The Pathless Path: Stepping Off the Default Script for Work and Life

Lenny introduces Paul Millerd as the author of the self-published book The Pathless Path, which Lenny says has sold more than 40,000 copies, a very high number for any book. Millerd defines the default path as the story in your head about what you should do: in the US, go to college, get good grades, get a good job, buy a house, start a family, and work continuously through adulthood. People who step outside it can trigger insecurities in others simply by existing.

Millerd stresses that there is nothing wrong with the default path. The difference is whether you are conscious of its costs and trade-offs and the implicit contracts you've created. He notes that when people quit their jobs, they often "forget to fire the manager in their head" and still behave as though they must work eight to ten hours a day, Monday to Friday, even when they could take an afternoon with their kids.

He has been surprised that the book resonates even with people in traditional roles, one of whom listed four priorities and realized his job delivered three of them. Millerd's "hot take" is that we are all on a pathless path, since careers are disrupted by shocks, shrinking stable jobs and personal events, and pretending we are on a smooth corporate ascent limits what we imagine.

Millerd deliberately avoids defining the pathless path too tightly. He describes it as a shift away from treating not knowing what you're doing as a problem to be solved, toward embracing discomfort and uncertainty, and from operating out of scarcity toward a sense of abundance. He says that naming it has helped readers, including one who emailed after seven years on such a path to say it was the first time they felt okay about it.

The umbrella includes short sabbaticals, creators who bet on themselves, independent freelancers, people who hop between jobs, and people in their fifties who have solved their money problems but lost a sense of aliveness. The shared ethic, he says, is possibility, opportunity and optimism. Lenny reads a line from the book: the goal is not to find a job or make money, but to consciously search for the work you want to keep doing.

Millerd describes how leaving his job was initially about escaping work, and he cut his cost of living in Asia to about $1,000 a month. Then he discovered a relationship with writing and creating that he enjoyed for its own sake. His big aha was that you can design around liking work, rather than assuming work must be endured. He says it was easy to turn down a publisher for a second book because he protects what he enjoys.

Millerd argues that a three-month sabbatical is more attainable than people think, since companies are desperate to retain staff. If you work continuously for about 500 months, he says, setting aside three of them to reconnect with yourself is a modest ask, and people routinely achieve bigger goals like saving for a house. Lenny confirms that his own sabbatical led him to stop checking email and realize his heart was no longer in his product job.

For people who really can't take that time, Millerd's alternative is three hours during a workday: block your calendar, go for a walk without a destination, or do something from childhood like basketball, painting or an instrument. Then pay attention. Do you feel bad about sneaking out, and where does that feeling come from? The point is to ask why you work at all and what scripts you absorbed about being a good person.

After talking with 500-plus people about their relationship to work, Millerd says the sabbatical is almost universally valued, and he has met only one person who couldn't wait to go back. Both he and Lenny found it takes six to eight weeks to unwind, with a deeper unwind coming after a couple of years. Asked about founders who fear losing staff, he says that reaction reveals an insecurity about work, and that people leave when they can't see a path to becoming who they want to be.

To discover a new direction, Millerd suggests a "path expert conversation": send a thoughtful message to someone a few years ahead on a path you're curious about and ask to pick their brain, or send written questions. He notes the possibilities for reinventing yourself, working online and flexibly are far greater than 25 years ago and keep growing with technology. Both men say a new path can mean income as well as satisfaction; Lenny earns significantly more than he did as a senior product leader.

Millerd's own income took until year five to approach his old salary, after years of earning roughly $24,000 to $50,000 while lowering his cost of living and exploring. He has seen people move abroad, live in an RV, dip into retirement savings, win grants, take loans, or convert their current job into a contract role with fewer days. Lenny set an explicit runway budget for his time off and treated it as a bet that might lead somewhere interesting.

Millerd likes naming the spending: it is a "life MBA", and few people would criticize a $150,000 to $200,000 business-school bill that also means two years without salary. Another reframe that worked for him was viewing earnings from his old consulting career as a gift from his former self. He says few stories actually end in regret, because without an income people spring into action, and people tend to regret what they didn't do.

Millerd observes that creative work can't be forced, and that much of modern work, including Lenny's product work at Airbnb, is creative. Companies often fail to give people the schedules and support that creativity needs. Lenny adds that sometimes the opposite works too, writing through the bad draft, and Millerd agrees that what lands on the page often surprises you.

Both describe leaving jobs after years of safe experiments rather than a sudden leap. Millerd read personal development books, coached on the side, helped people with resumes, and wrote on Quora for fun, without a goal. Each small thing gave him confidence that there was energy there worth following.

Lenny shares advice he got on sabbatical: after each call, hobby or piece of writing, check whether it energized or drained you, then do more of the former. Advising calls drained him, company ideas drained him, but publishing writing energized him. Millerd says that is hard because the pull to start a company after big tech is strong, and that you need a "boomer compatible story" for family, while Lenny's trick is to say you're "tinkering".

Drawing on Tim Ferriss' fear-setting, Millerd writes down his fears and reframes them around the cost of inaction. He recently hired a community manager after realizing that avoiding the hire, out of fear of creating a job for himself, would drain his creative energy, which is an existential risk to his path. He also learned from Lenny that someone else can be good at community management even if he isn't.

The big fears around money, health and importance don't go away; they become small daily visits that he talks to: "I see you." He draws comfort from the idea that something tends to last about as long as it already has, six and a half years on this path and four years of writing a newsletter. Taking a job to make the money fear disappear is off the table, so he has to live with it.

Millerd says his first ten years were spent jumping between jobs looking for his path in job-shaped containers. Lenny's frame is "ship, quit and learn", and Millerd began his podcast as a five-episode experiment. Both warn against creating jobs you hate, like writing about a niche you don't care about. Millerd keeps about 95% of his days free of work, uses asynchronous contractors, and sees the path as a commitment to constant reinvention, now exploring handing off his StrategyU business.

Responding to the critique that nobody would be left to build companies if everyone took this path, Millerd says most people react with "hell no" to his life. He also cites a long-run trend toward project-based work and notes that all labor market growth from 2005 to 2015 came from alternative work arrangements, citing David Deming's research. Companies, he argues, under-exploit freelance and creator talent.

His closing message is that the path might be hard, and might suck, but is worth exploring if you sense there's something more. It is not a "quit your job and get rich" pitch, and some people who try it return to jobs happier because they tested their boundaries. His practical next step is to find people on interesting paths and ask about their lives, since his own circle widened to include part-time workers and people who take three months off.

In the lightning round, Millerd recommends The Great Work of Your Life and Luke Burgis' Wanting, praises the Anthony Bourdain documentary, and says he looks for people who "come alive". His motto is "coming alive over getting ahead", which he repeated to himself before turning down a book deal. He advises podcasting only if you love the conversations, since it is the ultimate long game, and offers his book at author rate, around $4 a copy, at pathlesspath.com.