My Story: From Side Hustle to Thriving Business

jenna rainey

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I’m an artist, self-taught designer, and multi-faceted creative entrepreneur who is hell-bent on teaching everyone how to find their inner creative voice.

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My Story: From Side Hustle to Thriving Business

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This month, January 2020, marks 7 years since I launched my Etsy shop. From side hustle to thriving business, what started as doodling at our kitchen table to full blown career has completely surpassed my wildest dreams! I no longer have an Etsy shop where I sell hand-lettered quotes and painted prints, but that initial launch is kinda the marker of when I decided to try out having a side hustle.

Before I launched my shop, I worked random jobs. I was a nanny for a few years when I was in college, then I got a job waiting tables at a bar in downtown Chicago serving deep dish pizza and martinis to a bunch of locals and regulars and then tons of tourists.

My background is not in art or business or communications. I have a degree in psychology.

But in 2012, I was wondering what I would do with my life. I had just graduated college and I was basically doodling on my server notebook pad at my waitressing job when my uncle very, very generously, offered me a job. He offered a position as his administrative assistant for his financial planning office back near my hometown in southern California.

The salary wasn’t much, but it was more than I was making at the restaurant, so we moved out to California!

When all of our boxes got dropped off by our moving truck company that we hired, there was a box of art supplies that wasn’t mine, mixed in with our stuff. This box had calligraphy pens and nibs, watercolor brushes, paint, etc., so to get me through my long commute to my uncle’s office and the boring job I had there, I started painting in my evenings.

I quickly became OBSESSED!

It’s all I thought about when I was at the office. And then on my way home driving home, I would think about what could I paint next? What could I write next? I started doing calligraphy pointed pen calligraphy back then and I couldn’t think about anything else. It’s all I could think about. And back then, Instagram was not the beast that it is today. Eventually, after the prompting of my lovely husband, John, I started posting my work on Instagram. At the time, I had barely any followers, and most of them were either relatives or close friends. But it started off as a little trickle, or buzz. Friends were hiring me to do random one-off commission pieces for gifts or for their homes. I eventually listed hand-lettered quotes in an Etsy shop and continued to post my work on Instagram.

I can remember the feeling when I got the notification from Etsy that I made my first sale and I freaked out. I think I even posted a screenshot of the photo on my Instagram feed. If you have time on your hands, I highly recommend you scroll super far back on my Instagram and get back to the 2013 posts. If you’re feeling like your work isn’t good enough or you don’t know enough, you’ll see some work in my feed that is VERY beginner.

But, slowly, people started purchasing prints from my shop and a couple months after starting my job at my uncle’s office, I got my first wedding job!

I had a friend that was getting married in February 2013 who asked me to hand letter some vows and signage for her wedding and her photographer happened to get their wedding featured on a well-known wedding blog!

This created a little buzz! I don’t think I got any jobs from that post or that blog post feature, but it sent people my way to my Instagram and it gave me a huge surge of confidence. And the 23-and-incredibly-naive me said, “I’m going to reach out to as many people as I possibly can and send them my work.”

I got my hands on over 100 emails of wedding planners and photographers, and pitched my work to ALL of them.

Two out of the 100+ responded. One said, no thanks, then the other response was from a wedding planner who loved the work, surprisingly, and recommended me to one of her clients!

From this, I booked a Save the Date design job!

I didn’t know Photoshop, I didn’t know Illustrator. I taught myself through YouTube videos and I ended up being fired by the client from this job because I messed up the envelopes! That feeling of letting my first client down was worse than the dread that I felt every day going to my office job. I felt like a failure. And the thing with failure is it determines two different results:

You wallow and give in…

…or you do better next time.

I chose to do better next time. Through my failures, I learned the ins and outs of a stationery business. I scaled my custom stationery business to six-figures, was featured on numerous high-end wedding blogs, hired by A-list celebrity clients, and became a top designer for Vogue, and more.

From writing how-to books with Ten Speed Press to releasing online courses for creatives, I’ve not only been able to scale my business beyond my wildest dreams, but I’ve been able to help countless people with their art endeavors and creative businesses.



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  1. Hi Jenna,
    I just listened to your 3rd podcast and I just want to tell you what an outstanding job you did in describing how you started your business and how down to earth you are. I can’t wait to listen to the rest of them! You are like a twinkling star out there among many stars but you stand out because of your authenticity, humbleness, and humor.
    My fiancé and I are going to start a creative business right after he retires in March so I am going to be glued to your channel, you tube, Instagram, Facebook, and in the meantime I’m going to get your first book as well. It’s really crazy right now because I’m following Mel Robbins “Best Decade Ever” (I recommend you participate in it for the month of January) and Anne LaFollette’s “Turning Your Doodles Into Dollars” teaching us the basics of surface pattern design. OK, enough of the babbling. Jenna, you rock!

  2. Stephanie says:

    Still going through your old posts to find your first sale 😉
    Thank you for sharing your struggles and your encouragements !

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