In 2012, Professor Neal Roese made a powerful discovery in the science of happiness and motivation. He surveyed hundreds of people across the United States and asked them to describe, in detail, a time in their lives where they felt a significant amount of regret. People described incidents ranging from their education and career to romance, parenting, and more. ^[1]

He and his students dug deeper and asked them, “Does the regret focus on something you should have done, or something you should not have done?” As well as, “When did the event happen that made you feel regret?”

From the research, they made one key finding about regret:

The more time passes, the more that we're likely to focus on what we failed to do than what we actually did. ^[2]

These “regrets of omission” weigh more heavily than regrets of action. We're pretty good at rationalizing to ourselves when something we try ultimately fails. At least I tried, we'll tell ourselves. But we're bad at containing our disappointment at lost opportunities and all that could have been possible, if only I had done or said something!

Regret is often brushed off as a negative emotion. In this post, I'll share how we can actually use our feelings of regret to create a personalized feedback system that lets us lead more fulfilling lives and also become more effective leaders.

How to Make Regret Work For You, Not Against You

Despite regret making us feel bad, it does have an upside.

Faced with a decision, we can project forward the regret that we might feel for different decision branches. And then we can choose the one that leads to the least regret.

Amazon CEO Jeff Bezos calls this framework regret minimization, and it made his difficult decision to leave his successful banking career to start Amazon easy. ^[3]

"I wanted to project myself forward to age 80 and say, 'Okay, now I'm looking back on my life. I want to have minimized the number of regrets I have.' I knew that when I was 80 I was not going to regret having tried this. I was not going to regret trying to participate in this thing called the Internet that I thought was going to be a really big deal. I knew that if I failed I wouldn't regret that, but I knew the one thing I might regret is not ever having tried. I knew that that would haunt me every day, and so, when I thought about it that way it was an incredibly easy decision."

This idea doesn't just apply to the big decisions in life.

We all have days where we feel regret for something we did or failed to do.

Maybe we didn't speak up at a team meeting to push back on an aggressive deadline we disagreed with, and it ended up causing stressful and late hours for the team.

Maybe we felt uncomfortable from an inappropriate comment that a teammate made, but didn't summon enough courage to call out the behavior and ended up implicitly condoning it.

Maybe a teammate misprioritized critical work and ended up blocking others on the team, and we wished that we had checked in more or been clearer about our expectations.

I know that I've been in each one of those regretful situations more than once myself.

But what if we could create a personalized feedback system for ourselves that lets us identify the type of situations that lead us to feel regret? And then lets us codify the actions that would minimize regret?

This regret minimization system would then consistently lead to reduced regret over time.

How to Turn Regret Minimization into a Feedback System for Yourself

As an engineer, I think of things in terms of systems.

And for the past few months, I've been experimenting with the Self Journal. ^[4] It's a guided journal that provides a set of prompts to reflect on at the end of every day. What are your wins? What do you feel grateful for? And perhaps most importantly: What did you learn today about how you could've done better?

The question about the day's lesson fascinates me. I've always been drawn to personal growth and self-improvement. Every day, I can usually identify a moment, however small, where I held back on saying something I wanted to say or doing something I wanted to do — a moment of small regret.

When we don't take the time to reflect on these moments, it's easy to slip into the same patterns of regret again and again.

And so I'll instead make time to ask myself, “What would I want the best version of my future self to do in that situation?”

Then I turn that moment into a lesson to take away.

These lessons run the gamut of things. Sample ones taken from my actual journal include:

• When I'm in a funk, find a way to shift my perspective. (This was from a weekend where I was dreading to prepare for a talk that I no longer wanted to do).
• Mountain biking is scarier than I thought and maybe not something I want to tackle. (Or perhaps “the devil's gorge” isn't exactly a beginner route).
• When I have a day off, don't spend it on errands and logistics, or else I'll feel ungrounded at the end of the day.
• Create and protect my morning routines and rituals to help myself recover. (This was after two back-to-back workshop days where I felt drained and tired for the first time in a while).
• Don't worry about looking bad, and I'll have more fun.
• When I'm not sure about a decision, bias toward the choice that seems like an experiment that will give me more data.
• Ask for help sooner when I feel stuck, instead of being stuck in a loop in my head. (This was from a week where I felt overwhelmed by logistics and reaching out to friends to talk through what was on my mind provided such relief and clarity.)

Over the past 100 days, I've accumulated 100 such lessons — small and big adjustments to my mindsets to improve myself toward the person I want to be.

What I've created through this daily reflection is a powerful feedback loop for my own growth and for how I want to express my leadership in the world. In a way, it's not that different than how we tune products and systems that we build at work — except that the system here is ourselves.

When I notice patterns in the lessons, I reflect on them, share them with friends, and discuss them with my coach. And — thinking again as an engineer — I'll abstract the themes and patterns from the daily lessons into personal principles and rules to live by. I'll share those with you in a later post.

The impact of doing this personal work on my own happiness and fulfillment has been far-reaching. When I live in the knowledge that moments of regret are just opportunities to grow into the best version of my future self, I feel more agency to become the leader that I want to be in the world.

I want you to feel empowered to do the same.