Shifting career goals
I tell the story a lot, but just in case you’re new here…
When I first considered a career in design, I had a conversation with my wife, Emily, that went a little something like this:
ME [frustrated with work]: I think I want to really pursue this design thing.EMILY [super supportive]: You should! Where would you work?ME: I dunno. I could freelance, but I don't think I'd make much money.EMILY: Well, what about working full-time somewhere? So you could learn?ME: I think it would be cool to work for Target. Or maybe ESPN.
Obviously, ESPN ended up working out. I wasn’t exclusively pursuing it. I just happened to come across a job posting and landed an interview. A few years later, I visited Target HQ and (I think) came pretty close to getting a job there as well. I’m a firm believer in putting yourself out there and pursuing lofty goals.
I LOVED my time at ESPN. The people, the events, the quality of work — it was the coolest job I’ll ever have. There are moments when I wish I was still there, especially on days I’m working after 5:00pm. I don’t imagine my fondness of that place will ever leave.
I also knew it wouldn’t last forever.
Five year plan
The plan from the start was to earn enough renown — or “Career Capital,” as Cal Newport puts it — to rise in the ranks or be pursued by another company. I was naive and assumed that’s what all designers did, unless they were naturally gifted and/or extremely lucky. I figured I could stay in-house and reevaluate every so often if I ever wanted to try working for myself. In hindsight, this idea wasn’t too far off, but it would take just as long learning how to navigate the ins and outs of a giant company like ESPN as it would building up the skills (and confidence) to realize my dream of starting a studio.
I was always willing to reassess my timeline or revaluate my goals, but our initial commitment was five years. That was a personal goal of ours; nobody asked us to put a number on it, but we theorized that a secret getaway plan would relieve any pressure of feeling trapped or isolated in a new place. Five years seemed like a generous offering of ourselves to new friends, new jobs and a new part of the country where we were complete strangers. At the end of five years, if either of us weren’t completely content, we’d call it quits.
I wish I had some way to track my contentment from July 2015 to July 2020. It would have looked like a roller coaster, with extreme highs and lows. There were several stints when I imagined retiring as a Disney Cast Member — usually during the early Fall when New England became undeniably beautiful. There were just as many periods when I was hitting the job boards and taking calls — often just as ESPN announced layoffs, leaving hundreds of employees without work and making campus an awkward, sad place.
I was in constant flux, loathing my corporate work environment one week and imagining raising my kids in Connecticut the next. I guess that’s the beauty of a five year plan: it’s easy to straddle the fence. If we ever felt homesick, we’d simply stomach the status quo because the end wasn’t that far away. Anytime we felt content, we were so thankful because we had all the time in the world to enjoy ourselves with nothing forcing us out. It was like having our cake and eating it too.
COVID-19 and my inherent restlessness (which I seem to experience every half decade) definitely catalyzed our move, but when the opportunity arose to return home, we just happened to be coming down the last hill at the end of our ride.
Working there will look really good on a resumé.
After ESPN, I bet you can get a job anywhere.
Stay for a year, then do whatever you want.
These are a few examples of the comments I got after sharing I accepted a position at ESPN in 2015. It was my first real design job and I tended to believe what I was hearing. To this day I’m not sure if people were just obsessed about the next step for me or if nobody thought I would stay. Maybe some people didn’t understand why ESPN needed designers in the first place. At any rate, regardless of intentions, it never felt all that encouraging. It was also very false.
As I started looking for new jobs (late 2019), I was surprised at how few people I interviewed with wanted to talk about my work experience. I’m sure if I’d wanted to stay in sports media, journalism or UX design it would have been a different story, but I was interested in branding and illustration. Very few of the companies I was pursuing seemed to care where I’d been the last several years. If ESPN was even discussed, it was to ask about my favorite athletes I’d bumped into (Paul Pierce, Eric Hosmer) or which anchors I’d met and liked (Jemelle Hill, Bomani Jones).
As frustrating as this became, it was important to me that my next move was very different. I felt pigeon-holed as a “sports designer,” even though my coworkers would probably tell you I didn’t really fit that mold. I wanted to do branding and illustration, but my professional background was almost entirely web design. Luckily, I kept up a steady portfolio of freelance projects that helped get me a job (and later give me the confidence to start my own business).
Finding something else
Breaking into brand design was difficult. I could tell I was getting better at crafting identities on my own, but I still had a tough time finding a job. One of the things that pushed me to start a business was the inability to distance myself from ESPN on my own terms.
I’d hoped that the skills I’d been developing over the past several years would show potential employers that I could do a lot of different things. Editorial illustration, photo re-touching, art direction, copywriting, HTML/CSS, and designing web sites at ESPN; branding and identity design on my own time. I had gained experience and the portfolio to back it up.
When I finally landed a new job, I was frustrated to find that very little of what ESPN taught me translated and almost none of the work I’d done as a freelancer was relevant to my position. I was a senior designer in title only and the digital experience I’d brought to the table was ignored and replaced with production work. My managers struggled to match my expertise to the team’s needs and I was constantly reminded that the agency “did things differently than ESPN” to the point it felt aggressive.
The irony was that I wanted to do things differently. As a generalist evangelist (coining it!), I never want to be the authority on one thing. I constantly look for new skills to hone, like writing, coding and animating. I was under the impression that displaying a multitude of abilities would be more of an agency thing and less of a media conglomerate thing. I was wrong.
Had I finally broken out of this sports/journalism world only to wish I’d stayed?
Perks of the job
Even on my way out, it was hard for me to imagine leaving a Disney-owned company. Whenever a colleague in my department quit, I’d ask myself Why on earth would anyone ever leave? I often thought about the perks — free park entry and discounted hotels, for example — when I wasn’t happy at work, and that usually distracted me enough to suppress any frustration (more than once leading me to book a trip and use up some vacation days).
Perhaps not surprisingly, one of the biggest perks for me was telling people where I worked. In Connecticut it wasn’t much of a shock, but anytime I went home or to a design conference, I loved bragging about my job. I’m sure it got obnoxious. It didn’t help that my dad was super proud of me and told everyone about his son that worked for the world-wide leader in sports. Seriously, if it weren’t for him getting to see his grandsons every day, he might have wished I stayed at ESPN forever (jk, I think).
It was (embarrassingly) hard for me to give up my bragging rights. One of the biggest blows to my confidence was the noticeably fewer interactions I started having with some of my favorite artists once I announced I’d left ESPN. I don’t blame anyone for refocusing their attention elsewhere, and I’m extremely happy to have made some good friends through hiring, art directing, and collaborating; but I’d be lying if I said it didn’t sting a little. However, I think it serves me right for being so braggadocios, and I recognize how selfish it is to want to distance myself from ESPN while also retaining the some of those relationships.
I think one of the most frustrating parts about shifting careers was the confusion about where I “belonged.” The new job was a clear mismatch, but what did that say about my decision to leave ESPN?
At times, journalism feels like a fraternity. As someone who never really considered himself a reporter (although, I’m super proud to have a few bylines on the website), I struggled to appreciate what I was doing. I was so engrossed with the where that I failed to recognize how significant it was that I was, “Serving sports fans. Anytime. Anywhere.” Nearly everyone in my department had built their careers working for newspapers or magazines, so their paths often overlapped before arriving at ESPN. There were lots of inside jokes I didn’t get, especially from people who’d been with the company for a while. Sometimes it felt like the culture was something you had to be invited to be a part of, regardless of your employment status.
I made it a point to research what other outlets were doing and that came in handy when the team shared sources of inspiration. I also found a lot of comfort in my ability to recognize work from artists we frequently hired. The stuff that made me feel connected with my team required a little extra effort and usually came from outside of our office walls. Maybe that’s the case for any job — it’s just something I hadn’t ever anticipated.
One year later
Working there was an honor and one of the best jobs I’ll ever have. ESPN taught me how to appreciate things I never considered before, like conceptual illustration, investigative reporting and data visualization. It allowed me to take my sisters to Disney World. It gave me a chance to meet Ned Yost. It gave me the ultimate excuse: “I have to watch this game. It’s for work.” (Although, it’s nice to watch sports just for fun again; to be so wrapped up in the results and storylines of a season and know it affected your entire workday was exhausting.) Even though ESPN lost its luster after a while, I can’t deny the welcome presence it will always play in my life.
I was hardly the perfect employee. I said several things I’m quite embarrassed about now, some of which I’ve written about, but that’s not exclusive to myself or any job. I admit that maintaining a good working relationship with everyone in my immediate circle was more difficult than it should have been. I still harbor some grudges and have a difficult time seeing others thrive when I think about how great things at that company could have been; but, with as much growth as I’ve experienced in the past year, I often wonder if I’d be more content than before. Honestly, given the chance, I’d consider going back to find out.
I’d bet everyone that leaves ESPN, or any job for that matter, looks back with a mixture of wistfulness and gratitude. I tend to remember the good times much clearer than the bad, and even after only a year removed I definitely still speak highly of the place and the people. I still brag about working there, and I imagine I always will.
ESPN changed my life for the better, and I’ll always be grateful. Specifically, I wanted to give a quick thank you to Neil Jameison, Chin Wang, Heather Donahue and Luke Knox for hiring me, putting up with me, and teaching me. I miss the 4th floor.