10 Years, One Company

I never thought of myself as a "company man." Isn't that a term from the '60s, back when pension plans and the 9-to-5 were still revolutionary ideas? Maybe I've just watched too many episodes of Mad Men. I remember working at Jamba Juice in high school for about six months and thinking that was an eternity. Then I entered the tech world, where the conventional wisdom (ironic considering wisdom usually implies a long time horizon of knowledge) was to move as often as possible, as quickly as possible. Always searching for the next opportunity to climb the ladder, inflate your title, or at the very least, land somewhere with a more impressive logo on your LinkedIn. I tried that mindset on for a minute. It didn't fit. Most businesses move slower than anyone will admit in a job interview. It takes years, sometimes a decade, to build a culture that actually empowers designers to make impactful decisions without twelve layers of approval. Some companies never get there at all. And some designers spend entire careers watching their best work die in a backlog, never knowing what it could've been. Meanwhile, the advice keeps coming: stay hungry, keep moving, don't get too comfortable. I disagree with almost all of that. Here's what I've learned from staying in one place long enough to see my own work grow up.

With time comes: History and context Sure, you can learn history by reading the docs. The company wiki, the founding story, the "About" page. But really understanding what that history means, internalizing it, takes something that can't be downloaded. It takes time. I've heard the story of our founder organizing the New York City Veterans Parade to honor Vietnam veterans probably a hundred times. But somewhere along the way, I stopped just hearing it and started feeling it. And then I got to attend the parade myself, years into my time at the company, and the whole thing landed differently because I understood the context it came from. That's not something AI can replicate, and it's not something you can shortcut by reading faster. Those human connections accumulate slowly, and they quietly become the foundation of everything else you do. When I'm designing something for our members, I'm not starting from a user persona. I'm starting from years of being in rooms with the people who built this thing and the people it's built for.

With time comes: Status and respect There's a difference between learning the history and becoming part of it. The second one is where things get interesting. When you're new somewhere, you're expected to perform from day one. And that's fair. Every company needs to know what they're working with. But over time, something shifts. You've outlived enough reorgs. You've been around through the wins and the hard years. You've shown that you can be counted on when it matters, and you've risen above your own past mistakes. If you're doing anything interesting, you definitely have some of those. With that comes something that's hard to put a title on. It's a kind of internal credibility that doesn't show up in your job description. People stop second-guessing your instincts because they've watched those instincts play out. You become part of the institutional memory. New team members come to you to understand how things work and why they are the way they are. It's a little bit like building a character in a long story. The longer you're in it, the richer the character gets. And with that depth comes real clout. Not the performative kind, but the kind that gives you genuine flexibility, independence, and the ability to actually move things.

With time comes: Trust and creative latitude This is the one nobody talks about enough. Early in any design role, you're proving yourself on every project. Every decision needs a rationale. Every choice needs a slide. That's not a criticism, it's just how trust is built. But here's the thing: once you've built it, the whole dynamic changes. You stop spending half your energy on justification and start spending all of it on the actual work. At WeSalute, I've had the privilege of going from "here's my reasoning for this font choice" to "I think we should rebrand the entire company." And they let me. Not because I asked nicely, but because we'd spent years building the kind of relationship where they knew what I was capable of and trusted me to see it through. That's rare. Most designers I know are talented enough to do extraordinary work. They just never get the room to do it. They're fighting for approval on things that should be reflexive. Creative latitude isn't a perk. It's the environment in which great work actually happens. And you don't get it from a job offer. You earn it slowly, over time, in the same place, with the same people.

I'm not saying everyone should stay at one company for a decade. The right move depends on the company, the mission, and whether the people around you are the kind you want to grow with. For me, all three of those things lined up in a way I couldn't walk away from. But I do think the "always be looking" mindset has a hidden cost that nobody talks about: you never get deep enough to find out what you're actually capable of. You're always starting over. Always proving yourself from square one. Always inheriting someone else's mess without enough context to clean it up right. I'd rather stay long enough to make the mess, own it, fix it, and look back on it with some combination of pride and hard-won wisdom. That's the job. And ten years in, I'm still glad it's mine.