An All-Around Amateur
Why the shallow end is deeper than you think
TL;DR
Amateur-level engagement reignites the progress principle.
New skills keep the brain’s wiring pliable.
Visible incompetence builds humility and trust.
Prioritizing range over mastery can yield the richest outcomes.
Settling into the Shallow End
Not long ago I joined an introductory tennis clinic, naively confident that years of casual squash would translate. On my very first serve I swung clean through the air, ball totally untouched, while twenty strangers waited their turn behind me. It was a humbling experience.
Most of adult life conspires to keep us in the deep end of expertise. Once we have accrued a hard‑won set of abilities—negotiating M&A agreements, running a board meeting, balancing point and speed while steering a sailboat close-hauled—we tend to circle those particular waters for years, because it feels risky, even vaguely embarrassing, to thrash about in the beginner’s lane again. Yet the very people we admire for mastery often maintain a contrary habit of purposefully picking up unfamiliar pursuits. They accept the wobble, the awkwardness, and the smallness of their first attempts. The secret here is being aware (even subconsciously) that sustained excellence in one domain is nourished by periodic amateurism in others.
The Energy Hiding in Incompetence
The difference between comfort and vitality is stark: expertise wraps us in the former and amateurism jolts us with the latter. When we step into an introductory art class or our first low‑impact Peloton ride, the skill‑to‑challenge ratio resets to something slightly above our present capacity, and the effect can be enlivening. We’re likely to notice micro‑improvements from one session to the next, feel neurons firing in novel patterns, and, because the stakes are low, should be laughing at miscues that might have felt humiliating on more familiar turf. Psychologists sometimes call this the “progress principle”: visible, incremental gains release dopamine, which in turn fuels motivation. That loop, repeated often enough, spills over into professional arenas where plateaus are harder to perceive.
Neuroscience has a tidy phrase, experience‑dependent plasticity, for the brain’s penchant to re‑wire itself when confronted with fresh challenges. New motor sequences, vocabularies, or musical intervals coax dormant synapses into service. This process encourages fresh myelin (think of it as new insulation wrapped around busy electrical wires in the brain) so the result is a brain that adapts more quickly the next time novelty appears. Tennis is a textbook example with broad accessibility: public courts are plentiful, and a used racket can be found for less than the cost of a tank of gas. We do not need to pay for a country club membership to benefit from learning to hit with topspin; the mere act of coordinating footwork, swing mechanics, and strategic ball placement breaks our cognitive routines and plants seeds for future flexibility.
Humility as a Source of Credibility
Beginner moments also offer a social dividend of groundedness. Nothing brings hierarchy tumbling down faster than a shared struggle to keep a tennis rally alive. In those moments one’s title, résumé, and deal count fade behind the more immediate question of whether anyone can execute a clean backhand. The vulnerability required to be visibly bad at something breeds empathy: we remember how hard it is to learn, which in turn tempers our impatience when colleagues wrestle with a new model or an unfamiliar CRM workflow. Over time that humility becomes an under‑appreciated credential. People trust guidance delivered by someone who is comfortable admitting what they do not yet know.
By temperament and by schedule I have no intention of becoming a club champion or a certified sommelier, yet I try to keep a rotating series of modest explorations: Sunday morning tennis sessions, an intro‑to‑sailing series on Boston’s Charles River, and cookbooks so advanced that I struggle to decipher even the most basic recipes contained inside. Golf appears on the list precisely because it refuses to yield quickly. Every flushed 7‑iron is a reminder that progress often arrives disguised as repetition. The sport also rewards patience and punishes haste, a corrective force that every deal junkie occasionally needs. And while none of these pursuits has a KPI attached, each deposits a story, a new acquaintance, or a satisfying sense that last week’s version of me would struggle slightly more than today’s.
An Invitation to Drift
A common objection surfaces here: time is scarce, so why invest in skills that will never convert to expertise? The answer is that amateurism redefines return on investment. Instead of hunter‑gathering prestige, we cultivate range; instead of measuring output, we savor process. Try spending a couple dollars on an unfamiliar vegetable at the Saturday farmers market and dare yourself to turn it into dinner (perhaps best on an evening without dinner guests). Even a failed experiment pays out in self‑knowledge: we learn what bores us, thrills us, calms us, taxes us. Those data points sharpen future decisions about where to allocate the serious hours reserved for mastery.
Quit hunting prestige for a moment and gather a fresh first attempt instead. Pick a lane whose shallow end you have not yet waded into. Sign up for the neighborhood choir even if your voice cracks, audit that community college course on conversational Spanish, wander into the makerspace and let a teenager show you how to operate the laser cutter. You may discover a hidden aptitude; more likely you will discover a new friend, or a fresh metaphor to weave into Monday’s investment committee memo, or at the very least a party anecdote about the time you capsized a dinghy during man‑overboard drills.
So book one beginner slot. Whether that’s a dawn pottery wheel where wet clay coats your forearms or a twilight public‑court rally punctuated by the thwack of off‑center strings. The shallow end is always open.