Is THIS Keeping You From Trusting Yourself as a Creative Entrepreneur?

Do you ever feel like you’re getting in your own way as a creative entrepreneur? 

You’re in good company. 

Lately, this has become an all-too-common struggle among many of my coaching clients and for those of us in the creative and entrepreneurial spaces at large.

People who are struggling to reach their full potential because they’re…

  • Paralyzed by the fear of failure and judgment.
  • Navigating an internal battle between their aspirations and the relentless inner critic.
  • Questioning their every move, second-guessing decisions, and doubting their own creative instincts.
  • Waiting for the perfect moment, the flawless plan, or the external validation that never seems to come.

Nodding along?

I had a feeling…

That’s why I’ve decided to address the 800-pound gorilla in the creative business world—the obstacle that’s holding back way too many talented and visionary individuals, including you.


To be honest:

It absolutely breaks my heart to witness the chronic second-guessing and self-sabotage that are holding back too many would-be, could-be, SHOULD-be success stories. 

In fact, it’s what inspired my business in the first place. 

In this blog, I’ll explore three of the most common things that keep creative entrepreneurs stuck in self-sabotage. Then, I’ll provide practical advice to help you overcome the doubt so you can face the fear of failure, stop “shoulding” all over yourself, and escape the comparison trap for good.

You deserve to finally start trusting yourself again (or maybe for the first time ever) as a creative business owner.

# 1 Fear of Failure

One of the most common reasons creatives don’t feel they can trust themselves in business? The fear of failure.

It can show up in a wide variety of ways, but at its core, this fear is often universal. 

So, who typically suffers from a fear of failure?

High achievers, trailblazers, perfectionists, and those of us with anxiety or ADHD.

For you, and so many other creatives, your fear of failure may stem from one, some, or all of these factors. 

High Achievers

The culprit of your self-doubt could be the fact that you’re a high achiever. While setting ambitious goals is a noble cause, it often leads you to set unrealistically high standards for yourself that can lead to disappointment and burnout. 

This backfires even more if you don’t take the time to define what success actually looks and feels like in your own life. Often high-achievers act on what OTHERS tell them success looks like. These internalized messages often come from society, family, mentors, coaches, teachers, leaders, and even their culture (hello, people-pleasing).

Unrealistic expectations can cause you to feel like a failure because you’ve created a business you don’t truly love (chasing what other people define success as). 

Not only do high-achievers chase these goals, but they often measure success based on what others think of them and how successful the world deems them to be. When you base your self-worth or level of success in business on someone else’s perception of you, no matter who they are, it’s hard to realize your full potential or create a business that truly serves your unique needs.


These external factors, social conditioning, and outside expectations especially impact creatives– even if they don’t consider themselves to be high-achievers.

Outside perceptions can really do a number on your confidence if you’ve followed an unconventional path. You know you’re pursuing the road less traveled. But because of this, you often feel you need to prove to yourself and others that success is possible when you do what you love. That means the stakes feel high all the time! 


High achievement is often intertwined with perfectionism. If you struggle with perfectionism in any way, shape, or form, you likely know firsthand that even the most ambitious, talented individual can become paralyzed with fear that their efforts will never be good enough. 

As a self-proclaimed recovering perfectionist, this resonates with me BIG TIME! 

To this day I have to remind myself that done is better than perfect, otherwise I probably wouldn’t have even started my business in the first place!

It’s taken me a long time to really come to terms with the FACT that perfection is not attainable. Nor should it be something to strive for. Voltaire’s quote “Perfect is the enemy of the good.” reminds me that my perfectionist tendencies often cause more harm than good!

For my fellow Ted Lasso fans, the last Diamond Dogs scene really hit the nail on the head for me!

Higgins says:

“Human beings are never gonna be perfect, Roy. The best we can do is to keep asking for help and accepting it when you can. And if you keep on doing that, you’ll always be moving towards better.”

What if you replaced “perfect” with “moving towards better” in your business? How would that change your inner dialogue with yourself and the expectations you set for your work? If perfect were no longer the goal, would you be more willing to ask for and accept help?

Some food for thought.

Anxiety or ADHD

For others, a diagnosis of anxiety or ADHD may be at the root of their self-doubt and lack of trust in themselves. 

If this is you, anxiety may cause you to spiral. As someone with an anxiety diagnosis, who navigates the challenges it presents every single day– I see you! While it definitely presents its obstacles, I also acknowledge that without anxiety, I don’t know that I would be where I am today.

Similarly, while the tenacity, ingenuity, hyperfocus, and other typical ADHD traits offer a strategic advantage (a ton of these qualities are actually ideal for entrepreneurs), they can also make it feel near impossible to prioritize the “boring” admin or ops responsibilities, follow through on tasks, or shift gears– all things that are necessary to keep your creative business afloat! 

It’s no wonder the idea of failure looms.

COO Tip: While many creative entrepreneurs try to AVOID failure at all costs, I actually encourage my clients to lean into it! Instead of being afraid of failure, you can teach yourself to see it as the ultimate teacher. The key is to fail fast and forward. You can read all about it here

#2 The Shoulds

The second barrier that keeps so many creative entrepreneurs in self-doubt mode? 

All of the SHOULDS floating around in the business world!

It can be so easy to fall into formation, following what everyone else says is the “right” way to build a business. 

Sure, some foundational business practices are universal, but the idea that someone else may have the “answers” is like expecting entrepreneurship to be an open-book test!

Why would you try to fit your unique, never-been-done vision into a cookie-cutter framework that’s been used a million times before? 

It just doesn’t add up, and yet I watch my clients (both seasoned vets and newbies alike) trying to fit their square peg into a round hole again, and again, and again.

The problem stems from the relentless messages we encounter every day. We’re constantly bombarded by business coaches and gurus who insist that there’s only one true path to success, and if we’re not thriving, it’s entirely our fault (and let me tell you, I will NEVER be that kind of coach!).

But here’s the truth: 

There’s not a single book or Google search that can give you the perfect solution to your creative or business problems. 

Your situation is unique, your brain works differently, and your goals, challenges, and circumstances are specific to you. 

I remind my clients of THIS often:

You won’t achieve extraordinary results by following the exact same processes as everyone else. To create something truly original, you’ll need to break free of analysis paralysis and take imperfect action

So why are we wasting time looking for a one-size-fits-all blueprint? 

You started your business because you’re a trailblazer. This means deep down, you know what the right next step is, but you’re doubting yourself every time you let the “shoulds” hold you back!

#3 The Comparison Trap

Lastly, in the words of Teddy Roosevelt, 

“Comparison is the thief of joy.”

When you start comparing yourself to others in the creative industry, it’s a surefire way to lose faith in your own abilities and undermine your strengths. 

It’s disheartening to witness how many talented artists, designers, and writers initially feel confident in their creative talents, only to be intimidated by the business side of things and eventually start to think they’re not “cut out for entrepreneurship.”

I call BS!

What breaks my heart most is when these entrepreneurs, faced with business struggles, start doubting their talents simply because they lack access to better entrepreneurial resources. They question their abilities and are convinced they’re not good enough, or that the market is already saturated when really some fundamental business basics would make a world of difference. 

And it’s no wonder!

Our social feeds are filled to the brim with deceiving highlight reels showcasing our fellow entrepreneurs thriving. It’s hard to remember that often people only show the highs of their entrepreneurial journey, and the lows EVERYONE inevitably faces are often hidden in the shadows.

It reminds me a lot of how I felt as a new mom navigating the parenting world for the first time.

((don’t worry, I won’t delve into the whole “your business is like your baby” analogy, so bear with me!))

We’ve all heard the empowering sentiment, 

“No one knows better what is best for your baby than you, mama.” 

And guess what? The same applies to our businesses. 

It’s easy to get caught up in the comparison trap, looking at other entrepreneurs and their flashy frameworks, thinking they hold the key to success. But those experts don’t have the full picture and they can’t possibly understand the intricacies of your unique business and your creative journey. 

It’s time to stop comparing so you can trust in your own knowledge and intuition. 

Just like moms rely on their instincts to make the right decisions for their families, you need to let your intuition lead the way. When you let go of the comparisons, and embrace what makes you unique you can start to believe in your ability to create something truly remarkable and blaze a new path.

Move From Self-Sabotage To Trust

So HOW can you push past the fear of failure, the looming “shoulds”, and the ego-crippling comparison trap?

Look For The PROOF.

Let me explain what I mean by that.

When you’re living in self-doubt and struggling to trust yourself, you need to learn to believe in yourself again. This means you have to rebuild the trust you have in yourself 

And if you’re ever going to achieve that, you have to create a plan and commit to practicing. Look for past evidence that when you trust yourself, things work out! Because F.E.A.R. (false evidence appearing real) is simply a set of adopted beliefs that you have the power to debunk and change!

I coach my clients to do exactly that.


I literally give them a homework assignment. And now, I’m assigning it to you

  1. Start by brainstorming challenges you’ve faced in the past. Specifically, zoom in on situations that felt insurmountable. 

  2. When you take the time to reflect, you’ll probably realize that somehow, you made it through even the most overwhelming obstacles. Consider what helped you through (your support system, your skills, your work ethic, etc.)

  3. Claim those wins! They’re proof that you can trust yourself to tackle tough, scary things… and come out on top! You’ve got what it takes to not just survive but thrive! As Glennon Doyle puts it, “We can do hard things!”

  4. Rewrite your “failures” as successes. Those times you truly did let yourself down, what did you learn? Every “failure” is an opportunity to grow. How can you reframe it for yourself and confront this challenge with a new perspective and wisdom? Remember – nothing is ever a true failure if you learn from it.  

This exercise is something you can lean on again and again in both life and business to move from self-doubt, criticism, and imposter syndrome into a space where you feel more aligned, confident, and capable!

Remind yourself that you have succeeded before, delivered exceptional results, and made magic happen. That’s how you begin to trust yourself to do it all over again.

Your Creative Business Support System

As you learn to trust yourself and lean into your intuition, it can be helpful to build a support system around you of fellow entrepreneurs, friends, family, mentors, and coaches. 

Think of it like the scaffolding that supports a building as the architect’s vision comes to life!

I’d love to be a part of your entrepreneurial support system as you confront setbacks, criticism, and crossroads on your business journey!

If you’re looking to chart a path that supports your innovative, one-of-a-kind creative business, I’m here to help! 

No more following irrelevant blueprints or settling for the ordinary! Break free from self-doubt and build something that has never been done before. Schedule a 90-minute clarity call with me and we can dive into your unique goals and challenges. Together, we’ll uncover personalized strategies that embrace your creative vision. Say goodbye to doubts and hello to an extraordinary future for your business!


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