People ask me some version of the same question a lot. Not "what should I do with my career," exactly. More like, "how do I actually figure out what I want?"
My answer is never a framework you fill out alone at your kitchen table. It's a lunch.
I've told the story of how 50 Lunches started elsewhere. This is the other half of that story. Not why I did it, but exactly how you can do it too, starting with someone whose life makes you curious.
Who to invite
Pick someone whose story you're curious about. That's the whole qualifying question.
It can be a friend, a former colleague, someone you've admired from a distance for years and never actually talked to. The person who left the career you're scared to leave. The person who seems to have figured out something you haven't yet. You don't need a list of fifty names before you start. You need one name and an hour.
The message that gets a yes
Send something close to this:
"Hi [Name], I'm spending some time having real conversations with people whose stories I'm curious about, and yours is one I'd love to hear. Would you be up for an hour over coffee sometime this week?"
Almost nobody says no to this. People like being asked about themselves, and there's no catch buried in the ask. Nothing to sell, nothing to pitch, no favor to cash in later. That's what makes people open up once they sit down.
The 60 minutes
No script. A loose structure keeps you present instead of scrambling for what to say next. Three phases.
Your story first (10 minutes). Go first. Share where you are right now: what you're working on, what you're unsure about, what's actually going on in your life. If you've done a Life Report or mapped out your values, bring the page. It gives the other person something real to react to instead of guessing at your life from scratch.
Their story (30 minutes). Now turn it fully to them. Move from what they do to why they do it. Ask about purpose, turning points, the moment things changed. When something lights them up, go deeper instead of moving on to the next question on your list.
Brainstorm together (20 minutes). Bring it back to your own questions. Flip through the notes you took while they were talking and use them as prompts. What do they see in your story that you can't? What would they do in your position? Who else do they think you should be talking to?
Questions that actually open people up
Write your own before each conversation, tailored to the person across the table. These get you started.
For their story: "How do you spend your days? What does your life actually look like?" "To what degree do you feel you're living your purpose?" "Was there a moment that changed the direction of your life?" "What matters most to you? Not what should matter. What actually does." "When do you feel most alive? What were you doing the last time you felt that?"
For the brainstorm: "Given what I've shared, what would you recommend for someone like me?" "Hearing my story, what do you see that I might be missing?"
And before you stand up, ask one more, every time: "Is there someone else you think I should be having this conversation with?" Half the value of 50 Lunches compounds through that single sentence. One good lunch turns into three.
The part almost everyone skips
Take notes during the conversation. Not typing on your phone, just a few lines on paper as you go. Ask permission first if you'd rather record the audio, phone face down, flight mode on so nothing interrupts. Either way, those notes are what makes the brainstorming phase actually useful instead of turning into small talk.
Then write a few lines afterward, within 24 hours, while it's still fresh. What surprised you? What did their story make you think about your own life? When did you feel most alive in the conversation? Did any of your values light up? One thing you want to remember.
Do this after five conversations and you start noticing what no amount of thinking alone gets you to. Patterns. What pulls you in. What leaves you cold. The life you want, and the life you've quietly decided isn't for you.
Find the pattern
This is the fourth exercise, and the one that turns five conversations into an answer. Without it you have five nice afternoons and nothing to show for them.
After five conversations, put your notes side by side. Physically, if you can. Five pages on one table.
Then go through them three times.
First pass. Circle every role, industry or way of working that came up more than once. It doesn't matter who said it.
Second pass. Mark the moments you got excited. You'll remember them. The place where you interrupted someone. The hour that went too fast.
Third pass. Mark everything you explained away. Every time you heard something and immediately thought "yeah, but I couldn't." That one matters most. That's usually a belief, not an obstacle.
Now write one page. What keeps repeating. What gave you energy. What you keep talking yourself out of.
Pro tip: I dump my notes into an AI and ask what I'm not seeing. It's surprisingly good at this, mostly because it has no idea what I want the answer to be.
Your mindset going in
A few rules I hold onto every time. Curiosity, not performance. You're there to learn, not impress. Vulnerability is strength. Go first and people open up. Listen more than you talk, aim for 70/30. And nothing to sell. You're not networking. You're just showing up.
What this actually gives you
Ten podcast guests once told me the same thing about myself around a rooftop table in Malaga, without comparing notes beforehand. Other people can see things about you that you can't see yourself. Not because they're wiser. Because they're not standing where you're standing.
That's the actual mechanism behind 50 Lunches. Not networking, and not inspiration for its own sake. Borrowing someone else's eyes for an hour, on purpose.
I put the whole thing onto one page you can print or pull up on your phone before you sit down: the invite message, the question list, the mindset checklist, the after-conversation prompts. Grab the 50 Lunches Playbook here and take it with you to your first one.
Who's the person you'd invite first?
