How I Made $2000 While Vacationing in Rome: Freelancing While Traveling – Without the Guilt

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While I love to travel, I always struggle to keep up with my businesses while I’m on the road. In this week’s contribution, Jesse Gernigin explains how he gets it done and gives his advice on how to enjoy your trip AND make money; to have your cake and eat it too.

You might remember Jesse from episode 174 of The Side Hustle Show, where he gave his suggestions for writing attention-getting proposals on Upwork.

He’s a professional hypnotist, a freelance copywriter, and also helps run a local coin shop. (All about those multiple income streams!)

He blogs at

Take it away, Jesse!

Freelancing Abroad: Secrets to Succeeding Anywhere

Most freelancers love the idea of working remotely. After all, it the “laptop lifestyle” can be pretty glamourous. You’ve got the freedom, flexibility, and funds to live and work from anywhere.

But mixing work and travel isn’t easy.

Too often you get to where you are going, and everything falls apart. The Internet connection sucks, or there is too much going on during the day to focus on your work, or you are too tired at night to finish a project.

Nick’s Notes: One time in Thailand it took 3 different coffee shops until I found one with enough bandwidth to upload the podcast for that week. Not exactly how we’d planned on spending that morning.

Related: Why My 4-Hour Workweek Failed: My Digital Nomad Report Card

Related: The 125+ Best Work From Home (or anywhere else) Jobs

Podcasting in Hanoi.

The truth is freelancing remotely takes a lot of preparation.

If you freelance, you know how important being prepared is. Not only does it prioritize the time we use, it also keeps those weird negative thoughts about whether what we are doing matters away.

(Want to do work that matters? Cultivate the right skills.)

Nick talked about this recently in his 2016 annual review. Even though he is doing better than ever, he still mentioned this thought:

“Yet I’ve got some weird anxiety. Like I’m working every week, but maybe not on the right things. Like I could and should be taking on more or different projects. Like I’m letting people down who email me. Like I’m in maintenance mode and not growth mode — even though things are growing.”

You see the same issue when working remotely.

Recently, I took my father to Rome. The first couple days, I tried working from a local coffee shop, but make every imaginable mistake.

It took me nearly pulling my hair out in frustration to figure out what I was doing wrong. When I did, I changed everything and booked a $2,000 gig that paid for the trip of a lifetime!

I accomplished all of this by overcoming the biggest misconception freelancers have about working remotely.

Remote Work Misconception: I Won’t Have The Time

If you ask most freelancers if they work remotely, you’ll hear remarks like this:

  • “Work on vacation? Are you crazy?”
  • “I’m trying to relax, not work.”
  • “Why would I waste my time?”

Nick’s Notes: This is a serious challenge! You feel major guilt if you’re not out exploring and soaking in the culture every minute of every day. You didn’t come all this way to Tokyo or Prague or Madrid to work! 

Most freelancers don’t work remotely. They see it as a waste of time. The truth is there is plenty of downtime on your trip to get some work in.

While in Rome, we had tours, dinners, and train trips booked every day. Even with a full schedule, I managed to send out multiple proposals and finish a $2,000 landing page project–all on my self-imposed 2 hours of work a day limit.

Despite a busy schedule I managed to, as Nick says, erase my expenses. I did everything on my schedule, finished all my work, and enjoyed my vacation all with one simple trick anyone can do.

A Simple Trick to Find Time

Before I left for Rome, I sat down and did some research. I knew I would need time to work every day so I looked at the average Roman’s day.

I reviewed when they went to work, when they came home, and what time they ate dinner.


Simple. By knowing the rhythm of Rome, I could find time to work, rest, and enjoy my vacation.

Not your average Romans.

What I Learned

Romans are not big on breakfast, and they eat dinner late. That meant that every morning the cafes would have open seats, and at night, the hotel lobby would be quiet before dinner.

I scheduled work during that time, and I never missed a tour. I didn’t have to skip dinner, and I was able to work without interruption or having to look all over for an empty cafe seat  to work.

This works for any trip. Currently, I am planning a trip to Peru. I spent the last two days researching the social flow in urban Peru (where I’ll be spending most of my time).

My research shows that urban Peruvians enjoy a large noon meal and participate in afternoon siesta. That means the best time for me to do work is in the rest time that occurs after lunch.

We have to be careful. For instance, just because I found the right time to work didn’t mean I was doing the right work!

Earlier I mentioned it took me two days,  making every mistake in the book, before I got on track freelancing in Rome.

Here is what happened and what I learned.

(Want to learn to freelance like the pros? Grab Jesse’s $2k a week cheat sheet here.)

Mistake #1: Not Being Prepared

The first day in Rome, I went to the cafe to work. I had my laptop; I ordered my espresso, and I found an especially awesome seat by the window–only to discover the cafe didn’t have Internet.

No big deal.

I left the cafe and headed to the next spot (checking to make sure they had WiFi)–only to discover I forgot my notes at the hotel. I ended up nearly missing my tour that morning trying to finish a project.

Solution: That night, I decided to prep everything I needed for the next day and pack it all away with my laptop. This way when I sat down to work, I had everything I needed ready and in one place!

Nick’s Notes: In that sense, I’m probably more productive when working from the road. Knowing there might only be limited time or limited WiFi, I’ve got to make the most of those minutes and tackle only the most important tasks.

Mistake #2: Being Distracted

Rome is beautiful. Everywhere you look in the city center you see history, art, and unusual people.

Some of those unusual people :)

I had a hard time focusing on my work. It wasn’t until I had failed a half dozen times at starting a project that I knew something had to change.

Solution: I put in my headphones and turned my seat so it was facing the wall. These simple changes created a white noise space around my brain that let me focus on doing my work.

Nick’s Notes: When I’m away from my home office, I’ll sometimes use “productivity music” like or Focus at Will to help me concentrate.

Mistake #3: Overbooking

I made $2,000 in Rome working on a landing page project, but I could have made more. I had another client who wanted a sales sequence built from start to finish.

I wanted to take the project–it would have paid the cost of the entire trip–but I didn’t.


Taking the project would have meant canceling tours and train trips.

Solution: By limiting the amount of work I did I was able to enjoy the trip and deliver a great finalized product.

My Top 5 Remote Work Secrets

Since Rome, I have worked remotely from all kinds of places.

I’ve worked from high-end hotel lounges, airplanes, on the beach between paddle boarding sessions in San Diego, posh cabins, and dozens of coffeeshops.

I’ve learned a lot over that time. Below are my top five tips to freelance remotely. With these in hand, I learned to work comfortably, uninterrupted, and at my best wherever I am.

1. Carry Back Up Hardware

You ever get into a good flow only for your battery to run low and you realize your coffee shop doesn’t have outlets (it happens)?

If you want to work uninterrupted, pack backup hardware. Bring an extra battery, charging cords, external hard drive. They don’t weigh anything; the cost is low, and you will thank me the next time you need them.

2. Have a Notebook on Hand

You ever have a great idea while working only to forget it later? Or are you the type of person whose processor drags because you have thirty tabs open?

I understand. I am easily distracted. That’s why I keep a notebook. Anytime I have an idea, need to set a reminder or just want to keep myself from surfing the net reading nonsense articles, the notebook helps.

The notebook saves my ideas and is a great reminder to read an article without having to have a tab open.

Nick’s Notes: I typically just use the “Notes” app on my phone, ask Siri to remind me about it later, or send an email to myself. That way I don’t have to carry around an extra thing.

3. Consider a Premium Travel Card

I spent a lot of time in airports this year. I took advantage of the Chase Sapphire Reserve’s priority lounge access and often showed up early to work in posh airport lounges before boarding. By the time I boarded, I had got a lot of work done, had a great meal, and was relaxed!

If you are tired of working from uncomfortable seats, crowded food courts, or the tiny Starbucks ledge you see in airports, this is for you.

Note: This isn’t for you if you don’t spend a lot of time flying. The card carries a steep fee ($450 annually).

Nick’s Notes: We just got this one too, arguing that the benefits outweighed the annual fee. For instance, the annual fee gets cut down to just $150 when you consider the $300 in travel credits offered by the card.

Related: This Spending Habit Has Earned Me Thousands of Dollars in Free Money

4. A Resource Page

This is MAJOR. I discovered this working remotely but use it all the time now.

Create a resource page in Google Docs for proposals. Open the doc and put in your top ten testimonials with links to their projects. When you go to write a proposal, you don’t have to search all over the place to get links to articles you’ve written, testimonials for projects or other things.

I discovered this idea in San Diego during a proposal writing blitz, and the time it took to write a proposal dropped by half!

Nick’s Notes: Love this!

5. Send Lots of Proposals

I used to think this was a bad idea. I thought that I’d book too many jobs, not be able to enjoy my trip, and I’d be working a lot more than my two-hour a day limit.

I was wrong. The truth is that projects rarely start quickly. I’ve seen it generally take a minimum of three days for a project to get started. If it is a bigger project with multiple people on it, it can take up to five days to get everyone onboard

(This is only for new clients. If a recurring client asks for work, you would need to start right away.)

Don’t be afraid to send out a massive amount of proposals. There is nothing more rewarding than coming back from a trip with a full schedule.

Related: Jesse’s tips for writing proposals that get the job.

Your Turn

Working your side hustle remotely is possible. In fact, it can be a lot of fun and a great way for you to shore up the details on stuff you haven’t automated yet.

Is your business location independent? What tactics have you found most effective for getting work done away from the office? Let me know in the comments below.


Jesse Gernigin is an author and marketing consultant who has replaced his income working online. He shares how to gets more clients, raise your rates, and more in his Freelancer’s Insider List (it’s free to join!)

7 thoughts on “How I Made $2000 While Vacationing in Rome: Freelancing While Traveling – Without the Guilt”

    • Alexis it isn’t difficult to strike the right balance. I found my best balance came when I locked in a key time to work and made sure all the details were lined up before I started.

    • Thanks Stephen. It took a lot of trial and error before I found the right balance.

      That seems to be the story of my life though, lol.

      My goal with going the digital nomad route is to enhance the experience of my vacation while adding more income to my bottom line to free me up to do it more.

    • I’m glad you like it Brandon! Traveling is a big part of what drives me to freelance. I phased out my career as a full time stage hypnotist to create the freedom I want traveling.

      Last year was Peru and Rome. This year features Iceland, Ireland, Scotland and Europe.

      The best part? I am getting it all on the cheap! Check out Nick’s affiliate link for the credit card bonus. Using points I erased $3800 in fees last year and $5600 in fees this coming year!


  1. Great idea. So now you are familiar with the daily routine of local people wherever you went.

    Your guidance is very helpful for the bloggers as well as freelancers to keep a perfect balance between career and vacation.

    with best wishes,

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