Digital NomadWhen you hear, ‘digital nomad’, what picture comes to mind? For me, the picture to the left does a pretty unbelievable job of capturing the magic and allure of working remote. But it CAN’T actually look like that, right?

Well, it just so happens that is a picture of my husband working in Nicaragua, just one of the many stops we’ve had while working remote and traveling.

I would be lying if I said working as a digital nomad is all beaches and blissful sunshine. We’ve had our fair share of trials and tribulations. But overall, it’s even more amazing than we envisioned. If you can work remote and travel the world, DO IT.

Almost every day, I get a message on Instagram or Facebook asking, ‘how can you afford to travel so much’? From the lens of Instagram, I’m sure it looks like my husband and I are just trust fund kids trotting the globe.

My friends and family members constantly see pictures of beaches or exciting new cities, so it’s no surprise they think I don't work. I hate to break it to you, but I come from a middle-class family of educators, so I am NOT a trust fund kid. In fact, both my husband and I maintain our 9-5 jobs WHILE we travel, and we could not be happier.

However, there are a few key things to keep in mind. Luckily for you, I’ve done all the research and made all of the mistakes, so based off of my experiences, here are 7 tips for working as a digital nomad.


1.Find Jobs on Upwork

About a year and a half ago, I found myself in a position where I didn’t want to be buckled down to a particular geographical location, so I began entertaining the idea of working as a freelancer. I ended up creating a profile on Upwork and within one week of applying to jobs, I got hired by Michael Management. I worked for a few months as a freelancer for MMC and was lucky enough to be hired full-time as our Course Coordinator.  

 MMC’s CEO Thomas Michael feels very strongly about the ‘work from anywhere’ attitude and says it’s a big part of what makes our team so successful.  After working with Michael Management for about a year, I came to Thomas with a request: can I really work from ANYWHERE? Thomas is a very unique boss and encourages us to work from any geographical location. If we get the job done, he doesn’t care. This was absolute to music to my ears and has allowed me to work from numerous countries.

For the past few months my husband and I have worked from Costa Rica, Nicaragua & Panama, and we are gearing up to tackle Europe next. Working remote opens up a world (pun intended) of possibilities, and I am never looking back.

While all Upwork stories may not be as ideal as mine, it’s a fantastic platform for quality remote jobs. In fact, my husband found his current role on Upwork as well. He had a very similar storyline to me.

He got hired for a project, did well, got along with the team and then got hired on full-time. However, while it only took me a week to get a great job, it took Michael a few months to find something that worked well for him. So, don’t be deterred if it doesn’t happen instantly. It’s worth it—keep applying!



We were very careful to find accommodation with highspeed internet, but as with most things in life, reality and expectations were often misaligned. We experienced power outages, random internet blackouts, storms-- you name it and it happened to us.

Luckily, we decided to bring ‘backup’ WIFI in case the internet our accommodation didn’t work, and we ended up using it as our primary source of internet a lot of the time.

We purchased a Skyroam to bring with us, and overall, we were very impressed. Skyroam is a global mobile WIFI unit and is essential for any digital nomad. After you purchase the actual product, you have to ‘pay as you go’ for WIFI. Their customer service team is great and helped us set up a good plan. We started by paying per GB and quickly changed to the monthly plan since we relied on it so heavily.

The great thing about using a Skyroam is that it’s small enough to fit in your pocket, so we were able to take it with us everywhere which proved to be extremely helpful and convenient. Our biggest complaint is that the monthly plan is unlimited only up to a certain GB usage, and then they throttle it. If you have reliable internet in a café or accommodation, use that first, and then switch to the Skyroam.

Trust me and make the investment. It will be worth every penny, and even if you do all your homework and REALLY think your WIFI will be fast enough while you travel, there will be tons of instances where it won’t be. You need backup and Skyroam is your friend.


3. Test Out a New Place Before Committing for Too Long

We learned this the hard way. When planning our trip, we decided that it made logistical sense to stay in one place for a month. If you stay at an Airbnb for a month, it is significantly cheaper. We wanted to get to know the place we were in and not just feel like tourists. Staying in one place would keep our costs down since we wouldn’t be flying or traveling constantly. All of this seems reasonable, right? Well, it totally backfired!

We realized quite quickly that while a place may be interesting to visit for a week or two, a month is a long commitment, and expectation and reality are often quite different. For example, we started in Tamarindo, Costa Rica, and while it was lovely, it was super touristy. We ended up changing our itinerary and spending time in Nosara and Arenal as well, which we enjoyed much more.

We lost a lot of money changing our plans, and it happened multiple times. We ended up loving Panama City and stayed longer than expected. We strongly disliked Bocas Del Toro so we left 4 weeks early and rerouted to Nicaragua (which we LOVED). We veered so far from our initial itinerary and we lost a lot of money. Our nice and tidy plan did not go accordingly.

If you KNOW you love a place and will be happy for a month or longer, then go for it! There are obviously lots of financial advantages. But, if you’re just exploring a new place and are not 100% confident it will fulfill all of your dreams, book yourself accommodation for a week to start with, and then go from there. We will definitely be altering our travel planning technique going forward.


4. Put Blinders on During your Workday

I was concerned that I would be distracted from work knowing I was in a new and exciting place; however, I was highly productive and efficient right from the beginning. I mentally forgot that I was in a new place during the workday and then immediately switched to vacation mode after hours.

My husband and I became weeknight and weekend warriors, taking full advantage of our off hours. We both felt that were able to enjoy everything we wanted to and didn’t miss out on anything.

In fact, I found it quite refreshing that I knew I only had a bit of time in the evenings to explore, so I really cherished and took advantage of it. We had all of the benefits of traveling while still maintaining a semblance of day-to-day reality.

Don’t try to work on the beach, or surf during your lunch. Just put your head down, get your work done and then play to your heart’s desire afterwards. Life as a digital nomad means you can always travel, so don’t feel like you have won’t have enough time to enjoy your new locations. You will.

5.Things WILL Go Wrong

I am a big planner. I love event planning, planning travels, I even make travel itineraries for friends and family just for fun. I’ve had to learn that even if you plan and research about traveling for days on end, the reality your trip will be wildly different, in both good and bad ways.

We had several speedbumps during our travels. For example, as discussed, our itinerary changed almost daily. My husband is basically a walking pharmacy on trips, but we still both got sick at times. We even had to cut our most recent trip short (by 2 months) because I broke my nose while surfing and am back in California for surgery. Always be prepared that your trip may change drastically.

In addition, make sure to educate yourself about your surroundings in terms of safety, politics, weather, local healthcare etc. I always register at local embassies before arriving to a new location so that I can get email updates about any important updates or changes. And make sure you make an appointment with your physician to get any shots you made need to travel. Take all of the precautions you can, and then come to terms with the fact that you will still have to handle unprecedented scenarios.

Personally, I feel like this is part of the magic of traveling, but that was hard to remember while sitting on a beach in Costa Rica with a bloody broken nose. As the platitude goes, expect the unexpected.

6. Stay at Selina

As a big researcher, I spent hours finding the perfect Airbnb, hotel or hostel before our last trip. My criteria included good WIFI, comfortable working space, close proximity to everything, possibilities for exercise, good food nearby, and preferably, a ‘digital nomad community.’

What I didn’t realize is that this ideal digital nomad place ALREADY EXISTS. It’s called Selina and it’s essentially an adult hostel that is ideal for remote workers.

Selina’s tagline is a new way to stay, explore and co-work. They have locations all over the world (they started in Central America but are expanding to Europe and elsewhere). They are chic, affordable, community-oriented and all Selina’s offer beautiful co-working spaces at a very affordable price.

They have a kitchen, restaurant, daily yoga, nightly activities and FAST WIFI. We could have saved a lot of time and money if we had exclusively stayed at Selina. They have a hostel-like feeling, so we made lots of friends and felt very at home while there.

Going forward, we will always check to see if there is a Selina available!


7. Get Travel Medical Insurance 

I decided to keep my primary insurance through Michael Management and to also purchase cheap international insurance in case anything was to happen. Well, one broken nose later, I’m extremely happy I have both.

Even if you are planning to travel for a year, you never know what will happen medically, so in my experience, it’s always a good idea to keep good domestic insurance through work (if it’s offered).

And while medical expenses are often very affordable abroad, travel medical insurance is extremely affordable and therefore, I think quire worth it. We had travel insurance through World Nomads Travel Insurance, and it came out to a few dollars a month.

Since we ended our trip early due to my nose, we were even reimbursed through insurance for the flight. If you’re accident prone like me, do yourself a favor and take 30 minutes out of your day to read about travel medical insurance to see if it will be worth it for you.


Making the Most of Working Remote

We are so lucky that we live in an age where all you need to get your job done is a computer, and a good WIFI connection. I feel very privileged to work for a company that prizes itself on flexibility, trust and a ‘work wherever’ attitude.

If you have the possibility and desire to work and travel, you will be far richer for it. Working remote has completely shifted my idea of what a 9-5 should look like, and I’m afraid I’m not going to be able to go back to the old ways. Our CEO asked me how to keep Millennials happy in the workplace, and I said that flexibility and being location independent were my top values.

If you’re a company still on the fence about working from home, you’re doing yourself a disservice by missing out on great people who are looking towards the future of work.

Being a digital nomad is exciting, stressful, awesome, but most importantly, worth it! Get out and explore!! Oh, and remember to work super hard, because the only reason you can travel is because of your job.

Good luck!

Author Photo

Claire Albaum is the Training Manager for Michael Management. She recruits new SAP instructors in addition to fostering relationships and working with existing MMC instructors. She has years of experience in recruiting and project management within the field of education. Claire is passionate about connecting people with opportunities and facilitating learning initiatives.
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