Uncharted but ready
Like many people, I didn’t retire in the official sense. I left voluntarily—before the milestone age, before the formal send-off—because it just felt like time. I remember sitting with a mix of relief and fear—finally out of the day-to-day grind, but also thinking, “What the hell am I going to do now?” I had no clear plan. What I did have was a deep sense of what I didn’t want anymore. That part was surprisingly easy to articulate. What did I want? That was murkier.
Pushing through discomfort
So, I talked to everyone I could: friends, acquaintances, former colleagues, and new contacts. As an introvert, this was exhausting, but necessary. The structure of the MyNextSeason program was instrumental. It gave me a framework to process what I was learning from all those conversations. It helped me step back and identify not just options, but principles to shape my next season.
My guiding principles
After much consideration, my guiding principles boiled down to three basic needs:
Keep learning
Work with kind people
Have full control over my schedule
Agency over my time had been sorely missing in the past. I realized how much I craved the ability to decide when and how I worked. I’d spent too many years on conference calls under freeway underpasses, juggling impossible logistics.
A portfolio approach
In this next chapter, I’ve embraced a portfolio approach. I’m a venture partner in a consumer-focused fund. I advise a private equity firm on later-stage investments. I also work directly with founders, often in beauty and wellness, helping them with growth and strategy. Finally, I serve on two private company boards in the consumer space: one fiduciary, one advisory. All of these roles retain what I loved about my previous role—problem-solving on growth and the challenge and excitement of M&A—while delivering against my guiding principles.
I find the energy of founders and family entrepreneurs quite addictive. It’s exciting to work with people who are full of passion and conviction. They’re out there creating something from scratch, or building on a family legacy, and I get to support them with my experience and perspective. That’s a gift.
A real-world business lesson
That said, working in venture and private equity is no joke. It’s hard. Lots of people want your advice for free. You have to understand the business model—how value is created, what the economic levers are, and how to protect your time and contributions. If you’re raising money, even for a seed round, you’re already selling the business. There’s homework involved. You have to fight for your piece of the value you help create.
An unexpected identity check
I’ve learned a ton—met so many people, seen so many ideas. But more importantly, I’ve learned about myself. I always thought I had no ego. Turns out, I was lying to myself. I missed the title. I missed having an assistant. I missed the status. It’s humbling to start over. Three months in, people stop meeting with you because of your old job, and they start meeting with you for who you are. That’s both scary and liberating. It reconnects you with your values, not your resume.
A new kind of richness
These days, I’m around a lot more—for my wife, who is my best everything, and for our two daughters, who say I’m more fun to be around. My wife and I both work from home now, and there’s a flexibility and joy in our rhythm that I didn’t know I was missing.
I travel to see family in Scotland, something I did not do enough of before. I’ve built wellness into my routine—scheduled gym sessions I look forward to, not squeeze in. I attend meditation retreats twice a year. It feels like the real luxury now is time and space. No one needs me to make urgent decisions anymore. No one is pinging me for sign-off. And I’m not fitting in calls during family vacations or skipping events because of work travel. And yes, I miss Group 1 boarding. Now I fly in Group 6. But I sleep better. I laugh more. And I feel lighter.
Next season advice
If I could give advice to anyone standing on the edge of their next season, it would be this:
- It might feel awkward to go through a program focused on you. Do it anyway. There’s power in it.
- It’s going to be okay. It may be humbling. It will be different. But it will be alright.
- Reevaluate the value of your time. I used to have a bad exchange rate between pay and peace. That math has changed.
I’m so grateful for the more grounded life I am building now. I’m not just working differently—I’m living differently. And I wouldn’t go back.