The Path Expert Conversation
Find someone a few years ahead on the path you're curious about, and offer them written questions.
- Difficulty
- Starter
- Time to result
- ~weeks to results
- Steps
- 5
- Confidence
- 90%
Most people considering an unconventional path have nobody in their life who has done it, so their only reference points are colleagues on the default path. The fix is a deliberate outreach to a 'path expert' — someone two to five years ahead on the specific path you're curious about — with an ask engineered for a high yes-rate: offer written questions as the fallback to a call.
Origin
Paul Millerd's exercise for the curious, developed from his own practice of holding an open calendar every Wednesday for years, through which he spoke to 500+ people about their relationship to work.
Core principles
- 01You need real examples, not theory — people cannot imagine a life they've never seen up close.
- 02A few years ahead beats decades ahead: the memory of the transition is still fresh and legible.
- 03The written-questions fallback is the unlock — it converts a scheduling problem into a low-cost yes.
- 04Writers in particular say yes to written questions, because answering them generates new ideas for their own work.
How to run it
- 1
Identify someone a few years ahead on your specific path
Not a celebrity, not a generic mentor. Someone visibly a few years further along the exact path you're curious about — often found through podcasts, newsletters, or writing.
Pro tip Podcasts are Millerd's stated hunting ground: people who talk publicly about an unconventional path are pre-qualified and reachable.
- 2
Send a genuinely thoughtful message
Say plainly: you're a few years ahead of me on this path, I'm really curious about it, and I don't have anyone in my life who has done anything like this.
Pro tip The honest admission that you have no one in your life on this path is disarming and true for most people — it's why the ask lands.
Watch out Generic 'pick your brain' cold outreach with no specificity gets ignored. The specificity of the path is what makes it a real ask.
- 3
Offer the written-questions fallback
Ask for a call, and immediately offer the alternative: if we can't get on a call, can I send you a list of questions? Millerd says most people will agree to that, and the written version especially.
Pro tip Millerd no longer takes open calls (his daughter wins over strangers) but still always answers written questions — which is exactly why the fallback is the higher-probability ask.
Watch out Don't lead with a 60-minute call request. The calendar is the objection; remove it.
- 4
Ask about the inner game, not the tactics
Millerd's own podcast deliberately skips tactics and outcomes to ask how it felt, and how they dealt with it. That is the information you cannot get from a blog post and the information that actually decides whether you can do this.
Watch out Asking only for playbooks and tactics gets you content you could have Googled and wastes a rare conversation.
- 5
Widen your circle until your path feels normal
Repeat until you know a genuinely diverse set of people — those who work part-time, on weird schedules, nine months a year. Millerd notes that once he did, what he was doing simply started to feel normal.
Pro tip Find the weirdos. When all you know is full-time workers, the default path looks like the only path by construction.
In the wild
Before the pandemic, Millerd opened his calendar every Wednesday and invited anyone who wanted to talk about work to book time. Over years this accumulated into 500+ conversations about people's relationship to work.
→ It became the empirical base for his book and his advice — and demonstrates that people on unconventional paths are genuinely willing to talk.
Over a few years Millerd came to know people who work in restaurants, work part-time, keep odd schedules, or work nine months a year and take three off. Previously, surrounded only by full-time workers, his own choice felt aberrant.
→ His path started to feel normal — the social proof problem solved not by argument but by changing the sample.
Common mistakes
Only asking for a call
The calendar is the bottleneck. Offering written questions as an explicit fallback converts many nos into yeses — Millerd himself only answers in writing now.
Targeting people decades ahead
Someone a few years ahead still remembers the transition mechanics and the fear. A veteran has rewritten the story into a clean narrative that won't help you.
Asking only for tactics
The blocker on an unconventional path is the inner game — how it felt, how they handled fear and money. That information only exists in conversation.
Is it for you?
Best for
Someone curious about self-employment, creator work, or a career pivot who has zero examples of it in their existing network
Not ideal for
People who like their traditional job and are not curious — Millerd explicitly does not want to convert them
From the transcript
“have a path expert conversation reach out to somebody sort of like a podcast that's ahead of you on a similar path”
“can I just like pick your brain if we can't jump on a call can I send you a list of questions most people will…”
“I don't talk about tactics and outcomes as much as really just like how does it feel how do you how did you deal with…”
“try to find the the weirdos”
From the episode
Redefining success, money, and belonging
Paul Millerd (The Pathless Path)