The Side Hustle Life

Gosh, just seeing the title of this post makes me realize it could be its own website, hashtag, blog, or brand. That’s how a true side hustler’s brain works. Opportunity is everywhere! Maybe I need to park this domain and get it trending. It has a nice ring doesn’t it? #thesidehustlelife

What is a “side hustle?” Is it a hobby? A passion? A side job? Look to Uber and GrubHub as the poster children for the ultimate, legit side hustle. At its core, it’s a means of making money while fulfilling a need. Wait? Isn’t that the same as a job? Technically, yes, but a true side hustle is in a category all its own. If you Google “side hustle meaning,” this definition by The Balanced Careers comes up:

side hustle is a job that you can work on top of your full-time job. It is a flexible second job that brings in money, but it is also typically something that you are passionate about, that you don’t get to pursue in your main job.

I feel like I’ve been a side hustler my entire working life and in the current landscape of our economy, I couldn’t be more grateful. While I was in college, my first job was at the Kaua’i Athletic Club as a front desk attendant. I like fitness. Was I passionate about checking ID cards and ringing up random logo leotards and the occasional sweatshirt? Not really, but it paid $6.00 an hour. Whoa! A whopping $6.00! It was a huge jump from the $4.50 I made at my high school job at Blockbuster Video. (I am dating myself, but whatever. If you must know, it was 1995).

OK, let’s go back to before my first official job at Blockbuster Video. My mom joined a group of local people from Hawaii when we lived in Oregon. I was 13 years old and somehow, we put together a hula show and got hired to perform at company parties (Christmas parties to be exact. Don’t get weird). I probably made fifty bucks a show. I don’t really remember. I did it because my mom told me to. In this moment, I realize my side hustle was born when I was in the 8th grade. (Can you say “Child labor?”). I loved it, though. I got to be on stage and make people happy and in return for their happiness, I’d go home with fifty bucks cold hard cash in my wallet. Cha-ching! That’s a lot of money for an 8th grader. Trips to the mall were a blast. When that new Mariah Carey “Love Takes Time” single came out, I was one of the first to have it and I bought with my own money!

Fast forward back to college. Kauai Athletic Club required those same stupid khaki pants I wore at Blockbuster. Ugh! Why? Whatever passion there might be in a job, leave it to khaki pants to suck it right out like an airplane toilet.

I sang in a couple local competitions. I lost them; didn’t even place. I was devastated, but the opportunist in me tried one more time. A little voice in the back of my head said, “You never know who might be there. Just keep putting yourself out there.” I lost the third one with flying colors and cried myself to sleep that night. That evil voice in my head said, “Why on earth have people told me I’m a good singer? Liars! Every last one of them, especially my mom!” That week, I got a call from a man asking me if I’d like to record a song in Glenn Medeiros’ old recording studio in Lihue. My confidence was shot, but what the heck? The people seemed nice enough. I went. The demo I made that night fell into the hands of a producer in Japan and I recorded a full length album a couple months later.

Upon my return from Japan, there were little media blitzes in the local newspaper. Those little blurbs led to me modeling for Red Earth Clothing (remember the t-shirts dipped in red mud that were oh so on trend in the 90s?). I do not consider myself a model by any means, but I got paid to do it and it was easy. Meanwhile, my mom was screen printing t-shirts with hand drawn Hawaii images by my step dad. Soon, hundreds of people were wearing dresses and t-shirts with their designs picked up at local craft fairs. Dad was a cop. Mom worked the front dest at the Marriott. On the weekends, they hustled.

As a singer, I pretty much always had a day job while music was always my passion. There were times that I questioned which was the side hustle and which was the actual career. Once I figured out how to make music a sustainable career by carving a niche in the wedding industry, the day job was toast. My side hustle turned into a full blown career! I have realized, however, that a music career is really a whole lot of side hustle repeated over and over again. Some gigs are steady – set days of the week for example at a restaurant, bar, or hotel, and some gigs are concerts, weddings, graduation parties, retirement parties, etc. Hustle, hustle, hustle. There was also a time that I was teaching voice lessons. I had 30 students a week with a wait list! It was kinda nuts. Although it was another side hustle, it still afforded me the ability to boast, “I’m a full time musician.”

Full time musician turned into “entertainer.” Not only was I singing at events, I was emceeing. And then I was a spokesperson for Napa Auto Parts and a jingle writer for Hawaii VA Loans. Here’s who I feel like sometimes:

The chick who wanted to do everything from “Coming to America”

Then, one day I was casually asked, “Have you ever thought about officiating weddings? You’d be really good at it.”

“Noooo. No way,” I replied, thinking nobody should be allowed to do so many different things. Then, a totally different person in the wedding industry asked if I would officiate weddings. What? Why does this keep coming up, I thought? For the first time, I was running away from opportunity. Usually, I say, “Yes to all!” Well, I did it and all it took was one for it to turn into two and then four and then now where I’m doing at least 2 per month.

I do have a point. When I decided to be a full time real estate agent in 2016, I actually kept one foot plus my big toe on my other foot in my music career. The side hustle life has been awesome and really brings to life the saying, “You can do anything you put your mind to.” I really do believe that. At the same time, it can prevent a person from going all the way at anything.

2020 left musicians without gigs. It put what was once a major industry in Hawaii in ruins (the wedding industry, among others). The real estate industry, however, is booming. As for being a wedding officiant? People aren’t gonna stop getting married. They can’t have the big event, but they can still say, “I do.” Remember what I said at the beginning about a side hustle being something that fills a basic need while making money? BINGO. So there it is. I am a wedding officiant. I can marry you and then help you buy a house. How freaking perfect and opportunist is that? I wish I could take credit for crafting that, but I can’t. The truth is, I love both careers and didn’t even consider the thought of the two feeding each other. I love weddings and take it very seriously when asked to be the one who gets to usher a couple into marriage. I actually don’t even hound my couples about buying a house. Most of them know and I’ll casually bring it up, but I am hired to be their officiant. If they choose to let me be their realtor too, bonus!

In closing, here are my 3 tips to living a fulfilling side hustle life:

  1. If you see a true, repeatable, need that you can fill with a product or service that you’re passionate about, you’ve identified a side hustle!
  2. A hobby is not necessarily a side hustle unless you are fulfilling a need and identify a true demand for that need.
  3. Do it with excellence, but invest your resources wisely. When a side hustle seems like a side hustle, people know it. This is where it looks more like a hobby and you’ll see your friends and family buying from you or hiring you just to be supportive. That feels good until it doesn’t. Start too big, and your living room is filled with tchotchkes. Again, focus on fulfilling a need, solving a problem, helping people out, making them happy and if it puts a few bucks in your pocket, win-win!

Oh! Need an officiant? You can find my friends and me here: