How to Overcome Your Fear of Becoming an Entrepreneur

Caterina Kostoula

Is launching a business the best way to fulfill your purpose?

Are you dreaming of becoming an entrepreneur, but you are too afraid of taking the risk?

I know how it feels. It took me ages to decide to leave my job at Google to start my own coaching business. Abandoning corporate life is one of the toughest decisions you can make in your career. 

After leaving my cushy job to launch a company, I coached several other leaders to do the same. In this article, I share the amazing stories of three INSEAD Executive MBAs who transitioned to entrepreneurship. You will learn their best strategies in overcoming their fear of diving into the unknown world of startups. 

Skill up

Goulnara Aguiar first thought about entrepreneurship during a work assignment. She had to build a complex product from scratch. She made it happen in less than six months, and she enjoyed it. However, the political games within the company slowed down the product’s expansion. A few years later, a series of negative work and personal events made her realise that she needed to make a change. 

Goulnara’s biggest fear was whether she would be able to lead a company on her own.

She knew how to create and deliver a product. Being a founder and CEO involved much more, including strategy, financial plans, investor and media relations. She felt responsible for the people she was going to hire, and she wanted to know what she was doing. So she enrolled in the INSEAD Global Executive MBA to hone her skills. The programme enlarged her vision on the macro issues the planet was facing. Upon graduation, she decided to pursue a socially responsible business.

Goulnara tested several iterations of her business idea before she ended up with the right one. Now, she leads ORMEX, a tech solution that enables sustainable agricultural trading at scale. She advises aspiring entrepreneurs to surround themselves with mentors, teachers, coaches, and peers. “Entrepreneurship does not have to be a lonely path,” she says. 

Face your biggest fear

Fabrizio Crisafulli came from a family of entrepreneurs. After a stint in consulting, he took over the family business and drove it from strength to strength. As much as he enjoyed running an established company, he wanted to build something from scratch. Everyone was telling him that he was crazy to leave a CEO job in a lucrative business.

He was in his mid-forties and had two kids. What if everyone was right?

He did not know how easy it would be to go back after his successor had taken over if things did not work out. 

Fabrizio realised that most of his fears were irrational. He asked himself: “What is the biggest irrational fear I have always had? What is the last thing I would do in my life?” The answers were “heights” and “parachuting.”

In the fall of 2019, he travelled to San Fransisco to attend a joint INSEAD-Wharton workshop, as part of his Executive MBA. After the class, he rented a car and drove to Santa Cruz. Without anyone knowing where he was, he jumped in a parachute.

Within a week, he had finally left his job. Facing his biggest fear and surviving gave him the courage he needed to follow his dream. He is now developing two businesses and loving it.

He argues that the worst thing that could happen to aspiring entrepreneurs is to live with the regret of “I could have tried…”

Start with a side-hustle

Fatou Gueye was the oldest of five siblings, and since her early years, her parents instilled her with confidence and optimism. In parallel to her corporate work, she started experimenting with entrepreneurship. She was afraid of losing the money she would invest in her business, so she started with smaller amounts that she would be comfortable losing. She first launched a real estate business in France. Then, she invested in a commodity trading company in Congo. Now, she is working on a new venture dedicated to the African real estate market, her INSEAD final project

Along the way, she created a board of mentors and advisors who provide her with feedback and insight. Starting while she was still on a paycheck, reduced the risk for Fatou. She also set herself a deadline. If the business did not take off within two years, she would pull back. Fatou advises aspiring entrepreneurs to have a plan B, a pot of savings, and a board of advisors. A safety net will provide you with the confidence to be ambitious and go big with your vision. “Everything seems impossible until it is done,” she says.


If entrepreneurship is your dream, it is worth working on it.

There will always be risks when you embark into the unknown, but there is no reason to let fear be on the driving seat. Goulnara, Fabrizio and Fatou found people to support them in their path. Teachers, mentors, coaches, and fellow entrepreneurs can be your new tribe as you leave your old one. They managed their long-standing fears by building skills, networks, and working on their psychology. They now develop their businesses feeling more fulfilled than ever.

Life is short.

And as Jim Carry said:

“You can fail at what you don’t want, so you might as well take a chance on doing what you love.”