The book I wish I had written.

"I felt like a rebel, like I was doing something wrong."

I am currently reading Pathless Path¹ by Paul Millerd.

Ahh, on every page, my heart is melting. There are many things in that book that resonate with me very well. I am only halfway through the book, but I cannot wait to share my highlights from it so far.

This is the pathless path. Where the journey leads is to the deepest truth in you. - Ram Dass

Study hard, get good grades, get a good job. Then put your head down and keep going, indefinitely. This is what I call the “default path.”

It didn’t take me long to realize I had been on a path that wasn’t mine and to find a new way forward, I would need to step into the unknown.

After spending the first 32 years of my life always having a plan, this kind of blind trust in the universe was new, scary, and exciting.

The pathless path is an alternative to the default path. It is an embrace of uncertainty and discomfort. It’s a call to adventure in a world that tells us to conform. For me, it’s also a gentle reminder to laugh when things feel out of control and trusting that an uncertain future is not a problem to be solved.

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 don’t know anyone who has done that.” Many people fall into this trap. We are convinced that the only way forward is the path we’ve been on or what we’ve seen people like us do.

I want to see people live the lives they are capable of, not just the ones they think they are allowed to live.

With every internship offer, Dean’s list award, and scholarship I earned, the intoxicating feeling of success ran through my body. I felt like I had it all figured out.

I was becoming a hoop-jumper just like Deresiewicz’s students at Yale, internalizing the idea that education is “doing your homework, getting the answers, acing the test.” I had not developed a sense that “something larger is at stake” as Deresiewicz says, and only was playing the game of student, not using my mind.

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.

I tried to pretend I was happy to be starting the job, but I wanted more.

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.

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.

…many people who face crises often experience “post-traumatic growth” and that this manifests as an “appreciation for life in general, more meaningful interpersonal relationships, an increased sense of personal strength, changed priorities, and a richer existential and spiritual life.”

I had studied advanced math and physics thinking I would apply those skills, but instead I spent my summers doing simple math on Excel spreadsheets.

“The ultimate way you and I get lucky is if you have some success early in life, you get to find out early it doesn’t mean anything.”

After returning to work, I felt like I had gone through a major transformation, but to my colleagues, I appeared back to normal. I was physically present but detached. Rather than participating in meetings as a good team member, I observed them as a visiting anthropologist. I saw my colleagues with new eyes. Are they happy? What kind of pain or challenges are they dealing with? Is this how they want to be spending their time?

Without knowing it, I had embraced a question that would shape my decisions: “How do you design a life that doesn’t put work first?” The answer, my dear reader, is simple. You start underachieving at work.

I felt like a rebel, like I was doing something wrong.

I liked feeling like a fool and the excitement that comes with learning something new.

Based on the experiences of others who leave the default path, this stage of contradiction is common. You take a last stand, doubling down on the existing path despite all evidence that it is no longer working.

It was easier to aim toward another raise or promotion than daring to ask myself deeper questions.

I defined a leader broadly as someone that could be a “role model in all aspects of their life.”

…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.

…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.

At that last job, I wasn’t a team player and I could have tried harder to say the right things, dress the right way, or spend more time pleasing my manager. But I couldn’t do it. The norms of the organization were pulling me too far away from the person I wanted to be and the energy I used to manage this disconnect undermined anything good I had to offer.

Many self‑employed people are surprised to find that once they no longer have to work for anyone else, they still have a manager in their head.

The more experiments I’ve done, the more comfortable I have become, and this gives me more freedom to try new things without being afraid.

The headline, “Quits To Live on a Sailboat” seems more impressive and is easier to talk about than “Couple Slowly and Purposefully Tests Out a Life Transition while Aggressively Saving Money over Five Years.“ As a result, we hear fewer of the real stories, most of which include some kind of prototyping.

By experimenting with different ways of showing up in the world and making small, deliberate changes, we can open ourselves up to the unexpected opportunities, possibilities, and connections that might tell us what comes next.

To change would be to trade the known for the unknown and change brings discomfort in hard to predict forms. So people avoid change and develop coping strategies.

Uncertain Discomfort < Certain Discomfort + Coping Mechanism

Wonder is the state of being open to the world, its beauty, and potential possibilities.

Uncertain Discomfort + Wonder > Certain Discomfort

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.”

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Did you read this book? If so, please share why you like it. If not, please read it.

Cheers,

Sidika

1. You can buy it from Amazon using my affiliate link: https://amzn.to/4edYwfg