We recently connected with Rebecca Day and have shared our conversation below.
Rebecca, thanks for taking the time to share your stories with us today Earning a full time living from one’s creative career can be incredibly difficult. Have you been able to do so and if so, can you share some of the key parts of your journey and any important advice or lessons that might help creatives who haven’t been able to yet?
I’ve been a full-time entrepreneur since about 2011. I always knew I wanted to be a musician so as soon as I got a college degree, I dove right in to the creative arts full time. Running a business is hard enough, pair that with a creative aspect like music or writing and it becomes particularly tricky. It’s definitely not for the faint of heart. But it’s something I must do, not just something I want to do.
I learned quickly I wasn’t fit for the traditional route. Record labels and other traditional music industry companies look for very specific formulas they feel are a safe bet. I definitely don’t fit into that category. A few meetings in Nashville helped me realize my outspoken nature and stubborn independence were not in-demand qualities in the industry. As a creator, I tend to disagree more than I agree and that can definitely be viewed as problematic.
So I took the independent route, which I will always do now that I’ve been a full-time musician and writer for about a decade.
Though it’s rarely glamorous, that’s not why I chose my career in the first place. I’m in it for the blood, sweat, and tears. If it came too easy for me I’d probably get bored with it.



As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?
Because the live music aspect of being a musician is so important, especially in the industry’s current climate, I’ve played just about anywhere you can imagine. I’ve had the honor of performing across the southeast at festivals like Fernandina Beach, Florida’s Isle of Eight Flags Shrimp Festival, Palatka’s Blue Crab Festival, Jacksonville’s Porchfest, Jekyll Island, Georgia’s Shrimp and Grits Festival, and a ton of others. I also love playing for corporate events because I love being in a business environment. I’ve had the opportunity to play for companies such as Intel, Hewlett-Packard, and Purina. I’ve also played in the VIP lounge for a few country music shows at Coral Sky Amphitheater in West Palm Beach, Florida including tour dates for Tim McGraw, Florida Georgia Line, and Dan + Shay. Because I live in a tourist area, I get to play some really cool vacation spots. I love it when I get to perform at the King and Prince Resort in St. Simon’s Island, Georgia.
In between traveling year-round for shows I also release original music. I’ve released several projects as both a solo artist and with my band The Crazy Daysies. Releasing music with The Crazy Daysies is fun because it gives me an opportunity to work with my sister, Jen Thompson, who co-founded the group and plays viola and is a really talented songwriter.
All of our The Crazy Daysies original releases are available on all streaming platforms like Spotify, Amazon Music, Apple Music, and YouTube.
We also go live quite often on our Facebook page at Rebecca Day and The Crazy Daysies so we can check in our supporters and see how they are doing. As independent musicians, our supporters mean the world to us.
Even though I’ve been a full time musician for several years now I actually went to school for creative writing. I got bit by the writing bug pretty early on. My mom is a professional writer, poet, and author so I guess you could I say I somewhat followed in her footsteps.
When I’m not working on my music business, I switch gears and focus on my writing business. I enjoy writing for publications like Foundation for Economic Education, Zing Instruments, Newsbreak, and Indie Music Bus. I also enjoy writing at my own publication on Substack, Freedom Journal, and I published my debut novel, Derelict, in 2019. It’s a crime-mystery read and it’s available on Amazon.
While I pride myself on a few things when it comes to business including professionalism, communication, and work ethic, I am most proud of my grit and endurance. The creative arts is a marathon not a sprint. My stubborn ambition is what keeps me going when the cards seem stacked against me.



What can society do to ensure an environment that’s helpful to artists and creatives?
Freedom is essential to art. When artists and creatives are confined and constricted their end-product is mediocre at best. A society built on freedom of movement, freedom of expression, and freedom to disagree gives way to an artistic renaissance. History shows that with the Greek Renaissance and the romantic movement. And the reality of this hasn’t changed. which is why independent artists, who are free to create and express on their own terms, lead streaming growth in 2020 and continue to grow as a significant segment of the music industry. In the past year alone, the independent music market has grown 27%.
In the southeast, there’s a plethora of opportunity for artists because built into our culture is the desire for freedom. I am proud to wake up everyday and get to operate in a free market environment, where all of my interactions and business deals are rooted in voluntary interactions, which creates a win-win-win scenario for consumers, clients, and contractors (like myself).


Have any books or other resources had a big impact on you?
Quite possibly the most overlooked aspect of a person’s life is their philosophy. This is magnified when one is an artist. While reading up on industry news, marketing, and networking are important parts of running a successful creative business, what will get you out of bed in the morning when all you want to do is catch up on sleep, and what will help you power through an hour and a half set at a summer festival with a heat index of 108, is your philosophy.
A philosophy can make or break a mind. I knew early on if I didn’t want to get taken advantage of in my industry I had to be unapologetically mentally tough.
Because of this, philosophy is one of my favorite subjects to study.
My study of philosophy has directly impacted by art and business in many positive ways. It has made me a better decision-maker. It has improved my songwriting and creative writing. It has helped me get through both really tough days and really great busy days.
I enjoy focusing on a few different philosophies, each has merit in its own way which creates a well-rounded philosophical roadmap. Aristotelian and Socratic Logic is one of the most important philosophical subjects to study, especially if you’re a creative. Creatives often lead with emotion and reason is secondary, which results in impulsive, unreliable decision-making. Understanding that logic should come first and emotions should be tools of cognition is important to grasp.
A couple of other philosophies championing reason are Objectivism and Stoicism. Both will help you develop the mental toughness to weather rejection and criticism. The two philosophies also champion individuality which is another element essential to artistic creation.
Economic philosophy is just as important as personal philosophy. I have to constantly explain to upset musicians why people are okay paying $5 a day for a coffee at their favorite coffee house but don’t see the value in buying records anymore (it deals with the economic theory, The Law of Diminishing Marginal Utility). It can be hard to admit that being a professional artist means operating in a business environment a lot more than an artistic environment (especially if you take the independent route). Because of this, a thorough understanding of entrepreneurial economics (or the Austrian School of Economics) is extremely helpful in understanding consumer behavior and making the best decisions for your products and the services you provide.
Ludwig von Mises is the best economist you could read when it comes to understanding economic reality. Per Bylund is a professor of entrepreneurship at Oklahoma State University and recently released a primer on Austrian Economics that is useful for anyone looking to read more about the subject.
Even now, Austrian economics continues to be the only school of economics that places an importance on the entrepreneur’s role in society.
Economics doesn’t seem like a sexy topic, but it’s a crucial one to study if you’re a business owner of any kind.
Contact Info:
- Website: www.rebeccadaymusic.com
- Instagram: instagram.com/rebeccadaymusic
- Facebook: facebook.com/thecrazydaysies
- Linkedin: linkedin.com/in/rebeccadaymusic
- Twitter: twitter.com/rebeccadaymusic
- Youtube: www.youtube.com/rebeccadaymusic
- Other: thecrazydaysies.com – Band website
Image Credits
Durden Godfrey Joel Molotzak Photography

