Interview with a Barefoot Writer: Jason Holland

Jason Holland

“In the U.S., I spent half my life at Walmart just getting stuff. Here, we live in a small town … and my day-to-day is much more relaxed so I can really just concentrate on my writing.”
— Writer and Editor Jason Holland

I don’t often drool during interviews, but it was hard not to when I sat down with writer and editor Jason Holland. Not only is his writer’s life inspiring, it’s also tantalizing to anyone who appreciates a ribbon of white sand near crystal-blue Caribbean waters.

Our interview took place via video over Skype. Jason was in Costa Rica, in a home office where the open window showed patches of turquoise sky and palm trees waving in the breeze. It’s that breeze, Jason tells me, that keeps daytime temperatures around the mid-70s most of the year. He sat comfortably in a short-sleeved, tropical print shirt. I let my eyes flicker to the snow-covered, icy ground outside my own office window before gazing longingly at his sun-lit paradise.

Previously a resident of Florida, Jason tells me he loves waking up every morning in a place most people only get to visit for two weeks at a time. Grecia has a population of only 16,000 and sits about an hour northwest of capital San Jose, in the country’s Central Valley region.

Jason’s writing journey began in his U.S. high school English class with Mrs. Dorsey, a teacher he still appreciates. Her lessons in essay writing led to Jason choosing journalism as his college major — magazine journalism, specifically. Jason jokes that his initial writing goal was to be a Rolling Stones music journalist. He pursued it for a short time and completed a handful of pieces, even attending concerts for free. But, as he says, “That’s a hard field to break into so I would recommend most people not try that.”

He enjoyed journalism school, but it didn’t exactly fill him with high hopes of making a great living as a writer. “Every couple of months, the professors would say, ‘Most of you are going to end up at a small community newspaper for your first job. And you’re going to make an average of $23,000 a year.’ In my mind, that was a lot of money because I had zero dollars. So I got out of college, got a job at a small community newspaper in Kissimmee, Florida. And that average salary thing — he was right on the money.”

Writing for the paper wasn’t bad, says Jason. It was a great opportunity to learn from the editor there. “He was an old newspaper guy and taught me a lot about keeping my writing tight. He had a lot of good tips on research and interviewing.”

But the job itself was boring and unfulfilling. “I spent a lot of time at government meetings where they’d discuss land use and zoning regulations. There’d be government bureaucrats talking for an hour about residential zoning and a new development company coming, and it drove me crazy. And I would be at these meetings sometimes until two in the morning. I had to be there in case something actually happened.” That went on for about three years.

“I did write about some fun stuff,” he concedes. “I saw an alligator get captured in someone’s backyard, interviewed demolition derby drivers, and met a Vietnamese potbellied pig who played piano. I also got to drive a bulldozer at a landfill. So that was cool. But that was very rare. Mostly, I was at those government meetings.”

What made all the difference was the discovery of Agora Publishing and their popular electronic newsletter, Early to Rise. There was a job opening for someone with writing experience. Desperate to get out of his current position, Jason sent in his resume. He landed an interview and donned a suit in the sticky Florida heat. After an initial lunch meeting, Jason was taken to meet Mark Ford (known also by his pen name Michael Masterson).

As a bestselling author and entrepreneur, he’s well-known in the world of direct-response writing and is credited with generating over one billion dollars of sales through the mail and online.

After being introduced, Mark told Jason a riddle.

Jason answered correctly and was dismissed. He headed home, puzzled over the odd interview experience. Odd or not, it worked and he landed a job as research assistant to Mark. “I helped him with his projects and he mentored me in copywriting, which I had no concept of until I took that position. It was quite an education working directly for him and having his red pen all over my copy every day. I learned a tremendous amount in a very short period.”

Jason’s unique plunge into the world of direct marketing is what eventually led him to make his international leap to Costa Rica. Following employment with Early to Rise, Jason transitioned into writing for another Agora affiliate, International Living, a magazine that publishes information all about how to live, work, or retire overseas.

“Now I write for the print magazine, which goes out to 80,000 subscribers every month. I also write for the website; they have several e-letters, and I work with them on social media membership websites and some other programs and books. They have several conferences each year as well, so I do some public speaking.”

Jason confesses public speaking was a totally new thing. “I’m more comfortable behind the keyboard,” he says. Yet, he likes it. “The first time was terrifying, but after that it got a lot better. So the cool part about my job is I get to travel around the country and I get paid to do it. I interview expats living in Costa Rica, entrepreneurs, people doing cool stuff. They move down and open wildlife rescues or surf camps or hotels. All sorts of things.”

To date, Jason has interviewed a host of inspiring figures, from the Canadian expat who bought a cow pasture and turned it into a beachfront hotel to the German couple who moved from California to start a B&B and an art gallery.

In his work with International Living, Jason often writes about folks who go from hectic, 80-hour a week jobs in the States to pursue their passions, beachside. The communal goal down there is to get away from a life where you worry all the time about paying the bills and keeping your job. Instead, Jason and the other expats in residence indulge in their love of photography, making art, playing guitar, wakeboarding, fishing, craft brewing, and of course, writing.

“A lot of people work from home down here,” says Jason. “Not just in copywriting, but all sorts of other writing-related things. People have their own Money-Making Websites, or they publish travel guides, or they’re travel writers or financial writers.”

“So the great thing is, we all have flexible schedules. We’re not tied up from 9-to-5 every day. I work as many hours as I did in the United States, but it’s not all in one compact little block. I’m usually up by 5 a.m., I put in several hours before the kids get up, take them to school and everything, hang out with the baby in the morning, and then get back to work when he takes a nap. So it’s a very flexible schedule and a great lifestyle.”

Peaceful yet full of life is one of the best ways to describe life in Costa Rica. Howler monkeys are often visible in the trees along the road. Vibrantly-colored toucans fly overhead.

As I contemplate my own move south to the tropical haven, I ask Jason how he wound up in Costa Rica in the first place.

“We’d been to Costa Rica on vacation a couple of times in the past, my wife and I. We always said we wanted to move overseas, probably Costa Rica, maybe elsewhere, but it was just a dream. Something we talked about every once in a while. Then I went freelance and my wife said, ‘You know, we can live anywhere really, so why don’t we move to Costa Rica now and not wait?’”

“So then it became real. It started as a joke, just kind of throwing it out there. But when you have to start planning things, like finding a place to live, it starts getting very real. You’re like ‘Wow, this is really going to happen.’ And you start getting a little nervous, a little freaked out about uprooting yourself. But you know, the funny thing is, as you start to do those preparations, you get a little more comfortable and you’re like ‘It’s going to be great when we get down there.’

“So we didn’t know what it was going to be like, exactly. But we’re glad we did it. Just landing the job with International Living sealed the deal and made the move make sense. There wasn’t an alternative at that point; we just had to do it. We made the leap.

“The big reason was the cost of living. It’s a lot lower here. It’s a big reason that a lot of people move down here. A lot of retirees are living in Cost a Rica, Central America as well.

The funny thing is, it hasn’t affected my writing career at all. I have high-speed Internet, email, Skype, and even a U.S. phone number from a device called Magic Jack. It just plugs into your modem and basically makes it look like you’re in the United States. People can call you for free and you can call them for free anywhere in the U.S. There are no monthly fees or anything like that.

“And the funny thing is — and I’ve heard this from a lot of people down here and from writers living in other countries — most of the clients I work with have no idea that I’m in Costa Rica. That’s the thing about Barefoot Writing, you can be anywhere and nobody cares. It has no bearing on your writing or your clients or anything like that.”

I ask Jason if living abroad has affected his writing style in any way. “The cool thing about being here,” he replies, “is I’m much more relaxed now. Life in the U.S. is very busy, very stressful. You’re fighting traffic. You’re driving around all day. You have to do stuff, like go to Home Depot or Target. You know, in the U.S., I felt like I spent half my life at Walmart or Target or Home Depot just getting stuff. It was just crazy, all that rushing around and stuff.

“But here we live in a small town. My life is much less stressful and my day-to-day is much more relaxed. So I can really just concentrate on my writing and my projects for International Living. It’s been a great move.”

The lifestyle also provides plenty of extra time for Jason to write video scripts, landing pages, autoresponders, and other web-based writing projects for various clients in addition to International Living.

I tell Jason I’m ready to pack up my own family and join him. As a matter of fact, several writers I know through AWAI and The Barefoot Writer’s Club are already planning a move to Costa Rica or elsewhere abroad. Jason graciously adds, “If anyone out there has questions about moving down here, shoot me an email and I’d be happy to help. There’s a lot of freedom down here. So people who come to Costa Rica with a great idea can run with it. I’m also meeting a lot of fellow Barefoot Writers, actually.”

When asked where he sees himself going from here, Jason tells me he feels no need to change what he’s doing. Life is good, and he’s enjoying it. “So I’ll be here for the foreseeable future. Right now, we’re enjoying Costa Rica. We may be moving within the country, maybe next summertime or after that, but for the next couple of years, we’re going to be here. We just love it and we see ourselves here for quite a while.”

“Beyond that, I’ve always seen myself forming a little copywriting agency at some point, which I’ve seen colleagues do. I’d still coordinate with clients and do that sort of thing, but also pass work on to other people. Maybe in a couple of years.”

It makes sense, given Jason’s background as an editor and his ability to nurture writers. I ask him to share tips on how writers can work successfully with editors. “All the writers I work with are pretty good about this, but meeting deadlines is a huge, huge thing when you work with an editor. It’s not just a courtesy. We have publishing schedules that need to be met, publications and emails have to go out on certain dates, sales letters and product launches have to happen on certain dates. So as a writer, you have to submit stuff on time. There’s not a lot of wiggle room or saying, ‘Oh, we’ll just push back that launch date.’ There are schedules that maybe as a writer you don’t know about. Just trust your editor. They have a calendar they are following; they’re not just arbitrary deadlines.”

Jason’s next tip has to do with following directions, a common faux pas for new writers. “What I mean is, whatever the specs are for the project — number of words, or maybe subject matter — don’t reinvent the wheel. Follow the directions.”

His third tip focuses on style. “Learn to follow the style and tone of the publication or company you’re working for so you can match it. That just means checking out the website or checking out back issues of the publication to get an idea of what subjects they cover and how they do things so you can model your own work on that. You’ll see different styles and tones for each publication.

“As far as the editing process, the big thing is not to take it personally. I know when you get back copy with a bunch of tracked changes or red pen comments, it can be discouraging. Because as a writer what you sent the editor is hopefully the best you think you can do; you’ve poured your heart and soul into it. And when you get back suggested changes, you’re like ‘What? No, that was my best.’ And you just feel discouraged and you worry, ‘Am I good enough?’

“But every great writer has had an editor. Whether it’s Hemingway or Mark Twain, it’s just a relationship working back and forth. So don’t get discouraged if there are a lot of changes on stuff you submit. That’s just the name of the game. The editor is experienced in the niche or publication you want to write for.

“Final tip: don’t send your copy in with typos. That’s just a big red flag for editors that makes them think you didn’t spend the appropriate amount of time on the project. John Wood, another AWAI contributor, has a great suggestion for catching typos. He says to read your copy aloud. Not in your head, but actually out loud and slowly. Don’t skim through it. You’ll actually do some editing while you do that because it will help make your copy more conversational.

And you’ll also catch some typos you might miss otherwise.”

Given all he has going for him, I can’t help but ask what Jason considers the best thing about being a freelance writer. “Definitely the freedom. I have deadlines, I have projects going and stuff to do, but I’m not in an office somewhere with a boss walking around looking over my shoulder. I put in a decent amount of hours every week, but I’m not tied down to a certain schedule.”

He reminisces about his job at the newspaper, where he was limited to two-and-a-half weeks of vacation. “If I dared to take a trip for two weeks, everybody was like ‘You’re taking off for two weeks? What are you doing? Who’s going to cover your government meetings that week?’ Or my boss would say, ‘No, you can’t do that. You can pick a long weekend, but we don’t do long vacations here.’ And I’d say, ‘I know, but I have two weeks of vacation and I want to go somewhere long enough to forget I have a job.’”

Jason smiles at the fact he doesn’t have that problem anymore. “I take off in the morning if we have to go do something. I can take off and go to the beach in the afternoon if I want. I don’t have a routine everyday where I have to go to work and get everything done. We can take trips for a week or a couple of weeks if we want to, there’s no problem with that. As long as I have high-speed Internet and I keep in touch with everyone and get everything done, I’m good to go.”

This interview was previously published in the February, 2013 issue of Barefoot Writer. To read more interviews from fellow Barefoot Writers be sure to check out The Barefoot Writer's Club.

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Published: June 18, 2018

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