How to Leave Your Dream Job

or: How I Learned to Stop Worrying and Love Corned Beef

Lately in a wreck of a Californian ship, one of the passengers fastened a belt about him with two hundred pounds of gold in it, with which he was found afterwards at the bottom. Now, as he was sinking — had he the gold? Or the gold him?

– John Ruskin, Unto This Last; as quoted by Michael Lewis in the preface to Moneyball

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I was thinking about corned beef when I decided to take the other job offer.

When I was a kid, I loved macaroni and cheese. I still do, of course, because who doesn’t love macaroni and cheese? But when I was little, my passion for mac was on another level. It was my answer whenever I was asked what I wanted to eat. My friends’ parents knew to make it for me on playdates. I remember once reading a kids’ menu where every meal came with both an entrée and a side, and seeing mac and cheese as an option for both; I proudly ordered mac and cheese with a side of mac and cheese. When my mom was pregnant with me, she got uncharacteristic cravings for Stouffer’s frozen version. Even in utero, I was ordering in.

The point is, mac and cheese wasn’t just my favorite food, it was part of my identity. And it came with a recurring identity crisis.

Growing up in suburban Ohio, the closest thing we had to a good Jewish deli was a small diner called Jack’s. I was probably five years old when I discovered I liked their corned beef sandwiches — a major development in broadening my palate. But there was a complication: Jack’s sometimes featured mac and cheese as a daily special. And it was terrible. It was dry, it was bland, it had no creaminess or texture. The noodles seemed to be held together with paste rather than Mornay. 

Yet whenever Jack’s had mac and cheese, I always felt compelled to order it: mac and cheese was my favorite food, and in that moment mac and cheese was available to me. My preferences had been established, and breaking with them would have been irrational. (Shocking that this child grew up to major in economics.) I was the kid who loves mac and cheese, and I should act accordingly.

Of course I lacked the vocabulary (both literally and figuratively) to put this into words at the time, but I’ve never forgotten the strange sinking feeling of walking into Jack’s and seeing mac and cheese on the specials board. It didn’t occur to me that it was okay not to choose your favorite thing every time. So I’d order the mac and cheese, and I’d tell myself I’d have the corned beef another day, and I’d be left with an inarticulable confusion about why the thing I thought I wanted left me unhappy.

I could feel that happening again with the only other passion in my life that I have held as long and as strongly as macaroni and cheese: baseball.

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One day, long before I had a full-time job in the industry, I joined a small group lunch with a front-office lifer. As we sat down with our food, I started the conversation: What advice would you give to someone who wants to have a career in baseball?

He barely looked up from his sandwich as he flatly replied: “Don’t.”

While his delivery was unusually blunt, the point he went on to make is one that I heard from many other people too, and that I now try to impart when I talk to students and front-office aspirants myself: When you work in baseball, it can take over your life.

It’s no secret that the hours in baseball are long, and often include travel, late nights, and weekends. Even if you’re not required to watch your team’s games, you usually do. You plan your personal life around the numerous flashpoints of the baseball calendar, from dinners to vacations to your own wedding. (If we had a dollar for every time someone told us, in so many words, that we should get married at my office, we could have hired a videographer.) The industry is more cognizant of the need for work-life balance than it used to be, but it’s still hard to tell a coach or scout coming from a late game that you’ll get back to them during business hours, or to shake the feeling that you should be on call all the time if you want to be involved in making decisions.

But the grind is more than just the expectations. It’s the mindset. The sports industry is extremely competitive, shaped by the nature of the business and reinforced by the types of people who are attracted to it. Baseball is a zero-sum game that gives you results every night, and internalizing that urgency feels like a prerequisite for a job. Would I rather finish a project that could help with a time-sensitive decision or get an extra hour of sleep? I almost always picked the former.

The thing I struggled with most, though, was how much I cared. They say if you do what you love, you'll never work a day in your life; the flipside is that you’ll never live a day without work. The boundary between my job and my passion was swept away like the batter’s box after a slide into home. Baseball, it seemed, was all I talked about, all I thought about, all my life was oriented around. After almost a decade of working in the industry, even going to games was starting to feel like work.

When students ask me for career advice, I try to tell them in so many words: If you work in baseball, it can become your identity. That doesn’t mean you shouldn’t do it, or that you won’t be happy if you do — for many years I definitely was — but it’s hard to appreciate what it means for your job to be your defining trait until you experience it.

The problem, as I can tell you from personal experience, is that when such words of caution are presented to a competitive job-seeker eager to demonstrate their commitment to their passion, they don’t sound like a warning. They sound like a challenge. And so you approach your job like it’s a weed-out intro class for a STEM major, constantly proving your dedication not just to those around you but to yourself.

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I knew from an early age that I wasn’t cut out to be a baseball player, that I was better with a stat sheet and a scorebook than a ball and glove. When my tee-ball coach asked me what position I wanted to play, I replied, “general manager.” My mind was blown when I read Moneyball around my 13th birthday and I realized that there might actually be a place in the big leagues for a kid who’d hung up his cleats in middle school. 

My dream of working in baseball gradually became my identity. I wrote things online in hopes of putting myself on teams’ radars. I studied economics in large part because of how it aligned with then-contemporary sabermetric thinking. After nearly a decade of working in the industry, my claim to fame is still probably my college senior thesis, in which I made the honest but admittedly self-serving argument that front office personnel were undervalued in the baseball labor market. For so much of my life, there was no question about what my career ambition was, only whether I could achieve it.

I feel unbelievably lucky that I did. But I slowly started to realize that the things I valued had changed. For example, when people would ask me what the best part of working in sports is, I’d usually say getting to walk into a baseball stadium every day. No matter how tired or stressed or busy you are, I’d explain, it’s hard to walk into a place like that without a smile on your face. I still believe that very fervently. However, I also learned over the last couple years that I enjoy working from home. Wearing comfortable clothes, having the freedom to exercise or run an errand during my lunch, bookending my day by walking my dog instead of commuting and looking for parking — it turned out that I liked these things even more than seeing the stadium come into focus as I drove through the city to my office. Yet even that anodyne preference took a lot of time and self-reflection to acknowledge, because it was at odds with everything I thought I’d wanted.

A few months ago, when I heard myself say for the first time that I wasn’t sure I wanted to work in baseball anymore, there were tears in my eyes. It took weeks of increasingly frequent practice before I could get through a conversation about it without welling up. I had been so wrapped up in the pursuit of getting and then maintaining a front office job for so long that even now, two months after changing careers, I’m still quieting my instinct to see my life trajectory through that lens.

It wasn’t that I was afraid of other people knowing that I had doubts about baseball, though I was. What would I say to the colleagues I had grown close with and was now leaving behind? How could I break the news to my peers and mentors across the league, who initially got to know me through my career aspirations? Was I disappointing my friends and family who had watched me grow up and pursue my lifelong dream, often at the same time, and were proud of me for having achieved it? Yet these questions were small potatoes compared to the real problem: I didn’t know how to stop ordering the mac and cheese.

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Baseball isn’t very good at talking about these things. In an industry driven by passion, dedication, and constantly striving to get the marginal edge, it’s hard to start a conversation about whether your heart is really in it. Sure, you see people leave the industry to do things that seem more normal, where you work fewer hours and make more money, and you joke that it must be nice. But the ones who are still there at any given time? They’re pot-committed, you think. So the seeds of doubt about working in baseball don’t just make you question your passion for the game and your vision of yourself. They make you feel lonely.

That’s why I wrote this essay: So if you’re working in the sports industry, or if you want to someday, and you find yourself questioning whether you’re really committed to the path you’ve set out on, you can at least know that the feeling is normal, and you’re not alone.

In fact, I guarantee you that some of the people you’d be embarrassed to admit these doubts to feel the same way. While I expected the folks I knew around the game would be outwardly supportive — I probably talked this through with enough people to fill a full 40-man roster in the days surrounding my decision — I was afraid they’d be shaking their heads in disbelief on the other side of the phone. On the contrary, I discovered that these feelings are a lot more common than I’d thought (albeit not always this acute). Call it burnout, a need for more variety, seeing how the sausage is made, or just a consequence of turning a personal passion into a professional one — however you describe it, the fact that people don’t talk about it doesn’t mean they don’t experience it.

I found it equally surprising and validating that so many people in the game — across multitudes of teams, roles, and levels of seniority — could relate to my situation. Several industry veterans who I thought were fully committed to their professions told me that they, too, had searched or even interviewed for opportunities outside the game at some point. “Baseball is what we do, not who we are,” offered a friend whose résumé could have led you to believe otherwise. When I told another that I’d assumed he was immune to such feelings after all these years, he replied: “Nobody is.” I didn’t realize how much I needed to hear that.

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The truth is, I miss baseball. I miss my coworkers. I miss being close to the game. I miss walking by the field on my way to the office and having a place at the stadium that I could call my own. I miss getting up in the morning and realizing that I was doing exactly what I’d wanted to do since I was a kid.

I might try to get back in someday. Maybe tonight is the night when I’ll wake up in a cold sweat, kicking myself for walking away from baseball and praying that the past several weeks were just a dream. Ever since I gave my notice, I’ve been wondering if that day would come — but it hasn’t yet.

Two months later, I’m happy with my new job. I like my coworkers, the company culture, and especially the work-life balance. It turns out there are benefits of having a life outside your job, of closing your laptop at the end of the day and not worrying about what you’re missing or what else you could be doing. My wife and I are traveling more, doing things outside our routine, and enjoying the simple pleasures of saying yes to invitations from friends and feeling more present while we’re with them. (Apparently I’m also writing.) She keeps telling me how much less stress I’m carrying on a daily basis.

After dedicating myself to the game for so long, it’s humbling (though obviously unsurprising) to see baseball go on without me, but it’s also empowering to see myself go on without baseball. When I picture telling my adolescent self about my decision, I don’t think he’d be disappointed that I put my dream career on hold. I’d think he’d be amazed that I’ve found things in life I value even more.

On my last day of work, my wife suggested I pick a restaurant for some celebratory takeout. I thought about all my favorite foods: cheesesteaks, burritos, pad see ew. I could have ordered the fanciest, creamiest, most-indulgent macaroni and cheese in the city. But there was only one thing I was really craving: a corned beef sandwich.

If you found this essay relatable, you might also be interested in the follow-up: How to Leave Our Dream Jobs.