Stop Making Decisions Based on What You Want

Harnessing the utility of regret

Stop making decisions based on what you want.

Make them based on what you are most afraid of regretting. Doing so will allow you to lead a life of greater authenticity and agency.

Whereas our “wants” are mostly a confused mess of mimetism, an unheeded hunt for status and money - our regrets are deeply personal and illuminate our most genuine desires.

Regret has an abounding acquaintance with our mortality, intertwined with time as if two threads in a scarf. It serves as the body's emotional response to the knowledge that one day we are going to die. Consequently, it pierces through the haze of life, revealing the things that truly hold significance to us.

A deathbed wisdom, if you will.

Don’t get me wrong - pleasure is good. It makes life worth it. But it’s unreliable for decision-making, only a sail likely to steer you to treacherous waters.

As with everyone else, you have probably trembled at the feeling of regret, turning from it out of fear that it may swell and devour you whole.

However, it is a tool proferring existential wisdom. The only true resource in life is time, and regret is a purpose-made tool to extract that resource. If we instead turn toward regret and ask what wisdom it offers, we allow ourselves the chance of a life of greater meaning.

Consider the most common regrets that people express on their deathbed:

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

I wish I hadn’t worked so hard.

I wish I’d had the courage to express my feelings.

I wish I had stayed in touch with my friends.

I wish that I had let myself be happier.

Reflecting on these regrets emphasizes the importance of using regret as a guiding principle in decision-making, far before ever getting into any kind of bed.

But I don’t want to think about death!

Don’t fear - as many people as there are grains of sand in the Sahara have traversed that final sojourn. It’s entirely natural, and keeping death close in mind has been championed by many philosophers.

Marcus Aurelius one of them, noting its natural and inevitable nature as a powerful reminder to forgo the pursuit of meaningless material goods.

Similarly, “Memento Mori” is a philosophical concept translating to “death memory“, which suggests that one utilises death to trivialise superfluous wants. This concept underscores the idea of embracing mortality as a means to prioritize what truly matters.

Keeping death close in mind is not to grow depressed, but to ignite the fire of an authentic life. 

So how do we ‘turn toward’ regret? How does one wield this tool?

By reflecting and forecasting.

Reflecting on our biggest regrets provides a breadcrumb trail for the way forward while forecasting future regret helps us to choose the path that aligns most with our values and desires.

Allow me to give an example, focusing on the beast that many of us have faced off with before: 

What career do I want?

Reflecting

Do you experience regret around your career choice? Do you spend bedtimes imagining how that other career would have gone?

Don’t ignore that feeling. Honour it. That’s regret screaming out to you, telling you what you really care about. It might be time for a side hustle, joining a new community, starting a blog (go me), or a conversation with your manager about how you can interweave more of that other career into your current job.

Similarly, are there high school or university subjects you wish you had taken? Books you wish you had read earlier? Friends you would have liked in your life earlier? These each, pieces in the breadcrumb trail.

Forecasting

To illustrate this, let's consider a choice between two career pathways, a writer and a banker. In this exercise, you'll create three separate forecasts: one where both paths lead to poor outcomes, another where both paths lead to moderate success, and a final scenario where both paths lead to great success. This creates a breadth of data.

The example above is personal to me. I’ll take you on a quick run-through.

Going down the ‘Poorly’ forecast, I would imagine myself at the “end” of the writer pathway, at a point in which I have reaped the fruits (or lack of fruits) of that decision. In this case, the writing didn’t go well, things never took off despite my efforts.

I am going to bed one evening, pondering how life would have gone had I chosen the pathway of the banker. I don’t know exactly how the other pathway would have gone, as is the nature of life, and so I must only muse at it. That feeling of regret I feel, for not choosing a life promising more wealth, is the final output that I need to hold onto. 

Now, let's consider the alternative scenario: choosing the banker pathway. Imagining it didn’t go well, I find myself one night wondering what life would be like had I chosen the writer pathway, a life promising a greater sense of self-actualisation and creative expression.

Which bedtime draws more regret?

Interestingly, for each of the three forecasts - poor, moderate, great - choosing the banker pathway always draws more regret - especially in the ‘Very Well’ forecast.

Albeit a binary example (in the real world you can be a writer in addition to a corporate gig), the goal of the exercise is only to evoke your feelings of regret and to see what it tells you; in other words, this is not how to make decisions, but to give you existential data to inform your decisions.

The data from this exercise shows in clear terms that writing is important to me, so much so that even when I am a banker with an abundance of wealth in the ‘Very Well’ forecast, I feel substantial regret for not pursuing a career that meant something to me on a deeper level.

It’s your turn. You’ve been mulling on something, or twenty. It could be about career, relationships, or perhaps whether this is the year you do that big trip. Do some reflecting, do some forecasting. Imagine those two bedtimes, and discover what you actually want by tuning into your inherent existential wisdom - regret.

And if, when it’s time to depart . . . if it isn’t ceasing to live that you’re afraid of but never beginning to live properly . . . then you’ll be worthy of the world that made you.

Book 12,1 - Meditations, Marcus Aurelius

I would like to thank

Jen Hitze

for writing a post that gave me the courage to publish a piece that sought to provide solutions, and delve a little into that self-help world.

And to also thank

Jonny

and his book “Mini Philosophy” (which I have mentioned before) for providing me with the springboard of ideas for this post. Namely, his chapter on Momento Mori.