How to Stop Procrastinating on Big Scary Decisions

Source: Photo by Vladislav Babienko on Unsplash

Persi Diaconis, a professor at Stanford, is one of the most important researchers on decision-making. Yet, when faced with the decision of moving with his entire family from Harvard to Stanford, he couldn’t make a choice. A colleague suggested he use the method he teaches in class—calculating and comparing the expected value for both scenarios. Almost reflexively, Professor Diaconis replied: "Come on, Sandy, this is serious!"

We decide which project to start or which car to buy guided by analytic tools such as a decision matrix — of course, in balanced tandem with our intuition. However, for our big, life-changing choices, for the red pill / blue pill decisions that keep us up at night, an algorithmic approach, like Darwin's pros and cons list for getting married, is often ridiculous.

So what do we do when we find ourselves stuck at life’s major crossroads, such as: "Should I quit my job and start the coffee shop I dream of?" or "Should I have a child?" Unfortunately, we often get trapped in the same unproductive cycle:

1. Denial – We pretend the problem doesn’t exist. "If there’s no problem, there’s no need to make a decision!"
2. Silent Acknowledgment – We know we have to make a difficult choice but don’t talk to anyone about it—not even to ourselves. "Maybe it will go away."
3. Internal Rumination – We endlessly debate with ourselves, draining our energy. We lose weight. Or we eat compulsively.
4. Seeking Certainty – We search in vain for absolute certainty. We make spreadsheets, pros and cons lists, hoping for a method to guarantee a good decision. We find none—because none exists.
5. Fearful Procrastination – We understand what needs to be done, but we’re too scared to act. So we find excuses to delay.
6. Regret – After some time, we regret letting the opportunity pass us by.

Source: Kira Atanasiu / Used with permission

Sounds familiar, right? I know this cycle well. How, then, can we escape this draining loop that leads nowhere? Could any tool help us? Or even make the decision for us?

Don’t laugh—Steven D. Levitt, one of the authors of Freakonomics, conducted an experiment showing that people actually prefer someone else to make the big decisions for them, even if it’s just by flipping a coin. He created a platform with a virtual coin toss and invited people with major career or life decisions to participate. They would select their dilemma from a predefined list, flip the virtual coin, and then decide whether to follow its outcome. The results were astonishing, the coin was flipped more than 22,000 times. Not everyone followed the coin’s suggestion, of course, but many did.

I am not advocating for flipping a coin when faced with life’s crucial dilemmas, though poet Piet Hein famously suggests it might be a good idea, in order for the coin to reveal what we hope for before it lands.

How, then, can we approach these overwhelming decisions in a structured way? I propose a process based on five key questions:

1. Who am I, who do I want to become, what is my life about? Smart companies define their vision, mission, and values not just to display them on the website but as decision-making tools. We can do the same. If we articulate (and write down) a life purpose, a mission, then we can resolve tough choices by asking: "Which option aligns with my life’s goal? Which helps me grow into the person I want to become?"
2. Which scenario opens more doors? In our rapidly changing world, an essential criterion for life-changing decisions—whether personal or professional—is how much opportunity each option creates.
3. Which scenario benefits me in the long run? We often favor the comfortable, familiar scenario. But if the other option is clearly better in the long term, we should ignore short-term comfort, even if initially we will face difficult times.
4. What advice would I give a close friend in the same situation? We tend to give better advice to others than to ourselves. Asking this question can reveal the best solution, one we may have been avoiding.
5. Which option represents fear, and which represents courage? Often, we rationalize our fear of change with arguments about risks. But if we label our options simply as: "This one is fear and this one is courage", it becomes easier to be honest with ourselves.

This may seem like a simple process—just five questions—but it's not easy. It needs candid introspection. And pen and paper.

Of course, if after asking these questions you decide for a big change, test your options before jumping into the unknown. Don't just quit your job to open the specialty coffee shop; instead, spend a weekend working as a barista and see how it goes. Ultimately, though, I believe my friend S. is right when he says: "Between complication and complacency, I choose complication."

A version of this article appeared in Biz magazine.