Here's the funny thing about leaving a high-paying career - everyone wants to know exactly what you're doing next. But the truth is messier than that.

When I left my Managing Director role at BlackRock in 2015, my inbox was flooded with variations of the same text:

• "Are you starting a company?"
• "Did you get funded?"
• "Which hedge fund poached you?"

What really happened?

Looking back, I realize now that everyone was projecting their own escape fantasies onto my story. For my Wall Street peers trapped in the golden handcuffs, I represented a glimpse into what could be. For the entrepreneurs, I was another "finance bro" who would probably crash and burn.

But here's what was actually going through my head:

1. I was 35 and had just become a father
2. The next 10 years were what I called the "Magic Window" - when your kids actually want to spend time with you
3. I was staring down 20 more years of grinding just to "make it"
4. The math wasn't adding up: trade my daughter's childhood for more millions?

When people ask me about my transition, they're usually looking for tactical advice. Should they start a side hustle? How much runway do they need? What about healthcare?

What would I do differently?

But the real question isn't about tactics. It's about time freedom. Because at some point, you have to ask yourself: what's the point of being the richest person in the nursing home?

The truth is, I had no master plan. Just a deep knowing that there had to be a different way to design a life that didn't require postponing joy until retirement.

Sometimes the bravest thing you can do is admit you don't have all the answers.