Hi Reader,

For seven years at Google, I worked on the infrastructure behind Gmail. More than a billion people used what we built. When it worked, nobody noticed - that was the job.

That work mattered to a lot of people. I just rarely got to watch it change one person's day.

A few months into coaching, I did.

A client came to me with decades of experience in one industry and a clear plan to build her practice around it. Then she went to a big industry event and came back flat. The conversations felt like the same ones she'd been having twenty years earlier. A friend pointed out that she lit up talking about a side project, and about nothing else.

She was nervous to tell me she wanted to change direction. She thought I'd be disappointed. Instead it became one of our best sessions. The way she put it: "It's not a replacement. It's an addition." Keep what she'd built, and add the part she cared about. By the end of the call the worry was gone and she was talking about her next step.

That's the part I'd been missing: actually feeling that I'm making someone's life better.

What I'm noticing

Ikigai is a Japanese idea for your reason to get up in the morning. The version you've probably seen draws it as four overlapping circles: what you love, what you're good at, what the world needs, and what you can be paid for.

Coaching sits right in the middle of mine. It's why I added it as a service line, alongside the product and AI work I still do. Last week I was in Munich running an AI training for product managers. Either way, the job is figuring out the real problem, for a product or for a person.

Most of the senior people I talk to know what's in their middle circle. What they don't have is time for it. It's buried under everything else the day demands: the admin, the reporting nobody reads, the fourth draft of an email. The stuff you're good enough at but don't love, that pays but drains.

That's the most automatable work you have. Automate Yourself is about clearing out what's piled up around the meaningful part, so you can get to the thing you're here for.

Your next move

Three things to try this week:

1. Map your four circles. Don't overthink the middle - you probably already know it. If you'd like help, I turned the first exercise from my Fractional Kickstart into a prompt you can paste into your favorite AI. It asks one question at a time and pushes back when an answer is vague: https://www.chillaborate.com/ikigai​
2. List the work that sits outside all four circles, the pure drain. That's your automation list, in priority order.
3. Hand the top item to your favorite AI this week, and notice what you do with the hour it gives back.

Life beyond the screen

Lately I've been working on handwriting with my older kid. Right now it's numbers: the same ones over and over, erasing and starting again. It's slow, and then a number she's been fighting all week finally comes out right.

It's about as far from a billion users as you can get. One kid, one number at a time. And the moment it clicks is one of the best parts of my week. It's the same satisfaction I get from coaching: watching someone figure something out for themselves.

A question for this week: What's one thing sitting outside all four of your circles that you could hand off this week?

Come to the next Water Cooler 🚰 Thursday, October 29 (9am PT), Ian Irfan joins us on closing high-ticket deals without a proposal. Save your spot: https://luma.com/o737mad7​

Let's Chillaborate,

Dina

Founder, Chill Labs

PS: If you try the prompt, hit reply and tell me what showed up in your middle circle. I'd love to hear it. 💙