Are you entrepreneurial in your love life?

By Steve Fisher

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All photos in this post are from life and travel on Koh Samui, Thailand, Aug. 2013

“Playboy repent!” 

About three years ago, while living on Koh Samui, Thailand, I was walking the gorgeous, naturally pristine beaches of the island’s west coast. Famished after walking much of the 20 km of coastline, I wandered inland to find something to eat. I came accross a street food stand, really nothing more than a wok and a few tables beside the road. But the food was fabulous…and so was the proprietress. Beautiful beaches, tasty Thai food and a pretty young shop owner (see photos). Who needs heaven when this sort of thing happens in the actual world we live in! After eating, the mood was right so I asked her to give me cooking lessons at her shop. Her only condition was that I come every day. A beautiful young Thai woman demanding that I visit her shop and learn to cook her delicious food every single day for the remainder of my stay on the island. Grave hardship indeed but I was able to endure.


The beauty of failing fast and failing often in love

The tech capital Silicon Valley and the global culture of founders and makers who worship it are devoted to the concept of entrepreneurship. This includes starting one’s own business, of course, but in its contemporary usage the term has become much broader. It refers to an active embrace of risk taking and innovative change in any professional context. Starting a new business venture is of course entrepreneurial but so is quickly hacking together and launching a new product or service for your current employer.


In short, being entrepreneurial now means to actively embrace change, intelligent risk and innovation whatever your work situation, whether you’re an actual entrepreneur,  an employee in a huge multinational company or a local civil servant. “Fail fast and fail often” (as this is the way to find what works), “Move fast and break things” (to build something better in their place), and “Adapt or die”  are some of the commandments of this new faith.


Personally, I think this new broader concept of entrepreneurship is fabulous. Flexible adaptation to rapid change is essential to both how I make a living and how I live. In fact, I’m such a big fan of entrepreneurship that I wonder if we can apply this concept to other areas of our lives? In other words, if there are clear advantages to embracing change and innovative adaptation in our professional lives, why not be “entrepreneurial” in other important areas as well? If entrepreneurial careers are great, perhaps more broadly entrepreneurial lives would be even better?


For instance, perhaps we could be more “entrepreneurial” with the activities we pursue in our free time. Or with our friendships and social lives. Perhaps no area offers more fertile promise for an entrepreneurial approach than our love lives. Just as some people seek stable lifelong employment with one company or government agency, some people seek to meet The One, begin a relationship that will last their entire lives and start a family. Just as the lifetime employer is the sole source of financial support and professional advancement, in this model of love and family life, this one person is the spouse, co-parent, lover, best friend etc. Professional moonlighting is forbidden. And, so are extra-martial adventures. That’s the theory at least.


In considering a more flexible, “entrepreneurial” approach, it’s not my intention to throw stones at the stained-glass cathedral of lifelong monogamous marriage. I do think it’s fair to ask though whether this traditional model of love is really ideally suited to the modern world. And whether it works well for everyone.

Think about it. The ideal of stable lifelong employment dates to the early postwar period. Lifelong marriage for love is an even older custom, dating back more than 200 years to the industrial revolution. Are these traditional professional and romantic arrangements best suited to life in global, postmodern society? Is it realistic to have enjoyable and gainful employment with the same company until retirement? And, is it possible to be both monogamous and happy with one person for our entire lives? If your answer to one or both is yes, that’s great, but if like me you have doubts, what’s wrong with being open to a more flexible and entrepreneurial approach? With love, as with money.


My sense is that most people are more open to alternatives to longterm arrangements with employment than they are with romantic relationships. In other words, they recognize the benefit of at least some degree of entrepreneurship in their professional lives, but likely shudder when this logic is applied to romantic relationships. Why is this? Perhaps it’s because work and money are largely in the realm of reason, while love is deeply emotional, and for many people there are deep moral or even religious considerations involved.

But are lifelong relationships inherently more positive morally than other, more flexible and dynamic arrangements? According to whose morality exactly? What if the man and woman are unhappy? And what if they are not particularly nice to each other? What if the relationship creates a lot more pain than happiness? If we adopt a more inclusive, secular view of ethical behavior (be kind, don’t hurt other people and try to help them etc.), neither marriage nor more flexible arrangements have any inherent moral valence at all. Some swingers are nice, and some married people are nasty. Trust me, I’ve met plenty of both.


In the professional world, if someone is bad at his job, not happy and poorly paid, I think we can all agree on the need for a change. In love as well, if the traditional model doesn’t work for us, perhaps we should consider other options.

What exactly would it mean to be “entrepreneurial” in our love lives? To “fail fast and fail often”, to take perhaps the first commandment of entrepreneurship. I think it means to accept, and even embrace, change as a natural part of life. To be open to new opportunities. And to take risks. If a longterm relationship doesn’t work for you, I think it’s absolutely appropriate to think outside the romantic box. Or use the box for kindling and start a fire.


End the bad relationship or marriage. (What’s the problem? After all, you would think nothing of canceling the money losing project at work). Flirt with and date that intriguing coworker. Or guy/girl in your pilates class. Or Tinder match. Or do all of this at once. At this rather provocative juncture, let me emphasize that being entrepreneurial in love does not ideally involve an unwanted pregnancy or STD. Even as they embrace fast failure, professional entrepreneurs generally try to avoid death and destitution. In love as well we should naturally avoid actual catastrophe. But it is worth asking, “What is the worst thing that can happen?” When the actual risks are small and the potential rewards are great, it makes sense to go for it, with love and all areas of our lives.

As with all the ideas in this blog, I hasten to add that I’m very imperfect at this. Please don’t imagine me galavanting around the world, starting romantic flames like some dork James Bond. More often than not, my efforts in this area provide more comic relief than romantic satisfaction. I am, however, quite passionate about actively choosing how to work and live. In modern global society, the possibilities are endless! If the conventional model of working, living or loving doesn’t work for us why not choose something else?






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