I spent three years of my life trying to be the world’s leading expert on a specific type of freight auditing software that no longer exists. It was 2014. I was working at a mid-sized logistics firm in Des Moines, making exactly $42,500 a year. I thought I was being smart. I thought if I knew every single quirk of this one Oracle NetSuite module, I would be unfireable. I spent 400 hours learning the internal logic of that system, documenting every bug, and becoming the ‘go-to guy’ for the warehouse team. I was proud of my niche. I was the specialist.
Then the company got bought by a larger firm in Chicago. The new owners didn’t use NetSuite. They used a proprietary system they’d built in-house. In a single Tuesday morning meeting, my entire ‘competitive advantage’ evaporated. I wasn’t an expert anymore. I was just a guy who knew a dead language. It felt like I’d spent years building a really intricate sandcastle right below the high-tide line. I was 26, and I realized I had no actual skills—just specific knowledge of a temporary tool. It was embarrassing. I remember sitting in my car in the parking lot, staring at a Chipotle burrito, and realizing I’d been sold a lie about ‘niche-ing down.’
The modern economy doesn’t actually want specialists, even though every job description asks for one. They want people who can bridge the gaps. They want the connective tissue. If you specialize too early, you aren’t becoming an expert; you’re just becoming a component. And components are easily replaced when the machine changes.
The T-shaped lie and why HR is wrong
You’ve probably heard the ‘T-shaped’ person speech. The idea is that you should have a broad base of knowledge but one deep vertical of expertise. I used to think this was gospel. I was completely wrong. In reality, that vertical bar is usually a trap. What happens when the industry moves two inches to the left? Your deep vertical is now a deep hole you’re standing in, while everyone else is walking on the surface.
I know people will disagree with this—especially the ‘career coaches’ on LinkedIn who make their living telling you to find your niche—but I honestly think specializing early is a form of intellectual cowardice. It’s a way to avoid the hard work of understanding how a whole business actually functions. It’s much easier to hide in a spreadsheet or a specific coding language than it is to understand why a customer is actually angry or how the marketing budget affects the shipping department.
Specialization is a bet that the world won’t change. That is a bad bet.
The data on why ‘General’ is a better title
I’m not just talking out of my ass here. A few years ago, I started tracking my own productivity and income more closely. I tracked 18 months of my billable hours and projects across three different roles. What I found was startling: 64% of my actual value—the stuff that got me raises or bonuses—came from tasks that were officially ‘outside my job description.’ It was the time I helped the sales team understand the technical limitations of our product, or the time I used a basic understanding of psychology to fix a rift in the operations team.
- Generalists are 3x more likely to be promoted to cross-functional leadership roles.
- Specialists in tech see their core skill set become obsolete every 3.5 years on average.
- The highest-paid ‘consultants’ are almost always people who can speak three ‘languages’ (e.g., Code, Finance, and Human).
What I mean is—actually, let me put it differently. Being a generalist isn’t about being mediocre at a lot of things. It’s about being the person who knows why the different departments hate each other and how to make them stop. That is a skill that never goes out of style. I’ve worked at companies like Zillow and small startups you’ve never heard of, and the story is always the same. The specialist gets the task; the generalist gets the project.
Anyway, I digress. The point is that the ‘depth’ everyone raves about is often just a fancy word for ‘rigidity.’
I hate Monday.com and the cult of the niche
This brings me to a mini-rant. I refuse to use Monday.com. I know, everyone loves it. It’s colorful, it’s got the little animations, and it’s supposed to ‘streamline’ everything. But to me, it’s a colorful prison for people who can’t think for themselves. It forces you into a specific way of working that rewards ‘completing tasks’ over ‘solving problems.’ It’s built for specialists who just want to check their little box and go home.
Specialization is for insects. Humans should be able to change a diaper, plan an invasion, butcher a hog, conn a ship, design a building, write a sonnet, balance accounts, build a wall, set a bone, comfort the dying, take orders, give orders, cooperate, act alone, solve equations, analyze a new problem, pitch manure, program a computer, cook a tasty meal, fight efficiently, die gallantly.
I’m not saying you need to butcher a hog (though that would be a cool weekend project), but if you can’t write a decent email and also understand a basic P&L statement, you are a liability. I’ve met ‘Senior SEO Specialists’ who don’t know how to sell a candy bar to a hungry person. It’s pathetic. I don’t trust anyone who has a ‘Master’s in Digital Marketing’ or some other hyper-specific nonsense. You’re better off reading three books on history and one on basic accounting.
Total lie. That’s what the specialist path is.
The connective tissue
My career looks like a mess on paper. I’ve done logistics, I’ve done project management, I’ve done ‘operations’ (whatever that means this week), and I write this blog. But that mess is my safety net. Because I didn’t specialize early, I have what I call ‘connective tissue.’ I can see the lines between the silos.
If you’re starting out, or if you’re five years in and feeling like you’re stuck in a narrow lane, my advice is simple: Stop trying to be the best at one thing. Try to be the 80th percentile at five things that usually don’t go together. Be the accountant who can write. Be the coder who understands supply chains. Be the designer who knows how to read a balance sheet.
I might be wrong about this, but I think the liberal arts degree—the thing everyone made fun of for twenty years—is actually making a comeback in a weird way. Not the specific ‘underwater basket weaving’ stuff, but the ability to think critically across different disciplines. In a world where AI can do the ‘specialist’ part of almost any job (and do it for free), the only thing left for us is the ‘generalist’ part. The part where we decide what’s worth doing in the first place.
It’s a trap to think you can hide in a niche forever. The tide always comes in eventually. I learned that in Des Moines with a cold burrito in my hand. I’m never going back to that.
Do you actually like what you do, or do you just like being the person who knows the answer? I’m still trying to figure that one out for myself.