Why uncertainty has become so frightening to a generation searching for a vocation.
By Jill Szoo Wilson
Part 3 of a series on vocation, giftedness, and meaningful work. Click below for the previous essays:
Vocation Is a Conversation (Part 1)
Nothing Good is Ever Wasted (Part 2)
Every semester, I meet students who believe there is a correct answer to a question that has no answer key. They worry that choosing the wrong major, accepting the wrong internship, or moving to the wrong city will permanently derail the life they were meant to live. They are not simply hoping to make a wise decision. They are hoping to eliminate uncertainty altogether.
In the earlier essays in this series, I argued that this anxiety reflects a misunderstanding of vocation. We have inherited the modern assumption that meaningful lives emerge from identifying one ideal career, fully formed and waiting to be discovered. Increasingly, however, I have come to think something deeper is also at work. Long before these students ever chose a major, many were growing up in environments that gave them fewer opportunities to practice uncertainty itself.
Jonathan Haidt’s research offers a helpful framework. In The Anxious Generation, he argues that childhood shifted dramatically during the early 2010s as unsupervised play gave way to smartphones and constant adult oversight. The result was not simply more screen time. There were fewer opportunities to negotiate conflict, tolerate boredom, solve problems independently, and recover from ordinary failure. Childhood gradually became safer in many visible ways while becoming less effective at cultivating resilience in invisible ones.
Read alongside what many educators are observing, Haidt’s work helps explain an increasingly familiar pattern. In The Coddling of the American Mind, Haidt and Greg Lukianoff describe what they call safetyism: the tendency to interpret emotional discomfort as danger rather than as an ordinary part of life. It is not difficult to imagine vocational uncertainty being interpreted through the same lens.
Ambiguity, after all, feels remarkably similar to danger when uncertainty itself has rarely been practiced.
Jean Twenge’s research points toward a related pattern. Her work documents delayed milestones of independence, from driving and dating to living alone, alongside rising levels of anxiety and caution. Read together, Haidt and Twenge describe a generation that has often had fewer opportunities to build confidence through ordinary risk. The consequences extend well beyond childhood. They shape the way many young adults encounter work, relationships, and the future itself.
Yet uncertainty is not simply an obstacle to vocation. It may be one of its necessary conditions.
If life arrived with perfect clarity, we would have little reason to experiment, adapt, or discover capacities we never knew we possessed. We would choose once and simply execute the plan. But that is not how meaningful lives unfold. They unfold through countless small decisions, unexpected detours, closed doors, surprising opportunities, and responsibilities we could never have anticipated when we were eighteen years old. The uncertainty we often resist is also the environment in which wisdom grows.
In retrospect, few people describe their lives as the fulfillment of a carefully executed blueprint. More often, they describe a series of moments that only later reveal their connection to one another. The conversation between our gifts rarely reveals itself in advance. It becomes audible only after years of faithful attention.
The pattern appears repeatedly in classrooms and advising offices alike.
Students frequently ask whether there is some reliable way to know, in advance, that they are making the right choice. They hope there is a test that can reveal whether a career path will ultimately prove meaningful before they commit to it. The realization that no such test exists rarely brings relief. More often, it creates a quiet crisis.
They came expecting a map. What they are given instead is a compass.
A map promises certainty. A compass offers direction, but it still requires judgment, patience, and the willingness to walk before the destination becomes visible. The longer I teach, the more convinced I become that vocation resembles the second far more than the first.
None of this makes students’ anxiety less real, nor does it make them responsible for the conditions that helped produce it. It does suggest, however, that vocational guidance now involves more than helping people identify their strengths or explore possible careers. It increasingly requires helping them cultivate the resilience to remain inside uncertainty without mistaking it for failure.
Perhaps that is one of uncertainty’s forgotten purposes. It is not merely the space between decisions. It is the place where character matures, wisdom deepens, and vocation slowly learns its own voice.
The conversation between a person’s gifts—the conversation this series keeps returning to—cannot happen while every unanswered question feels like a verdict. It unfolds only when we become patient enough to trust that clarity often arrives not before the journey begins, but because we were willing to walk it.
Jill Szoo Wilson 