We were lucky to catch up with Jenna Rainey recently and have shared our conversation below.

Jenna, thanks for joining us, excited to have you contributing your stories and insights. The first dollar your business earns is always special and we’d love to hear how your brand made its first dollar of revenue.

When I started my business back in 2012, I was posting my work to my Instagram just as a hobby and it pretty quickly started picking up speed. There was no such thing as “Influencers” back then, and using hashtags and posting as many times a day as you wanted was totally acceptable. As my Instagram started growing and people started reaching out asking if I could design wedding invitations, I decided to send out 100 pitch emails to wedding photographers and planners. I only received two responses from those emails. One of them was a “thanks, but no thanks,” and the other was a “I think I have the perfect client for you!” Although I had no experience and barely knew how to open Photoshop, I was so excited to figure out how to make it work!

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

I started off as a pointed pen calligrapher doing envelope calligraphy for weddings and then eventually designing wedding invitations. The first few years were intense. I was working 60-80 hours a week most weeks, pulling all nighters and making LOTS of mistakes. I hustled and networked really hard, went to wedding expos to meet potential clients and I am so proud of all of the work I put in, but over the years I have had to pivot a lot in order to keep up with the output and create a business of my dreams. I now teach watercolor on YouTube and have four published books, my first book, “Everyday Watercolor” came out in 2017 and became a best-seller, which was totally unexpected and so fun!

What’s a lesson you had to unlearn and what’s the backstory?

I think a lot of us grew up believing that hard work = success. It’s definitely a part of the process in starting a business from scratch, but over the years, I’ve had to relearn and redefine what success looks like to me. I’m 35 years old currently, have a family and I don’t want to spend my life constantly worried about money or reputation or keeping up with the hustle, so I’ve recently stripped my business down to the studs and removed anything that didn’t feel aligned anymore to double down on what lights me up and how I know I can really make an impact in people’s lives through art.

Can you tell us about a time you’ve had to pivot?

I’m quite literally always pivoting. Staying stagnant is terrifying to me. My business has pivoted probably 10-12 times from weddings and calligraphy to in-person workshops, retreats, books, and now teaching online courses and YouTube. I think the most impact I can make is by sharing what I’m learning with my audience and showing them how to show up authentically through seasons of change.

Contact Info:

• Website: https://www.jennarainey.com
• Instagram: https://instagram.com/jennarainey
• Youtube: https://youtube.com/jennaraineychannel

Image Credits

Zach Sorensen