How a Millennial Remote Worker Gets Work, Affords Digital Nomad Lifestyle

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  • Michelle Checchi, 29, has traveled the world while working remotely since 2019.
  • She says her lifestyle is “much more affordable” than she’d expect to have in the US.
  • In 2021, over 15 million Americans described themselves as digital nomads, up 112% from 2019.

When Michelle Checchi, 29, left the US in 2019, she only planned to be gone for a few months — as long as it took to drain her savings account.

Today, she’s still traversing the globe, working remotely as a freelance writer and video producer — making $4,000 in the typical month while only working 15 to 30 hours per week, according to bank documents reviewed by Insider.

“Instead of just feeling stuck in my one place of living, I live in an international environment that’s international for me, where I am still a traveler and a visitor,” she says.

A growing number of digital nomads, or remote workers that travel for weeks, months, or — in her case — “for the foreseeable future.” Over 15 million Americans describe themselves as digital nomads, up 42% from 2020 and 112% from 2019, according to MBO Partners’ 2021 State of Independence study. Driving this trend is the growing flexibility of remote work, a longing to see the world, and the desire to cut costs.

As of June, over 25 countries had introduced digital nomad visa programs aimed at luring remote workers and their wallets. Per the World Population Review, only two countries — Bermuda and Switzerland — have a higher cost of living than New York City, where Checchi grew up. For her, living abroad has been a budget-saver.

Making more money than ever

After graduating in 2015, Checchi enjoyed her job as a local news producer for four years, but she says she had a persistent desire to “travel and experience freedom.” In September of 2019, she sold most of her possessions, drove cross-country, and hopped on a one-way flight to Tel Aviv, Israel.

In her first months abroad, Checchi traveled to Cyprus, India, and Nepal, where she tried to stretch out her savings as long as possible. But after about three months, when it looked like her fun was coming to an end, Checchi had a “spark of an idea:” What if she found a way to make money working remotely? She began browsing Upwork and other platforms for freelance writing gigs.

“I was thinking, ‘If I’m going to get a full-time job, it’s going to root me down to one place,’ she says. “I really wanted to create a lifestyle where I could maintain my location independence.”

While she found some work, money was “not good” early on — a few hundred dollars here and there — not enough to put off her return to the US for very long. But slowly, her workflow began to grow. After about six months, Checchi was making just as much as she had in her news job — which paid roughly $50,000 per year — and was working about half the hours, not to mention traveling the world as she did so.

She surpassed her old salary a few months later, breaking $10,000 in income some months, including $17,000 this past June — when she did on-site video production for a convention. Checchi also has over 68,000 followers on TikTok — where she posts her travel highlights and tips — though she says she only recently began to make “a little bit of money” via social media. Checchi says she used to wonder how digital nomads could possibly afford their lifestyle.

“I was really surprised,” she says. “I was like, “Oh, okay. So this can be sustainable.”

While she continues to do freelance content writing — “ghostwriting blogs, articles, and web copy” — she’s begun skewing more towards her video production roots. Although her clients vary, she often films and produces content for companies in the tourism industry — projects that typically pay for her travel.

Checchi says it’s strange to look back at her time as a local news producer, when she felt her skills weren’t transferable anywhere else.

“Now I’m like, ‘Wow, there’s so much that I can do with my skills when you think outside the box a little bit,’ she says.

The challenges of a nomadic life

When she’s not traveling, Checchi has a home base in Tel Aviv, which she chose in part for its accessibility to both Europe and Asia. While Tel Aviv can be quite an expensive place to live, Checchi only pays $871 per month to rent an apartment with a couple — and typically sublets her room when traveling for an extended period. She tends to stay in hostels and Airbnbs, which helps her stick to a monthly housing budget of roughly $900. That’s a big savings compared to the average June rent of $3,100 for a studio apartment in NYC, where she was previously based.

Airfare is her biggest expense, but given she doesn’t cross the Atlantic Ocean often to see her family, she’s able to travel relatively affordably from place-to-place. There’s also more competition in Europe’s airline industry compared to the US, which helps keep her flight prices lower.

It hasn’t all been roses, she had to return to the US and stay with her family in Staten Island, New York, for a time during the pandemic. Aside from that, she admits she doesn’t see her family often — though she’s now making an effort to return to the US every three to four months. These flight costs can add up, but she says they’re well worth it and that if need be, she can seek out extra work to offset them. While her best friends are in the US, Checchi says she has friends “all over the place” and that traveling alone has been a “great way to meet new people.”

While she doesn’t think a nomadic lifestyle is for everyone, she has no plans to give it up anytime soon: “I’m living for myself at this point in my life.”

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