Stop Waiting for the Plan… Start Running Experiments in Your Business

If you’re a multi-passionate or creative business owner trying to figure out what to focus on… this is for you.

Because the truth is, you don’t find your thing by thinking… you find it by experimenting.

And if you’re neurodivergent, highly sensitive, or have a million ideas at once, it can feel overwhelming trying to run your business by yourself. (And if that’s you, Hi… we’re twinning! 😊)

So in this post, I’m walking you through all the businesses I’ve started… and what they actually taught me.

Not because they “worked” or “failed,” but because they led me here.

And even though I cry in the episode below because this sh*t is hard, and you can FEEL like you’re failing, it’s really just experimenting… and taking what you learn into the next thing.

When I was an art teacher, kids would sit there saying, “I’m thinking,” just staring at their blank papers.
But the way you start is by sketching. By doing. By trying and seeing what works.

That’s how you figure things out… in art and in business.

Graphic with text “You don’t find your thing by thinking, you find it by experimenting” illustrating experimentation as a strategy for business growth and finding your niche

Just jump in, get started, and see where it takes you.

A Timeline of My Business Experiments (aka how I got here)

The Coolest Thing I Priced WAY Too Low: Missing Monsters

Custom plush monsters people “lost” that I’d find, make, and return with a whole backstory.

The Lesson: People loved the idea… but I priced it wrong and burned myself out.

Missing Monster examples around Richmond — Here’s a few of the monsters that I “found” around town.

Missing Monsters forms for people to turn in. — The very first “order form” when it was called Lost Monsters. The flyers I would hang around town and people could tear off a strip from the bottom. I’m old school y’all.

Monster mural on Cary Street by Deanna Seymour. — In 2013 I painted this mural with the ideas from friends and family on Cary Street, right around the corner from our first house on Parkwood.

Lessons About Building Your Audience with MissFit Aerobics

Punk rock aerobics classes I started after failing a Jazzercise audition and deciding to do it my own way.

The Lesson: One person showing up isn’t failure… it’s proof something’s working.

MissFit Aerobics showing a "you're beautiful" pin and a poster example. Plus scrunchies! — Body Positive Buttons. Flyers I hung around town to spread the word. Scrunchies I sewed from old thrift store clothes. I had a registration event at Rumors Boutique and I taught classes in the vacant building before it was for Quirk Hotel.

Building a Community Before I Knew That’s What I Was Doing: Pin Pals

A worldwide button exchange where strangers made art, swapped it, and accidentally built a tiny global community.

The Lesson: I was building community… but still measuring success by signups.

Pin Pals examples and my booth with Jason helping people make pins on First Friday. — One of Jason’s pins.
Me and Jason letting people make buttons during First Fridays.
And the google website I build to get the word out. I’m old.

Pin Pals art show at Gallery 5. I also got married here! — Here’s lil’ old me at the Pin Pals art show at Gallery 5 in Richmond to raise money for Art 180.
There are the pins we made for wedding party favors. We got married at Gallery 5 too!

The Business That Worked (But Didn’t Feel Right): LOL Richmond

A playful photo booth business built around props, parties, and making people feel a little less awkward in photos.

The Lesson: Just because something works doesn’t mean it’s for me.

Anniversary party at World of Mirth toy store — A fun anniversary party at World of Mirth, the toy store that also sold Missing Monsters, and the photo booth at the pool party that my cousin Denise threw for her husband Mike’s 40th birthday!

Educating Your Audience is Important: Wild Design Photography

Bright, expressive kids portraits focused on personality… not stiff family photos in a field.

The Lesson: People not “getting it” right away doesn’t mean it’s not valuable.

Wild Design kids — Kids being authentically themselves at Wild Design.
Ahhh… it seriously makes me so happy to look at these.
What cool kids, every single one I photographed.

When I Turned One Idea Into Way Too Many: The Lively Nest

An over-the-top creative lifestyle membership for families that tried to do way too much.

The Lesson: Sometimes less is more for you and your clients.

The Lively Nest graphics showing social justice art. — Dance Parties. Social Justice. Art.
They’ve always been themes in my life.

Imperfect Party: The One Where It All Finally Clicks… Or So I Thought

Daily dance parties, a podcast, and the start of building something rooted in fun, connection, and experimentation.

The Lesson: Sometimes less is more for you and your clients.

A cloud on a button. Imperfect party cover photo. And a rainbow that says "fuck it" across the bottom. — More buttons. My podcast. And the mantra that I tell myself when I start to feel perfectionism start to creep in and make me feel bad, or scared, or less than.

The Playhouse: Where a Lot of These Lessons Live Now

The Playhouse is where creative business owners host virtual events, coworking sessions, conversations, and hangouts designed to bring interesting people together.

It’s a place to try things, meet people, and figure it out as you go.

The Lesson: Keep going… you’ll get to where you were meant to be.

The Playhouse event hub for creative business owners, a community focused on networking, collaboration, and growing a business through live events instead of social media

Listen to the Full Story… Tears and All Cause Running a Business is Hard!

There’s a lot of feelings that come up when you’re reminiscing. But I can honestly say that as I put this post together I’m nothing but freakin’ proud of all the things I’ve done.

Not to mention teaching art this whole time. Fundraising over 10k for my students, being the SCA sponsor and being voted coolest teacher three years in a row. Just sayin’. 😎

I had my daughter when I was 35. A “geriatric” pregnancy. Haha.

I’ve done a ton of livin, and it’s all led me here. And I’m so excited to build a community of creative business owners who are doing the hardest (but super fulfilling job) of running a business by themselves!

If this hit a little too close to home… you’re my kind of person.

The Playhouse is where people like us experiment in real time, host events, meet collaborators, and actually get momentum without relying on social media.

Come hang with us inside The Playhouse! 🏠