Reading travel blogs as a high school student inspired Rocky Trifari to plan some long-term traveling of his own. "I had traveled a little bit here and there but never on any sort of a solo, long-term trip, which was really what appealed to me," he says.
The opportunity didn't present itself until the Parsippany, New Jersey, native graduated from Rutgers in 2017. At that point, he says, "I was looking for creative ways that I could work online to be able to fund those trips."
Trifari discovered VIPKid, a site for teaching Chinese kids 25-minute English lessons online where teachers earn between $14-$22 per hour. After working on the site for a few months and saving up about $1,000, Trifari took off in July 2018 and spent the rest of the year traveling in Greece, Poland, Spain, Croatia, and Bosnia and Herzegovina.
Trifari spent most of 2019 living in Madrid, studying Spanish. More recently, the pandemic has forced him to stay local. While at home, he's been building up his blog and doing some remote and hybrid substitute teaching in schools as he looks for a full-time gig — and plans his next trips.
Here are some of the steps he took to make possible, plan for, and afford his digital nomad lifestyle.
Trifari was meticulous about planning out spending for that first trip before he left. "I started out by making a spreadsheet, and I tried to estimate how much money I thought I was going to need in order to meet all of my basic expenses," he says. In addition to the $1,000 he saved to get started, he planned to work as needed to stay on the road.
His spreadsheet included costs such as travel from place to place, accommodations, food, and visits to tourist attractions. "There are websites and resources that you can actually use to find the cost of living in different countries," he says. He used sites including Nomad List and Expatistan.
Based on those calculations, "I knew I would need at least $1,000" per month, he says, "and I believed that as long as I made between $1,000-$2,000, I felt like I could probably spend 3 to 4 weeks" in a country.
Trifari started working for VIPKid in October 2017, long before he took off for Greece. He thought it could be a good way to earn money for his travels while he was on the road. "I wanted to have an idea of how much money I could make," he says. "Would it be enough that I would be able to afford my trip?"
After running the numbers, Trifari realized teaching a few classes every day could cover the $1,000-$2,000 he planned to spend every month on his travels.
While in Europe, he'd "wake up, do a few classes," then have the rest of the day to explore, he says. He often ended up making between $3,000-$4,000 per month on the site, and he invested and saved whatever was left over.
Trifari didn't skimp out on trying the local foods or going to the local attractions. But spending more time in each stop of his trip meant he didn't have to do everything quickly and make last-minute, potentially expensive decisions. He could plan ahead and keep costs low.
For example, he says, "if you're staying in an Airbnb, sometimes you'll get a better rate if you stay for a while." Not being pressed for time also meant he could wait to take cheaper flights.
When it comes to food, "a lot of times when people travel, they have to eat out at restaurants a lot or grab food on the streets," he says. These expenses can add up. But with a longer-term stay, and lodgings that include a kitchen, "you typically will start shopping in supermarkets, cooking for yourself."
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