Dealing with regret

The covid pandemic has given many of us more time, which is a double-edged sword. We use it for our hobbies, our errands, for the outdoors, for cooking, for reflection on our lives, and for taking fond trips down memory lane and revisiting the fun experiences we had when we could socialize and travel freely. Feasting on your lived life, your past, can feel satisfying. But for those of us that are perfectionists, we can become obsessed with analyzing, rather than simply observing or “reliving”, the past and we can judge many decisions we made as “wrong”.

How do you deal with this uncomfortable feeling of regret? First, it’s important to understand what makes us prone to regret, and secondly, use logic as a tonic.

What makes us prone to regret?

I have observed that our tendencies to regret are not correlated with actual bad life decisions but our perfectionism — you can have an amazing life and still have a lot of regrets, or have made a lot of ‘mistakes’ and have no regrets. You are more prone to regret if you are:

  • A perfectionist or an idealist – you aspire to greatness in all moments of your life and are constantly analyzing the ways you and your life could be improved
  • Very big on personal development, learning, growth – it’s true thinking about the past can uncover a lot of learnings, but analysis of the past is a double-edged sword that can also lead to you beating yourself up for stuff that can no longer be changed

Even regret about “first-world” problems is regret nonetheless and is painful. I sometimes regret things like not investing my savings earlier, not quitting a stressful job earlier, not quitting a dead-end relationship earlier, not going on holiday to foreign countries more pre-covid! None of these are really a big deal in the grand scheme of things, and my list of gratitudes and things I did right is way longer, but still…regret whenever it raises its head sucks and we must deal with it. I have developed a tonic of logic that I apply whenever I find myself analyzing the past and heading into “I should have done XYZ instead…” land.

The logic tonic to banish regret

I. Appreciate path dependency

The unique good things that have happened in your life may not have happened if the past, with all of its flaws, was different. For example, leaving a dead-end relationship earlier may have meant you may not have run into your current amazing partner at the time you did. If you’re happy with something now, consider that it may not have been possible if even one thing had been different in the past!

There is no way to predict what could have happened in the counterfactual parallel universe of something being different in the past and whether it would be good or bad, so don’t waste time trying.

In short, remember the butterfly effect!

II. Don’t judge past action against new goals

One of my regrets was not working more intentionally on getting promoted at one of my old jobs. In my first year as a post-MBA consultant, I picked projects based on travel to interesting cities where I had friends, where the team looked fun, where the topic was different and in a new industry. This was polar opposite of the types of projects that would fast-track my career: typically boring locations in the middle of nowhere, with stressed-out extreme type A teams, and a singular focus on one industry/function to build deep expertise and a brand in one area.

I was optimizing for fun and diverse experience at the time, and I picked well according to those criteria. But as I saw friends getting promoted faster, I was mad at myself for not having been more focused on ascending the corporate hierarchy earlier.

My goals had changed over time and with peer pressure: from prioritizing a good experience to prioritizing a promotion. And then I judged my past behavior on my new goals. This is a fundamental error that many people make that causes regret — judging past activity with new goals. You have to remember you had different goals then, and you optimized for those.

III. Remind yourself you did the best you could with the information, state of being and circumstances at the time

Most of us do the best we can all the time. If we made ‘mistakes’ when we were younger, it’s usually because we didn’t have the information, skill, self-esteem, or luxury of circumstance that we do now. Regret often comes about because your current self forgets key elements of a circumstance or state of being that your past self faced. Let me make it concrete with a specific personal example (you gotta appreciate how many personal examples I put out there for y’all!).

In my mid-20s, I dated someone for almost a year when 3 months in I knew I didn’t want to be with them long-term. I’m not alone – people of all genders do this often and in many stages of their life. Is it wrong? Is it dumb? Or is it sometimes just the best thing you could have done at the time with the circumstance, perspective and skill you had a the time? I think increasingly it is the latter.

My 30 year old self may say how dumb was that, I could have been travelling the world with my summer holiday, or deepening my friendships rather than spending time with this person. But at the time, I was a 20-something old with not much dating experience, who found it very hard to get a boyfriend, who was excited someone was interested in me, and had the hormones of a 20-something year old. That’s who I was then, and it makes sense to make the decisions I made then with that context.

Hindsight is always 2020, but remember you were making decisions in uncertainty back then. And you were always getting something out of it if you were doing it. May be not the best thing but you were always getting something.

IV. Don’t focus on things you can’t change, and you can’t change the past

Focusing on something that is done and irreversible is futile. No amount of rumination will allow you to change it. Time machines are yet to be invented!

V. The future is a blank slate – don’t miss future opportunities by being wedded to the past

Life is like a jungle gym or a game of snakes and ladders. If you’re behind in achieving a goal in some way now doesn’t mean you’ll be behind forever. You may find a very long ladder. Conversely, you may also get bitten by a very long snake through no fault of your own. You must carry empathy for yourself at all times, and hope, faith and gratitude in and for those small or big ladders you come across.

Dwelling too much on past regrets leads to sunk-cost-like fallacies. You don’t invest in a stock now because you regret you missed out on growth in the past, but there’s still plenty of growth ahead and you miss out on that because of your bitterness. Don’t let your past color your future so much, don’t let it define your identity. The more you are able to shake it off, the more of a blank slate the future is.

VI. Don’t sweat the small stuff… and it’s all small stuff

In the grand scheme of the universe, unless you have caused intolerable pain to someone or many people (I don’t want to console mass murderers, they should live with heap-tons of regret), it doesn’t really matter what decisions you made. No one in a hundred years is going to care or remember. We’re all going to die. Remember that when you get too caught in the weeds of your life! It’s morbid but it’ll help you have the right perspective to not get hung up on things and to live a little boldly once in a while!


Regret is an uncomfortable emotion that all of us encounter at some point, and especially when we are bored and not being forward-facing, as can be a tendency during the covid lockdowns when the future feels even more uncertain and the past invites you to visit more and more. Be kind to yourself and to others, and move boldly forward, it’s the only gear Life has.

Leave a Reply

Your email address will not be published. Required fields are marked *