Part 2 of “The Long Way to Rppl: What Positive Culture Actually Looks Like” — a series on two decades in the creative industry, and what they taught me about building a company on purpose.
Landing at The Seventh Art as Digital Design Director felt like another one of those milestone moments — the kind I’d chase a few times over the course of my career. This wasn’t just a step up; it was a chance to join a genuinely high-end design team making the exact kind of material I’d dreamt about creating for years, in exactly the space I’d always been drawn to: the intersection of art, design, architecture, and business. By that point I’d learned how to listen to the people around me — junior designers, art directors, peers. What I hadn’t learned yet was what that same principle looked like when the person across the table wasn’t a junior designer at all, but the CEO of a global real estate development firm.
The Seventh Art specialized in high-end digital branding and UX/UI for real estate — the kind of work where the “client” isn’t a marketing manager three levels removed from the decision-maker, it’s the decision-maker. Over those years I found myself interfacing directly with leadership at Douglas Elliman, Corcoran Sunshine, Brown Harris Stevens, Vornado, Tishman Speyer, Rechler Equity Partners, SL Green, JLL, and a run of overseas developers. These weren’t people who needed to sit through a junior designer’s polite deference. They needed someone across the table with an actual point of view.
That was a different kind of pressure than anything I’d felt before. It would have been easy to read the power imbalance in that room and default to just telling powerful people what they wanted to hear. Say yes to the notes. Soften every recommendation. Let the biggest signature in the building make every call, whether or not it was the right one. That’s a version of “listening” that isn’t really listening at all — it’s just compliance dressed up as service.
I decided early on that wasn’t the version I wanted to practice. If I believed a direction was wrong for the brand, I said so — respectfully, with reasoning, but directly. Not because I thought I knew better than the people who’d built these companies. I didn’t. But I did know the craft, and I’d been hired for that expertise, not to be a mirror. Integrity in that context meant the same thing it had meant with a junior designer at Berry Creative: treating the person in front of you as someone worth being honest with, regardless of which direction the power in the room was pointing.
I remember one meeting in particular — a room full of C-levels, VPs of marketing, and half a dozen outside vendors, all circling a brochure cover that wasn’t working and nobody could say why. The conversation was stalling, everyone talking around the actual problem instead of at it. I could see what was missing: the cover needed texture and restraint, not another color or callout. I suggested a blind deboss pattern — subtle, tactile, no ink at all — and watched the room go quiet for a second before people started nodding. It was exactly what the piece needed. That meeting could have gone another twenty minutes in circles if I’d stayed quiet and waited to be asked.
What surprised me was how often that landed well. The CEOs and principals I worked with hadn’t gotten to where they were by surrounding themselves with people who only agreed with them. Most of them had plenty of that already. What they didn’t always have was someone who’d push back on a bad idea — or step into a stalled room — before it cost them something. I learned that real trust with powerful clients isn’t built by telling them what they want to hear — it’s built by being someone whose “yes” actually means something, because they know you’re capable of saying “I don’t think that’s right, and here’s why.”
That’s not a comfortable lesson to learn in real time. There were meetings where I said something a principal didn’t want to hear, and I sat with the discomfort of not knowing how it would land. A few times it didn’t land well in the moment. But over the course of a project — and over the years I spent at that company — the relationships that lasted, the ones that turned into repeat work and referrals, were almost always the ones where I’d been willing to be honest early, even when it would have been easier not to be.
I started to understand integrity differently because of those years. It’s not a values statement on a website. It’s not something you have because you believe you’re a good person. It’s a habit you build one uncomfortable conversation at a time — the choice, made over and over, to tell someone the truth about their brand, their product, their idea, even when they’re the one signing the check and you’re not. Especially then.
That principle didn’t stay confined to work with CEOs. It became how I thought about every relationship where there was an imbalance of power — with clients, later with my own team, eventually with the people I’d go into business with. Treating someone as an equal team member isn’t about pretending the power dynamic doesn’t exist. It’s about refusing to let it change whether you tell them the truth.
I carried that into the next chapter of my career, at a much bigger agency, running a much bigger team, with much bigger budgets and much more at stake if I got it wrong. That’s where the culture lessons I’d been collecting — listening to good ideas regardless of title, telling the truth regardless of power — would get tested at a scale I hadn’t experienced yet.
Next: building and running a 14-person creative department at Big Drop, and what it means to treat everyone on a team as an equal, not just the people you like working with.
