This is how to overcome feelings of regret and go for it

Here is predicament many of us frequently face: How do you make the decision to do something uncertain? How do you know whether an opportunity is real or imagined, and if it is real, whether it’s worth the risk? The truth is, you can’t know in advance of trying. That’s part of the uncertainty. But you can figure out if you should try.

When Jeff Bezos came up with his idea to sell books online, it wasn’t obvious that it would work. The year was 1994, long before the dot-com boom of 1999, and most people didn’t even know about the internet—there were only two thousand websites in the world (compared with almost two billion today). Hotmail, the home of most people’s first email address, wouldn’t be founded until two years later. Bezos had a high-paying job at one of the most prestigious Wall Street investment firms, and when he pitched the idea to his boss, investment legend David Shaw, Shaw agreed about its merits but advised “it would be a better idea for someone who didn’t already have a good job!”

He encouraged Bezos to reflect for a while before making the leap. Bezos admits he struggled with the decision until he found what he called a regret minimization framework that made his decision “incredibly easy.” Bezos clarifies, “I knew that when I was age 80, I was not going to regret having tried . . . to participate in this thing called the internet, which I thought was going to be a big deal. I knew that if I failed, I wouldn’t regret that.” Then with emphasis in his voice, he continued, “But I knew the one thing I might regret was never having tried. I knew that would haunt me every day.”

Bezos wasn’t the first to come up with such a framework. Years earlier, researchers Amos Tversky and Daniel Kahneman argued that the one remedy to the biases introduced by maladaptive framing (i.e., framing that leads you to interpret an event in a negative way) is to ask “How will I feel in the future?” rather than “What do I want right now?”

Here is a list of clarifying frameworks to make sense of uncertainty you are facing:

Risk versus regret minimization: Most of us are taught to minimize risks, but that’s different from  minimizing regrets. Minimizing risks reduces negative surprises, but it also reduces the chances of new things happening. Regret minimization, on the other hand, is about identifying the right risks to take, the ones that define who you are now or who you want to become.

One-way versus two-way doors: Bezos talks about decisions in terms of one-way doors (irreversible) and two-way doors (reversible). Innovators try to turn “one-way door” decisions into “two-way door” experiments, usually by breaking a big decision into smaller decisions, taking short-term options on a longer decision, or creating backup plans.

Independent versus interdependent decisions: Some decisions affect us alone and some affect others. We should be thoughtful about the harm we may cause to others through our decisions, but also honest about it.

Apples versus apples: Lastly, one of the biggest mistakes people make is comparing the certain benefits of their current situation with the uncertain risks of the unknown. For example, in deciding to move, we compared our known comforts (e.g., salary, current schools, family) with the uncertain risks (e.g., culture, new schools, workload). This is an unfair comparison—one that’s particularly hard for our brains—because it compares known gains with risky losses. As Tversky and Kahneman’s research revealed, we tend to overestimate the benefits of preserving the status quo.

Ultimately, making remarkable and satisfying choices for ourselves and those who depend on us involves asking a pair of questions: First, will I regret trying and failing? And second, will I regret never having tried? Usually the answers to these go hand in hand: It can be an incredibly valuable lesson to try something and discover you don’t want it. So, if you wouldn’t regret trying and failing, then that is a good sign you should try. If you would regret never having tried, that is another indicator that you should take action. Bezos’s experience does not mean that the answer is always to try: Sometimes we ask the question and realize that we would regret either what we might lose or what it would mean for others impacted by the risk. In that case, regret minimization would mean not taking the risk. But recall that one of the top five regrets people express at the end of life is not having taken more risks.

Here are a few more tactics that might help you reach a good decision:

1. Write yourself a letter from your imagined 80-year-old self. What advice would you give from that perspective? When Susannah did this exercise, she instantly channeled a more compassionate, wisdom-filled older self that reminded her of the current things she was taking for granted (mobility, health, youth). She was also surprised at how feisty her 80-year-old voice was—encouraging her to be bolder, have more fun, and be more contrarian.
2. Advise the main character. If your life were a novel, what choice would you want the main character to make? What advice would you give him/her?
3. Compare apples with apples. Imagine what could go right on both trajectories—deciding to move forward or not—and compare those, as well as what could go wrong on both trajectories.
4. The right choice isn’t always to go for it. There are many things we have turned down and are happy that we did. Many advisers on decision-making, for example, talk about opportunity costs, or the cost of the opportunity you give up. Before you make a final decision, you may want to review the next chapter of the book to help you make informed choices about where you excel in uncertainty and where you struggle.
5. Adopt a decision framework. If you are still struggling, perhaps dig a little deeper by using well-thought-out decision frameworks.

Excerpted from The Upside of Uncertainty: A Guide to Finding Possibility in the Unknown by Nathan Furr and Susannah Harmon Furr with permission from Harvard Business Review Press. Copyright 2022 Harvard Business Publishing Corporation. All rights reserved.

Nathan Furr is an author and a professor at the INSEAD school in Paris. Susannah Harmon Furr is an entrepreneur, designer, art historian, and contrarian. They are the coauthors of including a coauthor of The Upside of Uncertainty.