Why Do We Do It This Way? Making Work Work, CEO Series Vol. 14

I don't consider myself much of a rule follower. I never have. In fact, it's probably getting worse with age. Not because I enjoy breaking rules (okay, I do a little bit). I've always been more interested in improving systems than preserving them. I try to always ask myself why we do things a certain way and if it’s the best way.

Why does every company need a headquarters?
Why do executives get access to daylight while everyone else sits in rows of cubicles?
Why do we measure professional commitment by commute time?
Why does every workspace have to look the same when the work itself changes by the hour?

As the de facto head of product at Workbar, these questions don't just cross my mind and disappear. They shape how I think about our expansion strategy, design decisions, and everything in between. It’s also one of the reasons I've always loved building a business in Boston.

As we celebrate America's 250th birthday, I've been thinking about how much of Boston's identity is rooted in questioning convention. The people who changed history here didn't rebel just for the sake of it. They looked at a system that no longer worked for them and had the courage to imagine something better.

Boston has been doing that ever since. Today we're home to companies changing healthcare, robotics, AI, higher education, and life sciences. Walk through Kendall Square, the Seaport, or Back Bay, and you'll find people challenging assumptions every single day. Innovation has always been part of Boston's DNA.

I think the workplace deserves that same mindset.

For more than a century, we built work around what was practical at the time. Everyone needed to be in one place because that's where the files were, the phones were, and the meetings happened. That made perfect sense. But we don't work that way anymore. We all carry the same powerful computer in our pocket. We collaborate across cities and time zones. We can jump on a video call from almost anywhere. Work itself has changed dramatically.

The reality is that real estate influences culture, but it doesn't create it.

I cringe when I hear someone say they need an office "for culture." I understand why people say it. For decades, the office was where culture showed up. It was where relationships were built, where leaders were visible, and where companies invested millions to signal who they were. Somewhere along the way, we started confusing one of the oldest asset classes in the world with the culture itself.

But those aren't the same thing. Culture isn't created by an address or an amenity package. It's built through the decisions people make every day. It's how they treat one another. It's whether leaders actually live the values they talk about. That's why Workbar doesn't have a headquarters. We work from whichever Workbar location makes the most sense that day, right alongside our members. And despite what conventional wisdom might suggest, no one has ever accused us of lacking culture. If anything, it's one of our greatest strengths. The workplace can absolutely reinforce culture. It can also undermine it. But it can't create it.

At Workbar, I've watched two companies occupy nearly identical spaces and build completely different cultures. Same walls. Same furniture. Same meeting rooms. Completely different organizations. That's why I think we're asking the wrong question. We're still debating where people should work instead of asking what kind of work they're trying to do.

A few years ago, my daughter's school moved nearly 50 miles from our home. Suddenly my days revolved around carpools, practices, and long drives through Boston. I could have viewed that as an obstacle, but instead it forced me to rethink how I worked.

Some of my best strategic thinking now happens in the car. I've negotiated leases between drop-off and my first meeting. I've reviewed financials from my kitchen table before the kids wake up. I've recorded podcasts in our studios and brainstormed ideas while walking through our coworking spaces talking with members.

None of those places is always the right place. Each of them is the right place for a particular kind of work. That's also how we've built Workbar. I don't believe one desk should support every type of work because that's not how people actually work. Deep work deserves quiet. Collaboration deserves energy. Calls deserve privacy. And sometimes your best thinking just needs a change of scenery.

Our spaces aren't designed around job titles. They're designed around activities because that's how work naturally happens. As Boston celebrates 250 years of independence, I've found myself thinking that progress usually starts the same way. Someone asks, "Why are we still doing it this way?" Sometimes the answer is, "Because it still works." But sometimes the answer is, "We've never stopped to question it."

That's where innovation begins. And I believe that's how we'll keep making work work for the next 250 years.