Chapter 2

Reverse Insurance

Many of us feel anxiety in the face of uncertainty and so we try to avoid it. But a world with too much certainty becomes a boring, repetitive cycle from which we long to escape. We forget that we actually need uncertainty, and if we don’t have enough of it, we will even pay to introduce more into our lives. As the leader of a major gambling organization explained it to us, “We sell reverse insurance…. Our ideal target customer is the forty-five-year-old person who wakes up in a job they hate, a relationship they hate, and realizes their life is always going to be the same.”1 They gamble to give themselves the chance that something new could happen.

Although most of us spend an immense amount of energy trying to make our lives more certain, in the process we forget how much we also crave uncertainty. In a recent survey of sixteen thousand people changing fields in mid-career, most didn’t give up their hard-won success because they wanted to make more money or they had a bad boss—they changed because they were bored!2 The boredom predicament invades our personal lives, too—as relationship counselor Esther Perel has found, the major challenge for maintaining relationships is reintroducing the uncertainty that keeps the spark alive.3

Clearly, too much uncertainty is overwhelming, but often in our quest to avoid uncertainty we forget that we need it to feel alive, happy, and challenged. Most of us are taught to create a predictable, stable life plan, forgetting that with every certainty we nail down, we eliminate other possibilities and add certainties that will be frustrating. For example, although we may aspire to buy a house, we forget that buying the house reduces the possibilities of living in other cities, discovering new areas, or making new friends while adding the headache of repairs, yard care, and taxes.

We aren’t claiming that the increased responsibility isn’t worth the benefits of owning your place but consider how doggedly pursuing certainty everywhere leaves no room for the invigorating “reverse insurance” sort of uncertainty that comes from not having every hatch battened down. Cautious and predictable choices often feel safer or morally right but when stacked up ad nauseum, they can leave you unfulfilled.

The same is true for organizations—they need uncertainty as well. In a recent study, Harvard professors found that when companies instituted quality-control systems like ISO 9000 to increase certainty in their production processes, they also eliminated the innovation that arose from mistakes, changes, and uncertainty.4 Tim Little, the entrepreneur who reinvigorated legacy shoe company Grenson, explained that reinventing the brand was only possible if he could, “take risks. If I hadn’t … it would have been a long, slow road to mediocrity.”5

Uncertainty is an essential ingredient for new things to happen. The innovation teams at some of the world’s top restaurants actually encourage uncertainty, injecting it into their processes by forcing themselves to use unknown ingredients, try new cooking techniques, reinstalling new kitchens, or adopting undefined roles for chefs.6 Likewise, Hamilton Mann, the head of transformation at Thales, which builds high-performance systems for space stations and electrical systems for megafactories told us, “To innovate, we have to seek risk, we have to seek uncertainty. If we try to avoid it like in other parts of the business, we won’t innovate.”7

When we start reframing uncertainty as a necessary reverse insurance against a boring checklist life, we will take bigger risks, tapping into uncertainty possibilities, which are the most interesting, valuable, and instructive possibilities. Jamie Rosen is an entrepreneur whose unusual journey taught him how important uncertainty really is to a fulfilling life. After finishing an undergraduate degree at Harvard, he had the sense that he wanted to do something different from the familiar career tracks in medicine or business. But he didn’t know what that something different was, let alone what to call it. As a student he had written travel guides for the Let’s Go series, and when a coworker suggested creating one for East Asia, they decided to write about Mongolia. Sadly the project fell through just before launch, so Rosen fished around for “that something” he felt was missing and came across a new program on invention and creativity that was sponsored by Jerry Lemelson—the late inventor who held 606 patents.

Rosen joined the innovation program and later worked with Lemelson, inventing creative toys like giant foam Lego bricks that could be used to build castles or ships. After his experiences with inventing, Rosen went on to found several entrepreneurial ventures, including WayBetter, which leverages behavioral science to encourage people to pursue healthier lifestyles. When we caught up at a small café, Rosen observed, “I used to see life as trying to get straight to my objective. And the periphery—those were the uncertainties, those were the distractions.”8 Then he hesitated, coffee cup in hand. “But, you know, the most wonderful and important things in my life have always come from the side, from the periphery. Every good and great thing that has happened to me—meeting my wife, meeting Lemelson, starting my businesses—it all came from the periphery.” Nodding to himself, Rosen concluded, “I still go toward an objective, but now I’m looking for the periphery, I’m looking for those surprises. That’s the good stuff. It all comes from the uncertainty. That’s the point of the journey.”

Not only do we need uncertainty, to introduce surprise, change, and enthusiasm into our lives, but uncertainty may be the only pathway to the possibilities many of us dream about. Uncertainty possibilities are easily forgone since they entail even more uncertainty and more of the unknown, but they are more satisfying and potentially life changing. They tend to come only after you face the unknown and, instead of backing down, live it into possibility.

Reflection and Practice

Reverse insurance reminds us that we can’t thrive without uncertainty. When thinking about our individual capability, or uncertainty ability, when facing uncertainty, it can be helpful to imagine a thermometer that registers the current temperature of uncertainty you are living with. To take the temperature of your uncertainty, consider both the planned and the unplanned uncertainties you are experiencing in five areas: relationships, career, health, personal growth, and time/money resources. Planned uncertainties could include starting a new venture, making a career change, moving to a new location, getting married, or undergoing some other exciting but potentially stressful change in your life. Unplanned uncertainties are any unexpected threat or disabling circumstances, such as a job loss, relationship breakdown, serious illness, natural disaster, depression, or other shock.

Taking your uncertainty temperature is subjective and requires some imagination and intuition—it will not be an exact measurement. Now consider that the heat of the uncertainty you are facing likely puts you into one of three development zones described by Tom Senninger (based on psychologist Lev Vygotsky’s original model): panic, learning, or comfort.9 If the heat of uncertainty is too high, then you are likely in the panic zone, in which case, your intention should focus on bringing the temperature down, as you would with a dangerously high fever. Simply reframing the unknowns you are facing—by finding ways to move them into the realm of possibility—often lowers your temperature a bit, bringing you down to the learning zone, where growth begins. If, on the other hand, the heat of uncertainty is too low, then you are probably squarely in your comfort zone and thus not really learning, growing, or developing. Obviously, the ideal is to introduce some novelty and uncertainty so you can reach the learning zone, where you grow and develop. We will discuss how to do that effectively in the discussion on frontiers in chapter 3. However, for most of us, the real problem is that we are so used to being in the comfort zone that just a little uncertainty ruffles our feathers. We then react by trying to escape from it in order to get back to our comfort zone rather than seeing how the uncertainty might be leading us to the learning zone. As you look at the uncertainties you face, is it really true that you are in the panic zone? Or is it possible that you are just feeling the normal discomfort of the learning zone? Ask yourself, What could I be learning from this? How is this making me more resilient, capable, and wise? Perhaps you will realize that you are actually in the learning zone, building your uncertainty ability and developing important lessons for the future.

  1. We coined the phrase possibility quotient to describe one’s likelihood of enabling positive change and transformation. Like all Reframe tools, reverse insurance increases your possibility quotient in the way it defangs the downsides of uncertainty and reveals the human need for uncertainty. Imagine our surprise when we googled “possibility quotient” and found Harvard assistant professor Srini Pillay using the idea in a slightly different way, one that is as informative as a temperature-taking exercise. He created the following checklist to measure factors that “could be masquerading as impossibility” and depleting one’s possibility quotient.10

    – How burned out are you?

    – How lost do you feel?

    – How much have you given up on your dreams?

    – How hard is it for you to change?

    – How depressed or anxious are you?

    – How much of a pessimist are you?

    – How difficult is it for you to clearly imagine what you want?

    If you have been avoiding risk and uncertainty at all costs, your possibility quotient will be low. If you are burned out, depressed, and have given up on your dreams, it may be that you aren’t allowing enough uncertainty into your life, which is the only way to imagine and live new ways of being into reality. We try to control situations to feel safe, but this chapter’s tool is a reminder that certainty in everything is overrated, making life dull and depressing. If we live all areas of life in the comfort zone, our uncertainty temperature will be low and our uncertainty temperature upper limit will remain equally low, since we aren’t taking steps to become comfortable at higher temperatures.

  2. Often innovators and others adept at navigating uncertainty get tired of high possibility quotients and “retire,” opting for calmer days within the comfort and learning zones. Taking breaks from introducing uncertainty can be a great idea, but reverse insurance is there to remind us not to stay there long. The most fascinating and inspiring individuals continue to learn and grow right up to the end of their lives, preferring learning zones over unfulfilling existences.
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