that “human existence is an infinitely unfolding process of remembering, forgetting, and remembering again.”
