As a kid in the 70s, I used to watch a guy named Charles Kuralt on CBS. His series, On the Road, pulled me in long before I ever thought about becoming a freelance travel writer. He wasn’t doing freelance travel writing himself, but the way he wandered into small towns, talked to regular folks, and highlighted odd corners of America stuck with me. Our country was celebrating the Bicentennial, and he was out there capturing the spirit of it. Americana at its best.
| The Freelance Journey | Actionable Takeaway |
|---|---|
| Early Inspiration | Influenced by the storytelling style of Charles Kuralt’s “On the Road”. |
| Overcoming Rejection | Transitioned from snail-mail query letters to digital submissions years later. |
| The Breakthrough | First byline achieved at age 63 with Go World Travel Magazine. |
| The “Metra” Method | Using commute time to draft stories, proving age and a full-time job aren’t barriers. |
Looking back, that’s probably when the freelance travel writing bug bit me. I just didn’t realize it at the time.
My full-time job as a technical writer doesn’t leave much room for creativity, but the urge to write stories never goes away. I scratched that ich wherever I could. I started a blog at danswords.com, writing how-to posts about blogging: headlines, social media, what makes a solid blog post, all that good stuff. It was fun and I learned a lot, but it didn’t hit the same spark that travel writing does.
At one point, I created a site called Empty Nesters’ Weekend Adventures. It eventually turned into an Instagram. I posted travel clips and little slices of everyday life. I liked it, but running two websites and two Instagram accounts started to feel like work. That project faded out, but the freelance travel writer itch stuck around.
I actually tried breaking into travel writing long before the internet was part of the process. Back then, you mailed query letters to editors (yes, real snail mail. Can you believe it!!). I sent a few. Didn’t get far, but one editor did write back with a short note:
“I don’t think so. Try again.”
So I tried again for a bit. Then life happened, work happened, and the freelance travel writer dream slipped into the background.
Years later, I was cleaning out the basement and came across that old note. I reread it and something lit up. Not nostalgia. Something more like, “Why did I ever stop freelance travel writing?”
Soon after, an idea hit me. I opened my laptop on the train (I commute to the city on the Metra) and started writing about my experience at Robbie’s Marina. When a story comes, you chase it. I wrote most of it between train rides and finished it that weekend.
Then I hit a familiar wall: what do I do with this thing?
Most magazines don’t accept completed articles. They want a query first. But while I was researching, I found that Go World Travel Magazine accepts full submissions. They don’t pay much, but I wasn’t hunting for a check. I wanted a byline.
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So I followed their guidelines and submitted the piece around 8 AM.
By noon, I had an acceptance email.
I just stared at it for a minute. After all these years, after false starts and old dreams stuffed in basement boxes, my first travel story had found a home.
And honestly, that moment changed everything.
Breaking into freelance travel writing didn’t happen overnight. It came from following the spark, paying attention to the moments that stirred something in me, and finally giving myself permission to chase it. And I’m just getting started. Come back for more—new stories are on the way, from Route 66 to the quiet corners of Americana.
And be sure to follow me on Instagram for behind the scenes stuff.
Peace, Love, and Happiness,
About the Author: Dan Swords
Dan is a content creator and technical writer with over 40 years of communication experience. He is dedicated to helping people over 50 master digital storytelling, overcome camera shyness, and build a lasting digital presence through simple mobile video.