Fear of Regret: A None Reason to live

I don’t think humans regret the fun they didn’t have. I believe the opportunity unseized, especially the impact left undone weighs more.

Why is the window closed in the morning? Is that why I have a running nose? Does the brightness of the sun damage my eyes? Am I missing out on fresh air ?

These are questions we ask in the present. In this case, me laying lazily in bed waiting for church service to start online and soccer shortly afterwards. No regrets though, I slept well. My Oura ring gave me a 70/100 score on sleep; which is better than the 35, I had the night before.


It is one of those words, feelings or whatever it is that pierces through the three forms of time.

I regret things I did in the past, which makes me regret not living in the present and guarantees regret in the future when I look at my past.

Read that statement again.

It’s fascinating because regret punctures living in all three facets but if you really truly observe it well. Regret only has a present form. The future and past part of those statements are consequences of an unintentional marriage between fear and discontentment masked as regret.

Those who live fully present rarely look too far back or too far forward. As such they rarely get swept up by feelings of regret because why?

  • Why do I really think that the purpose of living is to avoid regret?

The truth is, regret is like sin. Whether you are fully indulging in it or you are focused on running from it — you are enslaved by it.

I’ve heard many people say that they wanna live their best life so that they have no regrets on their death bed. But I dare say, if I am living my best life now to avoid regret, there is no version of my best life that I will be content with because I lived the best version of life I could in the past with what I knew about life and the opportunities it presented me; and yet, I am full of regrets.

Regret is not about Fun and Pleasure

I am paralyzed by avoiding regret. So this is not some message to a future self or anyone who reads. This is me, Dolapo, battling and wrestling with truth. I have lived a full life, one which I ought to be full of gratitude for.

But do you know what I spend most of my days thinking about ?

  • When I was in high school, I was so busy trying to be head boy (student body President) and have a good name. I didn’t date the woman I loved, and I didn’t break rules and have fun.

If you read that. You will see the mystery of regret. At every stage, you can imagine that I intended to not regret again yet I found myself at the exact same place. In my mind, behind. Late.

So often, I spend so much of my life trying to figure out how to fast track and catch up. Because by my own logic, regret is an inevitable momentum in full force destined to win on my sick bed.

Because I cannot go back, and by my estimation, I am already far behind. Time is something I cannot truly make up. So my plan is to retire earlier so I can enjoy the my old age sooner.

See what I did there? I did the same thing thing I have done all my life. I defined what a regretless life will look like in the future based on my next goals but more so to catch up and supersede my peers. Then I live my whole life discontent and frustrated when I feel life veer me off course even if it’s for a brief moment.

Here is the incredible thing. I have often times arrived at the goal set or the definition of no regrets. Only to feel regrets for all the things I discarded along the way to arrive in the future that had no regrets. Tell me that makes sense to you because it makes none to me. Let’s run over the last list again with the future definition of regret that drive my present then:

  • Becoming head boy will make my resume and portfolio very attractive and eligible for US based schools to see how distinguished I am and offer me scholarship since my parents cannot afford full price. Regret would have been to fail to get admission to a US school that my parents could afford paying me through after scholarship is applied.

The feeling of regret is not the truth. Have you ever heard stories of military commanders that averted huge disasters only to come home and beat themselves up over losing a faithful loyal skilled personnel in their ranks. Full of regret, they parse the past and analyze all the decisions made that led them to the loss.

Truth agrees:

  • Yes, you lost a friend

Truth says:

  • The equation of life requires balance. To gain, there must be loss. To go, there must be letting go. To remain, there must be resistance.

What am I really saying?

The YOLO generation is turbo charged by social media and entertainment. Regret is her most potent sales tool.

You should only permit regret a home in your heart if after reflecting on your part, you find no reason to be grateful.

There are many different ways to live. Many different things to focus on. Many different motivations for life. Regret should not be a major on the list.

  • Love the moments available

But don’t live to avoid regret. Because those obsessed with regret — to avoid it by doing more or less — are enslaved already.

Regret is the skewed perspective that minimizes the priorities chosen in the moments lived.