What regret teaches us about family, legacy, and love

Hi, I’m Omar, the founder and CEO of Kinnect. This blog is part of the From Omar series, where I share my personal reflections, thoughts, and experiences that are shaping the work we’re doing at Kinnect. These entries aren’t about polished life lessons — they’re honest, raw thoughts I’m working through in real time.

Today, I’m thinking about regret. It’s a heavy word, but it’s also one of the most human experiences we all share. Regret often creeps in after loss — when you realize the questions you never asked, the stories you never heard, and the small but meaningful moments you let slip away.

And for me, it’s personal.

My grandfather lived with dementia for 10 years before he passed. Ten years of watching him slowly lose access to himself. When I think about that time, I think about all the questions I wish I had asked him before dementia made it impossible. Not questions like, "Where were you born?" — but the deeper ones. The kind of questions that would have given me insight into the man he was, the dreams he had, and the moments he never shared out loud.

It’s that reflection that makes me think about regret differently. Regret isn’t about the big things. It’s about the small questions we didn’t ask, the quiet moments we didn’t take, and the connections we didn’t nurture when we had the chance.

When people talk about regret, it’s easy to assume they’re talking about the big, dramatic decisions. But that’s not the kind of regret I hear most often.

The most common regret I hear is: "I wish I had asked them..."

When you lose someone — a parent, a grandparent, a friend — you start replaying your conversations in your mind. You sift through your memories, looking for the moments where they shared something deeper. You hold on to the things they said, the stories they told, the reflections they offered.

But sometimes, you realize there was so much you didn’t know.

I think about the kinds of questions I would have asked my grandfather if I could go back

• What do you want to pass on about our Puerto Rican lineage?
• Are there health things I should know about?
• Why do I sneeze 10 times in a row?

How tools can help us avoid regret

If I’ve learned anything from building Kinnect, it’s this:

Sometimes, people just need a little nudge to ask a good question.

Think about apps like Spotify Wrapped or BeReal. They give people a reason to reflect and share, not because they’re being forced to, but because it feels natural. You see your year in music, and suddenly, you want to share it. BeReal prompts you to capture life in real time, and suddenly, you’re sharing more honest moments with friends.

What if Kinnect could do that for family relationships?

I think about how different things might have been with my grandfather. If I had gotten a nudge to ask him one of those simple but important questions, I would have done it. I know I would have.

Building a legacy that doesn’t rely on "someday"

A lot of people think legacy is something you build at the end of your life. But that’s only one version of it. There’s another way to build legacy — by doing it now, in real time.

Instead of waiting until the end, what if you were capturing reflections, memories, and stories every day? What if, without even realizing it, you were building your legacy right now?

This is the future I’m building for Kinnect. A space where the thoughts you share today become part of your family’s future. A space where your kids (if you have them) could one day look back and see your reflections from 10, 20, 30 years ago.

abrazos,
omar