Turn your side hustle into your full time business.

Turning My Side Gig into a Business

Turn your side hustle into your full time business.


It was not the plan. I’ve been a marketing and communications professional for 100 years (not literally, but almost), and I’d worked my way up to a Vice President position at an organization whose mission I loved. My content writing side gig was just a way to earn some extra money and stay creative. The plan was to stay at my VP job for another 10-15 years, then retire, and keep the side gig going part-time for extra cash.

That all changed in 2021 and 2022. A leadership shift at my job made working there untenable at best. Toxic was a better way to describe it. I tried to make it work. I stuck it out for almost a year. But eventually, I had to face the facts. As much as I loved my team and my colleagues and the good we were doing there on a daily basis, there was no way I could work for the current leader for another decade. My plans for my future would have to change. My mental health was at stake.


So, I decided to do the unthinkable.


I resigned from my job and became a full-time freelancer. It was unthinkable because it was so risky. I am not the risk-taking type. I don’t like to do anything without a well-thought-out plan, including documentation and timelines. I didn’t have any of that. I had a few loyal clients who had been with me for years, an Upwork account, a homemade website, and about 1500 friends and colleagues on LinkedIn. I didn’t have a business plan or a business bank account, but I did have savings to fall back on. So I did it. And I’m so happy I did.

That was May 2022. In the last eight months, I’ve learned so much about myself and about business. I’ve supported myself financially. And don’t worry, I now have a business plan.


What have I learned?


I’ve learned that when I don’t dread getting up for work every morning and meetings are not an emotionally abusive time suck, I am more creative, clear, and able to examine and accept new ideas and points of view.

I’ve learned it’s ok to admit I don’t know something (a holdover from my time working for other organizations) and to ask for help when I need it.

I’ve learned there is a vibrant and supportive network of freelancers, agency owners, and solopreneurs online who are willing and ready to offer advice.

I’ve learned that it is a gift to be able to pick and choose the projects I work on and the clients I work for. I’ve also learned that these projects and clients aren’t always the ones I think they would be at first glance.

I’ve also learned that the best clients are the ones that consistently give me solid and constructive feedback on my work and that feedback always makes my work better.

I’ve learned to take a step back from my writing and view it as a product, not as a creation. To me, writing has always been difficult in the best way possible. It comes from my soul and can be painful to get out onto paper. I always make the comparison to birthing a baby, although I’m not a mother, so I am only guessing. Anyway, there is no way to sustain that kind of creative process when running a business so I’ve learned to reframe my thinking about the content I write for clients as their content, not mine. It helps make the writing process faster, easier, and hopefully scalable.

I’ve learned that while I can build a creative and impactful marketing strategy for my clients in my sleep, doing it for my own company is a completely different mindset that I have trouble getting in.

I’ve learned to intentionally schedule a time to work ON my business because if I don’t, I will spend all my time IN my business.

I’ve learned to talk about my skills and experience more confidently and always be ready to present my business as the answer to any content marketing problem. ABC is an actual thing, y’all.


Why should you care?


My intent here is to help others who may be thinking about taking the big leap from side hustle to small business. Hopefully, these things I’ve learned will make your journey a little smoother. You will never be completely prepared for such a momentous decision but these smaller learnings can possibly make you feel more prepared. My advice would be to jump in feet first and start paddling!


What’s next?


Who knows?!?! But that’s ok. I’m having an adventure. I’m learning every day. It’s been a joy and a challenge to become a small business owner, even if it wasn’t planned. I can’t wait to see what happens next.




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