Fifteen years ago I left a job in New York and moved back to Sweden with no idea what I wanted to do next.
I didn't apply for anything. I didn't hire a career coach. I did something stranger.
I made a list of fifty people I wanted to have a conversation with. And I invited them all to lunch.
The rule that made it work
The first thing I'd say when I sat down was always the same.
"I'm not going to ask you for a job. I'm looking for inspiration."
That one sentence changed everything. It removed the awkward subtext. The other person stopped being a target and started being a person. And it made them open up in ways they wouldn't have if they thought I wanted something from them.
I'd ask them everything. How they had ended up doing what they were doing. What they thought happiness meant. Whether they were living the version of their life they'd actually wanted, or some version that just happened to them.
These weren't polite conversations. They were real ones.
And after about five of them, something shifted. I started noticing patterns. What pulled me in. What left me cold. The people I quietly wanted to be like, and the ones I quietly decided I didn't.
The flip nobody talks about
Here's the part most "have coffee with people" advice misses.
When their story was done, I'd say: "Can I borrow your eyes for a few minutes?"
Sometimes people were a little surprised. Nobody ever said no.
I'd have my Ikigai printed out on the table. Three minutes to walk them through it. My passions. My skills. What I cared about contributing. And then the question I'd really come for: given all of that, what do you think I should focus on? Who should I be talking to? What should I learn next?
What came back was extraordinary.
They weren't projecting their values onto me. They were genuinely seeing me. Reflecting back things I couldn't see myself. Doors opened. Names appeared. Ideas came up that wouldn't have come from me sitting alone with my journal.
The interview half was the warm-up. The flip was where the real work happened.
What kept happening
After about four or five conversations, people started saying the same thing without being prompted.
"Ken, it's obvious. You have to become a coach."
I didn't believe them.
I was sure I wasn't qualified. I was sure I wasn't good enough. I wasn't ready to charge for something I'd never been formally trained in. So the next ten lunches were, if I'm honest, me fighting that voice. Trying to talk myself into the thing fifteen people I respected had already told me was true.
After fifteen lunches I stopped arguing with myself. I posted on LinkedIn and on YouTube: "I'm giving myself thirty days to find my first paying client. After that I'll see if I can make it repeatable."
That was version one of 50 Lunches.
Why I keep coming back to it
This is the fourth time I've done it, in different forms. The first was fifteen years ago in Sweden, when I was working out what to do after New York. The current version is the coaching practice you're seeing build itself in real time.
The fact that I keep coming back to it tells me something. It's not a one-off trick. It's a way of finding direction when the inside of your own head has stopped generating answers.
You probably know the feeling. You've thought about it. Journaled about it. You've talked to your partner, maybe a friend or two. You've made spreadsheets. And it's not getting any clearer.
That's because you can't see yourself from the outside. Other people can. They have angles on you that you don't, and they're not trying to protect your story the way you are.
The version that's running now
The current one is a podcast. Same shape. Find people I'm curious about. Have a real conversation. Let what they see become part of what I see.
The only thing that's different is that I record it. So everyone else can hear what I was previously only hearing alone.
It's also where almost every paying client I've signed has come from. Not because the podcast is a sales funnel. Because the kind of conversations that show up there tend to make a particular kind of person, the kind who's been quietly asking themselves the same questions, recognise themselves and reach out.
If you're stuck right now
You don't need fifty lunches. You probably need five.
Make a list of people whose lives or work make you slightly curious. Not your closest friends. Not strangers off LinkedIn either. Somewhere in between. The people you've always thought "I'd like to know how they ended up there."
Reach out. Be specific about why them. Tell them the rule: "I'm not asking for a job. I'm looking for inspiration." If they have an hour for a coffee, take it.
Then do the thing most people skip. Bring your Life Report, or your Ikigai, or even just a half-page of "this is who I am, this is what I'm trying to figure out." Read it to them. And ask: what do you see?
You'll be surprised what they say. You'll probably be more surprised by how much of it you already half-knew.
You can't think your way to the answer. But you can usually find someone who can see what you can't.
