👋Hello, my friend. Sharing some thoughts today on my early-stage efforts to build an AI-powered ‘life operating system.’ I’m just kicking this process off in earnest, so the only thing I really know is that it’s going to evolve… but the plan is to build this in public, so hopefully that’s helpful in case you’re thinking about leveraging AI in the same way. Let’s get into it!
A few weeks ago, I downloaded my entire ChatGPT history — over 375 conversations spanning three years. I handed it to Claude (a different AI, made by Anthropic) and said, basically, “Tell me what you see.”
What came back was a mirror I wasn’t expecting. Health and wellness. Parenting. Career stuff. Side business ideas. Content creation. The same themes showing up over and over again, but scattered. No connective tissue. No system holding it all together.
And the volume told a story too: I went from 36 conversations in 2023 to 248 in 2025. I wasn’t just using AI more — I was leaning on it for increasingly important stuff. Career decisions. Health questions. Parenting challenges. But I was doing it all in disconnected, one-off conversations. Like having a brilliant colleague with pretty bad amnesia.
That’s when I decided to stop treating AI like a search engine and start treating it like an actual operating partner.
Before I get into what I’m building, a quick note about what I’m calling AI anxiety. If you’re anything like me — following the tech discourse, listening to the podcasts, trying to stay informed — the pace of AI releases right now is insane. New models. New tools. New capabilities. Every single week. And there’s this low-grade anxiety that comes with it. Like you’re falling behind. Like everyone else has figured this out and you’re still catching up.
I feel that. But I’m becoming more and more convinced that chasing every new release is the wrong game entirely. The real move is to pick your tools, go deep, and build something that actually serves your life and your priorities.
I sat down with Claude and laid it all out — I’ve got all these areas of my life that matter to me, and I need a system that helps me make progress across all of them without losing my mind. A legitimate operating system for my life.
If you’ve read my stuff over the years, you know I’ve experimented with identity-based systems before. I’ve been influenced by James Clear’s work in Atomic Habits — this idea that you don’t just set goals, you decide who you’re trying to become and then take actions that prove that identity. I’ve written about this. I’ve tried various versions of it. Some of it stuck, some of it didn’t. But the core idea has always resonated with me.
What’s different now is that AI gives you a thinking partner who can actually hold the full picture and help you execute against it week after week. That changes things.
So we started at the identity level. I landed on six:
Present, leading father. I want to be there for my kids. I want to lead by example. I want to be intentional about showing up.
Loving husband. I want to be my wife’s best friend. I want to listen. I want us to keep growing closer as we get older.
Successful executive. I want to keep raising the bar in my career, building relationships, surprising myself with what’s possible.
Intentional Wisdom creator. The podcast, the newsletter, this thing you’re reading right now. I want to build this into something real — a platform that helps leaders and high performers find balance across all the competing demands in their lives.
Active hobbyist. Golf. Pickleball. Things that are fun, that recharge me, and that give me a platform for building friendships.
Healthy, fit man. I want to maximize my healthspan. Not just live long — live well. Nutrition, training, all of it.
Then we built the operating system around those identities. Here’s how it works:
Sunday morning: The planning session. Every Sunday morning, I sit down with Claude and have a conversation — out loud, through voice — while I look at my calendar for the coming week. The question is simple: Does this week reflect who I’m trying to be across those six identities? If my calendar is stacked with work and there’s nothing blocked for my kids or my health, something needs to move. It’s maybe 20 to 30 minutes. It’s not about perfection. It’s about alignment.
Monday morning commute: The deep dive. My commute is about 35 to 40 minutes. Every Monday, I pick one identity and go deep on it. I’m talking to Claude through voice — having a real conversation in my car about what’s going on in that area of my life, what’s working, what’s not, what I want to focus on. We rotate through all six, so every identity gets a serious conversation roughly every six weeks. Nothing gets neglected for too long.
The voice piece matters more than I expected. I’m not sitting at a computer typing prompts. I’m talking. It feels like hashing things out with a colleague who knows my whole situation and is genuinely trying to help me think through it. That’s a very different experience than most people’s version of “using AI.”
One thing I’ve been thinking about a lot lately — partly inspired by a Tim Ferriss piece I read recently — is the risk of spending too much time looking inward. Always improving, always finding new things to fix, never actually feeling good about where you are. Ferriss has this great way of describing what happens when self-help becomes self-obsession — you end up so focused on fixing yourself that you forget to actually live your life.
So I’ve been trying to reframe the whole thing around two ideas: service and gratitude. Serve with intention. Strive with gratitude.
Every one of those six identities, when I really look at it, is about serving someone else. Being a great dad is service. Being a great husband is service. Building Intentional Wisdom is — if I’m doing it right — in service of helping other people figure this stuff out. Even the health and hobbies piece is about recharging so I can show up better for the people in my life.
And the gratitude part matters because keeping up with the Joneses is a real thing that I’m actively fighting against on the regular. A big part of focusing less on what I don’t have is making sure to be grateful for what I do. The striving is important — but so is appreciating what’s already here.
Right now, I’m the guinea pig. I’m building this system for myself, using it, tinkering with it, figuring out what actually works and what doesn’t.
But if this thing works — if it actually helps me make meaningful progress across these six identities while staying grounded in service and gratitude — then I think it could help other people too. Especially people who are juggling a career, a family, their health, and maybe a side project or creative outlet, and feeling like they’re constantly spread too thin. But I’m getting ahead of myself… right now, it’s an experiment.
So I’m going to keep building. I’m going to keep sharing what I learn — woven into what I’m already writing about here. And if something real emerges from this experiment, you’ll be the first to know.
Let me know if you’re experimenting in this arena, too. It would be fun to compare notes.
Thanks for reading, and have a great week.
Greg
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