When Your Career Pool Drains: Building Portable Skills

When the Pool Drains: Why Your Best Career Move Might Disappear While You're Swimming in It

Michael Phelps's training pool in Baltimore stayed open for two decades. The typing pool — once the entry point for hundreds of thousands of American careers — disappeared in about fifteen years.

That gap is everything Angela Duckworth's new book Situated gets right about success, and the one uncomfortable thing it doesn't address directly enough for those of us who work in fields technology keeps disrupting.

I read Situated last week and immediately recognized the pattern. Duckworth dismantles the mythology of pure grit — the bootstrap individualism that says success is just determination plus talent. She's absolutely right that world-class performance requires world-class situations. Phelps had the coach, the teammates, the Olympic training center an hour from his house. Grit got him in the water. The situation is what let that grit compound into 28 Olympic medals.

Then I got stuck on one question she doesn't spend much time on: What happens when the pool closes?

The Quiet Assumption Under Situational Agency

Duckworth calls it "situational agency" — the deliberate choice to place yourself in environments that amplify your effort. Find the great coach. Join the right team. Move to the city where your industry clusters. It's the difference between practicing alone in your basement and training at a world-class facility.

But there's an assumption baked into that framework, and it's a luxury assumption: the great situation you choose today will still be there tomorrow.

Phelps's pool stayed open for twenty years. That stability let his grit pay off. He could go deep. Specialize. Build expertise that compounded.

I don't work in swimming. I work in professional services — accounting, audit, technology advisory. And I've watched this movie enough times to know: in my world, the pool gets drained while people are still swimming laps.

The Pools That Disappeared

The typing pool didn't empty because the typists got lazy. It disappeared because WordPerfect, then Word, then email made the entire role structurally obsolete. You could be the grittiest, most situationally-aware typist in 1985 — positioned in the best secretarial pool at the best firm in the best city — and by 1995, your pool was a storage closet.

The junior tax analyst who spent three years mastering partnership K-1 forms found that expertise commoditized when software automated 80% of the work. The audit senior who built a career on sampling transactions watched that skill lose value when continuous auditing and data analytics made sampling feel quaint.

I'm not describing hypotheticals. I've advised clients through every one of these transitions. The people who struggled weren't the ones who lacked grit. They were the ones who picked a great pool, committed fully to it, and didn't notice when someone quietly started pulling the plug.

Disruption Is the Drain

Here's the uncomfortable pattern I've seen across four technology cycles: the better you get at swimming in one specific pool, the harder it becomes to notice the waterline dropping.

When I started in this industry, the path to partner was clear. You joined as an analyst. You built expertise in a specialty — tax, audit, M&A advisory. You went deep. The depth was the point. Firms rewarded vertical mastery.

That model assumed stability. It assumed the pool you chose at 23 would still be valuable at 33. For a long time, that was a safe bet.

Then software ate one specialty after another. Not all at once — that's not how disruption works. It starts at the edges. The most routine work gets automated first. Then the tools get better. Then what used to be "expert work" becomes "what the software does, plus judgment." Then the judgment piece gets smaller. Then someone realizes you don't need three people when you used to need eight.

The pool doesn't drain overnight. It drains slowly enough that the people swimming in it can convince themselves the waterline isn't actually dropping.

I watched a version of this play out with a client last year — a senior manager who'd spent 12 years building deep expertise in a specific compliance domain. Excellent work. Real mastery. The kind of situational agency Duckworth celebrates: she'd deliberately positioned herself in the best possible training ground for that specialty.

Then regulatory changes and new software combined to eliminate about 60% of the work. The pool didn't disappear. It just got a lot shallower, and a lot more crowded. Her expertise still mattered, but the leverage was gone. The firm needed two people doing that work, not seven.

She's fine — she saw it early and moved. But the ones who didn't? They're still in that pool, wondering why the career trajectory that used to be inevitable suddenly isn't.

The Skill That Outlasts the Pool

So here's the reframe: Situational agency isn't just about picking the right pool. It's about picking one you can leave.

The industrial economy rewarded depth. The knowledge economy still rewards depth, but only if you also maintain the peripheral vision to notice when your domain is getting disrupted, and the mobility to move before the waterline drops below your knees.

I've survived four technology disruption cycles in professional services — client/server, internet, mobile, now AI. The pattern repeats:

• Early stage: New technology creates new specialist roles. The pool is small but growing. Early adopters swim hard and get rewarded.

• Growth stage: The pool expands. Firms hire aggressively. Depth pays off. This is the golden era — usually lasts 5-10 years.

• Maturity stage: Tools get better. Work gets systematized. The pool is still full, but you need fewer people to do the same work.

• Disruption stage: Someone builds software, or offshore capacity, or an AI model that does 70% of what used to require expertise. The pool drains faster than people retrain.

The people who navigate this well aren't smarter or grittier. They just notice the pattern earlier. They build skills in one pool while keeping their head on a swivel for where the next pool is filling up.

But what do I know — I've only watched this movie four times.

The Uncomfortable Question

Here's what I'd add to Duckworth's framework, because I think the book is genuinely valuable: situational agency in a disrupted economy requires one more skill she doesn't name directly: the ability to walk away from a situation before it stops working.

That's psychologically hard. If you've spent five years positioning yourself in what you believed was the perfect pool — the right team, the right specialty, the right firm — admitting that the pool is draining feels like failure. It feels like you picked wrong.

You didn't pick wrong. The pool was great. Disruption doesn't care whether you picked the right pool. It drains them all eventually.

The typists weren't wrong to learn typing. The junior tax analysts weren't wrong to master K-1s. The audit seniors weren't wrong to build sampling expertise. Those were legitimately great pools when they chose them. The mistake was believing the pool would stay full long enough for the investment to fully pay off.

So the question isn't "How do I pick the perfect situation?" It's "How do I pick a great situation AND maintain the ability to recognize when it's time to leave?"

What to Do Monday Morning

I'm not saying don't specialize. I'm saying specialize with your eyes open.

Here's what I'd ask yourself — and if you manage people, what I'd want you asking about the people you're developing:

1. What's the half-life of your current expertise? If you stopped learning today, how long would your current skillset remain valuable? Five years? Ten? Two?

2. Are you building skills that transfer, or skills that only work in this specific pool? Domain expertise is valuable. But so is the ability to learn new domains quickly.

3. Do you know what the next pool looks like? You don't have to jump yet. But you should know where it's filling up.

4. Would you notice if your pool was draining? What's your signal? Client demand? Hiring patterns? The kind of work you're being asked to do? Don't wait until you're standing in an empty pool to start looking around.

The best career move I ever made wasn't picking the perfect specialty. It was learning to recognize when a great situation was becoming a good situation, and a good situation was becoming a trap.

Nobody gets fired the day the pool drains. You just wake up one day and realize you're standing in six inches of water, and everyone already left.

Your move: Look at your current role. If the waterline dropped 30% in the next two years, would you see it coming? And if you saw it coming, could you move?

Because grit still matters. Situational agency still matters. But in 2025, the pool you're swimming in has an expiration date — and you'd better know what it is.