The Book I Keep Recommending

The Book I Keep Recommending to Everyone:

In his book “The Pathless Path: Imagining a New Story for Work and Life,” Paul Millerd writes about his decision to walk away from a life of ladder climbing in exchange for a journey of uncertainty and wonder.

A former McKinsey management consultant living in New York, he felt disillusioned with the default notions of success but kept moving from job to job hoping to find fulfillment. Then a period of disability pushed him to change direction. Paul writes:

Most people, including myself, have a deep desire to work on things that matter to them and bring forth what is inside them. It is only when we cling to the logic of the default path that we fail to see the possibilities for making that happen…On the pathless path, the goal is not to find a job, make money, build a business, or achieve any other metric. It’s to actively and consciously search for the work that you want to keep doing.”

Paul’s story is relatable and insightful. He pulls in wisdom from philosophers, economists and everyday people who have made similar life changes. He also puts the default scripts of modern society into perspective by looking at the evolution of work and leisure over history (the takeaway: work didn’t always hold the central role in our lives as it does now).

As a fellow traveler on the pathless path, what I love most about Paul’s writing is its vulnerability. His tone is not one of: “Look at how brave I am for leaving the rat race and how awesome my life is now.” Instead, he shares honestly about his money fears, insecurities around success, and struggles with finding belonging. And yet, it’s clear that he’s found a life of deep meaning and connection that feels at once inspiring and within reach to anyone who is willing to embrace their own path. The book concludes with this:

We are living in a time when it’s possible for more and more people to design a life in which they can thrive. Yet many look at that possibility and say, “no thanks,” because it means discomfort, uncertainty, and a higher risk of failure. I shared my story because I want to show you that even though you may experience all of those things on the pathless path, the journey can still be worth it.

My Reflections

I first came upon Paul’s writing online when I was still in corporate mode and laying down the foundations for my own transition. I knew I wanted to get on a different path than the one I was on, but as my family’s breadwinner I also needed to manage our risk. My decision to leave salaried security came after a long period of experimentation and pragmatic planning.

Interestingly, Paul expresses a similar sentiment:

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.

For those of us who aren’t the “just have faith and jump” type, this should be a relief. Building up your savings, making a financial plan, experimenting with different ways of making an income, trying out different ways of living – these can give you the confidence to make a significant life change. It might sound courageous to quit your job without a plan, but financial stress has a cost. The reality is that it’s hard to actualize your best self if you’re worried about paying the mortgage next month.

At the same time, I can promise you that no amount of money will eliminate uncertainty and discomfort. Part of the pathless path is facing your fears but then making them secondary to the greater promise of living a life on your terms. When I met Paul over coffee in Taipei a few years ago, he told me that he could have stayed longer on the corporate path to build up more savings and that might have been “smarter” financially. But in the end he recognized that if he stayed, he’d only be making it harder on himself. Paul writes:

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.

As a financial planner, the work that I do is to help people balance these two truths: Building wealth can free you to pursue a life on your terms. But sacrificing your present happiness for the sake of building wealth in hopes of later affording that life can actually move you farther away from that which you seek.

In practice, what this looks like is taking a clear-eyed look at your financial situation and making a plan that aligns your money with what matters. It means getting a safety net in place and experimenting to figure out how to live a life that you want. And it means coming face to face with your fears and insecurities, and yet still moving forward in pursuit of meaningful work, deep connection, and your joie de vivre. After all, aren’t these the reasons why we care about having money in the first place?

Listen to our Interview on Pauls’ Podcast: Last summer, Lisa and I sat down with Paul to talk about the series of jumps that we’ve taken over the last decade which led us to passion projects, living abroad, and creating a business to help others achieve the financial freedom to live their best lives.