Regrets, or no regrets?

What is important for your important decisions

Life is all about decisions – those thousands of decisions that we take every single day. And luck – lots of luck in a world of randomness and serendipity.

A life-skill I have written about before “Luckily I am so lucky“.

Let me muse about that other skill – decision-making.

Basically, it should work like this: To make reliably good decisions, you simply weigh how right you think you are against how sorry you will be if you turn out to be wrong.

Whether you should take a risk depends not just on the probability that you are right but also on the consequences if you are wrong.

That sounds simple enough, right? But there is a small mental hurdle called ‘regret’.

Regret-Optimization

I personally know a lot of people – myself included – who ultimately made big life decisions largely based on the path of least regret. These decisions are almost always described as the best decisions they’ve ever made. Go figure.

Instead of basing my decisions around success/failure, or happiness/pain, I base them around regret-optimization.

Regret is part of life; an indispensable emotion; it’s not about living in the past or trying to turn back time, it’s about looking honestly at our choices because we can learn from them & use them to shape the next phases of our lives.

Regrets are usually the best measurement of what is actually valuable to me in the long run.

To get closer to that ideal I ask myself these questions,

“If I make this change and I am right, what impact will it have on my life?

What impact will it have if I’m wrong?

Have I been wrong before? For sure.

Did I regret it?”

That last question is crucial for running my life on a “regret optimization framework”.

My goal is to look back at age 60, 70, 85, or whatever it might be and regret as few things as possible.

Time horizon

Now, timeframe is another factor in decision-making.

I will fail with my decisions!

I definitely will.

Thus my sweet spot is to find the short-term failures that enable the huge long-term successes to happen in the first place. 

I need to remind myself often NOT to spend my life making up my mind.

While spending my life making decisions things change. My values change. My dreams change. What broke my heart or made my day at 16 is inconsequential at 50. What breaks my heart or makes my day at 50 was incomprehensible at 26.

And there will come a day when I would give everything I have left to have what I have right now.

Now are the ‘good old times’ I will look back at when I am old and frail.

Emotions

We are emotional creatures. Creatures that often avoid taking an action due to the fear that – in hindsight – it will turn out to have been less than optimal. Like leaving money in a bank account, rather than putting the cash in an investment with a higher return!

To put the finger in the wound it might help to bear in mind that someone who had invested in a lousy stock mutual fund 15 years ago – and stuck with it – is certainly better off today than someone who did not invest in stocks at all.

Ironically, it may be riskier to leave yourself vulnerable (to the devaluing effects and certainty of inflation) by keeping your savings in those steady Fixed Deposits than it is to subject yourself to the ups and downs of the stock market.

Stocks, although volatile, are still the average person’s best bet for long-term capital appreciation.

But I digress.

To avoid this emotional regret-aversion bias it might be helpful to remember that “it’s not always what you do that hurts your pocketbook, but what you choose not to do.”

And one more thought to hammer it in:

“Andy, please don’t make big decisions when you are emotional. The odds that you will regret them approach 100%.”

Ubiquitous Regrets – good ones and not-so-good ones

Everyone has regrets.

But try this: Talk to some people who are beyond their 70s and who have gathered ample experience in life. Ask those age-experienced whether they have any regrets and what they are.

My guess is—without having any empirical studies to back it up – that most people’s biggest regrets in life centre around things they have failed to do, not the things they actually have done.

“I wish I had” vs. “I’m glad I did”.

These four words will be the difference between a life well lived and a life filled with regret.

This is what I remind myself of when I struggle as an entrepreneur. This is what I remind myself of when I struggle as a father.

I don’t know the outcome, but I’ll keep on trying, because, in twenty years, while others say, “I wish I did”, I’ll look back and proudly say, “I’m glad, I did”.

So, ask yourself this question: “In twenty years, what will I regret?”

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Now, some might think you could make a calculated mathematical expectation for every decision in life. At a certain point, you have to take a risk and move forward with the information at hand, even if it’s incomplete. 

This is what makes rational decision-making such a difficult endeavor. You want the odds in your favor but the majority of the time you don’t know exactly what those odds are.

The problem with making decisions comes down to the fact that the past provides an incomplete guide because the future is always and forever unknowable. 

Intuition and judgment are necessary evils in an incalculable world.

As the saying goes: Wisdom is knowing what to do next, skill is knowing how to do it, and virtue is doing it.

Or in the words of Nike: “Just do it.”

Or in the words of Yogi Berra: “When you come to a fork in the road, take it!”

 “There are no wrong decisions. There are only right decisions and lessons learned. If everything goes right, we get a good experience. If everything goes wrong, we get a good story.” – Simon Sinek

“I did what I thought was right, given the circumstances, given my knowledge at the time, given the pressures on me at the time. That’s finished, done. I move forward. You keep on harking back, it’s just wasting time.” – Lee Kuan Yew

“The world is changing. Do what you think is right. You may not win but at least you tried. All people almost never regret the risk we take and fail. We always regret the risk we fail to take.” – Marshall Goldsmith

“I am not a product of my circumstances. I am a product of my decisions.” – Stephen Covey