5 Lessons I've Learned as a Female Entrepreneur banner image

5 Lessons I've Learned as a Female Entrepreneur

I have fond memories of my dad crafting a game of whiffle ball in our yard when I was a kid. Marking the bases, reviewing the rules, giving me pointers on my swing. The game would start, I’d take a few swings and quit. I hated "boys'" sports. I was a dancer. At the time, it really was a girl’s thing – most would not have called it a sport.

I tell you this to set the stage. I am and have always been "all girl". Tiaras and dresses and the whole thing. The best part was that I grew up believing that girls had the advantage. We were far smarter, sassier, knew how to dress better, didn’t smell bad, and could always talk ourselves in or out of a situation.

That was until my first real job.


Fresh out of college, I landed a job one of those big financial companies downtown. Four years of college, a business degree, and I was an administrative assistant to an SVP and 25 sales guys. It seemed unfair and it was. Nonetheless, I took the job and answered phones, ordered lunches, picked up dry cleaning, and much more.

I eventually proved that I could do more than take messages or write memos and got promoted to sales assistant. I accompanied the sales guys on sales calls and took notes, explained our process, and handed out collateral.

One day, we were at a prospect meeting. The sales guy had been working the deal for months. At the meeting, the C-level guy on the prospect’s side asked me a detailed question. I gave a detailed answer. He asked another question. I gave another great answer and we closed the deal.

I was gushing, feeling like I might have been part of the reason we closed the deal.

When we got in the car, the sales guy said to me, “Can I give you some feedback?” He then proceed to say, in a very superior and derogatory way, “So, when you do that thing - like smile and be nice and funny - you kind of act like a girl. You should try to change that if you want to move up.”

I felt like I was punched in the gut. I answered back, “So, are you saying I should stop acting like a girl and act more like a guy?”  

“Yes,” he said.

After that day, I swore to myself that I would never act like a guy to get ahead. I was my own unique self and needed to stay true to that. Yes, I smile a lot. And I’m nice. And I like to get to know people and joke around and have fun. I honestly don’t want to change those things. They are what makes me, me. One day, those guys would see that women are powerful, influential, and entrepreneurial.


I recently moderated a panel for the Boston Chamber of Commerce’s “Women in Tech” breakfast series. I was alongside accomplished, insightful women from Deloitte, Liberty Mutual, Hubspot, and more. I was humbled by the adversity all these women had overcome personally and professionally to rise in their careers and lives. I started the session by quoting a statistic from a recent Bloomberg article: women launch more than half of all internet start-ups in China. Here in the U.S., that figure is 17 percent. 

The big topic of discussion around the lack of women-led businesses and women in tech at the Chamber breakfast was the “barrier for women”. I never saw a barrier. I always thought I could do whatever I put my mind to. I told my story about my sales guy experience and staying true to myself. I talked about the mystical work-life balance, and being a working mom, and why people need to stop asking: “How does she do it?!” You just do it.

Here's my advice for women in tech, business, life, entrepreneurship, or otherwise:


In the words of that famous Caddyshack scene, imagine what you want for your life and your career. See yourself as that person or in that role.

Take steps toward that vision you have for yourself and make it real. Nataly Kogan, founder and CEO of Happier, calls this “being your own CEO,” which is exactly what you need to do. 


Every woman in business should have a mentor. If you don’t have one, go get one. Think about how you want to grow and the type of person who could help teach and guide you to make you better.

If you are in a position to be a mentor, share with someone else. My mentors are the reason I am who I am today and I am honored to be able to pass on the gift.


The adage goes, “If you want something done, give it to a woman.” We know how to get stuff done, but can often take on too much. Our minds are racing with a to-do list a mile long at any one moment (guilty!).

Your time is your most important asset. I get asked to be places, do things and contribute all day long. I wish I could say yes to everything. I have to pick and choose so I have time to get my son to hockey practice or carve out time to chaperone a field trip.

There is no work/life balance. It’s up to you to make the priorities and keep them sacred.


I worked for a woman once who was the master of networking and said your network is like a spider’s web. One person is connected to another, so you need to build your web.

Surround yourself with people who can help you learn and grow. Don’t be afraid to introduce yourself to people or ask for introductions. There is great power in strong relationships.


I mentored a smart young woman a while back who kept saying that her boss wasn’t giving her feedback, and she wasn’t getting promoted, and this and that weren't happening.

You are in charge of you. Be confident in who you are and what you can do. No one is going to hand you an invitation for the next step, so just take it.

Michelle Heath is a marketing consultant with Growth Street Marketing and the former CMO/VP of Marketing at Currensee and Matchmine. Follow Michelle on Twitter: @michelleheath.

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