20 Lessons from 20 Years of Freelancing

Don’t ask me how it happened, but somehow, I am marking 20 years as a freelance writer in 2023. I started as a new college undergraduate with a shiny new diploma and a desire to make a living from words, though I was unclear where the path would lead. I was lukewarm about the “usual” professions English majors gravitated toward—grade-school English teacher or journalist—and yearned for something more. Freelancing appealed to me on many levels.

I started as a stringer for a regional arts and culture publication. I truly enjoyed the work and loved interviewing the diverse range of creative folks that made up the vibrant arts culture scene the paper covered. I remember being blown away when a source from the Smithsonian Institution returned my call. Throughout various full- and part-time job changes, commutes, changing family dynamics, and other life “happenings”, writing has truly been a constant. I’m grateful for every project I’ve been assigned and every editor I’ve worked with.

From there, I've been fortunate to have my byline appear in over 50 consumer, trade, and custom publications. I've done a lot of research, asked a lot of questions, reached out to knowledgeable folks, and here I am. I've carved out a little niche for myself, and am thankful to have kept it going for so long.

As they say, it’s been a long and winding road. I continue learning and discovering more about this writing life. As I do so, I thought it would be fun to look back and put together a list of the 20 most important lessons I’ve learned over the last two decades (yikes! Did I just write that?)

To add a bonus lesson, I would add: Freelancing takes work. It requires a lot of legwork to find editors and sources. I've been fortunate to establish good working relationships with several editors over the years, but those relationships have changed, too. The writing itself takes work, as well. Sure, I'm not creating magical lands or multi-dimensional characters, but wading through source material and structuring words into a sequence that people will want to read takes work. The words don't magically flow from my fingertips most of the time, so yes, it's enjoyable work, but still work.

And now for the Top 20:

20. You don’t have to accept every project/assignment (although novice freelancers will take anything that comes along!)

19. Over time, you’ll learn to identify the “worthwhile” versus the “not worth it” projects. This will look different for everyone.

18. Cultivate good working relationships with editors and clients. Strive to be their go-to writer.

17. When reaching out to an editor for the first time, always send your most recent, or most relevant, samples. For instance, don’t send your article about in-home dog training techniques to the editor of a publication focused on operating organic bakeries unless it’s absolutely the only clip you have. Editors want to see you can write intelligently about a topic. Find something even tangentially related to organic bakeries, such as tips for working with local food vendors or a piece focused on running a small business.

16. Read your assignment carefully. Be sure your list of questions includes points your client or editor definitely wants you to include. Be clear on deadlines and word count, as well.

15. Send questions to sources ahead of time. Many appreciate the chance to get their thoughts together or track down noteworthy statistics.

14. Ask follow up questions to get less talkative sources to open up.

13. Ask “redirecting” questions to get talkative sources back on track.

12. Social media is a great place to find sources.

11. If it’s a topic you’re passionate about or a genre you want to break into, maybe accepting a lower rate is OK. For instance, you may accept less for those first few blog posts until you have a few under your belt.

10. In-person interviews will always be more impactful and meaningful.

9. Always be polite and professional, even if the other person is not.

8. Keep your editor informed of any roadblocks to the story—hard to reach sources, etc.

7. Stay on good terms with your editor. They are people, too.

6. Don’t hesitate to tell an editor when the working relationship is, frankly, no longer working.

5. Always check your work. Double-check spelling of names—people, places, events, etc.

4. Follow the publication’s style guide. Doing it right the first time will save you a lot of revising.

3. Use any feedback from the editor to make your next piece better.

2. Spreadsheets are a great way to stay organized and on track. (Sidenote: It took me far too long to learn this!)

1. Follow up. People are busy—editors, potential sources, business folks (aka, the people who pay you). Be proactive! Don’t assume responding to your request or issuing your check is next on their task list. I typically wait a few days after my initial request if I don’t get a response. And if that doesn’t get a response, don’t be afraid to get a little more assertive. This is your livelihood, and you often have to be your own advocate.

Longtime freelancers, what lessons would you put on your list?