Freelance After 50 Newsletter

F50 Issue #14: Start Your Digital Nomad Journey After 50

Published 5 months ago • 5 min read

F50 Issue #14: January 23, 2023

Rise of the Digital Nomad: Making the Most of Your Remote Freelance Career

Imagine sitting near the window in a cozy cafe, sunlight streaming across the table. In front of you sits a creamy cappuccino, a decadent pastry drizzled with chocolate, and your laptop.

As you sip the delicious Colombian coffee, you think about all the snow you should be shoveling at home. Except you can’t, because you aren’t there. Instead, you’re enjoying springlike weather in Medellin, Colombia!

Instead of snow-covered pine trees, you see lush green palm trees outside the window. Instead of dressing up in a toque and parka for your walk home, you throw on a light sweater.

The only thing that’s the same is your work. You’ve brought it with you on this exciting adventure, because you’re a digital nomad. Have internet, will travel!

This is our reality right now as we enjoy the freedom of location that comes with our online business. The world is our office, and we’ve traded a Canadian winter for several glorious months in the “city of eternal spring.”

Current Digital Nomad Trends

According to the statistics portal Statista, others are enjoying this lifestyle too. In the United States alone, the number of digital nomads rose to 17.3 million by mid-2023, an increase of ten million since 2019.

And the trend is expected to continue, with digital nomads holding a variety of remote jobs. Specifically, “an August 2023 survey revealed that around ten million of them held traditional jobs, while 6.6 million were independent workers.”

In a recent Further newsletter issue titled “The New American Dream,” Brian Clark discusses reasons why people of many ages are leaving the United States to do remote work in other countries. Often, they’re drawn by affordable healthcare and a lower cost of living.

And when it comes to those of us over 50, he explains,

“The key is doing work that allows you to live wherever you want. That’s the new American dream — all the promised benefits of retirement while maintaining an income and the purpose that comes from fulfilling work.
“We’re moving from retirement planning to ‘unretirement planning.’”

So, where would you like to travel? If you decide to plan your own digital nomad adventure, consider these popular and emerging destinations listed by Digital Nomad World. They’re likely to ”offer a good mix of affordable living, fast internet, and a vibrant community of like-minded individuals”:

  • Chiang Mai, Thailand
  • Lisbon, Portugal
  • Medellin, Colombia
  • Tbilisi, Georgia
  • Da Nang, Vietnam
  • Playa del Carmen, México.

Now, if you like the idea but are feeling nervous, never fear. Here are some tips to help you flourish in this rewarding lifestyle.

Five Ways to Make the Most of Being a Digital Nomad

1. Dream big.

We’ve listed some suggestions, but don’t feel you need to limit your dreams to the most popular destinations. Think about other places you’d enjoy calling home for an extended period of time.

This could be your trip of a lifetime, so dream big. Brainstorm a list of possibilities, and ask yourself these questions:

  • Are there some sights you’ve always wanted to see?
  • Do you have friends or family you could visit in another country?
  • What type of climate would you like to live in?
  • Is there a certain location that would inspire you and help you build a new freelance career?
  • Are there locations that would be better for your health?

2. Do your research.

Now it’s time to ground those dreams in reality. Once you’ve chosen your destination, research whether it’s the right place for you.

For example, according to Rowena Hennigan in an article titled “How to Become a Digital Nomad,” it’s important to determine whether you’re legally allowed to go to a certain place. In addition, remember to research and possibly consult a professional for more information about visas, taxes, health insurance, passport limitations, and other legal requirements.

She also recommends researching the local culture and asking friends or family to share any advice from their experiences.

3. Tie up loose ends.

And don’t forget to research what you need to do before you leave your current home. First of all, decide how long you’re going to go and whether you’ll be coming back:

  • Are you going to rent out your home while you’re away, or do you just need a house sitter?
  • Have you decided to sell your home and relocate for an extended period of time?
  • Would you even consider an extended home exchange through popular sites like

If you’re traveling temporarily, ensure you’re able to pay your regular bills online. Decide how you’ll handle any mail that arrives while you’re away and how you’ll continue any medical care and prescriptions.

Also, contact your current employer or clients and let them know your plans. Keep them informed about your availability and time zone so they’ll know how and when to get a hold of you.

Brainstorm any other loose ends you’ll need to tie up before you leave. Then you can relax and enjoy your time away.

4. Develop a routine.

Now, when you reach your dream destination, you may feel a bit disoriented — are you at work, or are you on holiday?

Well, frankly, it’s a bit of both, and we recommend developing a routine so you can make the most of your time. Although it’s important to be productive in your work, you don’t want to miss out on enjoying the activities you came all that way to experience!

If you’re working as a freelancer, you may be able to develop a routine based on what time zone your clients are in. But if your work can be done at any time during the day, we recommend using a technique like time blocking.

That way, you can plan to do focused work for a set period of time and reserve other time blocks for fun and relaxation.

5. Embrace the culture.

Most importantly, consider this wise advice from Rowena Hennigan in the article above about giving back to the local community:

“You don’t have to make any grand gestures to make a difference. You don’t even have to speak the language to communicate on a human level. Just show that you’re interested in learning more about people’s culture and needs, and you’ll be surprised at how profoundly you can connect.”

In Colombia, we’re embracing the culture by learning Spanish so we can communicate effectively and compassionately with those around us. We’re sensitive to our surroundings and have found many local cafes that welcome freelancers and provide a cozy place to work and socialize.

We’re enjoying life as digital nomads, and you can too!

Healthy Habits

To stay physically fit as you explore the sights in your new destination, be mindful of your posture. But not in the way you might think. Forget about simply sitting up straight!

In a video clip from a previous podcast episode, Dr. Peter Attia and Beth Lewis, a former professional dancer, discuss whether “bad posture” exists. The answer may surprise you:

"Beth does not believe in there being [such a] thing as bad posture. She believes that moving around and never maintaining a single posture for too long is more important than superiority of any one particular posture."

For instance, if you regularly sit while doing your work, remember to frequently get up and move around. And make sure you don’t sit in the same position for an extended length of time.

Handy Tools

The World Clock is a handy tool that helps you keep track of different time zones around the world so you know what time it is where your friends, family, and clients are. It’s available on desktop or as an app for iOS and Android.

It also includes a Meeting Planner so you can easily find the best time to get in touch with people.

Above all, remember, when you become a freelancer, the world is your office, and you get to choose where that office will be! Let’s dream big and make the most of the digital nomad lifestyle, both at home and abroad!

Until next time,

Co-founders of Freelance University

431B 41st Avenue NE - Unit 94, Calgary, AB T2E 2N4
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Freelance After 50 Newsletter

Craig & Kelly Cannings, Co-founders of Freelance University

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