How to Deal With Uncertainty

Three ways to counter ambiguity

Via Lucas Crespo.

Imagine two silk bags, each with a mix of 100 red and black balls. In the first bag, there are 50 red and 50 black. In the second, you’re not sure about the mix. If you draw a red ball from either one, you get $100. Which bag do you reach into?

If you’re like most people, you’ll reach into the bag with the known quantities of red and black balls. If you know someone is watching you make the choice, you are even more likely to pick from bag number one. 

Our tendency to favor known risk over unknown risk is called ambiguity aversion. The concept was popularized by Daniel Ellsberg (the same guy who leaked the Pentagon Papers) in 1961. Ellsberg found that people prefer choices with calculable risk, even in instances where the unknown alternative might produce a better result. 

In practice, ambiguity aversion discourages people from doing things like participating in the stock market or trying new medical treatments when risks are less known. This may seem rational—better to play with the devil you know—but our ambiguity aversion also prevents us from seizing the upside of possibility. To be a leader is to act in the face of incalculable risk. As OKCupid founder Sam Yagan puts it, “The single biggest predictor of executive success is how you deal with ambiguity.” 

I first recognized the effects of ambiguity aversion in my sophomore year in college. My friends had a wide range of interests—from urban studies to history, economics to poetry—but a disproportionate number of them sought out internships in two industries: consulting and banking. I wondered why so many wanted to become cogs in the machines of large financial institutions. Certainly, money played a role. But in retrospect, I believe a larger part of their decisions was the result of ambiguity aversion.

Finance and consulting each provide clearly lit paths, from intern to analyst to associate to manager to director. Much like school, they offer benchmarks for success and validation for drawing within the lines. Rather than dance with the uncertainty of pursuing passions in, say, the arts or tech, many of my peers opted for the least uncertain route. 

Our bias toward known risks doesn’t just plague anxious college students; I see it in business all the time. Fear of the unknown compels companies to cling to pre-existing strategies rather than adapt to new opportunities (see Blockbuster and BlackBerry). It compels leaders to hold onto employees who aren’t the right fit even when they know they might find someone better. And it compels employees to stay on safe paths, even if pursuing something novel might produce more personal and economic upside. 

If we are able to face the ambiguity, we can turn our fear and doubt into fuel for creation. Here are three tactics for becoming more comfortable with what we don’t know.

Create certainty anchors

In Jonathan Field’s book Uncertainty, he recommends creating “certainty anchors,”  things that add reliability to your life when you may otherwise feel you're spinning in a million different directions. These anchors can ground you so you have a greater capacity to sit with the unknown.

My favorite example from the book comes from legendary choreographer Twyla Tharp, who dutifully followed the same routine every day. She would wake up at 5:30 a.m., take a taxi to the gym, work out with the same trainer, shower, have three hard-boiled egg whites and coffee, make calls for one hour, work in her studio for two hours, rehearse with her company, return home for dinner, read for a few hours, then go to bed. Tharp attributes the creativity of her choreography to the regularity of her routine. 

For leaders, certainty anchors can help assuage the anxiety of uncertainty for your team. For example, if your business is facing economic headwinds or you are trying to figure out a return-to-office policy amidst an ongoing global pandemic, a weekly status update can give your team something to depend on—even if you don’t have all the answers.

Frame the possibility

One reason it’s so hard for us to sit with ambiguity is that our brain has a bias toward negative outcomes. If you are given a bag with a known mix of 50 red and 50 black balls and a bag with an unknown mix, it’s easier to assume that the unknown bag has worse odds than 50-50, even when it could just as well have better odds. While it’s easy to see the potential downside of turning toward the unknown, it’s much more difficult to see the potential upside.

In many ways, the job of an entrepreneur is to cultivate faith in the upside. Whether you are leading a company toward a new market or making a personal decision about your career, you can use what psychologists call cognitive reappraisal to counter the anxiety of not knowing. Cognitive reappraisal is a fancy way of saying “manage your mindset.” While you might not be able to control the future, you can control your perspective on the unknown. Exercises like Tim Ferriss’s fear-setting, which asks you to take a realistic look at the upside, downside, and cost of inaction of any given decision, can help counter your tendency to catastrophize. 

We tend to ask ourselves: what if things go wrong? What if the company fails? What if you reach into bag number two and find out later that the odds were not in your favor? But it’s also important to consider the upside—not only what might happen if things go right, but also what you could potentially gain even if you don’t get the outcome you wanted. The fear and doubt that come with facing the unknown are mile markers on the path toward creation—but only if you stay open to the possibility. 

Row through the fog

Back when I worked at IDEO, my colleagues and I often used a metaphor to describe client-facing work: innovation consulting is like sitting with a client in a rowboat on a lake shrouded in heavy fog. Neither of you can see too far ahead of the boat or know exactly where you’ll end up, but your job as a leader is to maintain faith that you will eventually reach land. The key is to keep rowing. 

Research shows that the anticipation of an uncertain future can often be more painful than dealing with a negative outcome. For example, breast cancer patients experience more pain during the waiting period after a biopsy than during any other part of the breast cancer journey—including when they actually receive a positive diagnosis. 

According to Dr. Kate Sweeny, the lead researcher of the breast cancer experiment, the best antidote to the stress of uncertainty is to seek out activities that put you in a flow state. In other words, the best counterbalance to the anxiety of not knowing is taking action. 

Avoiding ambiguity keeps countless people from embarking on nontraditional paths and finding unanticipated success. Learning to navigate the fog and hold the uncertainty incumbent in bringing any new creation into the world will help us better adapt to life’s inevitable twists and turns. Our job is to keep rowing. 


Simone Stolzoff is a San Francisco-based journalist, designer, and author of the book The Good Enough Job. If you liked this piece, you can buy his book, subscribe to his free newsletter, or join the next cohort of his course, Designing Your Next Career Step

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@muhuri.json 7 months ago

approaching life outcomes as a series of probabilities as opposed to certain outcomes is an important art. for ex. look at a project you are working on to have only a specific probability of say 0.6 to 0.8 chance of going some specific way. Doing this will help you prepare and be ready for unexpected outcomes which will almost always occur.

@fkurka 7 months ago

It’s difficult to trust the advice of anyone working out of San Francisco, silicon valley or California in general.

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