Photo: My mom and dad (far right) on stage at my dad's retirement party in Charlottetown, PEI on May 17. I was the only Hennessey kid who couldn't attend because I was consumed with working a deal in Toronto.
I recently celebrated my 29th birthday. When I was in my early 20s, if you had asked me when I planned to get married, I would have said I'd meet the girl of my dreams by 27 and be hitched by 30. And that I'd have kids by the time I was 32. I had it all figured out. In theory.
I'm not exactly on schedule. And I'm totally fine with it.
I have friends my age who are successful entrepreneurs and married. I also have self-employed friends who are boot strapping, in love and trying to figure out how to pay for a ring. How they'll support someone on maternity leave is another story.
Did you know Richard Branson is married? Probably not. He rarely talks about it.Michael Scissons of Syncapse got married in his early 20s and he says it was great for his career because he was able to focus on his company. Entrepreneur Kevin Johnson wrote a post for Under30CEO about his college girlfriend and why, from a business standpoint, getting dumped was the best thing that ever happened to him. Kevin O'Leary of Dragons' Den once told Chatelaine that people shouldn't get married unless they're going to have kids. "You are forming a business relationship," he explained, "not just an emotional one."
Successful entrepreneurs often wait until their late 30s to get married, postponing until after they sell their companies or when they are no longer needed to run the day-to-day operations. Some never get married because they're too into their careers, or themselves. No matter what the end result, every entrepreneur tells me they'd make more money if they were single (then again, the ones with kids say they wouldn't trade the experience for any dollar amount).
When I decide to take a solo vacation at The Body Holiday – no companions, no exceptions - or I cancel a date when I get a call at 8 p.m. about a new business opportunity, I ask myself: 'Who would put up with this shit?' I certainly wouldn't. What about the nights I don't sleep well, spurring me to fire up my laptop at 3 a.m., or go into the office at 4 a.m.?
I know it sounds selfish, but being an entrepreneur is sort of a selfish job. It's not easy to make time for someone outside of work. I still plan to get married and have kids, I just can't put a timetable on it. I had a very traditional family upbringing. I lived in the same bungalow my entire adolescent life. My mother was an accountant and my father was a manager with the PEI government. When I was eight, my mother decided that partner at her accounting firm wasn't for her, and my father took a severance package to start a technology company.
Eighteen years later, my parents are happily retired. They spend half the year in Florida and the rest at our cottage in PEI. My parents taught my sister, brother and I two things about life: be the hardest worker in the room, and don't forget where you came from.
My twin sister is a doctor in Halifax. She's in a serious relationship. Our younger brother is 27, he's single, and a very successful business-development employee at a technology company who travels on a weekly basis. I'm not in a relationship, which means I'm able to dedicate more time to running my companies. I don't have to spend long weekends at my in-laws or hang out with my girlfriend's friends with whom I might have nothing in common. I keep telling myself I'm going to build and stabilize my businesses, maybe even exit them, and then settle down.
But you know what? In the past, when I've dated, I often wished I was working instead of hanging out with my girlfriend. While I expect that attitude to change over time, it also got me thinking: If I were to sell a business for a premium price, would I then run the risk of attracting someone for the wrong reason?
There's the old saying: you'll know when you find her. Well, what if you're married to your business and not mentally committed to finding her? And what about the worst-case scenario, where your business fails in your mid- to late-30s, and everything you were chasing goes down the drain?
I'm taking a wait-and-see attitude. I'd like to hear your thoughts on this.