The Stretch

Monday morning. I open my calendar and count the empty slots. There are two, and one of them is lunch.

There’s a board request from Friday that needs a response by noon. A team member flagged something last week that I know is really a conversation, not a Teams message. One campaign shoot needs a decision on direction. And I promised someone I’d evaluate a White Paper — a promise I made in that dangerous fifteen minutes of optimism at the end of the previous week.

This is the stretch. Not burnout — I’ve felt that and this isn’t it. The stretch is the feeling that you don’t have enough surface area. Every responsibility is reasonable on its own. Taken together, they form a shape that doesn’t fit inside a single person’s week. Somewhere around the third calendar review, the specialist in me whispers: I could just go deep on one thing and it would be a good day. But that’s not the job anymore.

Pressure from both floors

The board pushes work down. This isn’t unreasonable — that’s the function of a board. But the requests arrive without awareness of existing load, and each one carries implicit urgency simply by virtue of where it came from. Saying “not this week” requires more trust than most professional relationships have built.

Meanwhile, the team needs me present. Not as a task-assigner — they know what to do. They need an obstacle-remover, a context-giver, sometimes a shield. When a stakeholder changes scope mid-project, someone has to absorb that hit before it reaches the people doing the work.

The middle manager is a translator. Board ambiguity becomes team clarity. Team concerns become board language. Both directions are lossy. Nuance disappears in each conversion, and the translator is responsible for what gets lost.

I’ll be honest: the downward part comes more naturally. Coaching is adjacent to doing — I can feel the work through it. Upward management is more foreign. It requires a different kind of performance, one I’m still learning to deliver without resentment. And my own work — the strategic thinking, the operational decisions that don’t belong to anyone else — has to fit in the cracks between translations.

Ten specialists, one fragile machine

Marketing used to be broader. A team member could cover for a colleague on vacation. The tools overlapped, the skills were portable. That’s no longer the case. My team of ten occupies ten narrow lanes, each with its own platforms, metrics, and specialized knowledge. One person runs paid search and analytics. Another does lead nurturing and automation. A third owns campaigns. Almost no overlap.

This works. Output quality is higher than it was when everyone was a generalist. But it creates fragility. When someone is on vacation, their function pauses. When someone leaves, their function collapses until a replacement is hired and onboarded — a process that takes months in specialized roles.

The manager becomes the backup generalist. Not the best at any lane, but surface-level literate in all of them. Enough to keep things moving, not enough to do them well. Here’s the thing I don’t often admit: this is the part I secretly enjoy. Jumping into a channel, solving a concrete problem, shipping something tangible. The specialist in me calls this “real work.” The manager in me knows it’s a trap — every hour I spend doing is an hour I’m not directing.

The career oscillation happens in miniature. Within a single week, I swing between doing and directing, and each mode makes the other feel like a compromise.

The firehose

New tools arrive daily. New platforms. New techniques. New trends with new acronyms that will be obsolete in eighteen months. AI alone has introduced a new “should I be doing this differently?” every few months for the past two years, and the pace is increasing.

This produces a specific kind of inadequacy. Not incompetence — I’m not bad at the job. But the job keeps expanding faster than anyone can track. A specialist can go deep on one new development and come back with a real opinion. A manager must triage which developments are worth the team’s attention, without having time to properly evaluate any of them.

The tinkerer in me wants to explore every one. The manager knows that exploration time is a luxury the calendar won’t grant.

Finding the seams

I don’t have solutions. I have directions — things I’m trying, things I’m thinking about. The difference matters.

Cross-training. If specialization creates fragility, overlap reduces it. I’m trying to build T-shaped¹ capabilities in the team — deep in one area, functional in an adjacent one. It’s hard in practice. People resist leaving their lane, partly from preference, partly because there’s no time. But the alternative is a team that breaks every time someone takes a week off.

Protecting depth. I block time for deep work — my own and the team’s. This sounds like time management advice, but it’s actually about boundary-setting with the board. It means actively declining or deferring ad-hoc requests, which requires trust that takes years to build and seconds to lose.

Naming the triage. Instead of feeling guilty about shallow evaluations of new tools and trends, I’m trying to make the triage itself a deliberate practice. “We’re choosing to ignore this for now.” Saying no as a stated strategy rather than an unspoken default. It doesn’t remove the guilt entirely, but it distributes it.

Embracing the oscillation. This one is harder to explain. I’ve spent my career swinging between specialist and manager roles — a few years in each, back and forth. For a long time I read this as indecision. Now I’m less sure. The manager who can jump into the work has a kind of credibility and situational awareness that a pure delegator doesn’t. The specialist who has managed understands the system around the work, not just the work itself. Maybe the swing is a feature.

None of these resolve the stretch. They’re pressure valves, not cures. But pressure valves are the difference between a system that holds and one that doesn’t.

The middle is a place

Middle management has always been a compression layer — pressure from above, pressure from below, and the expectation that you’ll absorb both without passing the distortion along. That compression has intensified. Specialization means more things to understand. The pace of change means less time to understand them. The middle got narrower and the load got wider.

I’ve oscillated between specialist and manager roles my entire career, each cycle lasting a few years. If I’m honest, I’m happier as a specialist. The work is cleaner. The feedback is more direct. But the roles I grow into keep pulling me back to the middle. Some people sit at the boundary between doing and directing — not comfortably, but productively. I think I’m one of them.

Monday morning. Calendar still full. Pulls still there. But naming the forces — the vertical pressure, the fragility, the firehose, the oscillation — is a kind of map. Not a map with a route marked on it. Just a map. And there’s value in knowing the terrain, even when you can’t see a clear way through it.