My Big Break at the #BosCon Bash

Image via BosCon member  Ben Lewis

Image via BosCon member Ben Lewis

This post was written by Elizabeth Wellington, a freelance writer and content strategist. Follow her, @wellington_liz.

By the time I landed my first paid writing gig at the #BosCon Bash, I had known for 10 years I wanted to be a writer. My room was always brimming with books and journals, bits of poetry and scraps of prose on napkins. As a teenager, Carrie Bradshaw confirmed my career aspirations. Even if my life did not include designer shoes, I still wanted the freedom to write and that skinny Macintosh computer. But as I forged a different path after college, the discomfort of dismissing my dreams became greater than my fear of leaping into the unknown.

If something I loved with such clarity was not worth the risk, what would be? And so, with a gallon of chutzpah and a pint of trepidation, I left my steady administrative job and embarked on a new path. I did not know how it would work out, but trusted that it would.

Moxie or Plain Old Foolishness?

A month into freelancing, I reassessed my moxie as plain old foolishness — and a lot of other people did, too. While at a health clinic because of an ear infection, a doctor asked me with a look of fear in his eyes, “Are you able to eat? How can you provide for yourself as a writer?” I cracked into a rare spit of sarcasm and told him my editors pay me in bagels. His comment hit a raw nerve, giving voice to my running anxiety. Just how would I support myself doing what I loved?

As fate would have it, my boyfriend Tyler works in content marketing — something I never related to my chosen vocational path. Days after my appointment with the doctor, Tyler asked me to go with him to the #BosCon Bash. I had spent very little time networking since my big leap, and Tyler knew better. He was convinced the best thing he could do was to introduce me to other people in the field: marketers, program managers, writers and editors. He was right.

Bathroom Drama

A part of me resisted going to the #BosCon Bash. OK, all of me resisted going. The vulnerability of stepping out into the world as “Liz, the writer” left me feeling exposed. In my 10 years writing behind closed doors, my aspirations grew in equal proportion to my fear of pursuing them. Despite how far I had come, having hedged my bets and left my job, walking through the door at the #BosCon Bash made me shake in my heeled boots.

Every time I told someone at #BosCon I was a freelance writer, I felt a little wince in my stomach, as if someone had poked me and said, “But are you?” I took a bathroom break, trying to shake off my cloud of anxiety. Looking in the mirror, I noticed a large piece of hair sticking up from my side braid like a cockatoo’s feather. My eyes widened as I realized my new shirt was sheer. Not only did I feel exposed, but I actually looked naked. My chin started to quiver, and I started to cry. Channeling my inner middle-school girl, I hid in the bathroom stall to pull myself together.

It wasn’t my shirt. It wasn’t my hair. It was that I was totally green. I was a beginner. I wanted to be two years into this rodeo, not at the starting gate. I questioned my own worthiness, but only because I held myself against a measuring stick that made me feel like a failure before I started.

I put on my coat to cover my see-through top, re-braided my hair and smacked on some lipstick. I still felt queasy, but I knew enough to start dancing.


One of the last people I met at #BosCon was a freelance recruiter from Skyword named Molly Berry. With a bouncing laugh and infectious positivity, Molly immediately cut through my fears. She asked me about my expertise and placed me on a list of “top priority writers.” One week later, I had my first paid gig, and with a Fortune 1000 company no less. The work perfectly suited my experience in higher education, acting as a bridge between my old career and my new one. It felt like someone had handed me an “Advance to Go. Collect $200” card, but it wasn’t Monopoly, it was my life.

The appreciation I felt toward Molly and #BosCon that night was only matched by a new dedication to facing my biggest hurdle. The most formidable challenge for most of us isn't out there in the world but is glaring at us in the mirror: our fears, our limiting beliefs and our self-doubt. By accepting and transforming those negative aspects every day, I armor myself with passion, ready to claim my dreams.