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Meet the Hustler Who is Navigating the Wild West of Remote Work

  • By Adela Belin
  • November 25, 2020

Nick Messina is a self-labeled remote work connoisseur—an enviable calling indeed—who co-founded YonderWork to help businesses build and sustain remote working cultures. Inspired by finding a perfect work/life balance, Nick and his team provide the necessary tools, guides and advice for people and companies wanting to lead more flexible and fulfilling professional lives.
After launching YonderWork in 2016, Nick’s team has led several retreats—with six new ones on deck for 2017—and he’s learned a great deal about travel and working independently along the way. Read to learn why Chiang Mai is his favorite remote work location, what inspires him on a daily basis, and his prediction for the future of freelance.

What are you working on right now?

I am working on a five-day remote work bootcamp. It’s a combination of live interaction, online discussions, and quizzes to help organizations assess if they are ready to implement a remote working program.

What’s your favorite remote work location?

My favorite place to work from is Chiang Mai, Thailand. The weather, food, Wi-Fi, and availability of places to work is just unbeatable. I am most productive in a coworking space, where I can feel the energy of other entrepreneurs and remote workers humming away. Also, the learning events and collaboration that happen in coworking spaces are a huge added bonus.

What’s the biggest perk of working independently? What’s the hardest part?

The biggest perk is the freedom to control when and where you work. When you don’t have to work nine-to-five in a fixed location, you can work when it’s most productive for you and where you feel most inspired. You can configure your day to fit your lifestyle, whether it be working nights or exercising at lunch.
The hardest part is being disciplined and focused. If you have multiple clients or projects, you have to be able to manage your time well and know when to call it a day in order to have some work/life balance. (We hear that.)

Where do you look for inspiration?

I talk to a lot of people. One of the best pieces of advice I received as an entrepreneur is to talk to 100 people. I think I have practiced that pretty well. If I read an article and come across someone with an interesting viewpoint, I always try to reach out and schedule a 30-minute conversation. It helps validate ideas, build connections, and it’s a great way to learn what others are working on.

What is the most important personality trait that one must have to find success as an entrepreneur?

Being able to focus. It is so easy to get pulled in a million directions, whether it be building your brand, pitching for investment, conducting market research, etc. You really need to figure out what you are going to accomplish in a given week and get it done. Tinkering is dangerous. Plan, execute, assess, and move on.
[Editor’s note: For more tips on how to be a successful solopreneur, check out our list!]

If you could be living and working in any year or era, which would you choose and why?

Some days when I feel like I need a digital detox, I dream of being a cowboy out west in the 1800s. Just driving cattle, with a gun and a horse. And maybe a cool moustache.

Where do you see the future of freelance heading?

I think freelancing is going to be on par with full-time employment by 2020. Multiple trends are converging to make that a reality.
First, employers are moving to contract-based work. This will only increase as automation takes hold. Additionally, traditional education is becoming absurdly expensive, and freelancing tends to be based on experience and capability as opposed to a fancy diploma. Younger workers are also looking for more balance and freedom in their lives. Finally, services like Toptal, Upwork, and are becoming more advanced to help freelancers and companies connect with each other.
All of these trends will continue to accelerate and bolster freelancing as an attractive option.

Know of an inspirational and interesting “hustler” among us? Send your nomination to

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