I was reading Inc. Magazine this morning and ran across an article about dating as a female entrepreneur or high powered corporate leader i.e. CEOs, etc. This gal nailed a phenomenon that I’ve personally experienced and that so many strong, successful women that I know have been subject to. Meg Cadoux Hirshberg writes, “[In business]Female entrepreneurs are often unfairly perceived as less serious, less aggressive, more likely to put family before business. But… I’ve discovered an opposite and equally insidious stereotype that batters women’s romantic prospects. The same woman who can’t persuade a VC she’s tough enough to build a business can’t persuade a guy she’s sweet enough to build a relationship.”
I read that and thought that is SO right on! In the article she talks about a CEO who started dating online after her divorce. She didn’t get a single bite on her profile until she made one small change. She changed her occupation from CEO to something simple like “sales”. Funny how that little change made such an impact, she was instantly bombarded with messages! Typically women who are entrepreneurial have the classic traits of entrepreneurs; grit, tenacity, strength and leadership. Problem is while women consider those qualities desirable characteristics in men; it seems men don’t find those same qualities as desirable in women.
So I started thinking about my own personal experience. I’m divorced. I got married super young, right out of college; to a man that was 9 years older than me. We were a disaster waiting to happen, but one of the greatest struggles in our relationship was the fact that I was extremely ambitious and he was a type B, do-enough-to-get-by kind of guy. Not a bad person, but I think ultimately as a man, being out earned, bred insecurity which only made the situation worse. As he felt more insecure, he stopped trying to be successful, kicked up his feet, played a ton of golf and decided to take on the extreme playboy lifestyle that married men simply shouldn’t be living, unless of course, they want their “sugar mama” to leave them… which is ultimately what happened.
Fast forward to when I put that chapter behind me and began looking for my perfect match, I found that dating was a challenge. #1 I was a single mama to a barely 1 year old little girl. #2 I was looking for a man who could not only be supportive of my ambitions but one that would find it sexy! I met a lot of nice guys while I was single. But I definitely experienced what this article talked about. “Many men are uncomfortable with, intimidated by, and ill equipped to handle a powerful woman. People assume that those with power aren’t necessarily nice, and women are supposed to be nice.” So I found that on first dates I’d downplay my career. I’d talk about my business briefly but move on so that we wouldn’t get real deep in conversation about it. As the author of this article said, “Ideally, someone gets to know you as a person before you wear the scarlet letter as an entrepreneur.”
She spoke of entrepreneurs exclusively with that statement and went on to articulate something I thought was interesting, “Of course accomplished women in any profession risk a similar response. But female entrepreneurs point out key differences between themselves and their peers in other high-powered pursuits. For one thing, traditionally employed women often have predictable schedules…Not so the entrepreneur, who is the first responder to any company crisis and the last to turn the lights off.”
So I was on a mission to find my soul mate. Laugh if you will. I did when people talked about soul mates. Silly really, one person to match your soul? Give me a break! But funny thing… I found mine. My first date with Jarritt was unlike anything I’d ever experienced. Our date was at a Thai food restaurant in West Seattle. I met him at his place, I pulled up on the busy street, called him to let him know I was there and he came out dressed all handsome in his designer jeans, sweater and boots that his female

Jarritt's Standard Attire
friends had dressed him in. I’ve since learned that my comic character t-shirt wearing man is more comfortable in a pair of 10 year old jeans and a Carhartt flannel. But he knew that to catch a fish you had to use something shiny so he dressed up in jeans he’d later tell me squeezed all the wrong places and a sweater that was arguably too tight for a straight man… The first thing that he said shocked me. I said, I’m happy to drive us since I’m already in the car. To which he replied, “I’m kind of traditional in that as the man, I’d like to drive you on a proper date.” I thought wow, that’s interesting. I don’t know why it seemed like such a nice gesture but after being married to the type of man I had been for 5 years it was definitely a change. And even after dating a lot of nice, successful men, I still found it strange because most of the time I’d just meet the guy at a restaurant, coffee shop, etc. So I parked my new Mercedes SUV in his garage and jumped in his Tahoe. I mention the cars for two reasons. #1 I had one date make a fuss about my “fancy car” and say that he wasn’t sure he could “afford” me. So the fact that Jarritt didn’t say something stupid was nice. But reason #2 that I mention cars is that he drove a Tahoe, which he called his “sweet bachelor rig” to which I still say, my first impression was, “Wow this is a great dad car! I could totally see Zoe’s carseat in the back. Is that a DVD player for the kids? How much cargo space is there for a golden retriever??” LOL!
From the Thai Restaurant on it was 1,000% clear that this guy was my 10. My absolute perfect match. Our date went on for 12 hours. Seriously. I’m not a night owl either, I’m usually asleep by 10:30. I met him at around 5PM, we closed down the restaurant, talking non-stop. When the restaurant closed I went back to his place where we sat on opposite sides of his couch, and talked until 5AM! (For the record, it was Zoe’s dad’s night, I wasn’t being irresponsible) We never kissed or anything. It was just the best conversation ever! Not to say we weren’t attracted to each other, we obviously were! But there was a level of respect for the situation because we both knew what was happening. It was like talking to the male version of myself. Jarritt is an entrepreneur and much like me, has learned life lessons that most under- 30 year olds haven’t learned. I believe he is more successful than me and smarter. I definitely met my match. My dad used to say that I had to find the man that I wouldn’t out-grow. That it takes a strong, secure man to be yoked with a strong, secure woman. Jarritt’s my strong, secure man. He’s so proud of me, 100% supportive of everything I do and because I believe he’s smarter and more successful I respect and value his opinions over anyone. I learned a valuable lesson, you HAVE to RESPECT the man you share your life with and he has to do the same. Insecurity causes all sorts of relationship trouble.
Our dates continued to be like the first. Fast forward 10 months later. Jarritt and I are married. Whirlwind? Of course! Any doubt in my mind that I made a rash decision? Absolutely not. I met my 10. And when you realize you are destined to spend the rest of your life with someone, you want it to start right now. People that know Jarritt well will tell you that he marches to his own drum. He’s patient and logical. But with us, we just knew. It’s been the best year of my life. We look at each other every day and say it feels like we’ve been doing this for a lifetime. And our friends and family say the same. My mom said the other day, “it feels like you’ve been here all along Jarritt.” We see the world through the same set of eyes. Opposites may attract, but for us, viewing life the same way makes for a peaceful life together filled with love and laughter. And I’ll tell you, being equally yoked with your partner is amazing. I feel like the two of us together could take over the world. When you’re a team with your partner it makes all the difference in the world. I believe that is what has made his parents so blissfully in love after 42 years of marriage. They are partners in every sense of the word.
I thought this article was spot on, but I had to share my success story because I was so cynical after my divorce. I didn’t believe it was possible to find the kind of man that a strong, female professional needs. But I did! And you will too. Just don’t settle. Mediocrity sucks. Better to be alone than with the wrong person because then you’re all tied up and not able to find the one.
Robin