ESPN’s Brian Windhorst recently described “aggressively middling” as both his strategy for winning the Hoop Collective’s win totals game and his career philosophy. It is a terrific phrase: honest, funny, and perfectly scalable.
Because aggressively middling is the perfect terminology for the 2020s: we are professionally sloppy; we are culturally uninteresting; we are aggressively middling.
Artificial Intelligence (AI) gives us instant competence, but not necessarily distinction or mastery One Stanford study found that Large Language Model (LLM)-generated answers were more homogeneous and positive than human ones: useful, polished, and suspiciously eager to circle back.The Atlantic recently asked whether this is the worst era of American pop culture and landed, sensibly, somewhere between “maybe” and “calm down, Grandpa.” Still, the warning is fair: unlimited content can create a lot of competent beige.
Work is not immune. More accurately, work perfectly epitomizes what it means to be aggressively middling. Many careers unfold in the broad middle of organizations, not the C-suite, not the mailroom, but the land of calendars, status decks, and meetings about better meetings. Gallup says managers account for 70 per cent of the variance in team engagement, while just 20 per cent of employees globally were engaged in 2025. That is less a talent problem than a daily-human-practices problem.
Relationships are wobbling, too. The World Health Organization (WHO) estimates that one in six people worldwide experiences loneliness. We have more ways to connect and more reasons to send “Sorry, just seeing this” three days later than in the History of civilizations.
Here is the hopeful bit: exceptional does not require a championship ring, a global following, or spectacular beard. It looks like exercising judgment instead of accepting the generated or curated average. Making the meeting useful. Giving clear feedback kindly. Calling your friend. Creating something only you would or could make. Noticing what others miss. Doing the small thing unusually well.
In an aggressively middling world, ordinary humans can become exceptional by practicing being more human. On purpose, every day.
