Teach Them to Be Shiftless Wanderers
July 23, 2025 – I have about a dozen reasons why my business is called The Shiftless Wanderer. Over and over, life teaches me that while we can—and should—set intentions and make plans, we must also hold them lightly. Because life turns on a dime. The best laid schemes of mice and men go aft astray, writes Robert Burns. A broken leg. An unplanned pregnancy. A cancer diagnosis. A chance encounter that leads to love—or to loss.
One of the hardest lessons many of us must learn is that control is mostly an illusion. We have far less of it than we think. This truth is especially important for those who work with, support, and advise teenagers. The pressure teens feel at the end of high school is enormous. They’re told they must make decisions that will determine the course of the rest of their lives—and it’s paralyzing. The irony? Every day we make decisions that shape our futures—we just don’t realize it.
What our adolescents need is a new framework, one that honors both planning and the inevitable chaos of living. A way to navigate between being goal-oriented and shiftlessly wandering. But first, we must learn this for ourselves.
Decision-making, after all, is not just about collecting information, assessing options, and being pragmatic. It’s also about surrender. Sometimes we simply throw our hands in the air and make a choice—even without knowing what comes next. Because we never fully know. How many times have you woken up in the morning only to have your world turned upside down—or redeemed—by nightfall?
We live in a time of deep uncertainty. Every day the news seems to bring another sign that the world as we know it—especially here in the United States—is unraveling. Never did I imagine I’d witness the unraveling of one of the world’s most iconic democracies. The world I say goodnight to is almost never the same one I woke up in.
And when change comes so quickly—with mercurial turns, destabilizing shocks, and heart-dropping tremors—it’s easy to feel disoriented, untethered, lost.
But this is life. Life is deeply personal, and also undeniably historical. Our lives are at once autobiographical and epochal.
That’s why we need to have different conversations with our young people. Conversations that go beyond goal-setting and achievement. Because, in the end, life is about something else entirely.
It’s about the Meander—the winding journey from our first breath to our last. It’s about learning to ask questions that don’t have answers. It’s about seeking meaning. Paying attention to the ways the world speaks to us. Noticing what crosses our path—and how we are changed by it.
The anxiety so many teenagers feel about making the "wrong" decision is both understandable and misguided. It’s unnecessary. It’s unhelpful. And it’s deeply human.
My work—the calling—is to help both adolescents and those who serve them learn how to be shiftless wanderers. To trust the compass of the gut, the heart, intuition, and the wild hands flung wide open to the world. To follow, like the Fool of the tarot, with courage, lightness, and animal wisdom. And to know that in doing so, we will arrive exactly where we are meant to be—today, tomorrow, and beyond.
That is a life well-lived.
In the end, we don’t wander because we are lost. We wander because that is the nature of life itself: uncertain, nonlinear, and beautifully uncharted. And so we learn to walk with intention, yes—but also with openness. With reverence for the detours, the unexpected turns, and the roads that disappear beneath our feet.
We may begin with a map, but sooner or later, we outgrow it.
The poet Diane di Prima captures this truth with spare grace. Her words are a reminder that the journey is the point—and that even when the map is gone, the direction is still ours to choose.
SECRET
you take
whatever direction you take.
Not out of indifference
or nonchalance.
You love the maps.
Tho they lied
they got you here.
MORE SECRET
perhaps you dreamed
the maps. perhaps you
burned them. Anyway
they’re not here.
And north is everywhere.
~ Diane Di Prima