The Clarifying Power of Regret

This week was Thanksgiving here in the states, so Jason and I flew back to Florida for the week to be with our families.

I spent the time away filling up on stuffing and mashed potatoes while simultaneously detoxing from social media a bit (both were equally satisfying.)

With all this happy family time, it might seem a bit odd then that this week’s topic of interest is regret, but in fact it’s this very topic that’s given me a new lens with which to view my experiences, including family holidays.

It first came to my attention as Jason and I were driving to the airport to catch our flight back to California. We were listening to an episode of The Tim Ferriss Show with guest David Heinemeier Hansson (also known as DHH, co-author of a favorite book of mine, REWORK, and co-founder of Basecamp.)

During this interview he made reference to something called the “regret minimization framework” which, as it turns out, is just a fancy term that Amazon founder Jeff Bezos applies to his approach to decision-making attempting to minimize that number of things he’ll regret at the end of his life (a framework that ultimately led him to take a chance on this crazy idea for “selling books on the internet.”)

I wrote this phrase down the second I heard it, mostly because I’m honestly so unaccustomed to thinking about regret and the very mention of it had my ears perk up.

I guess I’ve always thought of regret with a negative connotation. It conjures up some left turn in your life or event in your past (or perhaps post-tequila-shot decision) that you dwell on which ends up spoiling your present. That never seemed very productive to me.

I’m one of those people that believes every decision, every success, every failure, every path ends up leading you to who you are -- and really, making you who you are -- so what could there be to regret, I would wonder?...

But when I heard this term in the interview, it’s like I suddenly understood the idea of regret with a fresh perspective. I no longer saw it in the context of a present regret for a decision made in your past, but as a future regret for a decision made in your present.

In imagining a future version of yourself, perhaps even at the end of your life, suddenly you’re able to see more clearly which actions in the present support the deeper (often dormant) values that your inner core is longing for.

While considering this, I was reminded of a podcast interview I did with my friend Tiffany Han a few weeks ago and I remembered she too had discovered the clarifying power of regret.

When confronted with those big leaps that we often want to take but we're fearful of, she asks herself:

“Will I regret NOT doing this a year from now?”

Once faced with that question, it then becomes easier to sift out the difference between “I don’t want to do this because it’s not in alignment with who I am” and “I don’t want to do this because I’m scared.”

It’s funny though, whereas many people might find this idea of regret the thing that helps them get the courage to take a risk or conquer a fear or finally pursue a dream, in applying this to my own life, I discovered something altogether different and surprising to me.

I realized that my dormant values aren’t actually about expressing my creativity or stretching my boundaries; when I consider what I might regret at the end of my life, most of what comes up for me is about family.

As we rode along in the car on the way to the airport, I reflected on the Thanksgiving week we’d just had. Trying to balance my family, his family, seeing all my brothers and sisters, new nephews and nieces, trying to fit in a few friend visits. Trying to give everyone time, and attention, and yet still trying to carve out tiny pockets of self-care and introvert-crucial silence. And here’s the honest truth: it wasn’t EASY.

I don’t mean that necessarily in a negative way, I simply mean that when it comes to the routines of regular ol' everyday life that we cultivate, there’s a comfort there. There’s a rhythm. We know what our needs are, the needs of our partners, of our children or our pets, and for the most part, each day is simply our best shot at the delicate balance of meeting all those needs.

Family holidays, on the other hand, are kind of like an episode of Needs Gone Wild. There are so many more factors, so much more nuance and history and complexity that goes into the orchestration of all these various relationships coming together. And for me at least, all of that complexity comes with a little bit of unavoidable anxiety.

However, this lack of ease that I describe seems to fall away and the complexity matters so much less when I look back and frame the week around the context of REGRET.

I simply ask myself: Would I look back and wish I would have braved the uncertainty of the Needs Battlefield in exchange just a few more cherished memories with the people I call family? And when I sit with that question, I see the answer is almost always YES.

This “regret framework” allows me to peel away the subconscious label of obligation that family holidays often reflexively invite, and instead I can see them with a deeper perspective of gratitude and joy and even privilege. It may not make the scheduling or the navigating any easier, but at least I can bring attention to how lucky I am to have so many people pulling at my time and my attention.

And that’s the value that this whole idea of regret has brought me the past few days. It’s given me a new filter or test to hold my actions and decisions up against in order to get more clarity.

We can actually use regret as a tool for clarity in navigating life’s big decisions. 

We can actually use regret as a tool for clarity in navigating life’s big decisions.


The more I thought about it, the more powerful this idea started to become for me because it is advice that has the advantage of speaking to each person individually.

When you think about it, regret is actually a relative concept -- something that bends for each of us depending on what we value at our core.

So, the beauty of using Jeff Bezos’s “regret minimization framework” (we gotta get a sexier name for it, Jeff) is that for me, it might mean saying yes or making more time for family functions even if it means plucking me out of my comfort zone here at home because deep down I ultimately value family, connection, and shared memories.

For you, it could mean saying yes to that risky business idea even if it means overcoming your fear of rejection because deep down you value creativity and curiosity.

Regret is that rare concept that might exist in an ethereal space, but we seem to feel it and relate to it in a very tangible way. If you can tap into that not as a way of dwelling on your past, but as a way of ensuring the future that you really want, that’s when you can discover the clarifying power of regret.

Your challenge this week is to simply ask yourself: At the end of your life, what’s one thing that comes to mind that you think you’d regret not having done?

Bonus challenge: Go DO that thing. (Or perhaps take one baby step action toward that thing this week.)

Wishing you all a week filled with minimal regrets ;) and Happy It’s-officially-acceptable-to-listen-to-Christmas-music Week!