What Do You Wish You Did When You Were Too Scared?

What do you wish you did?

If there’s one thing I’ve learned in my 22 trips around the sun, it’s that we all live our lives in different ways.

We all have different ideas and beliefs. Different interests and hobbies. Different perspectives and experiences.

But with all our differences, I think there’s one thing we can all agree on:

No one wants to live with regret.

This is something I’ve talked about a lot in the past, but it’s a theme I keep coming back to. And for good reason.


Because it’s something we can all relate to. We all know the feeling of looking back and thinking things like…

“I wish I did that. I wish I wasn’t afraid to take that chance. I wish I didn’t miss out on that opportunity.”

More often than not, our fears hold us back from doing the things we wish we did (at least in my case).

Here’s the thing. If a year ago you asked me what I think of regret, I would have said that it’s one of the worst feelings someone can possibly experience.

Which in a lot of ways, I still believe to be true.

It weighs us down as we long to change a moment that’s already passed, an outcome that’s already determined.

We look back at these moments in time and think those dreaded words: I wish.

So yeah, carrying regret is no way to live your life.

On the other hand though, I’m at a bit of a cross-roads. Not because I don’t think regret is a burden no one should carry (it very much is).

But because I think it can teach us valuable lessons.

Look, the way I see it, life is just one big experiment of trial and error.

We do something, it either works or it doesn’t work, we (hopefully) learn from it, and we take what we learned and improve.

It’s an endless cycle that keeps repeating over and over again.

As for regret, you can wish you did something or didn’t do something. But the reality is that you can’t change the thing. It’s already happened. It’s already in the past.

So you may not be able to change the outcome, but you can change what you do in the future.

Because it’s not about the feeling of regret. It’s about what you do with it.

You still following? Cool, allow me to give a quick example:

You spend all day hiking and finally make it to the top of the trail to find a serene, crystal-clear lake. Your friend decides to jump into the frigid glacier waters while you and the rest of the group stand on the sidelines and watch.

In the moment, you’re glad you didn’t join. After all, why would you want to jump into freezing cold waters and put yourself through that type of physical discomfort?

But looking back, a part of you wishes you had jumped in. Not because it would have been fun (let’s be honest, it probably would have been pretty miserable).

No, a part of you wishes you’d jumped in because it would have been like a “stick-it-to-the-man” moment. You would have conquered your fear of the cold. You would have gotten out of your comfort zone and grown because of it.

If you haven’t guessed by now, this is a real life example (true story).

And listen, it’s not an example of one of those regrets that’s been weighing me down. I’m not thinking about it constantly and it hasn’t impacted the course of my life (at least I don’t think it has 🤔).

But whenever I do think back to that moment, part of me wishes I would have jumped into that lake. And I’m sure you have small regrets like this, too.

Look, it’s not about the regret itself. It’s not even about getting over that feeling of discomfort if I had jumped into the lake. It’s about what I learned from the experience.

So what exactly did you learn, Connor?

Well, I’m glad you asked. There are a few things I learned from that experience:

I learned that it’s always the things you didn’t do that you end up regretting the most. I learned that I want to conquer my fears even though it’s scary and uncomfortable.

And I learned that if I’m ever on a hike and find myself standing on the edge of a lake again, I’m sure as hell going to jump in (weather permitting, of course).

Yeah, yeah, I know this wasn’t the greatest example. But I can guarantee we all have small moments like this where we look back and think “I wish I did that…”

So while regret can be a burden that weighs you down, it can also be the perfect life lesson.

Learn, move on, grow, repeat. Life’s endless cycle of trial and error.

And you want to know the best part? This can be applied to every single area of your life: School, your job, business, cooking, dating… yes, even hiking.

So the next time you find yourself regretting something you did or didn’t do, think about what you can learn from the experience.

Because soon enough, you’ll look back and be proud of all the progress you’ve made.

Just keep learning and just keep growing. You got this, my friend. 💪🏼

Never stop dreaming,


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