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Yes, You Can – On Spitfire’s 15th Birthday

Dear future female entrepreneur,

I was 28 when I first became a chief officer of anything, 32 when I became the president of the company where I started as an intern, and 33 when I decided to found my own company. That was 15 years ago. My first client is still a client today. In between, I have hired and fired, survived a recession with no layoffs, lost my cool more than once but to this day can be in a room full of men and one will inevitably turn and ask me when the coffee is coming.

I recently met an expert on entrepreneurship who shared a startling fact: 75 percent of entrepreneurs are white and 80 percent are male. Stunned by this, I decided to kick-off Spitfire’s 15th anniversary year by giving a mixture of advice and pep talk to any woman out there thinking of starting her own thing.

We need you.

The three things you need most are courage, confidence and a good sense of humor.


Let’s start with courage. First, you need the courage to start. If you are waiting until it feels exactly right, get used to waiting. Starting something from scratch that you are totally in charge of is scary and risky. Nothing makes it less so. Not a rock-solid business plan, pat on the back from mentors or the perfect logo. What’s on the line is your reputation. You are either going to succeed or fail – unless you reset in your mind that simply starting is succeeding. Then, when you get going, you’ve already succeeded. You started a business. The sooner you start, the sooner you succeed.

You also need to have the courage to do it your way. There are a lot of books and know-it-alls who will make you think twice. I was told that paying my staff’s health insurance or exceeding what I had to do legally on parental leave wasn’t a financially savvy move. But my entire business is based on progressive values, including making workplaces family friendly and ensuring that people are economically secure. Right now, I have staff clamoring for pay transparency. “Experts” are telling me this will cause waves. OK, I may have to face that. But if pay transparency helps build an equitable workplace, and I want to do that, then I should take these risks. Part of being an entrepreneur is getting to build the workplaces you think the world needs. Have the guts to do that.

Last, as a female entrepreneur, you do need the courage to speak up. For that guy who asks me when the coffee is coming, I have the perfect response: Why are you asking me? I say it in a very light-hearted, curious tone. Then I watch as he tries to articulate why he picked me, realize why, not want to say why and then murmur something about finding the right person to ask. Does it get tiring? Yes. Every time someone makes a derogatory or discriminatory comment large or small, I think, “Why do I still have to confront this?” But you do need to do it. As you make your way in the world, use your growing power to shake up this dynamic. Because who else is going to do it? On those days when I think I am just going to let that discriminatory comment go, I look around the room and realize there are other women in the room fighting for their seat at the table. Maybe by speaking up and responding to every comment, that will mean one less time an up-and-coming female entrepreneur has to face unfair barriers and can simply focus on working her entrepreneurial magic.


What you have to say matters. Don’t undermine yourself when you are starting out by engaging in self-sabotaging behaviors like saying “um,” “like” and “you know.” When you are new, you are under the microscope. People wonder if you have what it takes. They are looking for small tells. Speaking in a hesitant manner might make people think you lack confidence. Being seen as confident even if you are shaking inside is going to get you through many difficult situations.

Be confident enough to have people call you on your shit. For this, you need a bossy posse in your life – in the office or outside of work. No, this is not when you get to lead a bossy group of people around. Quite the opposite, actually. This is where you gather people you trust, who really know you, and lay out whatever problems you are having. It may be staff morale, your inability to say no so you are always overbooked or overwhelmed, or that you aren’t growing the way you want. Pick people for your posse who are listeners. As the boss, you will get your chance to describe what you are struggling with. Now, here’s the tough part: sit back and take what your posse says. They will talk around you like you aren’t even there. You will want to say “but” and you will want to defend yourself, but you just need to listen. They are reflecting back to you what you aren’t seeing. And that’s the point. I am lucky to have a gaggle of girlfriends who do this for me, as well as a monthly co-ed forum where I can’t get away with anything. Your blind spots are inevitably what will hold you back the most. Anytime someone is willing to call those out, just sit back, listen and say thanks.

Confidence means facing your worst you and finding ways to keep that part of you under control. If you are in the position to start your own business, it is because you are damn good at something. Congrats. But sometimes what you are great at becomes grating. I recently read a book I highly recommend “Work Happy,” by Jill Geisler. In it, she talks about the concept of the evil twin. This is where you think you are enforcing high-quality standards but actually you are micromanaging and completely disempowering your team. Self-awareness is a must-have skill for an entrepreneur. You need to know how to hire to complement your weaknesses; you need to not let your best qualities become your worst traits; and you need to have people around you who will tell you when your less-than-great side is showing.

Confident people take a long view and don’t burn bridges for short-term satisfaction. Inevitably, the industry you are in will start to feel like a small town, and you’ll know everyone. Here’s the reality of a startup and growing business: Staff will quit – even your favorite ones. People will take their business elsewhere. This can feel humiliating, discouraging and might even piss you off. There will come a time when you want to curse or worse. But don’t. Ever. However mad you are now, set yourself up to work with people well over the long term. Take the high road every time. Believe me, in the end, you’ll feel better about it. …And you’ll be grateful you don’t have to hide behind a tower of cheese at a cocktail party when your nemesis shows up.

A sense of humor

A sense of humor will stand you in good stead. When you or your team face failure, levity will soften the sting. Find the humor in the situation. This doesn’t mean you are taking it less seriously, but rather you are sending a strong signal to your team that this isn’t the end of the world. Everyone will learn from it and, yes, even laugh about it. No one will die over it. This is what helps make failure less scary.

Humor can also help when it is time to learn new things. And when isn’t it time? As soon as you’ve mastered one thing, it seems like some newfangled management technique comes along and you have to get on top of that. Case in point, I know I need to be more empathetic. Books, coaches, my team, everyone tells me this. When I work on it, I am clunky. I am not good at it. And that’s the point. When learning something new, you have to get over the embarrassment factor, and part of that comes from approaching the lesson with a sense of humor and giving yourself, or your staff who is attempting to learn something new, a break.

“Be lifelong learners” sounds so nice. If the experts said instead “constantly do things you are really bad at in front of a bunch of people and see how that goes,” few of us would embrace learning. Think of your professional growth spurts a bit like paddleboarding. From afar, it looks easy. Then you get on and whoa … wobbly. Then you start to stand up and fall in the water. Some wiseass on a dock yells out, “nice one.” But eventually, undeterred and perhaps emboldened by the critic, you figure out how to get up, and in no time you are paddleboarding or managing or dominating or whatever it is you need to do. But when you are in the proverbial water after falling in, a smile and a little “yeah, I suck” goes a long way in taking the pressure off and getting you to try again.

A sense of humor also encourages you to play – with your team and with your free time. All work no play does lead to crankiness. I haven’t seen the study, but I have seen tons of test subjects who are working too many hours and not taking the time to recharge. Play is a great way to recharge. I have never regretted taking staff out on an unplanned field trip, dressing up like a flight attendant and passing out drinks from a bar cart or getting locked in a Sherlock Holmes-themed escape room with a team of colleagues (complete with loud Victorian-era music) and solving puzzles to get free. This is always time well spent. The time bellyaching about how everyone is too busy to play, not so much. If you want an inspired team and, just as importantly, a motivated you, embrace your role as play master in chief.

I realize there are a million more tips, cautionary tales and book suggestions I could offer, but these three pieces of advice will go far in getting you going and keeping you at the top of your game. If I can ever help a would-be female entrepreneur get going, just drop me a line. I am in your corner.

This blog post kicks off the start of Spitfire’s 15th year. There will be a new and improved Smart Chart® coming out, staff sharing lessons learned and other tools that will spark big change, and more. Thanks to all who have been with us on this journey. We can’t wait to see where it takes us next.


This entry was posted on Thursday, July 6, 2017 at 11:43 am and is filed under Brand identity and strategy, Spitfire anniversary and Spitfire culture. You can follow any responses to this entry through the RSS 2.0 feed. Both comments and pings are currently closed.