“The job — as well as the plight, and the unexpected joy — of the artist is to embrace uncertainty, to be sharpened and honed by it,” Dani Shapiro wrote in her beautiful meditation on the perils of plans. But while embracing uncertainty may be the cure for our epidemic of anxiety and the root of the creative spirit, it remains an art enormously challenging and uneasy-making for the human psyche. Instead, we try to abate the discomfort of uncertainty by making long-term plans and obsessing over everyday to-do lists.

There is hardly a better time than a month into a new year to behold the disconnect between our plans and our reality as even our most vigorously intended New Year’s resolutions crumble, despite all that we know about the psychology of self-control and the science of forming new habits. Indeed, of all the disappointments in life, there is hardly a kind more hazardous to happiness and more toxic to the soul than disappointing ourselves as we fail to live up to our own ideals and expectations.

The solution, however, might not be to further tighten the grip with which we cling to our plans — rather, it’s to let go of plans altogether. So argues British journalist Oliver Burkeman in The Antidote: Happiness for People Who Can’t Stand Positive Thinking (public library) — a fascinating look at how our conventional approaches to happiness and success tend to backfire as our very efforts to grasp after such rewards generate a kind of anti-force that pushes us further away from them. This counterintuitive, counterproductive proclivity is particularly palpable when it comes to plans and goal-setting. Burkeman writes:

What motivates our investment in goals and planning for the future, much of the time, isn’t any sober recognition of the virtues of preparation and looking ahead. Rather, it’s something much more emotional: how deeply uncomfortable we are made by feelings of uncertainty. Faced with the anxiety of not knowing what the future holds, we invest ever more fiercely in our preferred vision of that future — not because it will help us achieve it, but because it helps rid us of feelings of uncertainty in the present.

Indeed, Burkeman argues that we make a gobsmacking number of major life decisions under the duress of our discomfort with uncertainty. He offers a “potentially mortifying exercise in self-examination” to illustrate his point:

Consider any significant decision you’ve ever taken that you subsequently came to regret: a relationship you entered despite being dimly aware that it wasn’t for you, or a job you accepted even though, looking back, it’s clear that it was mismatched to your interests or abilities. If it felt like a difficult decision at the time, then it’s likely that, prior to taking it, you felt the gut-knotting ache of uncertainty; afterwards, having made a decision, did those feelings subside? If so, this points to the troubling possibility that your primary motivation in taking the decision wasn’t any rational consideration of its rightness for you, but simply the urgent need to get rid of your feelings of uncertainty.

The reason we do this is just as counterintuitive as the fact that we do: Rather than a failure to choose the right goals, it has more to do with the artificiality with which a goal singles out a specific aspect of life and attempts to separate it from that immutable interconnectedness of everything, which the poet Diane Ackerman so memorably termed “the plain everythingness of everything, in cahoots with the everythingness of everything else.” This, Burkeman reminds us, triggers the law of unintended consequences — any attempt to alter one variable in an even marginally complex system is bound to affect a number of other variables.

In considering what it might mean to lean into uncertainty and embrace it, Burkeman cites the work of psychologist Saras Sarasvathy, who studied the essential qualities that successful entrepreneurs share. In her extensive interviews with forty-five such people, who all fulfilled the same criteria for “success” — a minimum of fifteen years’ experience in launching businesses and at least one company they had taken public — she found a profound disconnect between the cultural trope of the innovator as a goal-oriented go-getter who brings her concrete vision to market and the reality of what these successful entrepreneurs did have in common. Burkeman writes:

We tend to imagine that the special skill of an entrepreneur lies in having a powerfully original idea and then fighting to turn that vision into reality. But the outlook of Sarasvathy’s interviewees rarely bore this out. Their precise endpoint was often mysterious to them, and their means of proceeding reflected this. Overwhelmingly, they scoffed at the goals-first doctrine of [management theorists Edwin] Locke and [Gary] Latham. Almost none of them suggested creating a detailed business plan or doing comprehensive market research to hone the details of the product they were aiming to release.

Instead, at the heart of the entrepreneurial spirit lies something else entirely:

The most valuable skill of a successful entrepreneur … isn’t “vision” or “passion” or a steadfast insistence on destroying every barrier between yourself and some prize you’re obsessed with. Rather, it’s the ability to adopt an unconventional approach to learning: an improvisational flexibility not merely about which route to take towards some predetermined objective, but also a willingness to change the destination itself. This is a flexibility that might be squelched by rigid focus on any one goal.

Sarasvathy has come up with a set of principles that underpin her anti-goal approach, which she calls “effectuation.” Her model distinguishes between “causally-minded” people, who take a specific goal and apply to it all available tools in order to achieve it. “Effectually-minded” people, on the other hand, consider the tools and materials at their disposal, but use them as a springboard for envisioning what new directions might be possible. Burkeman offers some examples:

The effectualists include the cook who scours the fridge for leftover ingredients; the chemist who figured out that the insufficiently sticky glue he had developed could be used to create the Post-it note; or the unhappy lawyer who realises that her spare-time photography hobby, for which she already possesses the skills and the equipment, could be turned into a job. One foundation of effectuation is the “bird in hand” principle: “Start with your means. Don’t wait for the perfect opportunity. Start taking action, based on what you have readily available: what you are, what you know and who you know.” A second is the “principle of affordable loss”: Don’t be guided by thoughts of how wonderful the rewards might be if you were spectacularly successful at any given next step. Instead — and there are distinct echoes, here, of the Stoic focus on the worst-case scenario — ask how big the loss would be if you failed. So long as it would be tolerable, that’s all you need to know. Take that next step, and see what happens.

In other words, “imagine immensities, don’t compromise, and don’t waste time.”

Burkeman, who cites Martha Nussbaum’s famous words on uncertainty as a prerequisite for good-personhood, puts it beautifully:

Uncertainty is where things happen. It is where the opportunities — for success, for happiness, for really living — are waiting.

The Antidote is a wonderful read in its entirety, existentially necessary in our age of constant striving after concrete results and absolute assurances. Complement it with Alan Watts on the wisdom of insecurity.

Public domain photographs via Flickr Commons / The Library of Congress