How To Work and Travel: What I learned to succeed around the world

Please enjoy this blog post about how to work and travel from Jesse Gernigin. You may remember him from the blog posts How I Went From Graduating College and Living in My Childhood Home to Running a Lucrative Coaching Business and Fast Start Freelancer Secrets: Getting Your First Client. Today, he is going to share his tips…

Michelle Schroeder-Gardner

Last Updated: December 28, 2023

Disclosure: This post may contain affiliate links, meaning if you decide to make a purchase via my links, I may earn a commission at no additional cost to you. See my disclosure for more info.

Please enjoy this blog post about how to work and travel from Jesse Gernigin. You may remember him from the blog posts How I Went From Graduating College and Living in My Childhood Home to Running a Lucrative Coaching Business and Fast Start Freelancer Secrets: Getting Your First Client. Today, he is going to share his tips on how to work and travel. Enjoy!

Interested in learning how to work and travel? In this post, I'll tell you all about my mistakes with work travel, my best tips for success, and more!One of the benefits of freelancing is being able to work anywhere.

You see blog posts, Pinterest boards, and more of exotic locations, far off locales, and people working from hammocks, lounges, and European cafes.

I love the freedom of traveling. I decided to transition from being an entertainer to a full-time online freelancer for that reason. Since then, I’ve worked from cool locations across the world:

  • Rome
  • New York
  • Florence
  • Nashville
  • Horseshoe Canyon Ranch
  • San Francisco
  • Chicago
  • Louisville

Along the way, I experienced a lot of hiccups, bumps in the road, late nights, and unhappy clients.

Since then I’ve grown. I no longer take Skype calls at 3 AM, miss out on tours or day trips to finish projects or worry about late payments.

Sound amazing? It is.

You want to travel the world, work from anywhere, freelance your way to freedom, all while avoiding making the stupid mistakes I did?

If you are ready to learn how to work from anywhere and want to save yourself the headache of getting started, read on.

Related read on how to work and travel: How To Become a Digital Nomad – How I Work and Travel 365 Days a Year


The Three Biggest Mistakes I Made With Work And Travel

When I started freelancing abroad, I made a lot of stupid mistakes. To keep you from making the same mistakes, ruining your trip, and losing clients, I am going to share the three biggest mistakes I made when trying to work and travel and how I fixed them.

Related reads on how to work and travel:


Mistake 1: Mixing up Time Zones

The internet has opened up freelancing to everyone around the world. I have worked with people from every time zone.

Time zones can be tricky for work travel, though. Even if you get used to scheduling meetings for your time zone, you can still get times wrong in other areas of the world.

That happened to me. I missed an important meeting while in Rome. I forgot my time zone had changed from home. Thankfully, the client was forgiving and we rescheduled.

If you are holding meetings in another part of the world, be sure to double check times for work and travel. Here is the site I use to double check times when traveling abroad.


Mistake 2: Scheduling Free Time For Work:

I have trouble turning off the industrious part of my brain. I am a product of to-do lists, schedules, and workflow.

At home, this helps me to accomplish a ton! In Rome it wasn’t as nice.

I made the mistake of scheduling work too close to tours and day trips. This meant I had little time to get into the workflow, and once I got into a good rhythm, I’d have to stop for vacation stuff.

During the tours and day trips, I was anxious I wasn’t working.

Thankfully, this only lasted a day and a half. My solution was to get up early and do my work in the bar (which was empty). By the time the day started, I had gotten work done, felt accomplished, and enjoyed the rest of my day.

Not a morning person? Before dinner is also a great time to do work. I’ve found that most trips would be over around 4-5 and dinner would be 7-8. That period in-between is a prime space to get work done if you don’t relish waking up with the sun.


Mistake 3: Scheduling too Much Work and Travel:

I made the mistake of booking too much work while on my trip.

On my second day in Rome, I booked a contract for a $2,000 landing page. I was ecstatic. The project would take me two days.

That meant I would come home having earned a third of my total cost of the trip while on vacation.

It nearly turned into a disaster. Halfway through my second day, I realized I wasn’t enjoying my trip. I was making money, but I was wasting money I had spent on myself and my father.

I ended up staying up really late one night to finish the project. I was tired the next morning but enjoyed the rest of my trip.

I know it is seductive to book a lot of work when it comes in. To avoid this, I came up with a formula. I allow two hours every day (either early in the morning or before dinner) for work.  

Afraid that clients won’t be patient? They usually are. If a client requests a rush, I send this message.

Feel free to copy and paste for your personal use.

“I appreciate the opportunity. This project interested me, and I feel my skills fit the impact you want.  For the next ‘X’ days, my schedule is limited. I’m traveling, and my available time doesn’t fit your deadline. I can finish your project by ‘X’. That is a little past where you set your goal, but not much. If you are okay with that, let’s move forward. If not, I understand. Best of luck.”

Copywriting Breakdown: This message works wonders! I use it all the time when clients want rush jobs or I can’t meet their desired deadline.

The email works for two reasons.

Related: 15 Of My Best Working From Home Tips So You Can Succeed


1. You are honest about work and travel:

Being upfront with a client is powerful. Clients are used to freelancers flaking out. By telling them what your schedule is upfront, you build trust. You also give them the deadline you can meet. This is powerful because it lets the client see a concrete time to get a return.


2. It is positive and client centric:

The email is upbeat. You express gratitude for their interest, show interest in their project, and sincerely state you can impact their results. By keeping the tone positive, clients will feel a deeper connection which increases your chances of keeping the project and being allowed to finish it on your schedule.

Even though I made all these mistakes, everything turned out great. I booked a $2,000 client in Rome, finished the job, and enjoyed my vacation.

I wouldn’t have done any of that if I had listened to other freelancers, though.

(Want to Start Making Money Online? How To Start a Blog!)


Why Most Freelancers Hate Working Abroad

When I talked to freelancers about working on vacation they scoffed.

They had three major complaints.


1) Clients don’t want to work with you when they learn you are on the road.

-Not true. This is a common mistake carried over from the corporate life. At normal jobs, your bosses didn’t trust you to work remotely. This isn’t true in freelancing.

Client aren’t interested in your location or schedule; they are interested in the results you deliver. It doesn’t matter where you are. What matters is what you give them.


2) Your work suffers because you can’t focus.

-Also untrue. Freelancers mistakenly correlate location with performance.  The landing page I wrote outperformed their existing test page by 17%. Doing good work isn’t about where you are.

If you have great systems, access to everything you need online, and a place to work,you can produce at your best no matter where you are.


3. You can’t make money.

-Nothing could be more wrong! Freelancers I talked to complained that the best clients are in American time zones. They told me if I didn’t respond instantly to questions or projects, I’d never book anything. They are wrong.

Your time zone doesn’t matter.

It also doesn’t matter if you are the 1st, 15th, or 52nd proposal your client receives. If you take the time to address the client’s needs, craft a proposal specific to the results your client wants, and you include relevant work examples or testimonials, you will book work!


Freelance Strategies to Succeed Around the World

I have developed multiple strategies, ideas, and methods to increase my success freelancing abroad.

Below I’ve shared three of my favorite tips so you can succeed no matter where you are! Work travel has never been easier.

1. Find Good Wi-Fi For Work and Travel:

If you read this blog, you know Michelle has talked at length about securing internet to work. If you want to work for long periods uninterrupted, make sure you have solid internet.

In my travels, I’ve found the worst internet is at the hotels (both luxury and plain). My best luck has always been at coffee shops or, in a pinch, McDonald’s!

(Want More Travel Working Trips? How To Make Money While Traveling)


2. Back up copies of everything you need in offline documents:

Let’s be honest. No one likes to carry tons of extra stuff on a trip. Between the rising cost of baggage and the pain and stress caring for business documents, you can lose your mind. To work and travel, backing up copies of everything can make life much easier.

My suggestion: Back up everything in digital documents you can access offline.

I use Word for larger documents and the downloadable version of Google Docs that comes with Google Chrome.

The service doesn’t matter. What matters is that you can access needed documents without internet.


3. Come Prepared To Work:

Freelancers aren’t as busy as they think they are. I’d venture 40-55% of a freelancer’s time spent working is wasted.

Working at home, we have that luxury. If you like to start slow, have that first cup of coffee or scroll through your favorite blogs before working, it is okay. You have all day to work.

You don’t have all day to work on vacation. To help with this, you should be prepared before you sit down to work.

What I Do: The night before, I prepare everything I need for the next day’s work. I make sure my sites, documents, and resources are ready to go when I sit down to work.

That means the moment I start working, I am ready. I don’t waste time looking for messages, documents, or follow ups. This allows me to work and travel better.


Final Thoughts on Work and Travel:

I love freelancing remotely. I struggled at first, but now my work is seamless.

You can freelance from anywhere if you approach your work prepared, with a specific goal in mind, and if you limit how much you are going to work per day.

Jesse Gernigin is an author and marketing consultant who has replaced his income working online. He shares how he gets more clients, raises his rates and more in his Freelancer’s Insider List.  Get an insider’s look at the psychology, strategies, and everything you need to achieve this today!

Are you interested in learning how to work and travel? Why or why not?

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Michelle Schroeder-Gardner

Author: Michelle Schroeder-Gardner

Hey! I’m Michelle Schroeder-Gardner and I am the founder of Making Sense of Cents. I’m passionate about all things personal finance, side hustles, making extra money, and online businesses. I have been featured in major publications such as Forbes, CNBC, Time, and Business Insider. Learn more here.

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  1. Mustard Seed Money

    I would love to travel and work at the same time. I feel like my eyes are slowly opening to the opportunities of freelance work. Once I reach FIRE, I’d definitely be open to taking on some interesting jobs to make some additional money and keep my skill sets sharp. It’s amazing what the Internet has created at times.

    1. Jesse Gernigin

      The world is more accessible now than ever! Traveling and working is such a rewarding experience.

      I suggest micro-testing it one month. Set aside a week, pick a close location, and head out! Freelance in the morning, enjoy the day, and send proposals before bed!

      You just might catch fire this way!

  2. Travis

    Jesse…great post and very inspirational.

    Unfortunately, I don’t think I’ll be traveling and working at the same time as I have 4 kids. However, I can relate to your tips & struggles b/c I work at home often. Like your work suffers b/c you can’t focus. LOL

    Here is to your success!

    1. Jesse Gernigin

      Travis congrats on the awesome family! 4 kids is two and a half jobs in itself!

      If you ever really catch the travel bug and want to go, kids and all, Tim Ferris has an amazing post that details how a family does just that.

  3. This post inspires me and also teaches me some important lessons. I like how practical you went. I am a new blogger and hoping to travel and bring my work along. ๐Ÿ™‚

    1. Jesse Gernigin

      You can travel and work! A ton of people do it. It is amazing but it takes focus, consistency, and dedication.

      My suggestion is to pick a source of revenue you can create with freelancing, grow that to a comfortable level (there are plenty of resources online on how to do this. Michelle has some great posts on here, some from ME, lol) and take action!

      Once you have freelancing income coming in pick a location and try working remotely for a week from there.

      You might fall in love with it! If so the possibilities are endless!

  4. There’s nothing better than being able to travel the world and work from your laptop, right? Some great tips here!

    1. Jesse Gernigin

      Glad you love the tips!

      Having coffee in the Sacred Valley of Peru while hammering out copywriting work for clients with the mountains beyond my screen, hard to say no to that!

  5. I mess up Timezones when I’m NOT traveling!

  6. Jesse Gernigin

    I have three suggestions. Follow them in this order.

    1)Build up a freelancing profile and portfolio:

    Don’t wait till you are free of your normal job to start freelancing. Start now! This way you can:

    A)see if you like freelancing:What if you hate it and don’t realize it yet! Make sure you like the daily grind before making it your only choice.

    B)Transition seamlessly into working full time. You won’t go from zero to fully booked in a week. It takes a few weeks of setting up clients, finding work, building relationships, etc. Get started now!

    2)Price yourself accordingly:

    Remember, you won’t be working on projects 40 hours a week. You will probably bill between 15-25 hours a week. Make sure your per hour fee reflects your needs.

    My suggestion is to double the rate you think you need. This makes up for time lost emailing and talking with clients, waiting to get paid, and the headaches you’ll experience along the way.

    3)Don’t get discouraged:

    Freelancing success is all about consistency. If you read about Michelle’s blogging history for the first couple months she barely made anything. Imagine Michell at month 6 and Michelle today. Michelle makes the money she does today because she focused on consistent adaption, growth, and learning.

    Bonus Tip:Make it a key point to learn something new in your field every week. Your success will last if you can always provide more to clients.

  7. Jesse Gernigin

    I know. I double check everything before sending out messages or setting up meetings.

  8. Aww Man
    What a nice article, when i am was reading it, the em feel so good
    Thank you for sharing your knowledge
    Thank you again

    1. Jesse

      Glad you liked it!

  9. Beth @ The Money Pixie

    While I don’t get to travel as much as I’d like to, I always work when I do. I’ve found that clients don’t care where I am as long as I meet my deadlines. I’ve even told clients before that I’m going to be in Florida, or wherever but I’m always working. They laugh and get it.

    As for making time to work, I’ve found that doing a bit when you get up and then making time later in the day works well for me. In fact, this past December, I was crazy busy, but I was able to get the work done and enjoy the beach all at the same time. It’s just a matter of scheduling and balance.

    1. Jesse

      It really is! I think setting aside time is key. It is rare to do anything in the morning on a trip so filling the time working is what I do!

      I earned back the cost for my last trip working mornings.

  10. Michelle
    I always had that fear that if a client finds me on the road, it is a sign of non-professionalism. But now that you have cleared that location does not matter till the results are coming and I am able to deliver them the best.
    I also want to travel the world. Thanks for the motivation.

    1. Jesse

      Location has nothing to do with quality. I’m glad you realized this! Most people end up shackled to their house or local coffee shop in fear of losing clients. The truth is the quality of your work is what matters, not where you do it!


  11. Love the tips in this post, Jesse! You know, I always liked the structure of corporate life, so I was a little nervous (well, downright lost, really) when my husband’s job moved us abroad and I started freelancing. But I’ve found ways to structure my days much like my old, comfortable 9-5 with lots of adventure time on evenings and weekends. No matter where we’re traveling, I work my 8 hour day, then enjoy myself! It’s really a perfect balance. And with your advice in this post, there’s no reason we can’t all live the dream ๐Ÿ™‚

    1. Jesse Gernigin

      Michelle the most overlooked words in the freelancing community are ‘balance’ and ‘consistency’. The freelancer that works hard, shows up every day, and masters those two words will succeed in any field that end up in.

  12. Jesse Gernigin

    Elaine i’m glad you like my content! Sorry for the late response a freelance client dropped a rush job on my desk at the last moment!

    I thought people would be interested in the real work behind working abroad. Don’t get me wrong i’m a sucker for beautiful Pinterest images and travelporn as much as the next freelancer.

    But if you are going to make it work you have to dial in the details (and there are a lot of them). I hope what I was able to gleam from my experience helps you take that next step!