I Moved Back in With Mom After Trying to Be a Comedian Didn’t Pan Out

“You can always move back if it doesn’t work out!”

I resented this response whenever I’d say I was moving to Chicago to become a comedian. It felt like everyone was doubting my decision.

At the time I left, I was confident that nothing would bring me back to my hometown of Milwaukee, but I was wrong.

I moved to Chicago in 2019, it was bad timing

In August 2019, my big dreams of going to The Second City, Chicago’s famous improv theater, and becoming a comedy writer were in full swing.

My fiancé of 11 years and I packed up our things and drove down. I didn’t have a job or many connections, but I was excited to be taking a chance on myself.

When 2020 arrived, I had just started to get my bearings.

I’d recently finished writing and performing in a program at The Second City Training Center, Sketchtest. I’d made a few friends, found my favorite restaurants and coffee shops, and had gotten a job that paid well.

However, the pandemic halted my momentum, leaving me isolated and anxious. That was just the beginning of a series of unfortunate events.

A lot happened in a short period

Three friends died between 2020 and 2022: one from a shocking brain disease that claimed them a month after diagnosis, one from long-term health complications, and another from suicide.

Meanwhile, my dad was battling serious health issues and losing. Waiting for “the call” of his passing sent my anxiety into a fever pitch.

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A glimmer of hope came with vaccines. I started going out to eat, finished the writing program at Second City, and even started doing stand-up again. Then, “the call” finally came.

My dad’s passing was expected, but no less devastating. The circumstances made a confusing cocktail of relief, grief, and self-reflection that had me asking if I was where I truly wanted to be.

My relationship began to unravel

Less than a year after my dad’s passing, I realized it was time for my fiancé and me to go our separate ways in September 2023.

Our relationship had been slowly eroding for years, due to unresolved resentment and unpredictable twists of fate.

I couldn’t fathom being alone, though, so just a few months after the split, I became entangled with someone else and his partner.

I fell for both of them, and we all moved in together into a new apartment. Because, hey, I figured if you can’t love yourself, try polyamory, right?

Meanwhile, my job situation was getting even better. I secured multiple contracts, including getting the opportunity to write gay lifestyle content, leading me to dub myself “Hairy Bradshaw.” It paid well and taught me even more about relationships and sexuality.

My new relationship was great, at first

For about a year, my partners and I were insanely, blissfully happy, except for the moments when we were poking our fingers in each other’s trauma wounds. It didn’t last.

The messy breakups started in January 2025, and I no longer felt comfortable being in the apartment, so I moved out.

It was that same month that my high-paying writing contract ended, and with it, my moniker of “Hairy Bradshaw.” There was no bad blood or people to blame, but I couldn’t help but wonder: Was this another sign I was moving in the wrong direction?

Last February, I realized I had no job prospects, only a handful of connections in Chicago, and nowhere to live. Moving back in with my mom in Milwaukee suddenly became inevitable.

I’m fortunate to have a mother who welcomed me with open arms

The series of losses and upheavals left me spending much of the past few months feeling lost and questioning how everything went so, so wrong.

As sad and dejected as I feel at times, I journal every day about how grateful I am, even if it’s just for having a roof over my head or my favorite snack of chips and salsa in the cupboard.

Writing my story has taught me to take responsibility for my actions and choices that led me here.

Too often, I let life happen to me, cursing what feels inevitable while forgetting I was holding the pen in my hand. There’s so much to look forward to, and I get to decide how my story continues.

I’m going back to school here in Milwaukee to study English in a few weeks, and I plan to move out on my own in October to be by myself for a while.

They said I could always move back. I’m glad they were right.