Photo credit: Mike Wilson via Unsplash

Perspectives on a year of change

I spent the last five years of my life starting-up and running a design agency in Chicago. A year ago, I left that agency and moved my family to San Francisco to work for Uber.

A lot of people ask about my about my transition to Uber. Polite people ask, “What drove you to Uber? How does it compare to running your own company?”, while others exclaim “Why would you leave your own shop to work there?!”

I want to shed light on my personal decision-making process and my transition from a small Mid-West agency to big tech Bay Area.

A tough choice

This was the toughest career decision I’ve made to date. I was extremely proud of my team and the work we were doing in Chicago. In some ways it was a dream job — I loved working with everyone on the team, they were like family, and I hand selected most of the projects we worked on.

After running the studio for a few years, I noticed I was growing distant from the work. The bigger we grew, the more time I spent with business operations: reviewing contracts, selling to prospective clients, and worrying about our sales pipeline.

I used to have an internal debate with myself — is this the natural step? I’ve spent so much time honing my design craft…do I hang up the gloves and get serious about operations? I even considered obtaining a law degree so I could save money on hiring lawyers. In a weird way, I started feeling selfish for wanting to spend more time doing work with the team rather than managing the operations of the business.

To my surprise, it was the people, not the work, that had the biggest impact on me.

Around that time, Uber reached out. I had a few introductory conversations that piqued my interest, and I eventually decided to spend a couple days getting to know the leadership team. I had no real intention of joining Uber at this time, but I was genuinely curious to learn more.

To my surprise, I felt a strong connection almost instantly. The work was very forward-thinking and exciting, but it was the people that had the biggest impact on me. I felt that I was surrounded by my peers and many people I could learn a great deal from.

Over the years, I had made the rounds through some of the big tech companies (consulting and interviewing), but never felt compelled to make the jump. Uber felt different, it was the first time I could really see myself in another company.

The right home for me needs to be a little chaotic — I need to work somewhere that doesn’t have it all figured out.

I’m a huge tech nerd and I write tons of code. But I’m a designer at heart, and I’ve built my career around combining the two. I loved the experience of building and mentoring a team and the thrill of running a business. I also taught at a university on the side and loved that too.

Long story short, finding a new home isn’t an easy task for me. The right home for me needs to be a little chaotic — I need to work somewhere that doesn’t have it all “figured out”….somewhere I can experience a lot of variety and not be pigeonholed. A place that affords the opportunity to impact culture, mentor others and shape the team. Most importantly, I need to work on something I personally connect with and believe in.

After a whirlwind tour and a bunch of inspired conservations, I headed back to Chicago. Even after a great experience at Uber, I still wasn’t ready to make the leap.

But something happened when I got back. All of a sudden, my whole world felt really small. I couldn’t help but feel distracted by thoughts of working on something “bigger”.

Around that time, out of the blue my wife also had a good opportunity to move her career to San Francisco. So after six months of mental toiling, we decided to take the leap.

My first 365 days at Uber

The first three months were a whirlwind of excitement and culture shock. I was taken aback by the speed and focus of teams at Uber. The best way I can describe it is looking into a fast flowing river and feeling hesitant to jump in. When I did jump, I was delighted by how much support was offered in those early days. I felt others genuinely wanted me to come up to speed as fast as possible, and they took the initiative to help onboard me.

During those early months I was a little homesick for agency life. I missed the feeling of a tight-knit team, pitching clients, and all the weird ‘n’ wacky things you do when a bunch of designers are in a room for 10 hours jamming on concepts.

Overall things were peachy, it felt like going to work at Willy Wonka’s Factory…but then it all hit the fan.

I found myself saying “well, in my old company we did…blah blah blah”, trying to shoehorn ideas and process that didn’t quite fit into Uber. I was constantly trying to compare agency life to the product world, and it was unhealthy. Over time I realized they aren’t comparable. There are pros and cons to each. But I’ve come to realize that my agency background is also an advantage. It gives me perspective that is uniquely valuable. I look forward to bringing more agency-culture into the product world.

Overall things were peachy, it felt like going to work at Willy Wonka’s Factory…but then it all hit the fan.

For the following six months, a series of difficult moments came crashing down on us. Some of the behaviors and events I read about made me sick to my stomach. I couldn’t believe it. It was increasingly difficult to square the notion that a place that I enjoyed working could have been the cause of trauma for others. I believe the design team was insulated from a lot of the organizational cruft I read about, but the feeling was alienating nonetheless.

It was getting harder to defend Uber to my friends and family when they’d ask me if I was doing okay.

It didn’t get easier. The blows just kept coming. It caused massive team disruption and some major organizational shifts. It was getting harder to defend Uber to my friends and family when they’d ask me if I was doing okay. Things were spinning out of control, causing people to leave and a putting emotions into overdrive. I decided to anchor myself and hold on for the ride.

It became clear the company must evolve. For me that meant doubling down on a few key cultural things — At the top of my list was ensuring everyone on my team had an open and respectful environment to work in. This is something I realized doesn’t automatically happen just by hiring nice people, it takes some work. I’m also working to build a stronger system for encouraging, supporting, and educating folks on the team so they can grow creatively and professionally with the help of their peers and managers.

This is pretty basic stuff, but it’s essential to get it right as it enables us to do great work that we’re all proud of.

In the most recent months, I’ve gained enormous perspective. I’m cautiously optimistic about the future. I see a multitude of healthy organizational changes happening week-by-week. I sense that the folks that work at Uber really want to be here and really welcome the changes. I believe we’ll shed this old skin and emerge as a world-class organization.

Despite it all, I feel like the best version of myself yet

During my year at Uber, there are a few things that have been exceptionally rewarding about my experience:

First, the breadth and depth of Uber’s reach has accelerated my personal growth. It’s been transformative to work with so many people across so many different parts of the organization — everything from Machine Learning and Maps to Data Visualization and Autonomous Cars. The problems we set out to solve are orders of magnitude more complex than anything I’ve tackled before. One year at Uber feels like the equivalent of three years in other places I’ve worked.

Second, the diversity of the team is really inspiring. That may seem counterintuitive considering the overall state of diversity in tech companies. However, the design team I work with is wonderfully diverse, and it absolutely helps me be more informed and aware. I learn something new from the team every day.

Lastly, the impact of the work is extremely humbling. Uber reaches over 600 cities globally. The sheer volume of riders, drivers, and trips is staggering. I’ve developed a much broader global perspective by simply being here. In just the past few months, I’ve been moved by stories of how Uber helps bring families out of poverty in Jakarta, improves mobility for women in Saudi Arabia, and gives back independence to seniors with our Uber for Business product.

Just like with any organization, my time with Uber has offered both the good and the bad. I continue to be incredibly excited by the progress we are making as a company, both in terms of doing groundbreaking work and, as importantly, improving our own internal culture to make sure that we are the best version of what we can be. I feel fortunate to have the opportunity to help make Uber a better company, and to help Uber shape the future of transportation.