My Life System #87: Regret – 2

At times, when alone, my pendulum swings from thinking forward to pondering regret. It is usually a response to a trigger – an email, a conversation, or something I saw. A memory from the past swings by and if I am not careful, I can end up opening door after door from a past long gone by. There is nothing I can do to change what’s happened and yet this game of alternate universes begins. What if I had accepted the offer an investor made? What if I had not refused the price point the customer wanted? What if I had said Yes instead of No? What if I had followed my doctor’s advice? What if I had been more careful walking (and therefore not tripped and fallen)? Some are trivial regrets, while others are more profound. Some don’t leave a mark, while others cause deep hurt.

Marshall Goldsmith writes in his book, “The Earned Life”: “Regret, in the words of Kathryn Schulz in her wonderful 2011 TED talk on the subject, is “the emotion we experience when we think that our present situation could be better or happier if we had done something different in the past.” Regret is a devilish cocktail of agency (our regrets are ours to create, they’re not foisted upon us by others) and imagination (we have to visualize making a different choice in our past that delivers a more appealing outcome now). Regret is totally within our control, at least in terms of how often we invite it into our lives and how long we let it stick around. Do we choose to be tortured or bewildered by it forever (as in the case of my friend Richard), or can we move on, knowing that regret is not finished with us, that we will surely live to regret again someday…Regret is the depressing counterweight to finding fulfillment in a complex world. Our primary theme is achieving a life of fulfillment—what I call an earned life.

An important point made by Goldsmith is that “our lives reside on a continuum that roams between Regret and Fulfillment.” He adds: “Something truly earned makes three simple requirements of us: We make our best choice supported by the facts and the clarity of our goals. In other words, we know what we want and how far we need to go. We accept the risk involved. We put out maximum effort.”

Control over one’s mind is key to dealing with regret. We must appreciate the good that has happened in the life we have lived and look forward with excitement to the life that is to come. We have control over many decisions. What we need to do is to make sure we choose the best possible option we have – based on the information available at that point. My approach is to always think that there is some good in all that happens, and at times that good may take time to manifest itself. Close the door on regret and open the door to fulfilment.

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While I had not intended it that way, the three themes of “Closing and Opening Doors”, “The Second Side” [Parts 82-85] and “Regret” form a triad of sorts . The common theme is to let the past go and look forward to a future we can craft by considering options which at times may not be obvious.

A few good quotes to think over:

  • “You can’t connect the dots looking forward; you can only connect them looking backward. So, you have to trust that the dots will somehow connect in your future.” – Steve Jobs
  • “For of all sad words of tongue or pen, The saddest are these: ‘It might have been!’ ― John Greenleaf Whittier
  • “Very few regrets in life are about what you did. Almost all are about what you didn’t do.” – Kevin Kelly

So ask yourself: Which doors do you need to close? In which current situations do you need to see the “second side?” How can you limit regrets and think about your “earned life”?

Published by

Rajesh Jain

An Entrepreneur based in Mumbai, India.

One thought on “My Life System #87: Regret – 2”

  1. Hi Rajesh,

    Interesting blog post, there is a lot of food for thought here.

    A related book that you might find interesting is Daniel Pink’s “The Power of Regret: How Looking Backward Moves Us Forward” – https://www.amazon.com/dp/B097XNT4RT. In this book Pink says that regret need not always be counter-productive.

    This is an excellent interview that Steven Johnson did with Dan Pink – https://adjacentpossible.substack.com/p/thinking-through-time-a-conversation ( In fact, Steven Johnson’s entire newsletter Adjacent Possible is very good).

    But one point that was missed in the above interview was there was no reference to Jeff Bezos’s “Regret Minimization” framework for making decisions – https://youtube.com/watch?v=jwG_qR6XmDQ ( I had also earlier tweeted about this – https://twitter.com/anirudhacharya1/status/1497503745604677632).

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