On August 19th, 2011, I wrote a blog post that easily became the most widely-read thing I’ve ever written. It was a surpise to me – I wrote the thing really quickly, late at night, as a reaction to a blog post I came across called “Date an Entrepreneur” (which was based on another post called “Date a Girl Who Reads“). You can check out my post from August 19th here.
The thing that’s funny is that I wasn’t yet an entrepreneur when I wrote that post. I was working at a startup, and we’d hosted our first Ladies Learning Code workshop, but I hadn’t yet taken the leap.
Now, of course, that’s all changed. Today, I’m definitely an entrepreneur – I make a living by working for organizations that I’ve founded. I’m responsible for paying salaries, carrying a commercial lease and remitting taxes, not to mention all of the fun stuff like making sure people love being HackerYou or Ladies Learning Code customers, defining and executing strategies, and working with my team. I’ve learned a lot since August 2011, and certainly matured as a person, a woman and an entrepreneur. Looking over my updated post below, and comparing it to the one from 2011, it’s pretty interesting to see what’s changed. And what’s stayed the same.
So, here it is. A reprise of my post about dating an entrepreneur from about a year and a half ago. Would love your thoughts.
Date an Entrepreneur, Female Edition – A Reprise
Date an entrepreneur. Date a woman who spends her money on programming courses and productivity tools instead of trips to the mall. A woman who doesn’t mind being told that her idea isn’t going to catch on. One who can scan the landscape and identify opportunities that other people just can’t or won’t see.
Find an entrepreneur. You’ll know she is one because of all the tabs she has open in her browser. She’s the one skimming industry blogs, the one who can’t stop thinking about how she could do more, be better. Yes, things with her business move quickly and yes, she has more ideas than any one person can reasonably handle. But that’s what makes her great. You see a woman writing thoughtfully on an empty page in her notebook, with a Google spreadsheet open and her iPhone out? That’s the entrepreneur. She can never resist exploring a new opportunity, but she’s learned by now that not every idea is ultimately worth pursuing.
She’s the woman wearing jeans while meeting with investors. Or customers. Or anyone, really. (Suits and blazers have seen nothing but the inside of her closet for years.) She’s on her laptop at the coffee shop down the street. Her coffee is cold because she’s kind of mentally occupied. Lost in a world where running a business and changing the world is really hard work. Sit down and chat. (She’ll give you a look because she’s working on some kind of deadline, as always.) Say something that will catch her attention (good luck), and if she seems engaged, ask her about what she’s working on. Let her talk about education, technology, and what she’s got coming down the pipeline. If you dare to interrupt her without a good reason, she’ll give you a look – but that’s just because most people don’t like being interrupted. Try giving her a problem to fix, but only if you really want it fixed and fixed right. Ask her for her help or advice if you need it – she’ll always help if she can. But she’s learned by now that she’ll be better able to help others if she helps herself first.
Let her know what you really think of [insert newsworthy startup story here]. Ask her for her honest opinion. Understand that if she says she likes calculus and video games and is learning Ruby on Rails at HackerYou she’s telling the truth – women don’t tend to exaggerate those things too much. Her economic predictions aren’t spot-on – but these days, whose are? It doesn’t matter, though, because she’d rather invest in people, like Katherine Hague, or in her own businesses. She’s obsessed with generating revenue and profit and does a great job of saving her piece of it. She knows that, in this day in age, she has to take care of herself. She’ll rub off on you, and before you know it you too will carefully compare grocery store prices by the ounce and stock up on household staples when they’re on sale.
It’s easy to date an entrepreneur. Give her Adafruit gift cards – and jewelry – for Christmas and her birthday. Enable her creative side while also making her feel special about being exactly who she is. Understand that, on your anniversary, she might be in New York speaking at a conference or in Halifax launching a new Ladies Learning Code chapter – and forgive her for it. She might be in San Francisco on the 14th, so don’t be shocked if she asks to celebrate Valentine’s Day a day later so you can be together. Let her know that you love the passion she has for what she does. Understand and trust that she knows the difference between the present and the future, but she’s going to change the world to make it reflect her vision for the future. Don’t try to stop her – there’s no point.
She has to give it a shot somehow.
Don’t lie to her. Honesty has never been more important. Don’t be one of those people who just tells her what she wants to hear.
She’ll fail sometimes, and that’s okay. Because an entrepreneur knows how to create opportunity from failure. Because an entrepreneur understands that nothing truly comes to an end. That you can always create something from nothing. That you can recreate again and again and that there are lots of ways to create value. That life is meant to have a challenge or two. Besides, it’s a good reminder that she has to focus on being the best she can be – for herself first.
Don’t worry about whatever you feel you lack. Entrepreneurs understand that people, like companies, grow. She will help you realize your potential. She will study you more than anyone. She’ll figure you out. That’s when you’re really in trouble.
You’ll want to propose to her long before she’s ready. She’s got a world to change, she’s always saying, and she’s in no rush. You’ll try to very casually slip it in dozens of times, always somehow losing your nerve at the last minute. Eventually, it will happen – via Skype. When you least expect it to. And the seconds before she says yes will feel like hours. But if you’re lucky, she’ll say yes.
If you find a woman who creates, keep her near. When you find her up at 2 AM wrestling with a bug on her websites that she’s already been working on for hours, make her a cup of tea and grab your laptop or a book and sit with her. You may lose her for a couple of hours but she will always come back to you. And when she does, she’ll either be absolutely frustrated, finally giving in to her sleepy eyes, or she’ll be on cloud nine because she did it. Either way, in the morning, she’ll be back to normal, so be sure to appreciate those precious moments of emotion.
Date an entrepreneur because you deserve it. You deserve a woman who can give you the most vibrant life imaginable. Share your dreams with her, let her show you better ways of doing things and let her know you love her for who she is. If you want the world and the universe beyond it, date an entrepreneur.
This post is dedicated to Shawn Konopinsky, the best partner I could ever dream of. So happy that we both found entrepreneurs to fall in love with.