How to Leave Our Dream Jobs

It turns out my story was relatable

I almost didn’t share the essay from the other day. I had written How to Leave Your Dream Job for myself, as a way to revisit the emotions I’d been working through over the last few months — the waning of a fierce passion, the identity crisis of leaving it behind, the challenge of shedding a long-held mindset — now that the pressure of doing something about it is behind me.

It later occurred to me that it would be nice to give my friends and family more perspective on my decision to leave baseball. Maybe if I shared it, it would also fall in the hands of someone in the industry who was afraid they were alone in their feelings, or a student trying to make an informed decision about whether to pursue a career in sports. But I was afraid that whatever I wrote could be misconstrued as bitter, that it would undermine my point about having a life outside of sports if I inaugurated my Substack by writing about working in baseball, and that publishing nearly 2,500 words about my job change was an exercise in vanity and self-indulgence. More than anything, though, I wasn’t sure people would find my story to be relatable.

To say I misjudged the last part would be a massive understatement.

I have been absolutely blown away by the response it has gotten. I had no expectation that my post would be read and shared so widely. From public shares to private DMs, folks in sports to those from totally different walks of life, accomplished industry leaders to those at the start of their careers, loved ones to acquaintances to total strangers, the outpouring of messages I’ve received has been at once humbling, overwhelming, and heartwarming.

The outside perspective and insight from readers has been so illuminating that I thought it would be worthwhile to share some of it in a follow-up. Here are a few morsels of wisdom and food for thought I’ve gathered over the last two days:

This is a very common phenomenon within sports…

Based on the messages I received, my essay made its way around the league. Friends and strangers alike said they saw themselves in my story. Others who left sports were grateful to find someone who understood why they did. Students and front-office rookies asked for advice on preemptively avoiding the rut that I fell into. Even folks around baseball who were perfectly happy with their situations reached out about the importance of recognizing if that ever changed. I don’t know that the industry will ever get to a place where people openly acknowledge these thoughts while they’re still in it, but maybe this week we got a little bit closer to that point.

…and outside of it.

Maybe it was naïve to think that sports are exceptional in their ability to draw people in and then burn them out; maybe they are particularly good at it, but not unique in doing so. Regardless, I didn’t expect my story to resonate so strongly with people in other industries: performing arts, media, education (I guess that wasn’t a surprise), academia (nor that one), health care (okay I should have known that people outside sports would get it), and historical archiving, just to name a few. If so many of us experience this across many professions, why do we all think our respective field is the exception? Why do we build up so much internal pressure to fit into the boxes we build for ourselves?

People need someone to talk to…

At one point, while reading through the kind messages people sent in response to my post, I took a step back and wondered: Why are people I haven’t talked to in years telling me about their identity crises? Why are total strangers trusting me with their career frustrations? (Please do not mistake this for a complaint — I am genuinely happy to be a resource for anyone who needs one.) The answer, I think, is that a lot of folks truly need someone to talk to about their professional aspirations, challenges, and disillusionments. It says something about our culture that people are more comfortable sharing these thoughts with an internet stranger than their coworkers or professors or supervisors.

If you work in an industry that lends itself to this kind of passion — and based on the varied professions of people I’ve heard from, there’s a good chance that you do — and you can create a space for your colleagues and mentees to share these feelings, it would probably mean a lot to them.

…and someone to hear this from.

A small sampling of the thoughts people have shared over the last couple days:

• "I’m glad someone is putting the human element out there for everyone to recognize."

• “People have shied away from making these feelings public but it’s good to hear someone put it all into words.”

• “The thing I try to explain to people … is just how consuming it can be over there. This is a good explainer.” (This one came from a pretty credible source!)

• “Your article definitely helped me find solace that I am not the only one.”

• “I never realized that others had the same thoughts in the industry and it makes me feel so much better to have read your words.”

I share these quotes not to stroke my own ego but to show how much it means to people to know that what they’re thinking and feeling is okay, and that they’re not alone or weak or insufficiently dedicated if their passion for their field wanes. The best way to do that — as I can tell you from my own experience on the other side of the conversation — is to normalize the notion that your dream job doesn’t have to be your dream forever, and you are no less you if what you do for a living changes. That starts by talking about it more.

We are more than our jobs.

It’s not a new or groundbreaking observation that, in our society, our identities are intimately tied up in our careers. When you’re meeting someone new, your job probably comes up within the first minute of conversation. If someone talks about you, they often describe you by your profession. We ask adolescents what they want to major in to start on a career path, and kids what they want to do when they grow up. In a sense, it’s logical that what you do for a plurality of your waking hours is a big part of your life. But it isn’t safe to assume that the thing someone does to put food on their table and a roof over their head is truly an expression of who they are.

I generally didn’t mind being introduced as “Lewie, who works in baseball.” After all, it was a really cool job, and every time someone said it I got to remember that being described that way was something I’d been working towards for my whole life. But the downside (beyond the occasional schmuck who would yell at me about a recent roster move and then ask for tickets in the same breath) was the fear that, if I changed jobs, I would lose the part of me that people thought was interesting.

How can we — both as a society, and as me writing this and you reading it — start to move past this? Maybe it starts with finding new default conversational topics besides work. When we ask young people what they want to do with their life, we could focus on where in the world they want to live instead of what they will do to afford it. We might consider describing each other not by our professions but by what makes us happy: “This is Lewie, he has the world’s sweetest dog,” “This is Lewie, he has a lot of opinions about cheesesteaks,” “This is Lewie, don’t make eye contact or he’ll tell you about his Substack.”

There are two ways to frame the fact that the story of my identity crisis resonated with so many people. The first is to see it as sad. It took a prolonged period of feeling like something was amiss and some painful soul-searching to realize I needed a change, to say nothing of the stress of looking for jobs and evaluating offers. I get a little bummed out every time someone tells me that they’ve been through something similar.

The second potential takeaway is that, if such feelings and experiences are this widespread, maybe we can rethink the stigma. Maybe we can put less pressure on ourselves to doggedly pursue our one true passion, and recognize the ways in which we contribute to our loved ones’ internalizations. Maybe we can be more open about our varying and evolving interests and values so that those around us feel a little less alone. Maybe we can all be better about focusing less on what we do while we’re on the clock than who we are when we’re off it. Why don’t we give it a shot?