Confessions of an Entrepreneur
We’ve all done it. You get a survey from a doctor’s office or a casual question from an acquaintance, and immediately the internal editor kicks in:
"Do I say I have a glass of wine every night? No, they'll think I have a drinking problem."
"Do I admit I’ve been sad every day for two weeks? No, they’ll think something is deeply wrong with me."
So you soften. You take those sharp, authentic edges, file them down, put on a polite smile, and present the version of yourself you think people want to buy.
When you start a business, that self-editing gets dialed up to eleven. Well-meaning mentors, marketers, and social media strategists step in with wildly conflicting opinions:
Advisor A:"You need to be strict, educational, and super professional so people trust your authority!"
Advisor B:"No, you need to be raw, vulnerable, and show behind-the-scenes content or you'll lose engagement!"
The result? Total creative paralysis.
Erin shared how she used to host "Wigging Out Wednesdays"—a unscripted, hilarious weekly video series that felt fun, creative, and genuinely connected with her audience. But after being told her content needed to be more "educational," she stopped doing it. The moment she tried to fit into the standard corporate mold, the joy vanished, and the social media burnout set in.
The Reality Check: If your marketing forces you to play a character, it isn't sustainable. Your ideal clients aren't looking for a polished, cookie-cutter clone. They’re looking for your exact flavor of weird, honest, and relatable. Sprinkle in the education, sure—but don't kill the magic that made you start in the first place.
The Invisible Identity Crisis: Transitioning from Expert to Unknown
One of the hardest parts of entrepreneurship that nobody warns you about is the sheer ego bruise of starting over.
Erin talked openly about leaving a high-profile career in domestic violence advocacy. In her previous world, she was the go-to authority in the state. People knew her name, respected her expertise, and sought out her counsel. But when she launched her new venture—and changed her last name after getting married—her digital footprint vanished.
Suddenly, searching her name brought up a ski clothing brand instead of her decade of professional accomplishments.
When those initial client slots don't fill up instantly, the spiraling thoughts hit hard:
"Was this a massive mistake?"
"Nobody knows who I am anymore."
"Should I just give up and go get a traditional job again?"
That imposter syndrome thrives on scarcity thinking. When you’re constantly looking for what isn't working, you fall into the Blue/Yellow Trap: if someone tells you to count every blue item in a room for 30 seconds and then asks you how many yellow items you saw, you won't have a clue. You weren't looking for yellow.
Business success requires retraining your brain to count the "yellow"—the small wins, the client breakthroughs, and the foundational growth—rather than obsessing over the missing "blue."
Red Flags in the Coaching Industry: Spotting the Quick-Fix Trap
When you're starting out and desperate for validation (and revenue), you become prime target audience for high-ticket business coaches promising immediate returns.
Erin and I broke down the major warning signs to watch out for which is basically anyone who guarantees specific financial goals ("Make $10k in 30 days!")
The Non-Linear Climb: Why Setbacks Aren't Square One
Progress in business is rarely a straight line heading up. It feels more like climbing a steep, muddy hill—you take three steps up, slip, and slide down a few feet.
But here’s the key mindset shift: When you slide back, you don't fall all the way to the base of the mountain.
Even on the days when you're too exhausted to journal, skip your morning walk, or fall off your social media routine, you still carry the knowledge, strength, and experience you gained on the way up. Slipping up on your routine doesn't mean you've lost yourself; it just means you need a rest day before taking the next step forward. Same with your business.
Fail of the Week: Unfiltered Chaos
To throw it back to old school Skirts Up ways, we wrapped up with our favorite ritual—admitting our biggest fails of the week:
Samantha’s Pig Heist: I bought a baby pig on impulse, built a puppy playpen on the grass, used half-hearted stakes, and called it "good enough." An hour later, the pig had rooted under the fence and vanished. It took 8 people, 5 acres, a soccer net and two hours to finally corner and net one tiny, slippery pig.
Erin’s Massage Chair Debacle: Trying to secretly get rid of her husband’s bulky vintage massage chair while he was at a workshop, Erin hoisted the heavy metal frame—only for it to fold in on itself, trapping her fingers in the metal hinges. Panicking and believing her fingers were literally severed, she screamed for her daughter (who refused to come downstairs thinking the dog had caught a mouse). After freeing her hands, Erin shoved the chair into the dumpster, went to urgent care, put on two splints, and still drove her kids to a Zac Brown concert that night. #dedication #Zac Brown Band
The Bottom Line
Stop trying to build a business that looks like everyone else's. Ditch the rigid scripts, give yourself grace when you slide back down the hill, and for the love of everything, watch your fingers around vintage folding furniture.
