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Minimizing Regret: 3 Questions You Should Ask Yourself When Making Hard Decisions

Winston Ibrahim

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How do you make a hard decision when neither choice is good?

There’s a great book called The Hard Thing About Things by Ben Horowitz (one of the co-founders of the renowned Silicon Valley investment firm, Andreesen Horowitz) that talks about this in the context of business. Sometimes, there is no easy or comfortable path forward. Both paths suck. And so leadership and decision-making are about figuring out which path is best for the business and parties involved.

Another great example of how to make hard decisions is Jeff Bezos’ Regret Minimization Framework, which he has talked about since the very beginning of his career. It goes like this: “If you project yourself into the future, and imagine looking back on your life when you’re 80 years old, will you regret this decision? Will you regret trying, or not trying?” Having this frame of reference helps put things in perspective—where even if you fail, you may still see it as a net positive for your life.

We are all faced with tough decisions in our lives, our careers, relationships, and so on.

The key is to have frameworks we can lean on.

Here are some questions you should consider when making these hard decisions so that you can determine which is the best path forward.

1. “Which direction will I regret more?”

Oftentimes, we try to solve problems by asking questions like, “Should I do this? Should I not do this?”

But these questions don’t really hit on the underlying emotion of the issue.

For example, there are lots of opportunities in life that, on the surface, seem great. But if you say yes, you are simultaneously saying no to a lot of other opportunities. So which do you do? Should you say yes? Or no?

A better question to ask would be, “Which direction will I regret more?” In this example, if you say yes to this new opportunity, will you regret all that you had to give up? Or, vice versa, if you say no, will you look back on your life and regret it? (And if you think, “No, I don’t think I’ll regret it if I say ‘no,” then maybe you shouldn’t say yes in the first place—because it shows the opportunity doesn’t actually mean that much to you.)

2. “How did I get here?”

Another good question to ask yourself is how you arrived at the fork in the road in front of you.

  • Have you been minimizing regrets up until this point? 
  • Have you been making decisions impulsively, and now things are coming to a head? 
  • What would it look like to start making different types of decisions? 
  • Have the definitions of what you would regret changed?

It’s important to remember that usually tough decisions come as a result of other decisions and moments that came before. So whenever you are confronted with a “no-win” situation, it’s worth reflecting on how this sort of dynamic even came to be in the first place.

This will help you better make forward-thinking decisions in the future.

3. “Am I making this decision from a logical place or an emotional place?”

When people are faced with this crossroads type of decision-making, emotions tend to be heightened. You feel anxious. You feel attached to the outcome, or the people around you, or the expectations on your shoulders. 

But these things impede your ability to think clearly and make rational decisions.

In addition, emotional decision-making tends to lead to what I like to call “sunk cost decision-making,” where there’s a level of attachment to the situation that you don’t want to abandon. You fear walking away because that would mean abandoning all the time, energy, effort, and money/resources you’ve invested thus far. 

Instead, you are far better off trying to create emotional distance from the situation so that you can think through things logically, first. Then, once you’ve come to a logical conclusion, you can check your gut, see how that feels, acknowledge the emotional consequences of the situation, and so on. 

But it’s a multi-step process—and usually not an easy, binary decision.

I am the founder and CEO of Hydros, an innovative water filtration startup with proprietary technology that works at five times the speed of standard home filtration systems. We strive to create beautiful, convenient, and competitively priced portable and home filtration products to reduce the consumption of single-use disposable plastic bottles.

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