Brandy Cavitt: ShoeFly

Brandy Cavitt has come out of the closet.

As an artist, that is.

After her long and successful career in graphic design and marketing was upended, practically overnight, due to the rise of AI, Cavitt made the call to take herself seriously as an artist and a creative.

Rather than trading her personal freedom for a 9-to-5 with a guaranteed paycheck in service of someone else’s vision, she chose to pivot and adapt, taking a bounding leap of faith and landing right in the cradled arms of… hand-painted custom shoes.

ShoeFly is the result of that leap of faith.

Cavitt’s custom sneaker vision scuffs the intersection where her personal passions meet: sick sneakers, hand-painting, and a keen eye for design.

Cavitt has fully stepped into the role of creative entrepreneur, all the while redefining what success feels like for her and reexamining her priorities against her values in real time.

At first glance, her decision to go rogue might read like a cautionary tale. The decision to strike out on her own has come with sacrifices, material loss, and its fair share of letting go.

Cavitt explained that she and her wife have made the choice to downsize their home and share one vehicle. For those of us who still measure our worth against what we have, this doesn’t sound promising. Begin to look deeper and it’s clear that Cavitt is anything but empty-handed.

The road to creating ShoeFly has brought her an abundance of empowerment, meaningful work, creative license, self-realization, and the opportunity to grow closer to her wife of 18 years—more in love than ever—as they walk hand in hand, navigating this unmapped terrain together.

So is her creative leap a cautionary tale after all? Maybe it’s more accurate to say it’s a daring question mark inviting more of us to ask ourselves “what if?”

What if we lose the things we were taught were important, but in their place purpose, joy, deeper connection, and personal freedom grow bountifully?

Lean in even closer and there’s a quieter and more pressing question underneath it:

Are we willing to come out of our respective closets to live more honestly and authentically even if it comes at a cost?

Just how willing are we to bet that maybe, there’s more to gain than there is to lose when we choose to follow our creative callings?

In Her Own Words

You’re a self-proclaimed sneakerhead. Describe your obsession with sneakers. When did that start?

There are pics of me wearing OG Nike Cortez sitting on Santa’s lap when I was maybe 2 years old. Greatness is sometimes thrust upon you.

I honestly don’t remember a time where I wasn’t chewing my mom’s ear off begging for Jordans. There was a year when I went to Carencro Catholic and my parents were juggling a new baby and private school and my mom told me I could literally pick between having an entire new wardrobe or a pair of Jordans I really wanted and I hedged my bet knowing that I had to wear a uniform. I opted for the Jordans.

What was the hangup that prevented you from openly identifying as an artist?

I never felt like I had made enough art to call myself JUST an artist, even though it’s all I’ve ever really made. I’ve never sent anyone a super duper proposal or a spreadsheet. I’ve never solved a giant crisis at a law firm. I’ve never run for any sort of office. I don’t even have a college degree.

All I’ve ever known how to do is to make small things that bring people joy, and I didn’t think that was an identity. I thought it was a series of hobbies and that I just didn’t have the goods to make it in corporate America.

In a way, I was right on both counts, but calling myself an artist is something I am just now able to say out loud. I’ve never fit anywhere else, I suppose it’s time to embrace that for better or for worse.

You talked about how your first sets of sneakers flopped and you had to redo them. What’s your advice for overcoming initial setbacks, and what kept you going?

There is no shortcut, there is only the work. Over and over. Ira Glass has a wonderful quote about taste that if you are interested, you should Google it.

Nobody tells this to people who are beginners, I wish someone told me. All of us who do creative work, we get into it because we have good taste. But there is this gap. For the first couple years you make stuff, it’s just not that good. It’s trying to be good, it has potential, but it’s not. But your taste, the thing that got you into the game, is still killer. And your taste is why your work disappoints you.

A lot of people never get past this phase, they quit. Most people I know who do interesting, creative work went through years of this. We know our work doesn’t have this special thing that we want it to have. We all go through this.

And if you are just starting out or you are still in this phase, you gotta know it’s normal and the most important thing you can do is do a lot of work. Put yourself on a deadline so that every week you will finish one story.

It is only by going through a volume of work that you will close that gap, and your work will be as good as your ambitions. And I took longer to figure out how to do this than anyone I’ve ever met. It’s gonna take awhile. It’s normal to take a while. You’ve just gotta fight your way through.

— Ira Glass

What’s been the evolution of ShoeFly?

There honestly hasn’t been much of an evolution. It’s mostly been a joyful struggle. I call it my “jobby” because it’s still somewhere between a hobby and a way to make a living, but I continue to invest my entire self into this knowing that I would regret it if I didn’t give it my all.

What are you learning about success and personal power on this road with ShoeFly?

I would be absolutely nowhere without my wife. Her approval is my success. She says I should pursue this, even when I feel like it is too indulgent and it doesn’t always pay the bills. She tells me to keep going.

You said it’s been worth it. Can you elaborate on what you’ve gained?

I no longer worry about what “everyone thinks.” I spent over 40 years trying to force people to like me through sheer charm and people pleasing, and it turns out the exact same people would have liked me if I hadn’t done any of that.

You speak so highly of your wife. What has she brought to your life, and how has your relationship grown as you’ve pursued self-employment and creative entrepreneurship?

We have been together for half our lives now, and our marriage has honestly aged like a fine wine. We have always really enjoyed each other’s company.

There have been times where my own pain has prevented me from being the best spouse, but I have to say a lot of it is the luck of finding someone who you sincerely don’t want to disappoint. That dynamic, whether it’s parent and child…student and teacher…spouse…it tends to allow you to become the best version of yourself when you serve a higher purpose within the dynamics of a relationship.

Making another person proud is about the highest high you can get.

What do you hope others will experience and feel by working with you and buying a custom pair of shoes from you?

I hope my clients come to trust that I will take a journey with them through my lifelong experience as an artist with my career of graphic design and branding and that together, we can create something very personal and special that will bring them joy for years to come.

What’s your long-term vision for ShoeFly?

I’d like it to be a factory of sorts. I want to be working on ten pairs a week. I’m happiest when I have my hands full.

What do you need? What help and support would be the biggest game-changer for you and your custom shoe-painting business?

I believe in the power of collaboration. My weaknesses and someone else’s strengths in business and profits/paperwork could be a powerhouse. I haven’t found the right partner yet.

I like painting alone, but I don’t love running a business on my own. Business is its own art form, and some people have that skill in spades. I feel like the right business partner is something that could really build a brand for the ages. I certainly know my weaknesses!

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