5 Lessons for the Fearless Female Entrepreneur The same challenges face anyone in business, but women encounter their own unique challenges.

By Jayna Cooke

Opinions expressed by Entrepreneur contributors are their own.


As female entrepreneurs and business leaders, we are often regarded as fearless. We've successfully batted away the outdated stereotypes and overcome obstacles that would derail many a man without even breaking a sweat.

Yet under that fearlessness, we face a myriad of challenges and difficult decisions just like any other entrepreneur or CEO. Sometimes those challenges are the same as our male peers and sometimes they aren't.

Related: Leaving a Long-Term Job Takes Courage, Especially If You're a Woman

As a female CEO and entrepreneur, I've relied on five key lessons to help me through these challenges and keep me fearless.

1. Dive in.

I really admire Sheryl Sandberg's famous "Lean In" mantra and I think the premise behind it is very valid in many situations -- especially when you are a woman in a male-dominated business world. However, I think many entrepreneurs -- especially female entrepreneurs -- would be better served by following a "Dive In" mantra.

When starting something new, we tend to be more cautious and analytical, which can lead to us over-thinking every detail in our quest for perfection. As an entrepreneur, you have to accept that the timing is never going to be perfect -- there is always going to be more research and testing to do, more edits, etc. Sometimes you just have to take a deep breath and dive in.

2. Get out of your comfort zone.

The fear of failure can have a debilitating effect on an entrepreneur or on any business leader. (Female CEOs are supposed to be fearless, remember!) In my experience, the best way to combat that fear is to force yourself out of your comfort zone.

After starting my professional career as a fashion buyer, a chance meeting with Brad Keywell (now co-founder of venture-capital firm Lightbank and Groupon) convinced me to take a leap of faith into the tech startup scene. I was a million miles outside my comfort zone, but I was also empowered by my choice and that helped me succeed.

Whether it's a career change or just forcing yourself to start making cold calls, pushing beyond your comfort zone will up your confidence and help you overcome your fear.

3. Learn to be a good listener.

It might sound cliché, but learning to listen to your clients, employees, mentors and/or investors is crucial to the success of any startup or small business. It also takes patience and lots of practice.

Related: 10 Apologies I Will Never Again Make as a Startup CEO

The most successful sales people (and aren't all entrepreneurs sales people really?) are the ones who get their potential customer to do the talking. For entrepreneurs and business owners, this can be hard because we tend to be very excited about our company and our product. Learning to truly listen to feedback, and validate it in return, can help you build loyalty and success.

4. Ask for it.

Growing up with five siblings, I learned from an early age to speak up. My mom often said "A closed mouth does not get fed" and that lesson has stuck with me. Early in my career, I would always try to be the first to ask "What else can I be doing?" and "How else can I contribute to the team?"

I saw this lesson come full circle once I became a manager as the most successful people were the ones who were always asking for it -- whether it be for more responsibility or more money.

5. Find a mentor (or two).

Starting a business is full of stressful decisions and challenging obstacles. A mentor can provide perspective, offer advice from the trenches and help you keep your ego in check. The beauty of the mentor/mentee relationship is that you don't have to be exclusive -- in fact, I would encourage the opposite.

I have a few different mentors (a mix of men and women) -- each with different backgrounds and expertise -- who I lean on depending on the situation. Local networking or business-practice groups are also a great resource that every entrepreneur -- male or female -- should utilize.

While there may many books on the subject, there is no clear-cut instruction manual for female entrepreneurs or business leaders. These lessons are born from my experience and have sustained me throughout my career, but every journey is different.

Identify your fears, find what works for you and then dive in.

Related: Shark Tank Star Lori Greiner: I Never Think of Myself as a Female in Business

Jayna Cooke


Jayna Cooke has been navigating the startup world as an entrepreneur, leader, philanthropist and investor for the last decade. A former vice president at Groupon, Cooke is currently CEO of EVENTup, an online marketplace that helps companies find the perfect venue for everything from movie and fashion shoots to corporate events.

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