• Hilary Young

Lady Bosses I Love: Kelly Courtney

Like several of the other amazing Lady Bosses that I've featured in this series, Kelly Courtney and I first met on Instagram. Aside from also being a champion of women and women-owned businesses, Kelly is unapologetic about being passionate about many different things at once. Her business, D20 Theory, was created to help encourage multi-passionate women invest in themselves, their self-care, and a growth mindset. This past fall, I participated in Kelly's Girls With Goals Productivity and Mindset Conference, where I was able to lead a workshop on personal branding and also participate in an honest conversation about how challenging it can be to stay focused as a working mom.


Kelly Courtney: D20 Theory



What is the name of your company and what do you do?

D20 Theory is a lifestyle brand for multi-passionate womxn who invest in their self-care and personal development through quality products, memorable experiences, opportunities for growth. I offer productivity and mindset coaching, workshops, speaking engagements, and subscription boxes. I help womxn to embrace all of their facets…like a d20 die! How long have you been in business?

I’ve been in business for a little over two years, but it feels like closer to four years because D20 Theory began as a blog in January 2019. It transitioned from a lifestyle blog to a lifestyle brand in March 2020 when I began offering workshop events. I officially received the LLC in July 2020. I have since launched a coaching program, accepted speaking engagements, and added subscription boxes. How did you decide to launch your own business?

I was unexpectedly laid off from my 9-to-5 job at a non-profit mental health clinic in 2018. While I was searching for a replacement for the stable income and benefits that literally disappeared overnight, I noticed a desire to connect with other women and share my passions outside of the mental health field. I started a lifestyle blog, which eventually expanded into a lifestyle brand for multi-passionate women. What challenges did you face in the process of launching your business?

None of my friends or family had ever owned a business or started a blog, so I didn’t have a model to follow or a support network to ask questions. Did you feel as though there were resources available to you, specifically as a woman business owner?

There are a lot of resources available for small business owners. However, finding the right resources when you need them can be challenging. Signing up for every email list, joining every Facebook group, and following every blog isn’t necessarily helpful.


Don’t expect to learn everything you need to know on Day 1 of business ownership. Do commit to a plan for continuous learning in small chunks. Do you have a mentor?

I am endlessly inspired by the women I meet at networking events and conferences, as well as through Instagram. Although I’m definitely not a business expert, I’ve found myself in more of the mentor role among my family and friends who have since started blogs and businesses of their own. These conversations allow me to reflect on my business decisions, even when I’m technically the one giving the advice. Books you recommend?

I am admittedly not much of a book reader—although I love any type of content from Brené Brown! I’m a big fan of docuseries, short-form articles, and live talks. I always encourage others who don’t identify as “book worms” to embrace the way they enjoy learning. What do you love most about running your own business?

As a self-identified “ideas person,” I appreciate the freedom to practice creativity every day. When you’re the boss, you don’t have to navigate organizational red tape or pitch your ideas to the management team. Business is a continuous game of trial and error. There is a different level of pride when your own idea succeeds and accountability when it fails—and you will fail at times. What is your least favorite aspect of running your own business?

Marketing and taxes. Most days I just want to come up with new ideas and put them into action. Communicating what I do to the right people at the right time takes the fun out of it for me. I’ve invested in different types of support with marketing over the years, and I’m still trying to find the best fit for D20 Theory as the business evolves.

Sales tax, quarterly estimated tax, and annual income tax can be a headache. My CPA is one of the biggest and best investments as a small business owner. What is your best piece of advice for other women who are thinking about launching a business?

Go for it! The world needs you and everything you have to offer, so be confident. Do your research and create a business plan, but don’t let the urge to figure out every detail keep you from getting started. Business ownership is a learning experience, and your business will evolve as you and your clients’ or customers’ needs evolve.