Hi Friend,
Today is the first in what I hope will be a series of interviews with successful freelancers (editors and writers). There are as many career paths as there are freelancers. Each person has an important story to tell with lessons for all of us.
An important lesson in freelancing is that you have to create your own opportunities, you can’t just wait for opportunities to fall into your lap.
Jennifer Silva Redmond is a great example of creating opportunities. In her interview, it’s apparent she created opportunities that opened doors for her. She started a publication, which led to her becoming editor-in-chief at a publisher, teaching writing and editing, and writing her memoir.
She’s also a fantastic example of living the life many freelancers dream of. Jennifer and her husband live on a boat, travelling up and down the Pacific. Her Substack, Honeymoon at Sea, is one I highly recommend. In it, Jennifer shares book reviews (some of her recommendations are now on my must-read list; she’s very supportive of indie books and less-known authors), podcast links, insights, and stories from her life at sea, including some gorgeous photos.
Plus, her dog Ready is absolutely adorable (sea photo above — you’re welcome for the awesome pun)!
Here’s your chance to learn from Jennifer (although I wish I’d asked if she ever makes her way up into Canadian waters!)
HF: What first attracted you to an editing career?
JSR: I was living on my boat in Baja, and I kept getting asked by friends to edit their stories, especially once I started the Sea of Cortez Review, an annual collection of writing about Baja. I found I liked helping people to focus and refine their work. My dad is an editor and my mom was a poet and writer, so it may have been in my genes!
How did you get started in editing?
We took the third edition of the Sea of Cortez Review to Sunbelt Publications in San Diego and they accepted it for publication and asked me about marketing ideas. Then they hired me to do marketing for all of their books. I slowly worked my way into editing and eventually up to editor-in-chief at Sunbelt. After working there for a decade, I found myself spending more time on P&L statements, contracts, and budgets and much less time on what I loved—editing. So I decided to go freelance. I am still Sunbelt’s editor-at-large.
Describe how your editing career has unfolded, and how you identified your specialities.
I always knew I was good at seeing what was missing in the structure of a book or play. At Sunbelt, I got the chance to expand on that ability and help authors to rewrite and reshape their books to make them more marketable and successful. Once I quit and started freelancing, I told people I could read their book and tell them what was wrong with the structure for a low price—I charged a dollar a page to start with! Then, if I liked the story and the client, I would do a line edit, once they did the rewrite, and I charged three or four times as much for that.
I started pushing the initial content edit much more as the years went by, because I could do more of them, it wasn’t so labor intensive and most important, it became clear to me that a lot of editors were going ahead and copyediting manuscripts that were flawed structurally, like putting lipstick on a pig. And the flawed content was getting published as really bad books that no one read.
What do you love about editing?
I love being able to spot what is missing or what there is too much of, like the typical problem of three chapters that open a manuscript that can become three paragraphs. I love being the person that can help tune in the author’s voice, like taking the static out of a radio signal, making their content clearer and less confusing. And I love when I can connect a writer with an agent or a publisher—though that step happens a lot less frequently, when it does, it is a real high.
What do you love about freelancing?
My life is a life of travel. My husband and I live on our sailboat. He taught school and had summers off so I wanted to be able to work from home so we could go sailing in the summers. Now we both work online so we’ve been able to sail up to the San Francisco Bay area and then up to Washington where we spent the last two summers cruising Puget Sound. I love being able to plan my days, to take a weekend or even a week off if I want. And this year, I loved being able to work less and concentrate more on my memoir while we were getting it ready to publish and also while I was marketing and promoting the book this fall.
What is a piece of advice you would share with other freelancers?
For beginning freelancers, it is key that you are willing and able to work a lot for less money to build a portfolio of clients. I started freelancing on the side while I was working a nine to five job, which meant a lot of nights and weekends were spent working, not playing. I really scrambled for the first couple of years of freelancing, but I eventually got enough testimonials on my website that new people sought me out.
For established freelancers, the big thing is keeping your feelers out to new clients all the time. I found the Southern California Writers’ Conference which I loved. After attending a few times I offered to teach classes on querying, which I knew quite a lot about by then, and taught many different workshops twice a year for a decade. Now I only attend SCWC in San Diego, even when it means a lot of travel and stress to get there and do the work of creating new classes as well as teaching at San Diego Writer’s, Ink, mostly online. It is always worth while to teach, even when it pays me pennies on the hour, because I never fail to add new clients from each conference.
Tell us about your Substack
Honeymoon at Sea is a newsletter about my life—sailing, living on a boat, writing and editing, and marketing my new book. Plus I write a lot of book reviews, especially trying to promote lesser-known books by indie authors and publishers.
What led you to a life on a sailboat?
I fell in love with a sailor. I was living in New York City, trying to break into acting, when I came home to San Diego for the Christmas holidays to see my family. I called my old boyfriend and the timing was right. He proposed two days later and offered to relocate to NYC so I knew it was true love. We got married a few months later and moved onto the boat that summer. In the fall, we took off for a honeymoon at sea in Mexico. We spent what turned out to be a truly wonderful, life-changing year in Baja’s Sea of Cortez. That year I discovered I was a writer and a few years later, back in Baja again, I started editing other people’s work, which lead to the creation of the Sea of Cortez Review.
How do you balance editing work with living on a sailboat? (How do you prioritize work and personal time? How do you find/meet with clients? How do you manage your career?)
I don’t have a hard time being self-motivated or making myself concentrate on work. In fact, I don’t really enjoy taking time off if I am behind with a project; that unfinished job will prey upon my mind until I have it finished.
Of course, I take plenty of time off each day for long walks and hikes (and sailing trips, during the summer) and basking in the sun or watching movies or going out to lunch or stopping work early for an impromptu happy hour. And if I feel punky and just want to read in bed all day, I can do that, though sometimes I am reading a book for work, even then.
I meet clients everywhere, but mostly at conferences or writers groups or other meetings where I teach or speak.
What other projects do you have on the go?
I have been working on a book of editing tips for writers for a couple of years, and I hope to have that manuscript finished next year. It will be more of a handbook, maybe 50 pages long. It will help me to put all my advice to writers in one place, and also be something I can sell when I am speaking or teaching a workshop.
Is there anything else you want to share with the readers of Happy Freelancing that we didn’t go into?
I think we have a great life—being able to work when you want to is quite a gift, but of course, you need to build up that customer base for a while before that will work for you. I am lucky that my husband has a job that gives me health benefits, or I would have to work quite a bit harder, or charge quite a bit more!
Contact info for anyone who wants to find you elsewhere
I am still the only Jennifer Silva Redmond on Facebook and I am jsilvaredmond or Jenny Redbug everywhere else—Instagram, TikTok, and Substack. You can simply type “Honeymoon at Sea” into a search bar and find my book and my Substack, too.
Cheers to your ongoing freelance success,
Heidi
Speaking of opportunities, I really appreciate this opportunity, Heidi! And yes, we will be sailing north into Canadian waters sometime next summer. Thanks again for asking me to be a part of this.