How can I avoid a life of regret?

Reframing critical decisions along the route to contentment

Freddie Kift
The Perpetual Student
4 min readNov 5, 2023

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Photo: Author, Rome 2013
Photo: Author, Rome 2013

I turned 31 this year.

Most of my friends are having kids, taking out mortgages, settling down.

A scant few are throwing caution to the wind, leaving the company they’ve despised working at for the last five years and moving across the globe or trading in a long term relationship in for a newer model….

There’s no doubt it that this moment in our lives feels like the biggest fork in the road yet.

Up until now the lions share of these life’s decisions been reversible, or at least correctible with the passing of time.

  • A failed business idea when no one is dependent on you is at worst embarrassing and a little costly.
  • A move to a new city that doesn’t pan out is soon fogotten amidst fresher, juicier gossip.
  • A painful breakup stings less once you meet your newer, hotter flame

These failures are more a rite of passage than irreconcilable life sentences.

When you’re an adolescent or a young adult, you sincerely believe you’ll have the time to do it all and that your experiences will just stockpile indefinitely — the good and the bad.

The emotionally charged word ‘regret’ that we attach to the shake-ups, trials and tribulations in this time has a half-life that increases the faster we see what else the world has to offer us.

After 30 however, the decisions that we have take get locked in and the ‘cooling off period’ clause on major investments gets struck from the contract entirely.

Cautious indecision becomes a weaknesses as, in some instances, the longer the decision is left unmade, the more the window of opportunity closes.

No wonder the big milestones bring with them such a dramatic reshuffle of the cards. This is it! It’s transfer deadline day on the rest of your life.

Interestingly the word decision comes from the Latin decidere. It means to cut off all other options.

As we get older choices have to be made. Most of the subtle variations that exist in our minds of who we could be have to be laid to rest. We realise that like a hall of mirrors, these uncanny constructions of the mind that lingered within reach were in fact completely fictitious.

It reminds me Steven Johnson’s idea — The adjacent possible.

The adjacent possible is a kind of shadow future hovering on the edge of the present state of things, a map of all the ways in which the present can reinvent itself….the adjacent possible captures both the limits and the creative potential of change and innovation.

We’re haunted by this spectre of what might have been in ourselves because only we recognise all that we could have been had things gone differently.

Yet this is to take the fatalist approach to living. It’s the equivalent of writing your tombstone before the doctors ‘you’d better come in’ diagnosis.

Regret is the feeling that a decision in the past has today reached its point of culmination and that there is nowhere left to go from here.

But time is a continuum, not a cul-de-sac.

The future is here but it is not evenly distributed — William Gibson

The idea that regret is an immovable emotion attached to a fixed, objective reality is entrenched in an absolutism that just doesn’t reflect reality.

Life is a process of change and evolution. It ebbs and flows and meanders in seemingly non-sensical directions.

It is made up of many chapters and epochs and what we perceive as a mistake laden with consequences in one of our many lifetimes might be the inciting incident that lit the fuse on the next.

When we perceive our less successful decisions as regrets rather than feedback for re-navigation, we allow them to be used against our rational brain going forwards.

Labelling an action that we have taken or not taken in the past as a regret therefore is a surefire way to guarantee that we will always regret it because of the significance we have falsely attributed to it.

Ultimately, we have a moral obligation to our future selves to renounce the negativity bias that is encoded so deeply within so many of us, not to hold our bad decisions so close to heart but instead to investigate where else having taken them might yet lead us…

Freddie Kift — I write about finding our own unique sense of purpose and meaning in life through skill acquisition, flow states, travel, communication, and navigating the lived experience

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Freddie Kift
The Perpetual Student

I write about skill acquisition, flow states, travel, language learning and technology Currently based in Aix. linktr.ee/freddiekift