Chris Wheeler
I’m a product leader, strategist, dad, recovering overthinker, and relentlessly curious person who’s spent a lot of his life figuring things out as he goes.
I’ve built a career by asking questions, challenging assumptions, connecting dots, and occasionally being willing to say, “That doesn’t make any sense.”
Somewhere along the way, I realized the same way of thinking I use to solve business problems is just as useful for careers, relationships, money, reinvention—and figuring out what the hell comes next.
The Backstory
My path here hasn’t exactly been linear.
I’ve been a UCLA fraternity guy, a musician in a rock band, a brewery employee in Northern California, a salesman, a corporate leader, a husband, an ex-husband, a sober guy who once wondered whether he’d still be fun without alcohol, and a dad trying very hard to get that part right.
I’ve built a successful career without ever having some brilliant master plan for it. Mostly, I kept getting curious. I learned things. I asked questions. I noticed opportunities. I figured out what I was good at, took some chances, hit a few ceilings, and eventually learned when it was time to find another ladder.
Life worked similarly. Some changes I chose. Others chose me.
Getting sober forced me to figure out who I was without something that had been part of my identity for years. Divorce forced me to reconsider what family, fatherhood, and the future looked like when the picture I’d had in my head suddenly changed.
Through all of it, I’ve become increasingly convinced that the uncomfortable feeling that something isn’t quite right isn’t always something we should silence.
Sometimes it’s information.
And sometimes figuring out what’s next starts by being willing to ask the question you’ve been avoiding.
I’m not here because I’ve figured everything out.
I haven’t.
I’m here because I’ve gotten pretty good at asking questions, pulling on threads, looking at problems from different angles, and helping people see things they may not have considered.
Friends have asked me to think through career changes. I’ve helped someone turn a restaurant idea into an actual business plan. Professionally, I’ve spent years turning messy problems and half-formed ideas into strategies that people can actually execute.
This is a place to do more of that.
Careers. Money. Business. Relationships. Fatherhood. Reinvention. Getting unstuck. Occasionally cars, science, music, food, or whatever rabbit hole has my attention.
If something here makes you stop for thirty seconds and think, “Man, this guy gets it. It’s like he was talking about me,” then this little experiment is working.
And if it makes you think, “Shit...I hadn’t thought about it that way,” even better.