I Left an Unfulfilling Life in the U.S. To Seek Joy and Freedom via Travel (Michelle Marie Checchi’s Story)

This post is brought to you by some of Michelle’s travel essentials: a portable battery pack, microfiber towel, coconut oil, and her favorite book – The Alchemist.

This is the latest interview in a series featuring digital nomads talking about their lives and lessons (click here if you want to be interviewed). The goal is to help demystify the process of making money online, wandering the world, and living an unconventional life!

Michelle has a relatable story of having a stable career she loved, but she felt like there was more to life. She made big moves and big changes and is now traveling the world as a digital nomad. Be sure to check out her YouTube Channel!

Thank you for hanging out with Freedom Is Everything, Michelle!

Key takeaways from Michelle’s interview:

“I initially thought I would travel for a few months, live off of my savings, and that I would return to the US when my travel fund ran dry. But I quickly discovered I had no desire to “return” to any previous life and only wanted to continue forward on this path. And if that was the case, I was going to need to hustle for some money.”

“Living as a digital nomad has helped me see that really isn’t the only way to live; it’s just the option that we’re handed. Once I realized how many possibilities were suddenly at my fingertips, it was game over. Unlike working in a corporate career, my income now has no limit, and I don’t have to negotiate my paycheck. I can live the life of freedom I always dreamed about while doing work I find truly meaningful and enjoyable.”

“Once you step outside your comfort zone, you’ll find tons of new opportunities that you would never have encountered by staying still.”

Introduce yourself! 🙂 Who are you? What do you do for work? And what is your nomadic story?

I’m a traveler, writer, and storyteller from Staten Island, New York. I worked in television news full-time for several years and was deeply committed to my career, but also always felt a lot of inner conflict. Was I supposed to slave over a career and work myself to the bones for the rest of my life to be happy? I always felt the answer to that question was “no,” but I wasn’t sure what else to do, and everyone else in my life seemed to be in a similar position, dedicated to the daily grind.

I always dreamt of creating a life of travel and sharing stories of beautiful places and cultures. After a few years of daydreaming and using short trips to quell my travel thirst, I decided enough was enough, and I set a solid plan to leave my desk job to hop a one-way flight. With a one-year timeline, I saved money, worked a second job to earn more money, did my research, and nervously awaited my departure.

I initially thought I would travel for a few months, live off of my savings, and that I would return to the US when my travel fund ran dry. But I quickly discovered I had no desire to “return” to any previous life and only wanted to continue forward on this path. And if that was the case, I was going to need to hustle for some money.

As I traveled, I started working as a freelance writer to support myself, mostly writing blogs and articles for low rates, to gain experience. After a few months, I was able to use that experience to land higher-paying clients and grow my income substantially.

Now I’m a writer, video creator, and I also produce live shows (drawing on my TV news background). I’ve lived in New York and Oregon, Israel, India, and Ireland, and because of the pandemic, I’ve been recently spending time in the United States. Starting in the summer, I’ll be based in the Middle East.

What inspired you to start nomading? And how has nomading changed your perspective on life?

I was inspired to live this lifestyle because I’m passionate about living a life of joy and freedom, and I felt so unfulfilled in my previous life, the one we’re “supposed” to live. Living as a digital nomad has helped me see that really isn’t the only way to live; it’s just the option that we’re handed. Once I realized how many possibilities were suddenly at my fingertips, it was game over.

Unlike working in a corporate career, my income now has no limit, and I don’t have to negotiate my paycheck. I can live the life of freedom I always dreamed about while doing work I find truly meaningful and enjoyable. Sure, not every day is paradise. But I truly believe I’ll never work 40 hours a week for another company ever again.

Please tell us the detailed story of how you started your freelancing business.

I began by writing articles and blogs, mostly finding my work on freelancing platforms (primarily Upwork). After a few months, I started finding more clients through word-of-mouth recommendations – there’s a lot of power in your network. These clients were much more high-paying, and I was able to be more selective in the jobs I took on. 

I also work as a freelance producer, which is thanks to my professional background in TV. I work with creative agencies and television stations on live broadcasts, ranging from corporate events to television news. This is sometimes location-dependent, and it’s a passion of mine since I love working on live shows (particularly news). 

What advice would you give to someone who’s thinking about nomading?

You don’t have to have all of the answers before you make the leap. Even just a small amount of savings and half of a plan might just be enough to get you started. Once you step outside your comfort zone, you’ll find tons of new opportunities that you would never have encountered by staying still.

There are always fears that can hold you back if you let them. Fear of being alone, finances, what people will think. If this is something you want to do, it’s definitely not a job someone will hand to you, so it will only happen if you take the initiative.

What are the 2-3 favorite places where you’ve lived/traveled to and why?

Israel: The Middle East is beautiful, complex and intense in many ways, and I absolutely love living there. Israel is small enough to easily navigate, has incredible food and culture, tons of rich history, and I love the desert landscapes & the Mediterranean Sea. 

India: India can be intensely overwhelming in every sense of the word: it’s huge, populated, and frenetic (at least to an outsider). But I love the energy, the spiritual traditions, and the food.

Canada: I think Canada often gets overlooked by Americans, but it’s actually an incredible place to visit. There are excellent national parks, vast wilderness, endless lakes, and streams, and it’s truly gorgeous. 

As a woman, what should other people who identify similarly (and who haven’t traveled much) know about traveling/nomading?

I definitely get a lot of questions about safety as a solo female traveler. I would say that overall I feel incredibly safe traveling solo as a female, but I also make decisions with my safety in mind. I stay in a lot of hostels to link up with other travelers and avoid traveling alone at night. While I feel safe, I also am careful not to let my guard down and take steps to prioritize my safety.

What is one of your favorite travel stories/experiences?

Trekking in the Himalayas in Nepal was an incredible experience. I did one of the shorter treks to a beautiful sunrise summit view, and while it was worth every step, this “beginner” trek left me limping for days after. Next time, I’ll definitely do a bit of training beforehand.

Since launching, what has been most effective to acquire/retain clients?

I really focus on retaining my clients because I like working with clients who require a higher volume of work. This means I get to know them intimately, which is important for me as a writer since I’m often writing in their voice. I make sure I’m available and communicative, even if I’m on the move, and always make sure that I get back to work on deadline or earlier than expected. 

As far as a typical workday, no two days are the same, and it really depends on where in the world I am and what clients I’m working with. I make my own schedule and can often work as much or as little in a day as I’d like. I’d say one of the bigger challenges is staying organized, with so many different irons in the fire. I have a running to-do list every day and create a weekly outlook, so I know what to expect for the rest of the week.

What digital tools do you use for your work/business?

Asana is a must, especially when juggling many different clients and projects.

What scale is your business at today, and what are your future goals?

What maybe surprised me the most about being self-employed while traveling is how profitable my own little business could actually be. After about a year and a half, I’ve surpassed my previous salary and am working far fewer hours per week. At this point, I’m more focused on taking on projects I’m passionate about, as opposed to scaling my business. For example, this year, I’m really planning to ramp up my travel video production and personal storytelling.

For someone interested in becoming a freelancer in your field, what’s the best advice that you would give? And what books, podcasts, thought leaders, or other learning resources do you recommend?

Don’t let your ego get in the way of getting started. When you’re first starting out, in order to get clients, you might need to undercut your competitors on cost and really go all-in for your clients. Hustling a little bit, in the beginning, can go a long way, though, because it’ll give you social proof and the base you need to really launch a successful business. So many people need decent content writers and will pay good money for good writing.

If you only had a few minutes to live, what are the most important life lessons you would share with the world?

It goes far too quickly. When you fail to act because of fear, you’re wasting precious time that you could be using to truly live your life.

What do you travel with that you couldn’t imagine traveling without?

So many things. Portable battery pack, microfiber towel (they dry much quicker than typical towels), a great backpack (I use a 65 liter from REI), and coconut oil (for hair, skin, and makeup removal) are just a few of the must-haves.

What’s your favorite book and why?

The Alchemist. It’s about one young boy on a wandering journey and should be required reading for any aspiring traveler.

Tell us about your content creation journey and share some of your favorite content that people should check out!

I was never really interested in being a content creator, especially not a “travel influencer,” because it seemed too inauthentic. But I really love two things: inspiring others and sharing stories. Because of that, I share tips for digital nomads on my TikTok channel (@michellemarietravels) and write articles on my website. This year I also have big plans to produce more travel videos for my Youtube channel.

How can people learn more about you and your work?

I share my work on my social media channels and love connecting with others interested in being a digital nomad! 

Lauren Allain
Lauren is a freelance journalist from Seattle. She travels the globe in search of the best grocery stores, bouldering gyms, and snorkeling locations. Her mission at Freedom Is Everything is to help others make the transition into location-independent lifestyles.