Rewind: Jessica Strassman

When the good job doesn’t feel good

Some jobs are easier to leave in theory than in practice.

The difficult ones are not always the obviously bad ones. Sometimes they are the jobs that still look good from the outside: the recognisable company, the title that makes people lean in, the role your younger self would have been proud to have reached.

There can be a strange kind of shame in questioning something you once wanted so badly. You know what it took to get there. You know other people might be waiting for the same opportunity. You know how easy it is to tell yourself that unhappiness is just tiredness, or that discomfort is simply part of being ambitious.

For Jessica Strassman, that question appeared more than once.

Her career has moved through several versions of what success is supposed to look like: a booking agency, a major label, big tech companies, music-adjacent startups, and now her own producer management company. On paper, it could read like a series of pivots. But when we spoke, it felt more like the story of someone slowly learning to trust herself.

Jess grew up loving music. She sang, loved musical theatre, obsessed over artists and songwriters, and eventually realised that while she might not want to be the person on stage, she wanted to be close to the people making the work.

“I didn’t know that you could work behind the scenes in music until I was almost graduating from high school,” she told me. “I just knew I had to figure out some way to work with creatives, even if I wasn’t the creative myself.”

That feeling carried her through college radio, internships, and eventually into her first job at a major booking agency. It was a foot in the door, but it also showed her pretty quickly what she did not want. The job involved a lot of negotiating and phone calls, and Jess found herself much more interested in sending music around, recommending bands, and following her own taste.

That instinct led to an introduction to someone in A&R at a major label. Jess started sending him music, one of the bands she brought in was signed, and suddenly she had the chance to move from LA to New York for an A&R job.

It was the kind of moment that sounds, on paper, like everything falling into place.

“I was like, what? This is crazy. I get to be an A&R,” she said. “I guess I’m moving to New York.”

At first, it felt like exactly what it was supposed to feel like. New York. A major label. A job that meant something to other people. Jess had gone from being an assistant to having the kind of role she had once hoped might be possible.

“I really did feel like I made it out of the mud,” she said. “I had a really cool job. I got to be an A&R.”

For a while, that was enough. Then, slowly, the feeling changed.

“I think that feeling lasted maybe about a year,” she said. “And then I was just like, okay, it’s a job.”

Jess stayed for seven years, and she is quick to say that she learned a lot. But over time, she began to feel the weight of the politics, the constant no’s, and the ways her identity had become wrapped up in the role.

“I was just like, I’m Jessica, I’m an A&R,” she said. “My identity was so tied to my job.”

That can happen easily in music. The work becomes more than work. It becomes a shorthand for who you are, where you belong, and how other people place you. A recognisable company name can make people lean in. A certain title can make you feel chosen. But it can also make it harder to hear the quieter part of yourself that knows something isn’t right.

When Jess began to think about leaving, people questioned it. From the outside, it looked like the kind of job you were supposed to keep.

“I had a lot of people that were like, why would you leave?” she said. “You had the best job.”

That kind of response can create its own pressure. If other people want what you have, it can feel ungrateful to admit that it is no longer working for you. But Jess was beginning to understand that external validation was not the same as feeling fulfilled.

“The title and where I worked were so much less important to me than how I felt at that job,” she said. “Having the title and the big company wasn’t enough.”

Eventually, she left music for tech, working in music partnerships. At first, the change felt energising. It offered a new challenge, a different kind of culture, and eventually a level of financial stability she had not experienced before. But at one major tech company, the pace and pressure began to take a toll. Within six months, she could feel how intense the environment was. About a year in, she found herself effectively doing two jobs.

The clearest signal came from her body.

“My hair was falling out,” she said. “I gained thirty pounds. I was unwell in a lot of ways.”

It was a turning point. Jess realised that the environment she worked in affected her physically, mentally and emotionally. She also realised that she could do good work without living in a constant state of stress.

“For me personally, it’s not healthy,” she said. “It’s not what I want my life to be.”

There is something important in that recognition. So often, especially in industries built around passion and prestige, we learn to treat depletion as part of the deal. We tell ourselves that stress is normal, that exhaustion means we care, that if we just get through this next launch, meeting, quarter, campaign or crisis, things will calm down. Sometimes they do. Often they don’t.

After another short chapter at a music-adjacent company, Jess was laid off. To her surprise, she felt excited. The idea of starting a management company had been with her for years, but she had always been afraid to make the leap without enough money saved or a clear sense of what would happen next. The layoff gave her the permission she had not quite been able to give herself.

“I never thought I would have said I was so excited that I got laid off,” she said. “But I felt like I was given the opportunity to be like, all right, I can fully just start my own company now.”

Coming back to music did not feel like going backwards. It felt like returning with more information. Jess knew she missed working with creatives and being close to the creative process, but she also knew she wanted to build something that left room for a life.

That is partly why producer and writer management made sense. It allowed her to work closely with creative people, while creating a business with more autonomy, more balance and more intention.

“A big part of it for myself was making sure I remembered to build in real work-life balance,” she said. “I wanted to build a company where I’d be able to take time for myself.”

Her definition of success has changed. At twenty, it looked like working at a label, doing A&R and signing cool bands. Now, it looks quieter. Good work. Real relationships. Clients she genuinely enjoys. Weekends that are not automatically swallowed by work. Walks with her husband where they leave their phones at home, even when part of her still wonders what might happen if someone needs her.

“Every time I leave my phone at home, nothing has happened by the time I get back,” she said.

There are still moments when the old habits return. Sometimes she finds herself sitting at her computer wondering if she should be doing more. If stepping away means she is not working hard enough. If enough is really enough.

“And then I have to sit with myself and be like, you’ve done enough,” she said. “You can step away. You can go on a walk. You can call someone. You can run to the grocery store and the world’s not going to end.”

When I asked Jess what she would say to someone who knows they need to leave a job but feels they are not allowed to because it looks too good from the outside, she came back to the same place. Think less about the company name, and more about how you feel inside your own life.

“As great as the company can look from the outside, at the end of the day, you are disposable,” she said. “You have to remember that you’re a worker, and you should first think of yourself.”

It is a hard thing to admit in industries built on passion, identity and belonging. But maybe that is exactly why it matters. A job can be impressive and still not be right. A title can open doors and still leave you feeling stuck. A company name can make people respond to your emails, without giving you the kind of life you actually want.

These days, Jess says fewer people may reply than when she had a big company name in her signature. But that no longer feels like the point.

“What I’ve realised is I have the right people responding to me,” she said. “And that’s what matters.”

Maybe that is the real shift. Not simply leaving music, going into tech, coming back, or starting a company. But moving from wanting to be chosen, to choosing. Choosing the work, the people, the pace, and a version of success that leaves room to be a whole person.