A career transition experiment

Let's have lunch.

I'm having 50 honest lunch conversations with people I admire... about meaning, work, and what actually matters.

26/50
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050 lunches

26 out of 50 lunches completed. Some are recorded. Others are not. The full conversations live on YouTube.

Reflections along the way

Instead of updating my CV, I ran an experiment: 50 honest conversations about meaning, work, and what comes next. These are my reflections from inside it.

What keeps showing up.

The patterns that emerge when I look across every lunch. Click any node for the conversations behind it.

Drag to nudge. Click a node for episodes.

Recent conversations

Each lunch is an honest conversation with someone I admire, about the choices they've made and what gives their work meaning. Full episodes on YouTube.

Life coach. Ex-Googler. Running the experiment.

I've spent 20+ years at the intersection of leadership, strategy, and coaching - from Google and startups to C-suite roles in Barcelona. Now I work one-on-one with mid-career professionals who are figuring out what comes next. And I'm figuring it out myself.

Why lunch?

Because the best conversations I've ever had happened across a table, not on stage. No script, no agenda, no pretending. Just two people trying to say something true about work, life, and what comes next.

Ikigai.

A Japanese framework for aligning what you love, what you're good at, what the world needs, and what you can be paid for. It's the lens I've been using to think about the second half of my career... and the question I bring to every lunch.

I'll be sharing mine, and exploring other people's, across these 50 conversations.

Ikigai diagram: the intersection of what you love, what you're good at, what the world needs, and what you can be paid for.

A micro-retirement, documented.

I've spent most of 2025 on a "micro-retirement"... travelling through Europe in a camper van, then through Vietnam, Cambodia, Laos, and the Philippines.

I've been reflecting on who I am, and how I want to spend the second half of my career. I'm documenting all of it on my YouTube channel, Re-Inventing Ken.

Watch on YouTube → Coaching with Ken ↗

The conversations raised the questions. Coaching helps you answer them.

Every lunch I've had circles back to the same themes... purpose, meaning, and what to do with the second half of a career. If those questions are already living rent-free in your head, coaching is a structured way to actually work through them.

Not sure where you're at? The Wheel of Life is a free 10-minute assessment that shows you clearly where energy is missing and where to focus first.

Does this sound familiar?

  • Work that once felt exciting now feels flat
  • You're doing well on paper, but it doesn't feel meaningful
  • You've been saying "something needs to change" for too long
  • Strong experience, but no clear story about what's next
  • You don't quite know what you actually want
Start with the free quiz - it takes 10 minutes →

Who should I invite for lunch?

I'd love to hear from you... whether it's about lunch, work, or just a hello.

Thank you.

I read every message personally. If there's a lunch to be had, I'll be in touch.