11 Entrepreneurs Share How to Overcome Business Insecurities

Entrepreneurs are likely to face many business-related insecurities. Overcoming silent business fears is essential to long-term success.

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Entrepreneurs are likely to face many business-related insecurities. At one point or another, a lack of confidence and self-doubt can creep in unnoticed and sabotage the best laid plans.

Overcoming silent business fears is essential to long-term success. So we asked eleven entrepreneurs to share how they overcome business insecurity. Here’s what they had to say.


1. Listen to your gut and just go for it.

“Don’t be afraid of what other people may think. If you overreach, you can always figure it out as you go. If you step on someone’s toes, you can always apologize later. You owe it to yourself to go for your dreams and live the life you deserve. I was an 18 year-old kid when I started working for a Fortune 500 company with no experience and no education. Three years later I was running my own business and became Entrepreneur of the Year. You too can live on your own terms – you just have to decide that from now on you will.”

– Sharif Khalladi, Founder of Complexant, @sharifkhalladi


2. Consider the worst case scenario.

“Once, when I was dealing with the fear of failure, a mentor told me that to try to understand the worst case scenario, in addition to evaluating the likely risk and reward of the options. If that worst case scenario is still acceptable and the risk and reward is attractive, then it probably makes sense. However, if you can’t handle the worst case scenario, then you may have to re-evaluate.

Related to this, was a story a fellow entrepreneur told me about one of his employees who was extremely successful because of his experience as a war veteran. This employee understood the risk and reward of his business decisions and took calculated chances at work that others may have viewed as risky. The veteran understood real risk as bullets flying past your head, not a bad sales deal.

This employee more properly understood business risk and true worst case scenarios than people without his experience, so he achieved better results from taking better risks.”

– Brad Morehead, the CEO and Co-Founder of LiveWatch Security@ LW Security


3. Celebrate your failures.

Celebrate your failures, recognizing they are a necessary part in the process of becoming successful. When I first started my own business, I was terrified of losing a client, thinking it would be the worst experience ever. Well, it eventually happened, and yes it was painful (mostly to my ego). But I analyzed what happened, made adjustments, and grew into a better person and a better company from the experience. Understanding that I will sometimes stumble, and that it’s okay when I do, has given me the confidence to run this crazy race of entrepreneurship!”

– Angela Leavitt, Founder & Managing Partner of Mojo Marketing, @MojoMktg


4. Be your own best cheerleader.

“No one can – or will – advocate for you and make it happen like you can. Exude confidence in your business and your capabilities, and others will see you as capable as well. If you don’t believe in yourself, no one else will, either.”

– Elle Kaplan, CEO & Founding Partner of Lexion Capital Management LLC, @ellekaplan


5. Set small, realistic goals every week.

“Starting a business from scratch isn’t for [the] faint at heart. Every entrepreneur is faced with periods of low self-esteem [and] lack of confidence, but most importantly, is uncertain of what is next. Am I on the right path? Am I doing the right things to grow the business? Is this normal? Am I panicking too early?

The way to combat this is very simple: set small realistic goals every week and conquer [them]. For example, when we first started our business we’d set goals of closing 2 deals a week. Now, that’s the norm for a day’s work. It’s amazing how much achieving such small goals can boost your confidence and motivation. As you build on winning small battles, the ultimate feat of winning the war will become real.”

– Zlatan Beca, Co-founder and VP of Sales at Repair Jungle, @repairjungle


6. Write a letter from your ‘future’ self.

“Being a young, female founder in a male-dominated industry, I’ve had plenty of moments when I questioned myself and why I was doing what I was doing. I took some time out a while ago to write a short letter to myself from my future self. I carry this letter around with me. In those moments when I question myself, I pull the letter out. I take a quiet moment, and revisit it to remind myself who I am – and to stay the course.”

– Shelli Trung, Founder of Investors Beat, @InvestorsBeat

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