The Year I Made the Jump from Freelancer to Agency Owner

The Year I Made the Jump from Freelancer to Agency Owner


When I started this year, I was a freelancer working by myself. In January 2021, I was determined to grow my business and switch from solopreneur to owner of a technical documentation agency. It was a rocky road, and I faced more negative feedback than working as a software developer. Folks who self-identified as allies made racist and sexist assumptions about my ability to run a company. I would commonly receive unsolicited questions like, “You need money to run a business. Where are you going to get the funds?” or patronizing tidbits of wisdom along the lines of “running a company is harder than you think.”

Happy to report in December 2021, I went from working by myself to growing my team to 3 people. I’m profitably and regularly enjoy 5 figure months. It was hard to do, but it was the best professional decision I made to date. Growing DocumentWrite has been the hardest and most fulfilling professional thing I’ve done to date.

Mindset Change

To be successful, I had to change was my mindset. When you’re worried about making the rent, you make financial decisions that never go beyond paying your bills. Once I decided to build a team, I started to value myself and chase after contracts that would put food on other people’s tables as well.

I think too many freelancers are operating in survival mode. Once I stopped being scared about making my day-to-day expenses, I became more ambitious. To date, I’ve worked with fintech companies, DevOps, and blockchain companies hailing from Silicon Valley, New York, Amsterdam, and India. 

The Why and How Behind Hiring

We can’t build an empire by ourselves. That’s why we scale and hire. If I maintained the mindset that “no one could write documentation better than me,” I could have never created DocumentWrite. If I’m providing an excellent service, it’s my responsibility to deliver my service to as many companies as possible.

When I started to hire, I didn’t know what I was doing. I had no processes or systems in place. Gradually, I instituted 1-1s, team meetings, and an internal guide outlining best practices and expectations. Contractors highlighted failures in my company that would have been ignored if I was just working by myself. I would not be where I am without my project manager’s hard work and insight.

When you build a team as a business owner, you are serving our clients AND employees. If employees couldn’t end the assignment with more skills than they started, then I failed. I’m happy to report back that this year my team learned about git, MarkDown, JavaScript, observability, and more. Growing my team’s skillset gets me out of bed in the morning, and I can’t wait to see them take on more challenging roles in 2022.

Dealing with Clients: With More Money Comes More Responsibility

The best part about running an agency is the radical accountability. If something goes awry, it’s not because I have a lousy boss, a lazy employee, or work at a terrible company. It’s 100% my fault. And that’s freeing.

When you’re running an agency, you have a chance of 5x your salary (even if you used to work as a developer). With more money comes more responsibilities. It’s not good enough to be a great writer or developer. You MUST deliver a great experience. This is NOT an option.

Project management === exceptional customer experience.

What’s the difference between a $1,000 project and a $10,000 project? Communication and excellent project management. I wish I knew this when I was freelancing.

Spending Money to Make Money

When I was a freelancer, I was obsessed with saving money. Quickbooks? Too expensive- I have google sheets. Proposals? I’ll just copy and paste something I found online. Why waste money on a CRM software?

The biggest lesson I learned from my transition from freelancer to agency owner is the importance of spending money to make money. It seemed like I was saving money by doing everything myself, but I was paying in time and mistakes. What good is a DIY yourself proposal if it doesn’t help you win the contract?

I also started to invest more in my education. 2021 is when I joined cohort-based learning courses, masterminds, and books. Ship30for30 taught me how to write for the web. My twitter following went from 300 to 1800. A bigger following helped me find clients, writers, and lifelong friends. Books like Deploy Empathy taught me how to craft services that companies actually wanted to purchase. My business wouldn’t have survived Q3 and Q4 without these invaluable resources.


Building DocumentWrite has given me purpose and confidence. Before starting my own company, programming bros and DEI specialists almost ruined tech for me. Running a company gave me the freedom to build things that I’m proud of and learn how to scale excellence. I’m grateful. 🥺🙏

owner of document write

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