The 5 Biggest Entrepreneurial Fears and How to Face Them

Jenna Kutcher 

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August 4, 2021


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Entrepreneurship often blossoms from a place of uncertainty, and with uncertainty comes fear. What if my business fails? What if I fall flat on my face? What if I get started, but lose passion or momentum or my success fades? 

This conversation with Kylie is all about the five most common fears entrepreneurs face at the beginning (and maybe even middle) of their business-growing journeys. Kylie is earlier on in her business endeavors so these fears are fresh in her mind, so we’ll walk through how I’ve faced and overcome the same fears she’s encountering now. We’ll cover the fear of starting, losing momentum, imposter syndrome, and more. 

Fear of Starting

We started at the beginning with the fear that keeps so many of us from ever crossing that starting line — the fear of starting. Diving into something new, creating your business from scratch, can put you right into a zone of discomfort. How do you get comfortable with being uncomfortable?

I think that a lot of the uncomfortable and unfamiliar situations would be a lot more comforting if we didn’t feel like we were thrust on a stage, whether digitally or in real life in front of people so that they were watching us. Social media making you feel like everyone is watching? Yup. That can contribute to the fear of starting.

I don’t know if I’ve ever necessarily gotten comfortable in entrepreneurship, but I think the discomfort can be a really good driver for you to create some level of certainty within what you’re doing, whether it’s how you create what you sell, the offers you offer your customers or your communication and things like that.

For Kylie, it’s about normalizing the feeling of discomfort versus trying to avoid it. It’s part of entrepreneurship — not a bad part, just a part. She said, “Yes, I feel like this. But I also know how to educate myself, reach out for help, turn to resources that can help navigate to a place of comfort.”

Fear of Losing Momentum

Kylie brought up a fear that I think so many side-hustlers and business owners encounter, but don’t necessarily realize the root of the anxiety that bubbles up in their bellies. Kylie told me that her biggest fear right now is losing momentum. 

“I am in this place with my podcast where so many things are happening. So many good things are happening at once. I’m experiencing growth that I never forecasted for. I have opportunities on the horizon that I never could have dreamed would be possible in the first six months,” Kylie continued, “Now I’m worried if I take a break, if I give myself rest that I’m going to lose this momentum I have, and then it’s all going to go away.”

My advice for Kylie and anyone else feeling this: We love to believe and write the story in our brains, that our successes are flukes. But what I’ve learned is that we don’t just get one shot. There are a hundred shots. There are shots that are waiting for us or for the right timing. 

Know this: You have been smart enough to get to where you are today, and you have been intuitive enough to make the decisions that have guided you to the success that you’ve found and those brains and that intuition are not going anywhere. When you can fully trust in your ability to figure things out, to start fresh, if that’s needed to make the right decisions to honor your talents, to define your own version of success, then you have nothing to fear when it comes to momentum.

Fear of Relying on Yourself

When you start your own business, you become the boss… As well as the HR director, accountant, marketing person, and so on. The success of your business, at least at first before you hire a team, relies on your own efforts. This is scary, especially if you plan to go full-time and put your entire livelihood on your own shoulders.

The best way to combat this fear is to admit that you don’t know what you don’t know, and work with someone who does know. When it comes to things like legal, accounting, and beyond, invest in a professional (even if the expense stings at first). 

Part of entrepreneurship is recognizing and accepting where you need help, and if your fears are rooted in relying on yourself, the good news is that you don’t have to. Team up with people who can support the areas that aren’t your strengths so you can focus on the areas where you shine.

More from This Episode

It’s so fun chatting with Kylie about these phases of entrepreneurship she’s walking through alongside you, and I hope this episode shows you that you are not experiencing these fears in a silo. We’re all there with you, or we’ve walked through it before, so know that you will make it through to the other side. 

What entrepreneurial fears are you facing right now? Drop me a DM on Instagram @goaldiggerpodcast so you can connect with other Goal Diggers who are experiencing the same thing!

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Before you get any further... Hi! I'm Jenna Kutcher!

A small town Minnesota photographer, podcaster, educator and puppy rescuer, my happiest days are spent behind my computer screen sharing my secrets with the world. I'm glad you're here.

I’m an expert at online marketing, a nerd when it comes to the numbers, and my obsession is teaching others how to make a living doing what they love (without it taking over their life). 

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