The Accidental Entrepreneur: A "Trial, Error, Adjust, Repeat" Approach to Finding Work

(This is part two in an ongoing series. Read part one here.)

As I wrote in the first part of this story, I left my part-time job for what I thought would be a freelance project writing and developing a comprehensive training course. But as I would quickly learn, plans change (especially when cost estimates come in and reality hits). That big project never materialized, which was quite a letdown after planning such a perfect transition. However, that first client did send me a smaller project that gave me something to work on while I looked for more work.

Some of the best advice I received came from other freelance writers. They encouraged me to create a Thumbtack account and also use Craigslist to advertise very specific services. I began running ads for resumes and cover letters, and also for web copy. These were tangible writing services that most people understand and many people need.

Very quickly, I began to get calls and small, one-off projects. When I started offering resume services, I thought it would only be layout and formatting, and maybe some editing here and there. But as I worked with people, I discovered that in order to craft a really solid resume, I needed to spend a bit of time on the phone with them. I needed to ask probing questions that would help me uncover and promote the skills and expertise that prospective employers would care about. Then I had to word it so that it was both true and compelling. It took quite a bit more time than I expected, and I began raising my rates accordingly.

That’s a theme that continues to repeat itself to this day, seven years later. I think I know what goes into providing a strong, quality service, but when I get into it, I discover there’s so much more required to really deliver results for my clients. I’m constantly tweaking things, applying what I’ve learned with one project or client to the next, and testing approaches to find the best one. Sometimes it’s exhausting to realize that this is a never-ending cycle. But to stop improving things is to effectively close my business. The world is changing, and in order to survive and thrive, we have to change with it.

Ethical questions began surfacing quickly, and not just around truthful resume-writing. A student initially contacted me for help with his resume and graduate school application. He was not a native English speaker, so I was happy to help him get his documents cleaned up. When he was accepted to grad school, he began sending me his assignments... except that he hadn’t done them yet. I had to explain that I could only offer editing services. I needed him to write a draft first, and then send it to me. Ghostwriting his coursework would have been helping him cheat. I did give him some advice and help as he tried to understand what was being asked of him, but it felt like a very delicate line to walk.   

My best leads came from people I already knew. "It's who you know" really does apply when you're growing a business. By reaching out to writer friends, I got introductions when they had more work than they could handle or when a request came in that they didn’t want to take on. That helped me build a network of clients who would also send me more work. I did some writing for my former employer, Children’s Hospital, and for my alma mater.

I also had a blog, which turned out to be an incredibly strong portfolio piece since my most essential skill is writing. Almost everyone who has hired me has found and read my blog in the course of our conversations and negotiations. At first, I wasn’t sure I liked that since it’s deeply personal, but being a real human being from the get-go, not just a name on a computer screen, has enabled me to build real connections with the people I serve very quickly.

By this point, about a year in, my business was humming along well. In the next part of this series, I'll write about learning the logistics of business.