The "Jack of All Trades" Trap: How I Turned My Biggest Weakness Into My Strongest Pitch
From Stammering to Strategic: Mastering Your Multi-Passionate Pitch
Dear reader,
"So... what exactly do you do?"
For years, this innocent question made my palms sweat and my mind race. I'd watch as specialists confidently declared "I'm a product manager" or "I'm a data analyst" while I stammered through a word salad that sounded like I was reading from a random job board.
"Well, I do social media management, but also project management, and I design websites, plus I write content, and sometimes I do brand strategy, oh and I can analyze data too..."
By the time I finished my rambling list, the person's eyes had glazed over. I could practically see them mentally filing me under "confused" or worse, "unfocused."
The breaking point came during a networking event last year. After delivering my usual chaotic explanation to a potential client, she smiled politely and said, "That's nice, but I need someone who specializes in what they do."
Ouch. Again.
That night, I went home and did what any reasonable person would do: I panic-googled "how to choose a specialization" while eating an entire pint of ice cream. Maybe it was time to finally pick a lane and stop this generalist nonsense.
But as I scrolled through advice about "niching down" and "becoming an expert," something felt fundamentally wrong. Choosing just one thing felt like asking me to cut off my own limbs. My diverse skills weren't a bug—they were a feature. I just sucked at explaining why.
The Epiphany in the Elevator
The shift happened during the most unlikely moment. Stuck in an elevator with a CEO during a power outage (because of course), we had fifteen minutes of forced conversation. When he asked the dreaded question, I almost launched into my usual spiral.
Instead, maybe it was the darkness or the mild claustrophobia; I said something different:
"I'm a creative generalist. I help businesses solve problems they can't quite categorise by connecting dots others don't even see are related."
Even in the dim emergency lighting, I could see his interest pique. "Tell me more."
So I did. I explained how I'd helped a client realise their conversion problem wasn't about their website design (as they thought) but about misalignment between their social media voice and their sales copy. How I'd spotted integration opportunities between systems that specialists viewing them in isolation had missed. How my broad perspective allowed me to translate between technical teams and creative teams who were talking past each other.
By the time the power returned, he'd asked for my card.
That fifteen-minute conversation taught me more about positioning my generalist value than years of networking events. The secret wasn't listing everything I could do—it was articulating the unique advantage of seeing across domains.
The Generalist Pitch Framework That Actually Works
After months of refining based on that elevator breakthrough, here's the framework I now use to articulate my generalist value:
The Problem-First Approach: Instead of leading with your skills, lead with the problems you solve. "I help growing businesses create cohesive customer experiences across all touchpoints" is infinitely more compelling than "I do marketing, design, and strategy."
The Connection Story: Share a specific example of how your diverse background allowed you to spot an opportunity or solution that specialists missed. This transforms "jack of all trades" into "strategic advantage".
The Integration Promise: Emphasise your ability to ensure different pieces work together. In our increasingly complex business world, integration is often more valuable than isolated expertise.
The Translation Skill: Highlight your ability to facilitate communication between specialists. This positions you as essential glue in any complex project.
Here's my current pitch in action:
"I'm a creative generalist who helps businesses achieve coherent growth by connecting the dots between strategy, operations, and customer experience. Last month, I helped a client increase conversions by 40% by spotting misalignments between their product development and marketing messages—something that became visible only by understanding both domains. I specialise in seeing the full picture and ensuring all pieces work together."
Notice what's missing? The laundry list of every skill I've ever acquired. Instead, I focus on the unique value that comes from my generalist perspective.
The Power of the Right Metaphor
One game-changer was finding the right metaphor for my work. Specialists are like laser beams—powerful, focused, and precise. Generalists are like floodlights—illuminating connections and context that focused beams might miss.
Both are essential. The key is knowing when you need which type of light.
I've used different metaphors depending on the audience:
For tech companies: "I'm like a systems architect for your business operations"
For creative agencies: "I'm a creative director who speaks fluent business"
For startups: "I'm your Swiss Army knife employee who can adapt as you scale"
The right metaphor instantly helps people understand not just what you do, but why it matters.
Your Pitch Challenge
This week, I challenge you to craft your own generalist pitch using this structure:
One sentence about the problems you solve (not the services you offer)
One specific example of how your diverse background created unique value
One clear statement about your specialization (yes, generalists can specialize—in integration, translation, or seeing connections)
Then, test it. Use it at your next networking opportunity, client call, or even casual conversation. Pay attention to the response. Do eyes glaze over, or do they light up with interest?
The goal isn't to hide your generalist nature or pretend to be something you're not. It's to articulate why being a generalist is exactly what makes you invaluable.
Today, when someone asks what I do, I no longer sweat. I smile and deliver my pitch with the confidence of someone who finally understands their own value. The reactions have transformed from polite confusion to genuine intrigue—and more importantly, to signed contracts.
Your diverse skills aren't a liability to minimise—they're a superpower to position strategically. You just need the right words to help others see what you've known all along.
Bye. For now,
Alexis