This is a new ~bi-weekly series where I share stories from others who’ve built or are building a portfolio career that align to their values, interests, and lifestyle. Want to be featured? Reply to this email and let me know!
When I went solo, I somehow came across Anna’s content and now I’m a super fan. She writes simple, valuable content that has helped the operations side of my business.
I recently was featured on her newsletter, and I’m so glad she agreed to be featured on mine.
If you’re a solopreneur or just someone considering a career pivot, you’ll enjoy Anna’s story.
Jump to:
Anna, thank you for chatting with me! Before working for yourself, what did your career look like?
I worked at a financial technology company for 15 years in three roles: Product Manager, Director of Customer Success, and part of the executive team.
In 2021, I quit to pursue content marketing and journalism. After 18 months at marketing agencies, I was laid off. The job market seemed bleak, so I started my own freelance writing business.
Now, I write for B2B tech companies, specializing in fintech, automation, and AI. I also create resources for fellow solopreneurs on improving back-end operations with tools and workflows.
When did it start to feel misaligned? Was there a specific moment that made you want something different?
The higher I climbed in the corporate ladder, the more disillusioned I became. I thought that I could enact change and make things better, but I couldn’t. When I started working closely with the other executives, I saw what happened behind the scenes, and I hated it.
It will sound cliché, but the pandemic pushed me over the edge. Working for a company that made me feel terrible all the time became intolerable with everything else going on.
How did you choose your new career path in writing and journalism?
I have a Bachelor's degree in English, but I'd never seriously considered writing as a career. When I graduated, the only viable paths seemed to be "work for a newspaper" or "write a book", and I didn't want to do either.
When I wanted to quit my tech job, I stumbled upon a marketing agency hiring freelancers. I'd never heard of content marketing as a dedicated job, but I started freelancing alongside my 9-5. By the time I quit, I had built up enough of a portfolio to get hired full-time at an agency.
Someone in my network also introduced me to the editor-in-chief at a banking magazine. My unique combination of financial knowledge, technical expertise, and writing skills landed me a monthly tech column.
Anna hosting a workshop in her home office!