The #1 Obstacle to Overcome in Business

blog business tips confidence mindset solopreneur

There are several obstacles to overcome as an entrepreneur, but here’s the biggest one…


Throughout the years, one of the most common issues I’ve seen arise for solopreneurs is questioning if they are good enough. Insecurity is a big issue and can paralyze even the sharpest, most talented people across all industries.

A natural reaction for most creatives

Previously, I attended the Becoming Boss, №3; which is an event organized by Sarah Knight of Roc Girl Gang, in Rochester, NY.

Even in Sarah’s opening welcome speech, she talked about negative comments running through her head when she first decided to start Roc Girl Gang (a local organization that is becoming quite the movement for women interested in entrepreneurship). She had questions like, “Who do you think you are to be doing something like this?” or “There is probably somebody way more knowledgeable and successful that could do a better job than you,” and many other self-sabotaging thoughts that ran through her head before she committed to taking the lead.

Can you relate?

It takes a lot of courage and tenacity to push through these persistent thoughts that can tank our ideas before they even get off the ground.

I see women struggle with a lack of confidence issues more often than men. Perhaps, it is a combination of how we are conditioned, the pressure of perfection from society/media, and the ingrained perception that the feminine has to please and serve. (More on insecurity and how to overcome it here).

Confidence in the collective

It’s awesome that organizations like the Roc Girl Gang are being created and supported. “We Rise By Lifting Others” was on the cover of the event booklet. This message is powerful and so is the example of seeing other women push through their fears, overcome obstacles, and achieve greatness beyond their wildest dreams.

The speaker panel consisted of Erika Sorbello of Gallery Salon, Tanvi Asher of Shop Peppermint, Jenny Rae Siplo of Flowerwell, and Cara Livermore of Chickpea Magazine. Each of these bright talents shared personal stories including overcoming self-doubt and criticism, which contributed to their current success. It was inspiring to be a part of 150 women uniting together, cheering one another on, and supporting each other along the windy path of the business journey.

On my way home, I was listening to Pandora. You Can’t Stop Me, from Andy Mineo, came on (a tune that I’ve never heard before). The timing was serendipitous! Here is a snippet of the lyrics:

“I’ll be living like woulda, shoulda, coulda, I’ll be paralyzed by fear
Huh, ain’t that the truth, if I quit the only way I lose
I got two choices when I do this, make moves or make excuses
Huh, if you know who I’m talking about, then you got me
My biggest enemy is me and even I can’t stop me”

Choose action over excuses

It’s OK to start small and take it a step-at-a-time…BUT do take action. Staying in your head, playing small, and resting in your comfort zone won’t bring you good results. That routine can keep you on the “second-guessing loop” for a long while. We’ve gotta nip that in the bud!

When we make friends with ourselves and the little tape in our head that questions our value, knowledge, skills, etc., we have a huge opportunity to express our true creativity. We can shine as our destiny intended, share our gifts, and flow through business-life in a way that is unencumbered and pure.

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