The Secret Insecurities of Three Successful Entrepreneurs

The Secret Insecurities of Three Successful Entrepreneurs

Leadership | Posted by - January 10, 2019 at 12:30 am

For the sake of anonymity, two of the entrepreneurs featured in this story requested to not be named.

Let’s admit it: we’re all insecure about something in our lives. For three leaders, who live and work in Toronto, their insecurities stem from a fear that they won’t live up to the responsibilities and expectations of their roles. 

YouInc recently asked these individuals: what are one to two fears or insecurities you feel that you’ve never shared with anyone? And, how are you overcoming these fears or insecurities? Here’s what they had to share:  

Investor, Toronto

I fear that people will discover, I’m not as good as people think I am. I fear that I’ll let down people on my team. I recognize that these fears are more emotional than rational, and I remind myself of my past successes. I recognize that these fears exist, but that I can’t let them stop me—I have to go forward despite these fears.

Entrepreneur, Toronto 
Diana Olsen, Founder, Balzacs Coffee

I have no formal education in business, so I spend a lot of time in high-level meetings trying to keep up with the conversation. Sometimes I “fake it until I make it.” Sometimes I’ll ask for clarification. Sometimes I’ll take notes and look things up later. A lot of times, I bring a fresh that may not occur to people working in the background. 

Let’s say I’m more comfortable as a worker bee than [I am] as an executive.

For the most part I rely on my team to fill in the blanks. Many of the people I hire and partners I choose, are vastly more educated and experienced in the corporate world, and I have no problem delegating jobs where I need help and trusting them to make decisions; they’re constantly teaching me. I don’t self-sabotage or doubt myself, because I know the skills that I bring to the table are equally or more important. 

As the company grows it becomes increasingly more daunting to manage the moving parts. Let’s say I’m more comfortable as a worker bee than as an executive. So far, we’ve successfully managed to scale up without compromising the quality and creativity.

Entrepreneur, Toronto  

I often worry that I’m going to fail as an entrepreneur. What if people don't buy the offering? What if I don't meet my targets? Taking on the responsibility for a large team is an abundant amount of pressure, and I always worry whether I’ll be able to succeed as I have envisioned and planned. 

I often worry that I’m going to fail as an entrepreneur.

I deal with this fear by breaking down my goals into tiny actions every day and celebrate the tiny wins. This is the only way I can deal with this: one step at a time.


In July 2018, I reached out to about 10 entrepreneurs in Toronto to ask one question: “would you be willing to share one to two of your secret insecurities? The story will be anonymous.” Most people replied, and even two to three leaders at well-known Toronto startups agreed, until I shared the questions—then they declined to participate. It’s not easy to put ourselves out there, for fear of judgement from our peers, so thank you to the people, who found the courage to share. 

So, what are you insecure about? Are you willing to share one fear with a close friend today? 

Tags: leadership, security, business advice, entrepreneur, motivation, startups, stress management

Kristen Marano

Kristen Marano covers women and their work for publications around the world. She has interviewed some of the most influential business leaders in Canada and the most passionate change makers in towns and cities as isolated as Perth, Western Australia. Most recently she interviewed Canadian businesswoman Zita Cobb about reinvigorating the economy in Newfoundland through the arts. Kristen's work encourages women to share honest and open perspectives about the emotional challenges of their journeys.

Patricia Coyne
October 7, 2018 at 9:23 am
Yes the above are all issues we FEAR... It's reassuring to know you are not alone!!!
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