Paul Millerd spent several years working in strategy consulting and on the “default path” before deciding to walk away to work on his own in 2017. His book, The Pathless Path, chronicles his own journey and deep dive into the history of work and has been read by more than 40,000 people. His podcast, The Pathless Path Podcast, highlights conversations with others following unconventional paths. He also runs the online training business StrategyU, helping people learn the skills of consulting without having to work in the industry. In our conversation, Paul shares:• An explanation of the “default path” and the “pathless path”• Signs you may be stuck on the default path• How to inch your way toward the pathless path• Why Paul suggests everyone should take a three-month sabbatical• Tips for embracing fear and betting on yourself• How to work through the fear of losing money and prestige—Brought to you by Sanity—The most customizable content layer to power your growth engine | Maui Nui Venison—The healthiest red meat on the planet delivered directly to your door | Wix Studio—The web creation platform built for agencies—Find the full transcript at: https://www.lennyspodcast.com/redefining-success-money-and-belonging-paul-millerd-the-pathless-path/—Where to find Paul Millerd:• X: https://twitter.com/p_millerd• LinkedIn: https://www.linkedin.com/in/paulmillerd/• Website: https://pathlesspath.com/• Newsletter: https://newsletter.pathlesspath.com • YouTube: https://www.youtube.com/channel/UCofS_FvauuHc-x6mq7yz6nA• Podcast: https://think-boundless.com/podcast/• Email: paul@strategyu.com—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:

Paul’s background

An explanation of the “default path”

Questions to help clarify which path you are on

Paul’s thoughts on “remixing your path”

An explanation of the “pathless path”

Examples of the pathless path

Why meaning is hard to find and sustain on a traditional career path

A case for the three-month sabbatical

A mindfulness and self-reflection exercise

Why Paul recommends three months

Advice to founders on offering sabbaticals

Other tactics for self-discovery

The variability of income in self-employed roles

Methods for staying afloat after leaving your job

Tips for reframing your thoughts around money

Why betting on yourself usually works out

The importance of setting aside time for creative pursuits

How to dip your toes in and find your path

Lenny’s personal journey

Advice on dealing with the naysayers

How to acknowledge and tame your fears

The “ship, quit, and learn” framework

Why the pathless path is one of constant reinvention

Paul’s response to criticism

First steps for getting started on your journey