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July 19, 2017

The Effectiveness of Regret

Regret is a tricky one. It’s clearly not rational, and its afterthoughts are impractical. Yet regret can be a fantastic and efficient impetus for making decisions.

I realized a lot of the choices in my life have been made by using regret as the metric to project how I would feel about potential consequences. There was a persistent trend underlying the source of a lot of dissatisfaction:

I was bothered by things I didn’t do.

More bothered by the things I didn’t dare try.

And most of all, hated the unforgiving curiosity of endless “what if’s” and “might have’s”.
Really, why live with this nagging feeling when it’s possible not to?

Weighing every choice with the intention of preempting regret does wonders. It puts an abrupt stop to unease tinged with fear of missed opportunity. When there is no definitive best solution, future-oriented hindsight adds so much perspective, especially if one of the choices is at odds with what is logical or with what feels like is expected by others.

As much as my decision-making relies on this, the problem with this strategy is twofold:

1. It’s ultimately a reactionary tactic. The course of your life is dictated by seizing what you would rather not want to miss out on than what you actually may want to do. It seems unnecessarily relativistic if what we value is objectivity.

2. The feeling of regret, at its core, is a dimension of sentimentality. By definition, that sentimentality allows emotion to trump logic.

So the question really is: can using a comparative, logical framework to make decisions based on predicted emotions still be logical in the end? But then again, how unfulfilling our lives would be if we allowed logic to be the supreme driving force in all our decisions?

If we believe happiness is synonymous with lack of regret, then this tactic would be all but infallible. It was particularly surprising to hear this was the very approach that prompted Jeff Bezos to take a leap of faith to launch Amazon, as he officially formalized into “The Regret Minimization Framework”. It seems like a systematic method, but I’d also be curious to see if it would always lead to the optimal outcomes we’re looking for. Arguably, regret minimization deals with consistently avoiding the most negative results but doesn’t necessarily generate the most positive.

Looking back, I can pinpoint that this was the underlying motive that drove me to do a lot of things that seemed strangely ambitious or even out of place. But it’s also the same rationale that has gotten me a lot of things I couldn’t have fathomed attaining otherwise.

I’d rather do more than wonder if I missed out.

I’d rather risk looking foolish than avoid dismissing something before it’s even had a chance to happen.

Seeking a regret-free conscience requires the conviction that there’s nothing to lose. It simply makes more sense to just go for it.

If nothing ends up happening, then it won’t matter. But if something does work out, it just might mean the world.

And the fact that that possibility exists is worth everything.

The Power of the 6 Month Test

Every once in a while, I like to take a moment to reflect with what I call The 6 Month Test. I find it incredibly illuminating and motivating to benchmark things into perspective.

The test is simple — there are only two questions: Am I a fundamentally different person than who I was 6 months ago? and Is this difference a good thing?

Try it.

Let your mind wander to half a year ago — What were you doing, working towards, hoping to have? What were your concerns? What did you want to be better at?

Now fast forward to where you are today — Has there been measurable progress towards those things? Are you now facing a new set of challenges? Are the walls towering in front of you different than those that appeared before? Do you feel any differently?

Most of the time, I’m astounded by how much of a difference 6 months can make.

I’m intrigued by the sheer volume of new experiences I’ve had, people I’ve met, and ideas I’ve come across. It’s fascinating to relive how and why these events have impacted me. A few times, I truly question why I said or did X, Y, Z things just a mere few months ago and feel so relieved to have moved beyond that.

If the answer is no, not much has changed, then I also know I’ve been spinning my wheels and need to be more deliberate in architecting my life or putting myself in situations to be exposed to more opportunities.

I love this test because it’s so revealing. There’s no hiding from your progress. The only question more powerful is, “Where do you want to be 6 months from now?”