# The Gift of Regret

I don't know why, but I've been thinking a lot about regret lately.

It's strange how universal the feeling is. No matter where we come from or what we achieve, regret finds its way into the quiet moments. The decisions we replay in our minds. The roads we didn't take. The words we left unsaid. The jobs, relationships, and adventures that might have been.

Some regrets stick with me more than others.

I think about not applying myself more in high school. Maybe I could have gotten into better colleges, or opened doors I didn't even know existed.

I think about leaving the mainland after just a year of college—homesick, mostly chasing a relationship. At the time, it felt right. After we broke up, I spent a while wandering, unsure of my direction.

I regret not spending more time with my mom, especially before and during her battle with ovarian cancer. She passed away while I was still in my early twenties. Some days, that regret still feels heavy.

I think about finishing college in Hawaii and choosing to stay. I built my life and career on the islands for almost two decades. There were plenty of chances to go back to the mainland and take my career in a new direction, but I didn't. Life in Hawaii was steady and comfortable, but sometimes I wondered about the lives I might have lived if I'd taken a different path.

Eventually, a personal passion created an opportunity, and I took a leap of faith.

I left Hawaii for a job in San Francisco, leaving behind home and friends to join a startup. It was scary. I didn't know anyone. The transition was tough and lonely. Then, one weekend, I was looking for a place to get my hair cut. I called around and found a neighborhood salon. I booked a random Saturday.

While I was there, a friend of the owner stopped by to drop off some boba and catch up. We got to talking and hit it off. That friend ended up becoming my wife.

Looking back, the odds of all those choices coming together feel beyond improbable. Moving to San Francisco when I did. Choosing the right neighborhood. Picking a random salon on a random Saturday. Each piece had to fall into place. Honestly, it makes winning the Powerball feel easy.

Not long after meeting my now-wife, I had the chance to join a different startup as one of their first employees. That company is now valued in the billions. I still think about that decision, because there's something special about being there from day one, building alongside the founders and the earliest team. I'd be lying if I said the potential equity payout doesn't cross my mind. Money's not everything, but it's definitely something. That "what if" lingers.

With all these regrets and what ifs drifting through my mind, they all fade when I look at my son. When I see him, things become clear. Every decision, every hesitation led to this point. There's absolutely no other path that could have brought him into my life. Even the hardest moments and the biggest regrets were part of it.

I know not everyone has a child or a partner to look to for meaning. For some, it might be a close friend. For others, it might be a job, a small ritual, or just realizing you've changed. I'm not sharing this as advice. It's just my story.

But if there's anything to take away, maybe it's this: Wherever you are today, you're here because of every choice, every misstep, and every unexpected turn that came before. The present isn't perfect, but it's yours. And it couldn't exist without the path that brought you here.

Also published on Medium.