What My Worst Business Mistakes Taught Me About Confidence
Establish Yourself® Podcast | Episode 29
What if finding confidence in business takes getting it wrong first?
If you’ve ever looked at another successful entrepreneur and thought, “They must know something I don’t”, you’re not alone. Most seasoned business owners don’t talk about the things they got wrong—only what worked in the end.
But behind every smooth brand and confident message? A trail of messy mistakes - myself very much included.
In this episode of the Establish Yourself® podcast, I’m pulling back the curtain on some of the worst (and most embarrassing) business mistakes I’ve made over the last 11 years—and how those exact moments helped me become more confident, clear, and successful.
You Don’t Have to Be Perfect to Be Powerful
From a major SEO misstep that hid years of content from Google to offering too many services to the wrong people, I’ve had my share of what-was-I-thinking moments. And still—2024 was my best year in business yet.
That’s what this episode is really about: normalizing the messy middle, so you can stop waiting to feel perfect before you feel powerful.
Because building confidence isn’t about avoiding mistakes. It’s about learning from them, laughing at them, and making better decisions next time.
Confidence Comes From Surviving the Setbacks
In this episode, you’ll hear:
✅ The mistake that hid 100+ pieces of content from ideal clients for 3 years
✅ What happened when I launched an offer that totally flopped
✅ How an awkward elevator pitch cost me clients
✅ The mindset shift that helped me stop spiraling and start experimenting
✅ A surprising metaphor from a Disney cruise water slide that will stick with you 😉 🦎
Here's the truth: you don’t build confidence by getting it all right— in my experience, you build it by staying in the game when you get it wrong.
🎧 Tune in now for a fresh perspective on what real business growth looks like (hint: it’s not linear)
This is Part 4, wrapping up our “Greatness, Not Perfection” series👇
Free Gift 📕
Dive into my best (hard-won!) best practices with a free chapter of my bestselling book, Establish Yourself. Start reading now!
Find more fun in your business at this free event ✨
Join me and fellow strategist, Quinn Tempest, for a relaxed, valuable roundtable on “Bringing Fun & Fulfillment Back to Your Business” on July 24 via Zoom. Zero pitch, all value.
RSVP for free here 👇
🎧 Listen to all 4 episodes of my “Greatness, Not Perfection” Series
And go deeper with this episode on the major marketing mistake I made for 4 years (and what the mixed results taught me)!
