A Framework For Making Bold Decisions Without Regrets

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.'
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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.'

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.

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 traveling and learning. Time is the ultimate leveler. 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 backward do we realize 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."'

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 rationalizing big decisions. The basic concept is this:

  • Take a sheet of paper and split it into 3 columns (or 3 sheets of paper if you're fancy.)
  • In one column write out all the worst possible consequences of the decision.
  • In the second column, figure out how you can reduce the risk of each.
  • 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 minimizing short-term regret.

Pay attention

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 recognized 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 realized 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.