Episode 137: What If I Fail? And Other Fears That Are Blocking You from Building Your Dream Business

"If you plant beautiful thoughts now, if you work on your confidence now, if you work on your kindness, and your generosity, and your compassion, and your integrity, then everything you do is above the fray."

I know what it’s like to sit on your couch (snuggled up with a pup or two), looking at your creative dreams and feeling a wave of “What if I fail?” wash over you. I’ve been there. I’ve stared at canvases in my studio, worried that my next big idea wouldn’t land. I’ve torn up dozens (okay, more than a hundred!) unfinished pieces just to clear the energy. And yet, something inside still tingles with excitement for what’s possible. If you’re feeling stuck, disconnected, or scared to step forward, you are not alone!

Building a Remarkable Creative Business Starts with YOU

You might be here because you want your art to become more than just a hobby. You dream of courses, workshops, mentorship, or even running your very own creative business. But something’s keeping you sitting still, and, if I had to guess, it might be a fear of failure, a dip in confidence, or that all-too-familiar voice of self-doubt.

Newsflash: Every successful artist, mentor, or creative entrepreneur you admire? They’ve been there, too.

Like I always say:

“Having fear is part of the life experience. But letting your fear hold you back from doing that big audacious thing that you’ve been wanting to do, well, that’s going to be a bigger regret than actually taking the chance and betting on yourself.”

The Confidence Crisis (And How To Start Busting Through It)

A recent survey I sent to my community revealed something BIG! Confidence, mindset, and clarity are the top struggles for most aspiring creative business owners out there. Yes, more than figuring out your niche, audience, or shiny new marketing strategies, it’s confidence that holds us back!

Here’s what keeps popping up in our answers and how to bust the big fears:

• “What if I fail?”  “What if no one buys?”
  Honestly, failure is part of the path. You will make mistakes. Some launches won’t go as planned. But each “failure” is feedback, not a final verdict.
  

• “What if I look silly on social media?” “What if someone judges me?”
  They might. But for every one critic, there are ten people grateful you showed up.
  
  

I get it. Confidence isn’t a one-and-done win. It’s an everyday muscle. That’s why I’m sharing some of the most common excuses and real fears I hear (and have faced myself!), and how to break through them.

“If we live our whole life trying to avoid failure and trying to avoid looking dumb and trying to avoid people judging us, we will do nothing. We will make no steps towards the dreams that we have.”

Taking Action: Your First Steps to Remarkable

So, how do you get unstuck and move from fear to action? Here’s what I recommend:

1. Find Your Creative Spark Again

• Clean up your studio space. (I’m still in process after a year—and that’s okay!)

• Try a new class or medium. Community and energy feed creativity.

2. Just Start Showing Up

• Don’t wait for perfect. Start posting, emailing, or sharing now.

• Each post or email is practice, and every small step is progress.

3. Grow Your List

• Your email list is your business backbone!

• Don’t wait for the “perfect offer”, start gathering people interested in your vibe today.

4. Get Support

• Ask for feedback. Take surveys. Lean into community.

5. Call in Mentorship

• Free content (podcasts, videos, blogs) or deeper support (like mentorship or joining Build It Remarkable) can help you break through plateaus.

The Power of Mindset (and Why You’re Already Remarkable)

Building a soulful, profitable creative business isn’t about hustling 80-hour weeks, being a “bro marketer,” or reinventing yourself as someone you’re not.

It’s about:

• Embracing fear but acting anyway.

• Rooting yourself in your “why.”

• Showing up authentically, mess and all.

Plant seeds of generosity, integrity, and courage, whatever “rains” down (success, challenge, change), that’s what will grow.

Your Next Steps:

• Take my business survey so I can better help you with your next step.

• Get on the Build It Remarkable waitlist if you’re ready to step into more confidence, clarity, and community.

Remember:

You don’t need to be fearless, just willing to be “remarkable” anyway.

If this post resonated, drop a comment or share with a fellow creative soul who needs a nudge. The more successful artists we foster, the brighter and better this world becomes.

Follow Kellee on her Instagram account @kelleewynne

Follow the podcast and great business advice @maderemarkable

The easiest way to listen to the podcast is via Apple Podcasts  

Visit our YouTube Channel, Kellee Wynne Studios, for other trainings and recordings.

Click here for the full written transcript