Somewhere right now, a marketing manager is muting one virtual meeting to sit quietly through another. She’s not slacking off. She’s job stacking – holding down two full-time roles at once, both paying full salary, neither one aware the other exists. A few years ago this would have sounded like fraud. Today it’s common enough to have its own vocabulary, its own subreddit, and its own acronym: OE, for overemployed.
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Your turnover dashboard looks great this quarter. Nobody quit. Nobody got poached by a competitor with a nicer parking lot. HR isn’t scrambling to backfill three roles before the holidays hit. By every traditional metric, retention is a win. You might think it’s time for some job hugging… but that’s not quite the same thing as team high-fives. And if you aren’t sure what it is, it’s time to dig in.
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There is a number that has quietly run a lot of hiring decisions for a long time. Not a budget number. Not a productivity metric. Just a headcount. How many people are on the team. Are there vacant cubicles? Whether the org chart looks the way the org chart was designed to look – it becomes a headcount trap.
It’s a reasonable thing to track. It becomes a problem when it starts standing in for something it was never designed to measure: whether the business actually has the capability it needs to do what it’s trying to do.
Those are different things. And the gap between them has gotten wider.
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Here is a question worth sitting with for a moment: when a business stalls, what actually went wrong?
The most common answers tend to involve the usual suspects – cash flow, market timing, leadership. And sure, those things matter. But there’s a subtler failure mode that doesn’t make the autopsy report as often as it should. It’s not that the talent didn’t exist. It’s that you didn’t have access to expertise – the right expertise – when you needed it most.
That’s a meaningful distinction. And once you see it, you can’t unsee it.
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A week before his birthday, Nathan sat down to enjoy breakfast and nonchalantly mentioned, “I really like the turtles.”
That was it. That was his whole story. It wasn’t a masterclass in project scoping for freelancers, but it was his proclamation for the day.
To be fair, he’s not quite ten years old and was about to scarf down a short stack of pancakes before running to catch the bus to school. You can’t really hold the quality of his project brief against him.
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Everyone has that aunt. You know the one. She still has a rotary phone hanging on her kitchen wall – not ironically, not as décor, just because it works. And right next to it, a notepad. Notes from long friendly phone conversations. Who she should call back. Errands she needs to run. People she wants to send a letter – yes, a letter, with an envelope and a stamp. Everything written down, orderly, a list with no real order, but crossed off when done. She’s not particularly tech-savvy. She’s not type-A. She just figured out a long time ago that a good day doesn’t happen on its own. It has to be organized into existence.
She has never worked remotely. She has never managed a distributed team. But if she had, she would have been very good at it. Not that she would tell you so, you just know it.
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It’s Tuesday evening, and your actual work is waiting. The kind that has your name on it, the kind that moves things forward. But instead of doing that work, you’re rewriting a job description for a freelance project manager you need next month. You’ve already rewritten it twice. You’re not sure it’s right. You post it anyway, to three different places, because that’s what the freelance hiring process has become: yours to manage, yours to run, yours to finish when everything’s done. So you do.
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I’m betting there is a pot of coffee in your break room right now.
Maybe it is fresh. Maybe it has been sitting on the burner since before the morning standup and some well-intentioned co-worker keeps meaning to make a new pot but the day keeps happening. Either way, it’s there. It’s always there. Because that is what coffee does – it’s reliable. It fuels the team; it absorbs whatever the morning throws at it – but it also gets burned sometimes and overflows other times. Frequently, it just ends up empty.
Your core team is that coffee. Not because they grind – although I’m sure they do – but because they’re there. They’re showing up day after day.
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There’s a specific kind of exhaustion that sets in at week five of any project that was planned – and budgeted – for three. It’s not dramatic. It doesn’t announce itself. It just settles in quietly – in the fourth rescheduled deadline, the apologetic client email you draft and redraft, the Sunday afternoon you spend doing the work that Friday afternoon was supposed to hold. You’re not failing. You’re just running a marathon that started as a sprint, but kept getting longer while you continued running it – and doing it without the freelance talent support that could have made all the difference.
Most people push through. They redistribute the load, lean into the team, ask too much of the people who can least afford to give more, and eventually deliver something that’s good enough but not what it was supposed to be. Then they take a breath, declare it a win, and quietly file the whole experience under “that was rough” – without ever stopping to ask why it had to be rough in the first place.
That question, “why?” is worth asking. Because the answer, almost every time, is the same: there wasn’t enough flexible talent support in the room when the walls started closing in.
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There’s a particular kind of chaos that sets in around day three of managing a remotely distributed team.
You ping your designer in Istanbul at 8 AM your time. She’s already wrapped up for the day. Your developer in Portland won’t be online for another four hours. Your content strategist in Austin just sent eleven voice memos – all of them important, none of them short. And you’re sitting there, the supposed orchestrator of this whole operation, wondering how anyone gets anything done when everyone’s clocks are pointing in different directions.
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