#061 Steve Roller on How to Successfully Run Your Freelance Business While Traveling the World

One of the biggest reasons freelancers love being on their own is the flexibility it affords.

When you’re your own boss, you set the schedule. You pick whom you work with and what projects you take on.

And, ideally, you pick where you work.

Unfortunately, most of us don’t take full advantage of our business portability. Some people have young kids. Others have aging parents to take care of. Or a medical condition that limits travel.

Recently, after talking with my colleague Steve Roller from CopywriterCafe.com, I realized that (for me, at least), it’s mostly an issue of both commitment AND fear.

I haven’t made this a priority. And I’m a bit fearful of the unknown.

There’s a third reason that stops many solos…

The belief that you have to go to an exotic location — and that you have to do it for an extended period of time.

If you’re even remotely interested in travel, I urge you to listen to this episode. Steve talks about his motivation for getting out of his daily environment and seeing more of the world. He explains how he’s able to make it work. And he offers many useful tips and tricks for successful “vagabonding.”

The notes that follow are a very basic, unedited summary of the show. There’s a lot more detail in the audio version. You can listen to the show using the audio player below. Or you can subscribe in iTunes or on Stitcher to get this show delivered straight to the Podcasts app on your smart phone, tablet or iPod.

Tell us about yourself

Steve spent much of his career in direct sales. About 10 years ago, he discovered copywriting and decided to combine his sales and writing skills and create a portable business. In March 2009, he left his full time sales job to freelance as a copywriter full time.

He specializes in writing for the fitness, travel and publishing industries, but he also writes in other areas, such as real estate and finance.

What attracted you to long-term working vacations?

In 1989, Steve took a semester off college to backpack through Europe for three months. He’s had a serious case of wanderlust ever since.

When he worked in sales, he was limited to four or five weeks of vacation a year, and he couldn’t take them all at once. He wanted travel for longer periods of time.

He was sold on taking long-term working vacations after reading Ralph Potts’ book Vagabonding. It made Steve see that it was possible.

Where have you taken these working vacations?

For his first trip, Steve spent three weeks in Nigeria.

In 2011, he and his family spent a month in Ecuador. Most of his clients didn’t know he was away. He communicated by email and kept up his normal routine.

clicktotweetFreelance writers can work from anywhere in the world—all they need is Wifi and a laptop.

What stops them from doing it is their mindset, not the logistics.

Tell us about your most recent trip

This year, Steve and his family spent nine weeks in Ecuador. They rented an apartment through Airbnb. They arrived in the morning and by 10:00 a.m. his office and laptop were set up and ready to go.

Every other week, he and his family would take a short trip to other parts of the country.

Describe to us a typical work day when you’re on this kind of trip

Steve gets up at 6:00 or 6:30 a.m. and starts work. He gets in two or three hours of writing every morning before his kids get up. He and his family then spend the day exploring.

In the evening, he works from 7:00 until about 10:00 p.m. He puts in six to eight hour days but spends the bulk of the day with his family.

Tell us about the affordability of this kind of trip

Steve spent less money in Ecuador while vacationing than he would have spent if he’d stayed home. He didn’t have the usual home expenses such as gas, car insurance or utilities.

Ecuador is also very inexpensive. A gallon of gas costs $1.48. The five of them could eat a three-course dinner for about $13.00. They could take a taxi from one end of the city to the other for $2.00.

What are some of challenges of working away from home?

One of the biggest challenges is focusing on your work. You want to spend all your time exploring. But in a way, it’s easier because you don’t have the distractions of home so you’re more productive.

Most of Steve’s clients pay him via PayPal. He transfers money from PayPal into his accounts, and he can then withdraw it from an ATM. He pays his bills online.

When and where are you going to next?

Steve wants to go back to Ecuador next year. Next April, he’s going to spend a month in Paris. At some point, he’d like to do a six month trip.

Are there places worth exploring places closer to home?

You don’t have to leave the country or go for weeks at a time. You can take a week and stay in a cabin in the woods. You could go to New York City and find an apartment on Airbnb or VRBO. You could do a driving trip to a National Park.

clicktotweetWhen you write in place that inspires you, you’re more creative and productive.

Whom is this lifestyle for? Whom is it NOT for?

You have to enjoy traveling. You have to be able to detach from the comforts of home. Can you leave your friends? Can you live without Starbucks? Can you leave your car?

You have to be able to write without the rigid structure of a nine to five work setting. You have to want to explore the world and see new things.

Tell us about Copywriter Café and where listeners can learn more about you

About two years ago, Steve started copywritercafe.com. It’s a place for writers to get together virtually and swap ideas, get feedback and offer encouragement.

Steve also offers training for writers, including The Ultimate Writing Retreat. It’s a three-day, small group retreat to help writers build their businesses.

Steve Roller’s Copywriter Café: http://copywritercafe.com

Copywriter Café on Facebook: https://www.facebook.com/CopywriterCafe

The Ultimate Writing Retreat: http://copywritercafe.com/writing-retreats


  • Good to see others living this sort of lifestyle. I made a conscious decision to move my business online a couple of years ago and now spend a couple of months a year living and working in Cape Town – the flexibility and freedom my business gives me is fantastic!

    • edgandia

      Oh, I bet it’s beautiful in Cape Town right now, Ali! What time of year do you spend there?

      • Ali Marsland

        I went Feb/March this year and March/April last year and am going again in a few weeks – mid Nov to mid Dec. I do my best to escape a chunk of the British winter!

        • edgandia

          I love it! Have a fun trip, Ali!

  • This idea of the working vagabond is one of the reasons I started my own business. I want to be able to do that as well, travelling & visiting friends and family as I work. My ideal mix would be a few months here in Toronto, a few in Vancouver, and the rest in Italy/Europe. =)

    Steve’s experience this summer has really got me thinking about this even more. My plan is to take some small trips in 2015 to get my feet wet and see how it works for me. Perhaps explore more of Canada and the US for a bit. Then once I get my administration & work modes sorted out, really dive in for a longer trip to Italy. Can’t wait!

    Thanks for having Steve on the show Ed. It was nice to hear more of the details about how he did this working vacation. (We had a chat about his trip last month, but we didn’t get into all the nitty gritty like you did here.) =)

    And thanks for the inspiration Steve! I know Ed and his listeners appreciate it. So Ed, where are you going to go for your first working vacation? =)

    • Glad it got you thinking of doing it yourself, Julia! I know Italy is calling your name again. Best wishes, and let me know if I can help you in any way.

    • edgandia

      Oh, Italy! That would be ideal for me.

      My family and I are going to transition into this idea. Our little one is not very portable right now (he’s a real firecracker!). So places that require a longer attention span are out for now.

      I’ve been thinking that doing the Airbnb thing in the U.S. for 1 or 2 weeks a time is a good way to transition.

  • Tom Bentley

    Thanks Ed and Steve. As you suggest, it’s more of a mindset thing, getting over the discomforts that sometimes happen with travel. (And of course your work has to be adaptable to the road.) In the last couple of years, my girlfriend and I have house-sat for 2 months in the Bahamas, 6 weeks in Panama and recently came back from 3 weeks in San Miguel de Allende, Mexico.

    We’re both freelance copywriters, so we (with some occasional glitches) are able to get the work done online. And see beautiful, intriguing places. Check out mindmyhouse.com for opportunities all over the world.

    • edgandia

      Thanks, Tom! Good for you guys — living the portable lifestyle. 🙂

  • Sharon Brodin

    Thanks, this was fun to listen to! I’m just starting out as a copywriter but have hopes to “take it on the road” now and then, too.

    For starters my sister and her family live in Puerto Vallarta, MX so I could hang out there anytime in the winter. My brothers live in Colorado with their families, which would be another possibility.

    My family and I have spent several weeks of our summers for the past 10-12 years in our camper in the northeast corner of my home state of Minnesota. That’s the place I’d hope to spend extended time, although it sounds more remote than Equador as far as being connected!

    The campground we’re at is about 20 miles past any cell reception. And I’ve tried wireless at a local lodge nearby but speeds were as slow as dial-up! I might have to drive the 28 miles to the nearest town in order to be able to get online with any speed, but I’ll probably try it.

    Our three kids are in the late high school/working/college years so it’s hard anymore to get away with them. And my husband doesn’t have that wanderlust, so this might be more down the road for me…but the idea that it’s even possible is exciting!

    • Hello there, fellow Minnesotan! My husband and I just spent 10 days in a campground in California in our 5th wheel. Our daughter’s family moved there last spring. We loved it! I was also amazed at the amount of work I could get done while we drove down the road with my laptop plugged into the auxiliary and using my iPhone as a hotspot connection when I absolutely needed to connect to the internet with the laptop in route. Also, learned to save research pages to my Evernote ahead of time to have access. We plan to do much more of this.

    • edgandia

      I wonder if there are any viable and affordable satellite Internet options for mobile users (?). I know there was a lot of talk about that technology for a while, but I haven’t heard anything in years.

  • Marc-John Brown

    Wow, this was probably my favourite B2B launcher podcast to date! 🙂

    Massive thanks for the inspiration, Steve, and massive thanks for pulling this together, Ed! 🙂

    I myself was on the verge of being a lifelong radical hippy; I spent around 2 years in South America, visiting Uruguay briefly, spending lots of time in Buenos Aires, and then hitch-hiking from there through Chile and Bolivia into Perú. This is where the more serious, responsible inner voice started to kick in, as I met the woman who would later become my wife.

    This travelling spirit has never, EVER left me; I constantly have itchy feet and a burning desire to get back out there and kill my cultural curiosity once more!

    Partly thanks to Ed – and The Wealthy Freelancer book – I established myself as a freelance translator and interpreter in March 2012. That’s when I realised I’d hit the jackpot. I had my wife by my side, and a job which allowed me a good flow of cash whilst travelling the world!

    In December 2012 we decided to go for two months to the Far East. We spent around 5 weeks in South Korea, travelling around the place using http://www.couchsurfing.org. Then we had around 2 nights in Shanghai before spending 3 weeks in Malaysia. I was working all the way on an ongoing project I have (still to this day) in medical translations for an agency client.

    Because the workload from this agency can be a bit sporadic, I never really had a fixed schedule. But I don’t really like having fixed schedules anyway;). Maybe one of the negative points of working whilst on the move, on this particular occasion, was that I’d make plans a day in advance and then have to shuffle those plans around a little, or possibly cancel them all together if I was sent a large workload. For example, one day we planned to meet our Couchsurfing host at 3pm to then be taken to her place, but I received a HUGE batch of files to translate that day, so we had to re-schedule for 7pm, which turned out to be not so convenient for our lovely host as she had a baby son who normally went to bed around that time.

    All in all, though, I’d HIGHLY recommend taking such adventures, and I really enjoyed listening to Steve’s experiences here, especially since they were so closely linked with South America! 🙂 Thank you for the opportunity to be inspired and REMINDED of this reality!

    Now we have a 1 year old baby daughter – the magic of those South Korean airs 😉 – so things are a little bit… different to say the least – for the time being. But I am building myself up steadily as a copywriter, hoping to replace 100% of my translation income by this time next year, and maybe also by this time next year we’ll be back on the road somewhere else in the world?

    Returning to live in Perú and opening a retreat centre is a concrete plan for us within the next five years, though, so maybe we’ll get to meet in the Amazon somewhere between Cuzco and Quito, Steve? 😉

    Huge gratitude to you both once more. This was a DIME!

    • edgandia

      Wow, thanks for sharing this, Marc-John! Love what you’ve done — and love what you’re cooking up. I see some amazing adventures in your future!

    • I love your story, Marc-John! I have a preference for South America myself, including Buenos Aires, one of my favorite cities anywhere. Best wishes.

  • Steve, as a technical writer living here in Ecuador for 6 years now, I have to say thanks for your info. I’ve never heard of the hostel in the caldera.

    Ed has my email address. When you come down next (real estate shopping), drop me a line and I’ll give you the insider view of real estate here in EC. We live in Cotacachi, between an extinct volcano and a dormant one!

    And Ed, thanks for doing the interview. Steve has me pumped about getting on the road again. Maybe I will spend a month down at the coast during the hot season!

    • edgandia

      Heck, I’ll join you guys!

      Thanks for checking out the show, Jeff.

    • Jeff, I’ll definitely try to connect with you when I’m in Ecuador again. Hoping to spend most of January, February, and March 2016 down there.

  • Sandra

    This podcast reminded me of one of the reasons I wanted to freelance in the first place: to be able to work from a warm location from November to April and return to Canada from May to October. I worked a bit on a trip to Cuba, but I wouldn’t recommend it to anyone because Internet access is difficult and expensive.
    I don’t have a specific location in mind, but I’ve looked into Honduras, Ecuador, Belize, Peru and Costa Rica. But honestly, I’d be happy working from a tropical location with Wifi access and as long as English, French or Spanish are spoken, I’m good.
    Thanks for sharing your experience – it’s clear that many of us are interested in trying this.

    • edgandia

      Sandra — Why wouldn’t you want to be in Canada in Jan/Feb?? 😉

  • For my 30th birthday next year, I wanted to do a road trip of the East Coast, visiting friends and historical locations. This podcast was really inspiring in that sense–I hope by the time my birthday rolls around, I’ll have my freelance business fully up and running (not part time as it is now), so I can do this!

    I also want to go to London and to South America to go bird watching. I can see it now: A couple days working, then a day or two to go look at birds.

    Great podcast as always, Ed.

    • edgandia

      Great! Love your plan, Jessica. What a great way to celebrate your 30th. But don’t hope — plan as if it will absolutely happen. And it will be so. 😉

      • When I read this, I could almost hear “there is no try.” Thanks, Ed! 🙂

        • edgandia


  • Pat Bass

    Several summers ago I started going out to Colarado to escape the Louisiana heat. My family spent 5 weeks out there this past summer. It is great because we can get a 3 bedroom condo in ski town for the same as we pay for a week at the beach.

    Much like on the podcast I was able to get the majority of my work done before the kids get up in the morning. I hope to next try this internationally.

    I would also love to hear if people are able to “write off” part of vacation if you are working.