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.

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.

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.

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.

I’d been raised on the narrative that self-employment is inherently riskier than a full-time job. However, I don’t think that’s true anymore. When I lost my full-time job, I lost all of my income, overnight. I immediately made the decision (the next day) that scrounging up some freelance work could better support my family.

Honestly, losing my job just pushed me down a path I was headed for anyway. The tech industry has been brutal. Working for myself gives me more control over the outcome, something I didn’t feel I could get working for an employer. 

That being said, there were some practical fears, like “Can I get enough clients to sustain myself?” Turns out, I could. I’d also been freelancing alongside my 9-5 jobs for two years at that point, so I wasn’t building from scratch.

I learned how to use Zapier when I was working in fintech, and that has been the backbone for a lot of my systems. I can get more done without putting in more hours because automation handles a lot in the background (currently around 1,500 tasks per month).

I also use AI a lot. I’m a writer, so it’s never replacing my voice or my ideas, but I use AI to speed up parts of my writing process. AI can help with outlining or act as an editor for feedback when I’d otherwise be relying on self-editing. AI can also handle some things within my Zapier workflows that would otherwise be impossible through automation alone.

I love writing, so that helps! I write for clients and I produce about 3-4 longform pieces per week across my own platforms. And I write a lot of social posts.

I’m usually up around 4:30 am, but that’s my body’s natural rhythm. I use the time in the morning to work on my own content for the day. So Monday might be a blog post, Tuesday might be my newsletter, etc. I think it helps that I prioritize my own writing before moving on to client work for the day. 

Writing for clients pays the bills. But writing for a fellow solopreneur audience (or people who are thinking about going out on their own) gives me a lot of creative satisfaction.

Sustainability, to me, means two things: having control over my time and not feeling overwhelmed. It's running a "right-paced" business. That means working in a way that allows me to show up for my kids. It means automating tasks so I don’t feel burdened by the admin-type work. 

Sustainability also means building a business that can weather slow months. I’m an intense saver. I squirrel away money when I have a really profitable month, so that I don’t have to panic if I lose a client. I can also step away from my business for vacation and not have to worry about a dip in my income for the month.

In 2025, I found out that I had a brain tumor. It was thankfully benign, but I still needed surgery to remove it. That took me away from my business for about half the year. Even when I was able to work again, I had to focus on paying work for clients. 

Going through a major medical crisis changes you. Preparing for a lengthy medical leave as a solopreneur isn't something people talk about enough, so I'm sharing what I learned about getting ready—both personally and in business.

I host a lot of free webinars for solopreneurs and had planned to launch a course/cohort in 2025. I still have some lingering vision issues, so now I have to ask myself, “What’s possible, given my current limitations?” 

In the meantime, I’m maintaining my current ecosystem of content. I’m just not sure what the “next thing” will look like.

(Yes, I write A LOT)