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I quit corporate and turned my side hustle into a 6-figure dream career — here's how

Perri Ormont Blumberg   

I quit corporate and turned my side hustle into a 6-figure dream career — here's how
  • Jason Nelson, a musician in Hoboken, earns $175,000 a year by performing at weddings and events.
  • Nelson transitioned from email marketing to full-time entertainment in October 2020.

This as-told-to essay is based on a conversation with Jason Nelson, a 29-year-old musician and entertainer in Hoboken, New Jersey. It's been edited for length and clarity.

I'm a saxophonist, pianist, and business owner with a marketing degree and a certificate in recording arts. I earn around $175,000 a year in revenue playing events. I don't pay a manager, but I have limited business expenses related to gear, marketing, and transportation.

After graduating in 2017, I worked as an assistant strategist and then as an email marketing coordinator. When I took my side hustle full-time, I started making around $125,000 more than my last salary.

Since October 2020, I've been a full-time entertainer for weddings, private events, and nightlife.

I started music as a side hustle in March 2019

I've played the piano for 21 years and the alto saxophone for 18. From an early age, I learned that my pitch is perfect, which allows me to play any song by ear.

During my free time in college, I spent hundreds of hours mixing dance tracks in my DJ software program for my friends, and I DJ'ed myself occasionally.

Around 2015, I started an Instagram account where I posted short videos of popular songs on the piano and sax. I eventually was hired by a friend's sister to play cocktail hour piano at her wedding. She also had me play along with the DJ for the intro to her reception, and I ended up staying for the entire wedding.

I was so attracted to the adrenaline rush that I became obsessed with replicating the feeling

I contacted several entertainment companies in my area and started getting booked to play at events. In addition to compliments about my musical talents, I kept being told I had so much energy and I was the life of the party. I realized my greatest passion was entertaining others.

While playing several events each weekend and still working my email marketing job, I built relationships with DJs, event planners, photographers, videographers, and other entertainers.

I also gathered content from my events to grow my Instagram and TikTok accounts, from which at least 50% of my event leads now come. I can reach virtually anyone worldwide, which has led me to incredible destination events in places like Puerto Rico, St. Maarten, and, later this year, Aruba and Dubai.

I wanted to leave my 9-5 marketing job at the start of 2020

When the pandemic hit, I lost practically all my event bookings lined up for the rest of the year.

I was fortunate to still have a paycheck and work from home when most full-time event industry professionals were shut down completely. I continued to grow my side hustle by networking virtually, posting content, and working on the administrative part of my business because I knew it was only a matter of time before events came back.

A surge of events started in 2021, and I knew I made the right decision to leave the 9-5 world the previous October. Thankfully, I had enough savings that if I failed, I could support myself for a decent amount of time or return to corporate work if need be.

Most of my live music packages start at $2,500 and peak toward $5,000, while the average is around $3,500. I play around 50-60 weddings a year and have had multiple occasions where I play two weddings in one day.

I saw a lot of growth in August 2022

Since I don't have an agent or any employees, when I started receiving an increase in demand, I was overwhelmed with how manual the booking process was.

I used to send out contracts and invoices using Google Docs and Sheets templates, converting them to PDFs, and having clients manually sign and scan them back to me. After hearing about HoneyBook from a friend, I upgraded my technology, which increased my revenue. My business looks more professional now and I'm saving time.

I've played more than 400 events, including more than 200 weddings

Some of my career highlights include the New York Jets' official 2023 team roster party and Teresa Guidice and Luis Ruelas' one-year anniversary dinner cruise, which was filmed for "Real Housewives of New Jersey" on Bravo in 2022.

I love it when couples share their must-play list with me, but it's not mandatory since I read the crowd to determine the best times to make an impact. I often rehearse songs on the piano how I want to play them for a ceremony, but my saxophone practice is built entirely on the fly at each event.

If you're looking to go into the entertainment industry full-time, find your strengths and triple-down on them

You can always hire or outsource other parts of your business that aren't easy or natural to you. What sets you apart from the rest will be your "it" factor, so clients will want to hire you for you.

This is my dream job. I love seeing the joy on the faces of every guest I interact with. My success isn't measured by playing all the right notes — I win by bringing the energy to the dance floor and couples telling me they had the best night of their lives.

I have no regrets about quitting corporate work. My life has been much more stable over the past five years. If I had let a few hundred dollars a month of health insurance hold me back from quitting my full-time job, I would never have had all these incredible experiences.



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