You might need to specialize out of your generalist role
Feeling stuck in your current ops role?
👋 Hey there, remember me? It’s been a while. My son’s sleep regression collided with me running Fundraising School this year, and my well-planned writing cadence didn’t survive the storm. But, hey, it’s better late than never, so here we go.
Every now and then I talk with my friends in operations, and the inevitable question of being a little bit stuck creeps up. It’s common in all careers, but operations in particular tends to suck you in and it might feel like career progression is just not in the cards.
Boo, wrong. Let’s get you unstuck.
The two traps of generalist careers
#1: The utility player
You’re too good at too many things, even things that people do not know need to get done. You quietly keep the company running, sometimes you do three people’s job at once. Especially common in very small teams. Replacing you feels impossible. Which means your company is not incentivized to promote you, because then who’d do your job?
#2: The jack of all trades
The other common trap is the jack of all trades. And it’s not a bad start. You can handle a bit of everything — finance, people, sales, customer ops. But when it’s time for your next role, you’re often up against specialists who’ve gone deeper, and they win with a clear story.
The way out: become T-shaped
I believe there is a way out of the traps, and it is becoming T-shaped. It’s a borrowed idea from Jason Yip, a T-shaped operator has depth in one discipline (the vertical bar) and working fluency across many (the horizontal bar). In reality, it’s likely you have more than one vertical over your career, but as the author noted, T-shaped is a better analogy than M-shaped or comb-shaped.
Just like you wouldn’t want to have a stock portfolio with a single stock in it (that’s a very risky investment strategy) you shouldn’t have a skills portfolio with only one specialty. So, pardon the finance analogy, a T-shaped personality is what will hedge your career risk by combining generalist capabilities and expertise in particular areas.
Depending on where you go deep, your end game might look in different ways:
CFO, if your vertical is finance, FP&A, and metrics
Chief People Officer, if it’s people ops, culture, and talent retention
Chief of Staff, if your strength is strategy and C-suite partnership
COO, if you’re a strong systems thinker
VC or Advisor, if you’ve built strong pattern recognition and finance acumen
Founder, if you want to do all of the above AND get the kick out of building things
So, my take is simple here. If you feel stuck in your current operations role, you might need to start specializing out of your generalist seat.
That’s it for today, thank you for reading.
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