The Regret Minimization Framework or "How To Live So That You Can Die With No Regrets

I talk a lot about 'winning at life'. This is a deep and complex question with many layers. I find the 'regret minimization framework' is a useful heuristic to think about when considering this.

Using this concept, the goal of life is to live in such a way that at the end of your days, whether that is tomorrow or in 100 years' time, you have no regrets.

Let's make it even simpler - you want to get to the end of your life and think "Fuck yeah, I rocked it."

Will you regret spending the vast majority of your life working?

What about backpacking around Asia?

This is an individual decision to make but I find that it shakes you out of the bullshit you are telling yourself.

I spent most of my life saying "Once I hit x amount invested, I'll be able to live happily and do what I want." And although delaying gratification is an important life skill, this needs to be balanced with living in the moment. More on this in a bit.

How do we know what we will regret?

One way of approaching this is by looking at those before us.

Bonnie Ware, a carer for terminally ill patients, wrote a blog post that turned into a book titled: The Top Five Regrets of the Dying where she outlined the five recurring themes that haunted people at the end of their days.

A lot of my thinking uses this core concept and you'll see recurring themes through the website.

You may be familiar with these but I find that you can't be exposed to them enough. I have them written permanently on my whiteboard as a reminder:

A reminder is always worthwhile so I'll expand on them below.

1️⃣ I wish I had the courage to live a life true to myself, not the life others expected of me

This was the most common regret. We float down the river of life, buffeted along by conditioning and base emotions, being influenced by society and the desires of expectations of others. We think we have time so we make excuses.  

When we really think about it, the risk of living an unfulfilled life is catastrophic. It doesn't bear thinking about, so most people don't. But let's be real, we only get one shot.  Because rocking the boat in the moment is so much more immediate, we put off our needs and desires, fooling ourselves into thinking we have time. This works, until it doesn't.

Health brings a freedom very few realise, until they no longer have it.

2️⃣ I wish I hadn't worked so hard

Another product of societal conditioning is work - we sacrifice doing what we want to make money so that we can do what we want... it makes no sense.

However the conditioning is strong and society validates heavily for material things, career progression, and status so we forge on without questioning it.

People who work less or try to break away are ridiculed, our peers behaving like crabs in a bucket, pulling any dissenters back in, lest they succeed, forcing those who remain to question their life choices.

All of the men I nursed deeply regretted spending so much of their lives on the treadmill of a work existence.

3️⃣ I wish I'd had the courage to express my feelings

This is about unashamedly being yourself with all the messiness, emotions and needs that we largely suppress. Not only does this lead to a fraction of the experience available to us, but suppressed emotions lead to physical symptoms.

Poor boundaries and unmet desires accumulate over time as we try to 'keep the peace'. Easy choice in the moment, but with dire consequences.

If someone gets upset about my feelings or boundaries then I need to trust them to be able to work through it. This is something we can always improve and communication is a core skill here but "if in doubt, get it out" is a pretty decent rule of thumb. You will only get better with practice!

Many people suppressed their feelings in order to keep peace with others. As a result, they settled for a mediocre existence and never became who they were truly capable of becoming. Many developed illnesses relating to the bitterness and resentment they carried as a result.

4️⃣ I wish I had stayed in touch with my friends

Close relationships in life are fundamental. We often let them slide as life gets busy - again, this is prioritizing the wrong things and a product of the society we will in.

I resisted the need for connection for a long time and thought I was a robot and that I didn't need anyone. On reflection (and a lot of therapy), I realized that all of my best experiences in life were about the people I shared them with. I was just protecting myself from getting hurt. It took humility to understand that I needed connection and this became easier as the positive feedback became a virtuous cycle.

I am now very intentional with connection and friendship, despite the difficulty caused by my lifestyle, and my life has blossomed in quality because of this.

Everyone misses their friends when they are dying.

5️⃣ I wish that I had let myself be happier

This is what happens when people bullshit themselves into thinking they are happy and trying to convince themselves and others that this is the case. We feel like we SHOULD be happy because we've done what society told us to do and then put on a performance because of course, we would feel stupid if we went to all this effort and weren't. The issue is MOST people are performing, and you have to be honest with yourself first and foremost to be able to rationally assess the situation and take action.

Often this is mistaking comfort, routine, and checking boxes for happiness. The potential discomfort and 'risk' of change stops people from taking action.

The irony is that if someone is at a 2/10 in life, it's a no-brainer to change. However, 6/10 is dangerous, because the perception is that there is more to lose. This couldn't be further from the truth.

Moving towards 10/10 and genuine happiness and fulfillment despite the fear is the goal of Ultrawinning.

Many did not realize until the end that happiness is a choice.

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My Reflection and Takeaways

When I came across this concept, I had already started to make some moves and so when I really thought about it, I had no regrets.