Tutoring took off very quickly. In my hometown of San Luis Obispo, California, I taught math, physics, and statistics for the SATs and other admissions exams at rates of $135 to $155 an hour.

Working the tutoring into my travels

In June 2017, a friend asked if I wanted to go on a trip to Japan.

At that point, I'd been doing all the tutoring in person, and I realized I could do all the tutoring online and travel longer.

We went to Japan for three weeks. Then, I continued to Southeast Asia, tutoring the whole way. During that time, my student base expanded throughout the US, including some international students.

I got into a rhythm of spending three months abroad and three months back home in California. I traveled to Western Europe and jumped around North Africa, South America, and Central America until the pandemic hit. By that point, I had earned a six-figure salary from tutoring.

I work the tutoring job into wherever I am. I settle down in the same place for a week and open up the hours I want to be available for tutoring. I spend the rest of the day exploring.

One of my favorite pictures from my travels is of a tiny village in Guatemala that doesn't appear on Google Maps. There was great cell service, so I made some openings in the calendar and connected to my cellphone's Wi-Fi hotspot. There's a picture of me sitting in a chair in the jungle, tutoring. It always makes me smile.

Boutte tutoring at a remote village in Guatemala



Matthew Boutte




The pandemic gave me a chance to try new things

My tutoring slowed down significantly at the beginning of the pandemic, so I had a lot of free time. I decided to teach myself data science.

My family friend's farm near my hometown was short-staffed, so I agreed to help harvest cilantro for about two and a half weeks. It was very hard work and less financially rewarding, but I've always been fascinated with agricultural fieldwork.

Boutte always wanted to experience "the miracle of food"



Matthew Boutte




Weaving work, life, and travel together

One dimension of wealth I struggled with was choosing freedom over time. When a student pays me for the hour, it's money for my time.

Practicing law was the same thing. At the law firm I worked at, I billed in six-minute increments, which messed with my perception of time. I didn't like thinking of time as having monetary value.

With my travels and tutoring, I could have buckled down at home and been more efficient, but I wanted to weave work, life, and travel together.

In 2021, I started a new career as a data scientist, working at the intersection of law and data science. But after I moved to Chicago, I started getting more inquiries about tutoring. Now, most of my students are in high school, and I help them with taking standardized tests to get into university.

I've recently started learning web development; maybe I'll also find ways to monetize that.

I have no regrets about going to law school, but I realized pretty quickly the practice of law was not for me.

Looking back, I wish I had tried more things. I've heard the analogy of a sail on a ship: You can't guarantee the wind will come, but the more sails you put up, the better off you'll be when the wind does come. So putting yourself out there, taking more risks, and learning new skills are all ways of putting up more sails.