Paul Millerd
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.
Career Skills
Transitioning from full-time to contract work within the same company can provide the flexibility needed for a career pivot while maintaining income.
"A big move that a lot of people do is turn their current job into a contract job, which a lot of employers are a lot more open than people would think... You say, 'Hey, I want to work three days a wee..."
Cold outreach to 'path experts' is more effective when you offer a low-friction option like written questions.
"Reach out to somebody, sort of like a podcast, that's ahead of you on a similar path, and just send them a message and say, really thoughtful message. Say, 'Hey, you're on a path a few years ahead of..."
A three-month sabbatical is a small, manageable fraction of a 500-month career that allows for essential self-reconnection.
"A three month sabbatical is much more attainable than people think. Companies are desperate to keep people and are much more open to things like this these days. And the way I frame it is if you're as..."
The psychological transition away from a high-pressure job requires nearly two months before true exploration can begin.
"I've found it takes six to eight weeks just to unwind."
When transitioning to unconventional work, use traditional labels to satisfy the social expectations of older generations and reduce friction.
"I always tell people you need a boomer compatible story for what you're up to, as just give them something. Just say, 'I'm an entrepreneur,' or, 'I'm a business owner.'"
Treat career experiments as short-term projects designed to be abandoned after they provide the necessary data for the next step.
"I call it ship, quit, and learn, which is what is the quickest way I can ship something designed to quit, but as soon as I ship it, I learn about what to do next?"
Hiring & Teams Skills
For creative or unconventional roles, a candidate's intrinsic energy and alignment with the work are more important than their technical resume.
"I'm always curious about, what makes you come alive? I want to work with people that are alive, and connected, and inspired... I'm always looking for that energy first and skills second."
Leadership Skills
To avoid turning your solo venture back into a management-heavy job, delegate via asynchronous systems and highly specific roles.
"I have contractors, but I hire contractors for very specific roles. And I create systems such that we can do it asynchronously. And of course, I'll have conversations with them if they want to jump on..."
Effective decision-making in career pivots requires weighing the cost of staying in a soul-crushing job against the risks of leaving.
"Tim Ferriss' fear setting, and he basically forces you to write down what are your fears, how could you mitigate these. But more powerfully, the second part is... And you're framing them around action..."
Both the guest and host discuss a specific, tactical framework for career direction based on tracking what 'energizes' vs. 'saps' energy after every interaction or task.
"Pay really close attention to what gives you energy after you do the thing. Say you have a call. Did that give you energy or did that sap you of energy?"
Marketing Skills
Sustainability in content creation depends on intrinsic enjoyment of the format rather than immediate financial or growth metrics.
"Podcast is the ultimate long game, so you need to find some intrinsic connection to what you're actually doing. If you don't love the conversations or the format you're doing, don't do it."