Regret Minimisation — 5 regrets of the dying

Rajiv Srivatsa @telljeeves
Published in
5 min readMay 17, 2020


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The first strategy of living your #OneLife as per the OneLife Theory is to live your life without any regrets.

(Introduction to OneLife Theory is here and here)

Thankfully for all of us, we don’t have to wait till our very end to discover this. There’s enough literature that talks about the 5 biggest regrets of the dying here and here.

I am quickly going to run through the 5 with my interpretations on it added —

(1) I wish I had the courage to live a life true to myself and not what others wanted me to do

This is one of the toughest ones to do, especially in a country like India, where we are always told to compare ourselves against our peers from a very early age. Progress in all aspects is seen as a very specific defined path — get into the IITs / IIMs / get a great job / get married / get a kid / get a home / fancy car / etc. There are very few people who really get out of this rat race and establish their own paths — which they want to or are proud of. There’s nothing wrong in having this path as the model — if you are fully convinced about it yourself. But comparing your life against that of your peers, or getting of this oft-treaded path in fear of what parents might say / friends might say etc. is a load of silliness.

I have personally treaded the beaten path, and every time — either by force or by choice I have gotten off it — despite all the ups and downs in those journeys — have been the best experiences of my life. I am sure I will continue to abide by some while challenge status quo / the norms of success and failure super-imposed by society in general.

(2) I wish I had not worked so much

Most people — including proud workaholics — at some later point in their life — realise this and tell this to people. Unfortunately, if you realise this too late in life, then you probably have no life or energy left to correct it. The conscious way to correct it earlier on is not to overcompensate and work less — it just means you are conscious of what time you are spending where, and whether you are doing justice to other commitments in life including health, relationships, hobbies etc. As long as you consciously prioritise and give the right time commitments to all axes of life (based on the anchor of life — check Episodes 11–15 on this), then you are doing a fair and fine job.

(3) I wish I had the courage to express my feelings

This probably applies to much younger in life or even later — for the first love that you never expressed, or even the gratitude or the sorry or the thank you that you never had a chance to tell people. It’s better to express these feelings at whatever point in time — and even if you didn’t at that point in time — to share honestly much later as long as the situation allows it. Too many suppressed feelings can make life feel half lived. The worst cost of letting someone know your feelings is a tiff — nothing — or in some cases — a long-lasting silence. That’s better than living in denial or living without knowing what might have happened.

(4) I wish I had been in touch with my friends (& family)

As we get older and busier, we start becoming less connected. While we may have hundreds or 1000s of social media friends, connecting / being in touch with them is a completely different paradigm. It’s also impossible to be in touch with so many. So while you can go wide in staying connected on social media (a birthday wish here / a like there / a comment here on specific life events), staying deeper connected with certain special networks / people either as a group (at least once in 6 months or a year) or once in a while (1 on 1) is critical to establish those connections. It does not matter how old you are or how long back you were in touch with a particular group or a person, it’s never too late to get back in touch with them.

I can give a personal example where after 20 years, a bunch of us decided to renew our connections with our school friends (who had hardly been in touch) and the result of it — is a gang of around 100+ people being far more in touch than ever before in the last 20 years.

(5) I wish I had lived happier (& less stressed)

Happiness, at some level, is the crux of pretty much the entire #OneLife Theory podcast. However, I would alter this particular one as being less stressed in life. We all take too much stress and pressure for things around us — including complaining about the weather, the traffic, the pollution, the maid not coming in, the food not being cooked the right amount, and just about anything and everything. Once you get a larger perspective of living and life in general, then all these smaller episodes just about vanish from our purview and we don’t allow these to come and alter our moods and happiness.

Every time I have gotten some perspective and let these pass, my days have been far better than when I have let myself react to these seemingly inane situations.

Additionally, you should add any regrets that you would have and compile a list of your top regrets. For e.g. these may include —

  • Starting up — maybe you have always dreamt of starting up one day
  • Having a kid — in case you would love to be a parent and want to have a kid / spend time with the kid in her early years
  • Travelling the world — if you are a wanderlust and want to explore many different cultures / people etc.

Whatever it is, that you will additionally regret if you have not done well enough, you should add to the list of the top 5 and keep that as a strong basis.

Here’s Episode 4 of the OneLife Theory Podcast that covers this in more detail.

Here’s the Spotify podcast link to it —

Do send me any feedback on the podcast as comments on any of the above channels or on email to



Rajiv Srivatsa @telljeeves

Partner at @Antler India. Co-founder Urban Ladder. Write on Startups and Happiness. Podcast @OneLifeTheory. Jack of all trades, master of none!