This as-told-to essay is based on a conversation with Austin Nasso, the 30-year-old comedian and cofounder of Tech Roast Show, based in New York City. His employment at Microsoft has been verified by Business Insider. This story has been edited for length and clarity.
I’ve been doing standup for 12 years. I went to UCLA, studied computer science, and started a comedy organization there. When I graduated, I went to Microsoft to be a software engineer in Seattle.
In 2018, my friends and I started Tech Roast Show, which is a crowd-work show making fun of tech people, that we perform in tech hubs in the US, Europe, and India.
In 2021, I left Microsoft to pursue comedy full-time. Now, when I perform locally, I’m at New York Comedy Club and Westside Comedy Club, and a bunch of smaller ones. I just released a comedy special, and I’m about to go on tour in India for Tech Roast Show.
I can’t imagine doing anything else — but I approached the career change methodically, and pursuing this life isn’t always as glamorous as people often fantasize about.
I thought of my life as a startup
When I graduated from college, I read “The 4-Hour Workweek,” a book about how to make income on the side and live the life you want. It taught me three key learnings that I took with me as I juggled my full-time job and comedy.
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One of the main things I got from it was figuring out how to work remotely as soon as possible. I worked at Microsoft for four years, and after the first year, I convinced my manager to let me work remotely. In 2018, I moved back to Los Angeles, worked in a WeWork during the day, and did shows at night.
Another key principle I gleaned from the book was learning how to minimize my workday. I needed time to code, so I prioritized that first and made sure not to schedule meetings during those focus blocks. It’s easy to get caught up in a bunch of miscellaneous tasks that are low-priority.
Luckily for comedy, it’s mostly at night, but there was still friction. Sometimes at 5 p.m., my manager would be like, “Do you have two hours right now?” I would be like, “No, I’m going to go film a sketch. I can’t.”
The book also taught me to view my life like a startup, and thinking like that made me more comfortable with taking the leap. My income was at its high point at Microsoft, and I knew it would go down when I quit. I knew I could go a few years without making money from comedy, as long as I could offset some of my expenses by renting out a condo and an Airbnb.
A hobby is not a career
When you leave a job to follow your passion, you need a sense of validation that you’re good at it. There also has to be some indicator that you can monetize it. You have to recognize the difference between a hobby and a career.
People think it’s so brave and cool that I quit my tech job. At the end of the day, I just have a different job.
I went viral on TikTok before I quit, which is part of the reason I left. I thought you could succeed at standup if you’re good and have a lot of followers. I’ve been doing standup for 12 years, and that’s just not how it works. Even if you have a lot of experience doing standup, are good, and have followers, you still have to know each of these club bookers.
It’s not always glamorous. I get to do cool stuff and travel to places like India and Japan. My life is probably slightly more interesting than a regular corporate job, but there’s always a sense of obligation. If I book a show in two months, I have to do that show, even if I don’t feel like it. Finding a balance is hard. No one hands you a schedule — so you have to figure out how much you can commit to and at what pace it’s sustainable.
I think success here comes from being able to commit to a routine and habits that you do over and over again.
But if you show up exactly the same each day, you’re not necessarily going to be successful. You have to constantly look for ways to get better in your writing and performing. Success will follow, but you have to measurably improve.
