I picked up Scott Galloway's The Algebra of Wealth expecting the usual bruising honesty he's known for, the kind of book that tells you things about money and ambition you'd rather not hear (or wish you had decades ago). And it delivered. What stuck with me wasn't a revelation; it was something closer to embarrassment.
Most of what Galloway lays out, I already knew. Save early, diversify, avoid debt that doesn't build something, don't confuse a good year with a good decade. Some of it was new information, but not all. But what surprised me when I finished it was how much distance there can be between knowing something and actually operating from it. I'd read entire chapters nodding along, thinking yes, obviously, and then catching myself wondering when I'd last actually done the thing I was nodding at.
That feeling followed me straight into our last leadership quarterly. Typically it's planned as a strategy session, where you talk about where the business is headed and what bets to make next. Instead, we spent almost the entire day on things that, on paper, our team should have already had locked down. And Jay was dreading it.
We reset expectations that had shifted without anyone deciding to shift them. We talked through how AI was changing the actual shape of people's jobs, not in the abstract, but in the specific tasks that had crept into or out of someone's role over the past year. We looked at meeting structures that had multiplied past the point of usefulness. We talked about tool creep, the slow accumulation of platforms and dashboards that made sense one at a time and had become, together, a mess nobody signed up for. We walked through client meeting processes, pre and post, and realized half the room had a different understanding of the output. None of this was glamorous. All of it needed to happen.
Nobody in that room was new or careless. This is an experienced team that runs a real agency well. And we still needed a full day just to get back to fundamentals that, by any reasonable measure, we already knew.
The easy explanation is that people get lazy or distracted, that the basics slip because someone stopped paying attention. I don't think that's what happened, and I don't think it's usually what happens anywhere. The basics didn't get abandoned. They got buried.
Every year StringCan grows, we add something. A new tool, a new service line, a new way of structuring client work, a new hire who does things slightly differently than the person before them. Each addition makes sense on its own. But complexity doesn't announce itself. It gathers in the gaps between decisions, and eventually the simple, obvious things that used to run on autopilot need someone to consciously reset them.
That's a different problem than the one people usually diagnose. If you think the basics slipped due to neglect, the fix is a lecture on discipline. If you understand the basics get buried by growth itself, the fix looks more like maintenance. You build in time to go back and dig them out, on purpose, on a schedule, before the mess gets expensive.
I've stopped thinking of days like that quarterly as a sign something went wrong. They're closer to what a growing company owes itself. The size of the reset isn't proof that we lost the plot. It's proof that we've been building enough for the basics to need re-excavating.
I'll probably be having some version of this same conversation again in a year, and probably the year after that. Not because we didn't learn the lesson the first time; in fact, it's because growth keeps adding layers, and every layer buries something that used to be obvious. The goal was never to fix the basics once and be done. It's to know they'll need digging out again, and to make peace with doing that work every time we grow enough to need it.
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