Early in your career, the game is straightforward: work hard, develop your skills, deliver results. Technical excellence is the currency and it spends well. But at a certain point — usually somewhere around the time you start moving into leadership — the rules quietly shift. And if nobody told you they were shifting, you find out the hard way.
I found out the hard way.
When I was early in my career, like many young people, I didn’t like to rock the boat. I listened, stayed quiet in meetings, and knew I had to pay my dues before I’d earned the right to push back.
Then my confidence grew — and tipped into volatility. I became dominant because I thought that’s what surviving in corporate America required. If something didn’t make sense, I made sure everyone in the room knew that I knew. I’m not proud of it, but at that point in my career I made a few people cry with my unapologetic directness. It’s not personal, it’s just business became my mantra.
I thought I was playing to win. I didn’t realize I was playing the wrong game.
The moment that changed it came during a promotion cycle. I was asked to provide feedback for a colleague I believed was ready. The form had two sections: “strengths” and “areas for opportunity”. I filled in the strengths and left the second section blank.
A few days later, his manager called.
“I noticed you left a section blank. Can you fill it in?”
“I don’t see any areas of opportunity, so no.”
“I need it for his promo doc. I’d really appreciate it.”
“That’s just silly. I’ve worked with him for years and I don’t see a reason not to promote him.”
“Ashley — I know this is silly. You know this is silly. But sometimes you just gotta play the damn game.”
I went quiet.
My whole mid-career had been about pointing out what was broken, calling out injustice, being vocal about my disagreement. I believed that was integrity. What I hadn’t understood was that there’s a difference between being right and being effective — and that in leadership circles, the latter is often what moves things forward.
That conversation was the beginning of a different kind of education. Not the kind you get from skills or credentials, but the kind that comes from learning how rooms actually work. Who holds influence and why. How to challenge the status quo without making people defensive. How to be a calm presence instead of a disruptive one.
Looking back, I understand now why I skipped straight to volatility. I didn’t know the rules well enough to play them strategically, so I compensated with force. That’s not a character flaw — it’s what happens when you’re figuring out a game nobody explained to you while everyone around you seems to already know the rules.
For first-generation professionals, this is often the second gap — the one that shows up after you’ve already proven you can do the work. The first gap is information: knowing about equity, negotiation, how compensation actually works. The second gap is cultural fluency: understanding the unwritten rules of how leadership operates, how decisions really get made, and how to move within systems without losing yourself in them.
Nobody puts this in a job description. You absorb it growing up, or you figure it out in real time, usually after a few costly mistakes.
I don’t regret the volatility phase. It came from somewhere real — from passion, from having to fight to be heard, from operating in rooms where the rules weren’t written for people like me. But I wish I’d learned sooner that influence isn’t always about being the one who names the obvious. Sometimes it’s about patience, nuance, and knowing which battles are actually worth fighting.
Play the game strategically. Change the rules when you have the power to do so.
And if nobody told you the rules changed — now you know.
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