May 2, 2026 May 2, 2026 2026-05-02

In 2009 I wrote 33 questions and pretended to interview you, the reader. Now I want to take the interview myself and answer them honestly — because a lot of the answers have changed, and a few of the questions have become better questions than I knew how to write.

I’m not going to answer all 33. That would be an act of endurance rather than insight. I’m going to pick the ones where my answer has shifted the most — because those are the ones that reveal something real about the gap between 2009 and now.

“What Do You Do For a Living?”

In 2009 I would have said: blogger, writer, early-stage entrepreneur. There was pride in the novelty of it — being someone who made a living online felt like a real identity statement back then. Now I say: I build iOS apps, I write, I coach. But the more honest answer is that I’ve stopped organizing my identity around what I produce for money. What I do for a living is just something I do for money, it doesn’t define me as a person.

The question itself has aged strangely. “For a living” assumes a cleaner separation between work and life than most people I know actually experience anymore. The question might now be: what are you building, and for whom?

“What Do You Regret?”

I wrote in 2009 that I tried to live without regrets. That was partly true and partly a performance — the kind of thing you say at 35 when you’re trying on the persona of someone who just moves forward.

I have regrets. I regret specific moments of hesitance, half cooked decisions that rippled for decades, relationships I still maintained when they didn’t deserve maintenance anymore, and sticking to free-falling projects and businesses with a ridiculous amount of pride and stubbornness. What’s changed isn’t the fact that I do experience regrets — it’s getting the guilt out of them. If you just leave out the guilt, regrets become useful information, helping you navigate life with less suffering. They are really just lessons.

“What Are You Afraid Of?”

In 2009 my fear inventory was mostly about failure — failing at the business, losing the independence I’d worked hard to build, or being proven wrong in public.

In 2026 the answer is significantly different. I’m less afraid of failure because I’ve failed at enough things to know it doesn’t end you. What I’m actually afraid of is irrelevance — not in the social media sense, but the deeper sense of becoming someone who just takes life for granted and doesn’t ask questions anymore. That fear is useful. I try to stay close to it. Keeps reality fresh, and life tasty.

“What Would You Do If You Weren’t Afraid?”

This question has aged perfectly. It’s still exceptionally useful. The answer, though, is completely different from what I’d have said then.

In 2009 I would have named a specific business, a specific place, a specific ambition. In 2026 the answer is more interior: I’d write more honestly about the things I actually think rather than the things I expect to land well. I’d disagree in public more. I’d be more me – which, to be honest, I’m getting better at it.

“Who Are the Five Most Important People in Your Life?”

This one I can’t fully answer publicly. But I can say: the list has changed more than I expected, and in directions I wouldn’t have predicted. Some of the most important people in my life in 2009 are no longer in it. Some of them I just met in the last 2-3 years.

What I notice is that the list has gotten smaller and more certain. At 35 you’re still collecting important people, people that will bring “relevance” into your life. By 50, you already know which ones actually are. And you stick to them.

Which Question Aged Worst?

“Where do you see yourself in five years?” I was still asking people that in 2009 with a straight face. The pandemic proved it’s nearly meaningless as a planning exercise, and the accelerating pace of change has made five-year visions mostly fiction. I’d replace it with: what are you oriented toward, regardless of timeline? Where are you going? And why?

Which Aged Best?

“What would you do if you knew you could not fail?” Still perfect. Still revealing. The answers people give to that question tell you almost everything about what they actually want versus what they’ve settled for.

Seventeen years is a long time. Long enough to have real answers instead of aspirational ones. I’d recommend everyone answer these questions on a ten-year cycle — not to track progress, but to see clearly how much of who you are now you couldn’t have predicted from who you were then.