A Simple Framework For Avoiding Regret And Making Confident Decisions


Regret is one of the most painful feelings any of us can experience. It hurts because regret is, more often than not, based on our own choices and not external events.  We can’t fix it in retrospect and it’s hard to know what the catalyst will be. As Kurt Vonnegut put it, the saddest words anyone can say are ‘It might have been.’

In the novel Watt, Samuel Beckett brilliantly sums up the downwards spiral of regret:

‘Personally, of course, I regret everything. Not a word, not a deed, not a thought, not a need, not a grief, not a joy, not a girl, not a boy, not a doubt, not a trust, not a scorn, not a lust, not a hope, not a fear, not a smile, not a tear, not a name, not a face, no time, no place, that I do not regret, exceedingly. An ordure from beginning to end. And yet, when I sat for Fellowship, but for the boil on my bottom… The rest, an ordure. The Tuesday scowls, the Wednesday growls, the Thursday curses, the Friday howls, the Saturday snores, the Sunday yawns, the Monday morns. The whacks, the moans, the cracks, the groans, the welts, the squeaks, the belts, the shrieks, the pricks, the prayers, the kicks, the tears, the skelps, and the yelps. And the poor old lousy old earth, my earth and my father’s and my mother’s and my father’s father’s and my mother’s mother’s and my father’s mother’s…’

And so on. I came across an interview with Jeff Bezos (founder of Amazon) a while back, where he discusses his ‘regret minimization framework.’ He developed the idea when he made the decision to leave his high paying job and risk everything by starting Amazon. Since reading that, I have been working on building my own framework from the wisdom that smart people have already figured out.

As with most of my essays, I first wrote this for my own benefit, then decided to share it. Here’s what is helping me to avoid regrets, in the short term and hopefully long term. This is going to be a quote-heavy post as it is based on other people’s knowledge, not my own.

Look at decisions from a distance

The first question I ask myself when I make a big decision is this: how will I feel about this when I’m eighty? Bezos asked himself the same question when he founded Amazon.

When I was making the choice to drop out of university, I asked myself that and knew the answer straight away. If lacking a degree held me back too much (and so far it hasn’t) I could always return and finish the one I started. At 80, I wouldn’t care if I got my degree at 22, or 27, or 40 or never. But if I stayed at university for another 3 years, miserable, unfulfilled and not learning anything, I would end up regretting it. Even if I only took a year off (as was my initial plan), I knew I wouldn’t regret spending that time travelling and learning. Time is the ultimate leveller. In his TED talk, Daniel Gilbert puts it this way:

‘The bottom line is, time is a powerful force. It transforms our preferences. It reshapes our values. It alters our personalities. We seem to appreciate this fact, but only in retrospect. Only when we look backwards do we realise how much change happens in a decade. It’s as if, for most of us, the present is a magic time. It’s a watershed on the timeline. It’s the moment at which we finally become ourselves. Human beings are works in progress that mistakenly think they’re finished.”’

For his book, 30 Lessons for Living: Tried and True Advice from the Wisest Americans, Karl Pillemer interviewed a diverse group of 1000 elderly people to figure out what knowledge they could share with younger generations.  In a beautiful interview for Farnam Street (I strongly recommend reading the whole piece), Pillemer covered some of the key lessons:

‘At the core of their lessons for younger people is one major insight…This lesson is one that almost everyone expressed. And they did it vehemently. It is kind of like one of those nightmares where you are yelling and no one can hear you. What they want younger people to know is this: life is short… They say this not to depress younger people, but to get them to be more aware and selective about how they use their time… As one man told me: I wish I’d learned this in my 30s instead of in my 60s; I would have had so much more time to enjoy life.’

So they tell young people to stop wasting time and instead to use it more carefully. Some implications of this insight are to say things now to people you care about, whether it is expressing gratitude, asking forgiveness, or getting information; spending the maximum amount of time with children, and savouring daily pleasures instead of waiting for “big-ticket items” to make you happy.’

‘Another piece of advice comes from this idea that life is much shorter than you realise: Take a chance. People in their 70s, 80s, 90s and beyond endorse taking risks when you’re young, contrary to a stereotype that elders are conservative. Their message to young people starting out is “Go for it!” They say that you are much more likely to regret what you didn’t do than what you did. As one 80-year old, successful entrepreneur told me: ‘Unless you have a compelling reason to say no, always say yes to opportunities.’

‘When asked what they regret in life, many of the oldest Americans said: ‘I wish I’d travelled more.’ They recommend that people embrace travel, and especially when they are young. So if young people right now are wondering what to do with those graduation gifts, elder wisdom says to look into some travel (and low budget is fine) before you begin that first job.’

‘Another of their biggest regrets made a real impression on me. I need to admit that I’m a world-class worrier. So for me, a particularly striking lesson for avoiding regret – and a nearly unanimous one – was this: Stop worrying. The elders deeply regret the time wasted worrying about things that never happened. So looking back at the end of life, they take a radical view of worry. As one elder told me: Worry wastes your life.

Looking ahead is the perfect way to get a sense of perspective.  I also use a meditation technique which involves imagining yourself zooming out from your current location, seeing the whole town from above, then country, then continent, then the whole planet, and then let it fade away. The effect is powerful.

In a Guardian article which I reread every few weeks, Bronnie Ware, a palliative care nurse, recorded the regrets she hears most often from people on the verge of death:

  1. “I wish I’d had the courage to live a life true to myself, not the life others expected of me.
  2. I wish I hadn’t worked so hard.
  3. I wish I’d had the courage to express my feelings.
  4. I wish I had stayed in touch with my friends.
  5. I wish that I had let myself be happier.”

Each time I read that list, I try to do one thing to mitigate the risk of each item; taking an afternoon off, getting in touch with an older friend, allowing myself to just relax and appreciate life for a moment. It is hard to know how any of us will feel in the future, so it’s helpful to learn from the mistakes of others.

Pay attention to procrastination

Procrastination. It is the ultimate first world problem in a society obsessed with productivity and achievement. It’s a topic I have long found fascinating. Why do we all seem to do something so illogical and detrimental? I see the battle to just get shit done play out non-stop in my own life and that of just about everyone I know.

One of the reasons why procrastination is so prevalent is how misunderstood it is. There is an incorrect view of it as a character flaw- an internal issue.  It is widely assumed that someone procrastinates because:

  1. They are lazy and/or
  2. They are bad at whatever it is they are deferring.

In fact, that is rarely true. If it were, the sudden motivation produced by an impending deadline would not occur. A student, having put off an assignment until the last minute, would not work all night to complete it. An author would not lock themselves away to complete a 50,000-word manuscript in a short time. Someone who cannot be bothered to clean their apartment would not happily work 18 hours a day to code their start-up. If procrastination were a character flaw, we would not universally be able to conquer it when necessary. In fact, we procrastinate because of two key reasons:

  1. A lack of a clear idea of what to do and/or
  2. A lack of a reason to do it.

Laziness and ineptitude have nothing to do with it. I view procrastination as a warning sign that I need to change something. When I do work I love, I never procrastinate because I know what I am doing and am highly motivated to do it.

Procrastinating something is a good sign that we will end up regretting it later on. Yes, sometimes we have to do unpleasant things like tax returns and hoovering. Yet, putting off studying might be an indication that you are on the wrong course. Putting off doing anything at work might be a sign that it’s not the right career for you. Putting off meeting up with someone might be a sign that there are problems in the relationship.

Practice ‘fear setting’

I learned this technique from Tim Ferris and it basically changed my life. It is a means of making avoiding regret by rationalising big decisions. The basic concept is this:

  1. Take a sheet of paper and split it into 3 columns (or 3 sheets of paper if you’re fancy.)
  2. In one column write out all the worst possible consequences of the decision.
  3. In the second column, figure out how you can reduce the risk of each.
  4. In the third, write how you would handle the potential negative consequences, and how you would get back to normal.

Fear setting has helped me to make choices I would not otherwise have considered because, in most cases, the worst case scenario is reversible and improbable. I also developed my own technique for minimising short-term regret.

Take more chances

Even when I look back on the last few years of my life, I find that I don’t regret the chances I took, only the ones I didn’t – which is what people often say when they look back on their lives. As a teenager, I was mostly paralysed by anxiety, but I am grateful for the times I pushed through it. I don’t regret kissing someone I had a crush on for the first time, I do regret taking 6 months to summon up the courage. I don’t regret the nights I stayed up with friends, watching the stars and drinking wine, I do regret the times I went home to bed. I don’t regret the times I showed people my art (even if they made fun of me), I do regret the times I hid it away or destroyed it. I don’t regret spending a year in a hospital to recover from various mental health issues, I do regret not getting help sooner. I don’t regret all the lazy days with family, playing board games and drinking tea, I do regret not spending more time with my grandfather before I lost him.

Machiavelli urges us to make mistakes of ambition, not mistakes of sloth. Arnold Bennett wrote in 1910 that the man who journeys to Mecca, even if we never make it there, will be better off than the man who never leaves Brixton. Seneca reminds us that the voyage of a ship which is merely tossed about my waves in the harbour will never be considered great. Ted Hughes writes that the only thing people regret is not living boldly enough because nothing else counts. Simone De Beauvoir said that she could never know where the paths she didn’t take would have lead her, yet was grateful for where the ones she did take lead her.

Pay attention

“My uncle Alex Vonnegut, a Harvard-educated life insurance salesman who lived at 5033 North Pennsylvania Street, taught me something very important.

He said that when things were really going well we should be sure to NOTICE it. He was talking about simple occasions, not great victories: maybe drinking lemonade on a hot afternoon in the shade, or smelling the aroma of a nearby bakery; or fishing, and not caring if we catch anything or not, or hearing somebody all alone playing a piano really well in the house next door.

Uncle Alex urged me to say this out loud during such epiphanies: ‘If this isn’t nice, what is?'” – Kurt Vonnegut

In 1914, a fire broke out in Edison’s New Jersey plant. More than half the site was destroyed in a blaze fuelled by chemicals which fire departments were unable to put out.

According to Edison’s son, Charles, the legendary inventor’s reaction was the exact opposite to what you might expect. Instead of panicking and lamenting the loss of his life’s work, he told his son: It’s all right. We just got rid of a load of rubbish. Go get your mother and all her friends. They’ll never see a fire like this again. Edison was 67 years old, yet he told reporters at the scene that he would just start again tomorrow. He did exactly that. Within a few weeks, the plant was running again, despite a loss of $23 million in today’s money.

It brings to mind a phrase I have adopted as a sort of motto: find the snowball in any bad situation. This is a metaphor which I first drew from BJ Miller’s extraordinary TED talk. In it, he describes his experience in a burn unit – usually regarded as the most horrific and unpleasant part of any hospital. During that hellish time, a nurse brought him a snowball during the winter. He sat and felt it melt onto his raw skin, feeling wonder at the sense of connection it created. I refer to that scenario a lot because it has stuck with me.

For me, the snowball represents the art of finding something worthwhile, beautiful or useful in ugly situations. Edison recognised that the fire was something unique, which people were unlikely to see again. He could have been wracked by regret- instead, he found something meaningful. When I find myself in a bad situation, I always think about the snowball and start looking for one. I have realised that finding the snowball makes me much less likely to regret even the most unpleasant times. Sometimes we can only find it in retrospect, looking back and seeing the value.

It is not the number of positive experiences that dictate our enjoyment of life. It is the intensity with which we pay attention to them that matters. A parent who spends hours with their kids each day is not going to look back on the time as valuable if they were always preoccupied. A person who has their dream job is not going to feel fulfilled later in life if they ignored their success and focused on the failures. Some people derive no joy from wonderful circumstances, while others find happiness in shitty time.