How Rory Gardner Balances 4 Careers (Musician, Comedian, Software, Real Estate)

by | Aug 24, 2020

Meet Rory Gardner. He is a multi-talented and creative force. He embodies the hyphen. He is a singer-songwriter-artist-comedian-software consultant-real estate investor. I know that sounds like a lot. Even by the standards of this newsletter, Rory stands out because of his raw talent and ability to alchemize his gifts into pure gold. And by gold I mean finding balance and satisfaction. He understands how each of his careers are mutually supportive, and herein you’ll find his thoughtful take on his life. I’ve known Rory for a few years, and I’ve even seen him perform. I’m a big fan.

Rory’s careers

  • Musician
  • Comedian
  • Software Consultant
  • Real Estate

On his motivation for having many careers

“When I was younger, the multiple careers were driven by money and because my parents forced me to get a ‘real job.’ Today, the variety is how I create balance in my life. Being creative lights me up, but you can’t maintain that high 24/7. Having another career where you can use your left brain for a change, is a well needed vacation from creativity. When I use to go ‘all in’ on the entertainment career, I would run out of motivation. I needed the perceived adversity that the ‘day job’ brought to fuel the imagination.

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Advice to aspiring multi-careerists

“Don’t over think it. Just do it. Too often people don’t want to pursue something because they are afraid of failing. Long before having my comedy featured on Funny or Die, SiriusXM, or Americas Funniest Videos, I was the guy in the audience just trying to get the nerve to go on stage. Once we push past our own insecurities, vulnerabilities, and consistent feeling of inadequacy, the road ahead is laid with discovery and life long experiences. My only regret is not starting earlier.”

On overcoming obstacles

“In the beginning, the side hustle doesn’t create as much income as the main gig. But when your side hustle eventually becomes your main gig, it becomes ‘a job,’ and the joy slowly get sucked out. What was once a pursuit of passion, becomes a tool for survival. When I started making more money in music licensing than software consulting, I felt like I had to lean more into writing songs for TV and commercials, but I didn’t find that creatively fulfilling. That’s not why I got into music.

I overcame it by focusing on writing a country album full of authentic songs that I wanted to write, for me, rather than writing for contemporary radio. The Be You record ended up getting nominated for my first CCMA (Country Music Award).”

How multiple careers are mutually beneficial

“The greatest benefit is the skill stacking. Combining comedy into my music shows has opened up several international touring opportunities as a ‘variety act.’ As a real estate investor, I never need to worry about touring for extended periods of time because no matter how well my albums are selling on the road, my multi-family rental properties back home are creating positive cashflow and building equity.”

On managing personal time

“I incorporate loved ones as much as possible. I try to line up winter tour dates in tropical climates, so that I can take my family on ‘paid vacations.’ My kids are young, and they’ve inspired me to write multiple children’s music albums. When I’m home, I play more afternoon shows so that they can come be a part of the experience, then after they go to bed, I hit the comedy clubs to work on new material.”

On what he wished he learned earlier

“I wish I had learned to embrace the balance sooner. For years I would resent the 9-5 consulting gig because it was taking away from my creativity. Now I am grateful for it, because it puts less pressure on my creative work, allowing me to enjoy it for the art, rather than a vehicle for putting food on the table.”

On what he tells his day job colleagues

“I rarely share my ‘secret identities’ with anyone. When someone in the corporate world figures out what I do evenings and weekends, they can’t comprehend that lifestyle. When a comedian or musician finds out what I do during the day, they just can’t comprehend that lifestyle. After opening up for Keith Urban (10,000+ people) one night, I had a meeting in the office the next morning at 9 am to go over agile methodology in the work place.”

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A Day In the Life

  • 8 am – 12 pm – For creative space or deep focus work. I have the most mental energy during this window
  • 12 pm – My first meal of the day as a result of intermittent fasting
  • 1 pm – Work out. Exercising body, to give brain a break.
  • 2 – 5 pm – Perform all linear tasks that don’t require creativity. Phone calls, emails, research, errands.
  • 5 pm – 10 pm – FAMILY

Where to find Rory




Kabir Sehgal is a Multi Grammy & Latin Grammy Award winner, as well as New York Times bestselling author of fifteen books. His latest work is Close the Loop: The Life of an American Dream CEO and His Five Lessons for Success (Hachette, 2020) with his father Raghbir Sehgal which is a Los Angeles Times & San Francisco Chronicle bestseller. Follow him on LinkedInInstagramFacebookTwitterSpotifyYouTube.