➡️ Before we dive in, if you want to learn the exact mindset and habits that turn aspiring writers into published authors, you can download it free: The Author’s Code: 10 Proven Mindset Shifts and Daily Habits That Transform Aspiring Writers Into Published Authors

If you hang out in the online world of alternative careers and “off the beaten track” life paths, you’ve probably heard of Paul Millerd and his bestseller The Pathless Path, a memoir-manifesto for people who feel misaligned with the traditional script: get the fancy degree, get the prestigious job, keep climbing, feel dead inside, repeat.

I read his book a few years ago, and it genuinely shifted something in me. It recalibrated how I thought about work, security, and the life I was building.

So when Paul joined me live from Taipei on the Substack Writer Salon podcast, I wanted to ask him all the questions people are too polite to ask.

* Do you really not regret leaving McKinsey?

* How on earth do you turn down a Penguin two-book deal?

* How do you not obsess over money when you have a family?

* And is this “pathless path” actually practical, or just romantic?

Here’s a lightly edited version of our conversation.

Leaving McKinsey (and the “Prestige Path”)

Paul started his career in what many would consider a dream trajectory: GE → McKinsey → business school → high-paying consulting roles.

And yet, the higher he climbed, the worse he felt.

“My salary definitely kept climbing. But my curiosity and sense of aliveness kept going down. That disconnect just tore at me.”

He loved consulting early in his career, especially at McKinsey, which he still describes as the “best job” he ever had.

“McKinsey was fast-paced. Great managers, great mentorship. I learned a lot. It was really amazing.”

But after business school, things shifted. More money, more status… and less life.

“I didn’t know what I wanted to do. I just knew that if I stayed on my current trajectory, I was heading almost assuredly toward a life I was not satisfied with.”

So he did the unthinkable: he stepped off the default path.

Does he regret it?

“No. I wish I left earlier.”

If he could rewrite his story, he says he would have skipped business school, stayed a few years at McKinsey, then gone off to travel and explore, before taking on debt and doubling down on a path that wasn’t right for him.

The Spark Behind The Pathless Path

Unlike a lot of “build your brand” nonfiction, The Pathless Path wasn’t written as a strategic product. It emerged as the obvious next step in his experiment with a different way of living.

In 2018, Paul moved to Taiwan without a plan.

“I was just looking for distance from my old life, both metaphorically and literally. In that first month, I decided I would do the opposite of everything my brain was telling me to do: make money, pursue impressive things, start stuff.”

Instead, he wandered. Read. And discovered that what he most wanted to do every morning was write.

“I enjoyed it so much. I thought, what if I just make this the aim of everything? So I decided to build my path around writing as the core activity.”

For years, that’s what he did, without a clear promise of success:

* He wrote.

* He talked to people about his ideas.

* He lived in a way that would give him energy to keep writing.

Only after three and a half years of this did he finally publish The Pathless Path.

And the book… took off.

Why?

Partly because it’s not the usual “do these five things and you too can be free” business book.

“I didn’t write a popular nonfiction ‘how-to’ book. I wrote a memoir-ish book. It’s my personal journey, with side quests into the history of work and reflections on why people feel so weird about work today.”

Above all, he says, he wanted the book to say one thing:

“You’re not crazy. The way you feel about work makes sense. I just spent three and a half years mapping this all out.”

Why He Self-Published (Twice)

Here’s where it gets spicy.

Paul didn’t pitch The Pathless Path to agents or publishers.

“I had a tiny audience. I didn’t even try. I wasn’t interested. Writing a nonfiction proposal just to get permission to write a book on a topic a publisher chooses—that was fundamentally opposed to how I was living.”

Instead, he self-published and spent about $7,000 doing it, on editors, design, ISBNs, and audiobook production.

“If you want to do it well, with good editing and design, you’re probably looking at five to ten thousand. Anything less and you’ll need to bring a lot of the skills yourself.”

His second book, Good Work (published in 2024), cost even more—around $10,000—because he paid existing collaborators better and cycled through several cover designers.

Has he made a profit?

Yes—but modestly.

“I’ve probably made about $5,000 to $10,000 profit on Good Work in a year. Not amazing. The Pathless Path still sells better.”

And then came Penguin.

Turning Down Penguin

About a year after The Pathless Path launched, Penguin came knocking with a two-book deal:

* $70,000 to buy the rights to The Pathless Path

* $130,000 to write a second book on a topic they would choose

And he said… no.

“At that point I was selling about 2,000 copies a month and making around $10,000 per month from the book. After the agent’s cut, I’d net maybe $52,000 from that advance—and then I’d have to earn it back with a smaller royalty percentage.”

Worse, they planned to take his self-published version out of print.

“It was just a bad match. I didn’t connect with them energy-wise. So it was a pretty easy no.”

This is where other authors often raise the “but what about reputation?” argument. Don’t traditional publishers still give you legitimacy?

Paul doesn’t buy it.

“Who published your favorite book? Do you know? You probably read it because someone recommended it, not because of the publisher’s logo. We care about our friends’ reputations, not the publisher’s.”

What does matter, he acknowledges, is speaking.

Traditional publishers have relationships with PR firms and conference organizers—and that’s often what they quietly sell authors: not royalties, but access to speaking circuits.

“That’s exactly what Penguin told me. ‘We’ll get you on the speaker circuit. You’ll make money from speaking.’ But I like writing. I don’t want to be a professional speaker.”

His stance is simple: if you own your audience, it’s insane to give away marketing and rights control to a company that will own your book, your merchandising rights, and your options, often for a deal that doesn’t make financial sense.

What Actually Sells Books (Hint: It’s Not Hacks)

People love to ask him: What’s your secret? What’s the playbook?

His answer is almost disappointingly simple:

“There’s one thing that sells books: people buy it, finish it, and then share and gift it to others.”

There was no grand launch strategy. No mass outreach to influencers. He didn’t even ask Ali Abdaal to promote it.

“Ali just happened to be a reader of my newsletter. His brother sent him my stuff. He supported my presale, I offered to send him free copies, he read the book, liked it, and started recommending it. His behavior was almost indistinguishable from other readers who loved the book.”

Paul’s “strategy,” if you can call it that, is radical generosity:

“I see my creative work as a gift. I don’t feel like I deserve money for it. I already feel paid in the privilege of being able to do it. So if someone loves my book and gifts it, I’ll often say, ‘Can I send you five copies?’”

He also shares all his numbers publicly—royalties, foreign rights deals, percentages, everything—so people can judge his opinions in context.

“Most traditionally published authors won’t tell you the size of their advance or how many books they sell. Without that, it’s hard to learn from them.”

Money, Family, and “Is This Sustainable?”

At this point in the conversation, I pushed him on the thing many people are quietly thinking:

Okay, this all sounds very spiritual and poetic, but… you have a family. How sustainable is this?

Paul doesn’t pretend to have a neat, practical framework. What he has instead is clarity of priorities.

He and his wife have organized their entire life around creative work first, and they’re willing to sacrifice for that.

“We are not saving to send our kid to private school. We are not trying to buy a house. We don’t own a car. We live in Taiwan partly because it’s cheaper. We start with: what’s the life we want to live? What are our constraints? And then we design around that.”

He defines success in simple terms:

“When I quit, I had enough savings for about a year. I told myself: success is breaking even each year.”

Some years he made very little (around $30K). He cut expenses aggressively and trusted the frugal, cautious version of himself he’d cultivated in his 20s.

He also tracks his finances quarterly:

“If I’m burning $2,000 a month and I have $50,000 in savings, that’s 25 months of runway. If I look at that and see I still have a buffer, I say: screw it, keep going. At the end of my life, I won’t wish I chased safety more. I’ll wish I’d pursued my bold creative dreams.”

And if it all stops working?

“I’ll just get a job. It’s not that big of a deal. I’ll fight like hell to avoid it, but uncertainty is not a problem to be solved—it’s something to be embraced.”

Not for Everyone (And That’s the Point)

Paul is very clear: his writing is not aimed at the average corporate professional who wants a more flexible schedule but also the house, car, private school, and stable salary.

“My writing is not for the person who wants the cozy upper-middle-class American life. You shouldn’t be reading my stuff. My book is for the weirdos who must find another way.”

He places himself in a lineage of misfits across history:

“From the poets who escaped Confucianism to get drunk in the forests, to Walden, to mystics in the Middle East, there have always been people who had to live differently. I realized I am one of them. I’m not wired like the suits I was surrounded by.”

Life on the Pathless Path (Day to Day)

So what does day-to-day life look like when you refuse to optimize for traditional stability?

For the last couple of years, much of Paul’s time has gone into parenting and helping his wife with her book.

“All of last year I was the lead parent three to four days a week while my wife wrote her book. We decided as a family that we’re going to put creative work above everything else. Book royalties gave me enough cushion to work less.”

Now, living in Asia near his in-laws, his days are loose by design:

* Mornings with his daughter

* The occasional podcast or call

* Writing when the energy is there

* Very few fixed commitments

“I sort of just make it up as I go. I love writing, so that happens most days, but there’s no rigid structure. That’s how I’ve designed it.”

He runs a small community on Circle for readers of The Pathless Path—not as a big revenue stream, but as a way to help “the weirdos” find each other. Members get:

* A monthly call

* A space to connect

* A WhatsApp group

* Access to some of his courses (on freelancing and reimagining work)

It mostly breaks even, and he’s okay with that.

Why He Doesn’t Have a Paid Substack

This surprised me: with 25,000+ subscribers, Paul could easily turn on paid subscriptions and make a steady extra income.

But he doesn’t want that.

“I don’t want to be a weekly newsletter writer. That’s not the job I want. If people pay, I feel pressure to deliver something specific to them. I’d rather they buy my books or a one-time course.”

He prefers one-time payments (like his community or courses) and freedom from the “I owe you a post” feeling.

“I didn’t leave the paycheck world to create another paycheck for myself.”

He’s even considering taking four months off and likes knowing he doesn’t have to explain that to paying subscribers.

The Future of Work (Spoiler: He Doesn’t Know Either)

Given his background—MIT, McKinsey, consulting—you’d think Paul would have a neat TED-talk answer to “What is the future of work?”

He doesn’t.

“If I were smart, I’d lean into that topic, talk to corporations, and morph myself into a Simon Sinek or Adam Grant. I’d make a lot more money. But the truth is: I don’t know what the future of work looks like.”

What he does know is that most people’s stories about work are outdated, and that the big “future of work” discourse is often a distraction:

“The now of work is radically different than it was 30 years ago. We already use AI. We already have more flexibility. We already do creative work. But people haven’t updated their scripts to match reality.”

So instead of obsessing about the distant future, his advice is to update your story about today:

* What are you actually doing now?

* What constraints do you have?

* What do you want your days to feel like?

* What trade-offs are you willing to make?

And then build from there.

“I’m mostly just trying to figure out what I’m going to do today and tomorrow.”

What’s Next for Paul

Paul’s immediate focus isn’t another solo book—it’s his wife’s.

“We’ve really been focusing on my wife’s book for the past two years. It’s about Asian identity, emigrating to the U.S. as an adult, moving between social classes, finding her work path, and becoming a mother. It’s going to publish in Chinese first, then we’ll translate it to English.”

He also has three book drafts of his own simmering in the background—and a big experience coming up:

“Next year we’re joining something called The Traveling Village—twenty families traveling to three countries in Asia. I’ll probably write about that.”

He admits that since becoming a parent, he hasn’t quite found a new creative groove yet.

“I don’t know exactly how I’m going to make it all work in the next few years, but I’m excited to find out.”

Final Thoughts (and Where to Find Paul)

Talking to Paul was a refreshing break from growth hacks, funnels, and “10 steps to build your personal brand.”

He doesn’t promise that everyone can—or should—copy his choices. He doesn’t pretend the pathless path is easy or neatly scalable.

What he does offer is something rarer: a lived example of someone who prioritized aliveness over status, designed his life around writing and family, and is willing to absorb more uncertainty than most people would tolerate.

“I’m not aiming at a future potential life. I’m living the life I want right now.”

If you want to go deeper:

* His site and newsletter live at pathlesspath.com

* His books are The Pathless Path and Good Work

* His Substack newsletter:

And if you’re one of the “weirdos” who feel like they must find another way, you might find a language for your own longings in his work.

If you enjoyed this conversation, feel free to share this post, forward it to a friend who’s stuck in their own “default path,” or hit reply and tell me: what’s your version of a pathless path?

Read and Write with Natasha is a reader-supported publication. To receive new posts and support my work, consider becoming a paid subscriber, and you will get lifetime access to some of my free courses (Worth over 300 dollars), in addition to free access to my webinars on writing

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit natashatynes.substack.com/subscribe