This will change how you think about regret

Bondi Icebergs: Sydney, Australia

I regret _____.

How many times have you thought or said this? Did you mean it?

Regret is tricky. It’s both deeply complex, and yet seemingly nonsensical. It’s something that sneaks up on me. It is always triggered by the present, but it keeps me living in the past.

At least it used to. But not today. Not anymore. I’ve had enough!

Instead, I’m wondering…

What if we position feelings of regret as important signals for how to live today?

I regret not quitting my job when I was in my early 20s to travel the world or move to Australia. (See above for a photo of the Bondi Icebergs pool — need I say more?).

It’s something I felt really compelled to do, but I didn’t. There are a host of reasons why. Financial and emotional. Relationships that got in the way, and career ambition that only saw a traditional ladder-climb as the means to advance.

Ultimately, though it was fear of the unknown that killed those plans. On one hand, I’m sad about that, but on the other hand I curse myself for even having that thought.

Today I am living the life I’ve always dreamed of with a partner I surely wouldn’t have met in Australia.

So what’s the use in having a regret about the past?

Isn’t the past responsible for what we all have now?

If we are fulfilled with the present, is regretful reflection on the past a direct slap-in-the-face on our lives today?

No, it’s not.

Regret isn’t something we can completely eliminate. But it is something we can channel into positive for the present. Our filter for what it means, and what it makes us feel can change from one of negativity to one of hope.

If we can all expect to feel regret, then we can all use it as a signal to live our best lives. Today, and tomorrow.

What do I mean?

A regret that surfaces with emotional intensity is a proverbial flashing light. A beacon telling us to, “pay attention!”.

I regret not throwing caution to the wind and traveling in my early-20s.

What is your biggest regret? Don’t think too hard about it. What immediately surfaces in your mind?

(I’m waiting for you to think about it.)

Okay, good. Now that it’s top of mind. What can you learn from it to direct the course of your actions today. Don’t even wait for tomorrow.

I live with this regret of not traveling while I was younger. I don’t see it as an anchor that keeps me rooted in the past, but as a jet engine propelling me towards what I felt I left behind. What I craved then, is what I’m building my life around now. Adventure, novelty, uncertainty, mobility, and freedom.

Solo hike at Mount Sanitas Trail in Boulder, CO

Today I am actively finding ways to live my dream life, with my regrets reminding me of what matters to me. What I desire may change, but the core of what interested me in the past is likely to stay a part of me forever.

I like to explore. I like variety. I like the mysteriousness of the unknown. I love to travel. Today I am finding ways to fulfill all of those desires in a way I never could have imagined at 22.

Today at 33, I’m actively working to design my life. It’s a process. It’s a journey. I’m realizing these things take time to build.

I’m using everything I learned in 10 years as an advertising strategist for global consumer brands to plan the world’s most important brand and campaign — who I am and how I spend my time.

Your life is no different. What you regret, may actually be what you’re curious about.

Has that curiosity left you, or is it still burning inside of you? Don’t be afraid to look inside for the answers of where you should go next. They are there.


We can’t change the past. This we know. We can’t stress over what we did or didn’t do. We must embrace the decisions we’ve made and flow with them.

Let go of past decisions. Stop seeing them as barriers for allowing you to live the life you want today, and tomorrow. Instead, begin leaning on your regrets. Trust them as signals for what you value.

I’m doing my best to live with the knowledge gained from yesterday, applied to today. I hope you’re doing the same too.


If this resonated with you. If you’re looking to go deeper, and to learn first-hand how to apply regret to living your best life. I’d love to share an approach for doing so.

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