Why generalists are underestimated — and why that’s a mistake
How to talk about your career when it doesn’t fit into a neat little box
How to use range as your superpower
🔧 The Resume That Doesn’t Fit in a Box
This is one of the most common things I hear from my clients:
"How do I pitch myself when I know how to do a lot of different things?"
This hits for me SO HARD. I've been in the same boat. I started my career in private equity and affordable housing. I could underwrite a real estate deal in my sleep, build investment models, and speak the language of analysts (aka finance bros...) fluently.
Then I became a founder — and learned everything else.
Product development. Supply chain. Packaging. Marketing. Legal. Customer service. Bookkeeping. Content creation. You name it.
Suddenly, I wasn’t “just” one thing anymore. I was everything.
And when I tried to re-enter the job market after shutting down my first business? I realized I had become the person recruiters didn’t know where to put. Too broad. Too experienced. Too…hard to categorize. Tonnnnns of interviews, and hardly offers to follow.
While I was a super interesting and dynamic interview candidate, I had become something many companies didn’t know how to evaluate: a generalist.
🫣 The World Wants Specialists...Until They Don’t
Here's what no one tells you:
Generalists are the ones who thrive when things fall apart.
We're the ones who step in when plans go sideways, when teams are in transition, or when there's a brand to rebuild or a new challenge no one else wants to tackle.
In today’s market — with layoffs, pivots, and companies trying to do more with less — the ability to wear multiple hats isn’t just helpful. It’s a survival skill.
Generalists often worry about how to tell their whole career story in 60 seconds — but that’s the lens.
You’re not just a collection of past roles. You’re someone who solves problems. And the best way to show that? Tell the part of your story that solves the problem in the room.
When I’m talking to a founder, I lead with my founder experience. When I’m talking to a strategist, I talk about systems and ops. When I’m talking to a finance exec, I pull out my analyst roots.
When I’m pitching myself to a new client?
I’m a chameleon. I showcase my strongest asset in real time — my ability to adapt, improvise, and create value no matter the situation.
You’re not meant to tell your whole story every time. You’re meant to read the room.
That’s what makes generalists powerful — we can meet people where they are and speak their language, without losing our own.
Reminder: the way you tell your story can be a strategy.
💬 Your Challenge This Week
🎭 What parts of your story are you underplaying — or over-explaining? 🪞 How do you want to be known right now? 🛠️ What version of your story will land best in the rooms you’re trying to enter?
🤝 Want to Sharpen Your Positioning?
If your career looks like a mosaic — not a ladder — I see you.
I work with founders, execs, and creatives who’ve done a little bit of everything, and need help making it make sense.
In just one Power Session, we’ll:
🧩 Rework your narrative so it reflects your actual depth
🛠️ Clarify your positioning for the rooms you’re walking into
🗣️ Build confidence in how you talk about your experience
This is strategy, not fluff. It’s how you go from “I’ve done a little of everything” to “Here’s exactly why I’m the one for this.”
If your story doesn’t fit in a box, don’t pitch it like it should — let’s rework it so it lands in the right rooms.
