07/10/2013 05:31 pm ET Updated Sep 09, 2013

Is This the Most Entrepreneurial Dater Online?


A few weeks ago, a woman named Linsey posted a comment in a LinkedIn dating and relationships group to which I belong. Tired of online dating and expensive matchmakers, she had taken matters into her own hands and created her own personal website, where people could learn more about her and get in touch if they were interested in getting to know her. She was soliciting feedback on her site from all 562 members in the group and asking for our help in spreading the word. I wrote to her with a few suggestions for her site (some of which she made, some of which she disregarded) and mentioned that I wanted to write about her idea for my blog on the Huffington Post. I absolutely loved her resourcefulness and entrepreneurial spirit.

How could I not? After all, I started a dating coaching business (The Love TREP) based on dating entrepreneurially and innovating in one's love life. The idea is to help women find the type of healthy, happy, committed relationship they desire by infusing the entrepreneurial spirit, mindset and approach into their search for love. Ultimately, women see that the power to create change lies within them; that they can create, build and shape their love stories in much the same way a traditional business-oriented entrepreneur creates, builds and shapes her venture. When a woman takes on the persona and approach of an entrepreneur, a Love TREP, moving her love venture forward, she feels more energy, more motivation and a sense of purpose in her dating life as opposed to going through the motions or wallowing in victimhood.

Part of what I help singles work on in their entrepreneurial dating journeys is the practice of creating opportunities -- entrepreneurs are known for seeing possibilities where others see headaches. In fact, adversity is not a burden to an entrepreneur; it's an opportunity for growth and discovery. So, instead of being passive observers in their dating lives, burdened by their "bad luck" in love, I encourage women to roll up their sleeves and start problem-solving, not only with regard to internal obstacles (limiting beliefs, low self-esteem and the like) but also how they can start thinking differently about the ways they can meet and interact with men. In the world of entrepreneurship, this type of creative thinking is known as "blue-sky thinking" (the origin of which traces back to, of all places, the Eisenhower administration!)

Blue-sky thinking in your dating life is all about breaking boundaries, pushing past self-imposed constraints and limits. Your feet can still be on firm ground, but as you look up into the blue sky, stretching endlessly above you, the possibilities are endless. You can then frame your opportunity by asking yourself: How might I break free from my predictable, status quo dating existence? The higher in the sky you look, the wackier, sillier and more inane the idea should be. Sometimes, the zaniest ideas are often catalysts for progress in love and business (to wit: PooPooPaper, a successful line of recycled paper products made from poop!). Entrepreneurs engage in these types of brainstorms and often find that not being limited by current thinking or beliefs helps stimulate the kind of creative thinking needed to come up with novel, reality-based products and services. Check out this example.

Linsey's on the right track with her idea. Like a true entrepreneur (she's also one in her career life), she experimented with a new idea, is testing the results and will make pivots accordingly (maybe she gets new pictures or changes some of the language, or maybe she ultimately decides to take the site down and try something else). Sure, the naysayers will be out there ready to pounce, but throughout history, that's always been the case when someone steps forth with a bold, new idea: How many people balked at the notion years ago that one could find love through a computer? Linsey's idea also managed to get the attention of me. And look what happened: I'm now writing about her site for thousands of people to see. And maybe out of those thousands there are a handful of men who say: "This gal's got spunk; I like that; I want to get to know her!"

Adam Orna, who I write about in my forthcoming book (Skin In the Game: Unleashing Your Inner Entrepreneur to Find Love), also engaged in blue sky-thinking when it came to his love life. Remember this guy? Orna, a 39-year-old postal worker, was so tired of waiting for love to find him, constantly striking out through the usual approaches -- bars, online dating and the like -- that he took the bold if rather peculiar action of taking to the streets with a sign listing his personal statistics -- "$55,000 plus benefits, loyal, straight, marriage-minded, a marathon runner and a vegetarian" -- followed with the words "Please Date Me." In the story, a married woman by the name of Carol Dersarkissian who chatted with Orna one afternoon told him she was married, to which Mr. Orna responded by giving her his card so that she could give it to a single friend.

"There have been nights I've cried I was so lonely," he said in the piece. "You've got a good job, good hobbies, but what good is it if there's no one to share it with?" While Orna didn't seem to have much luck at the time -- more than likely being seen as desperate by most women -- I had to applaud him. His entrepreneurial spirit was something I could appreciate. He was dedicated to a vision and decided to take action, even on the wackiest of ideas.

"Don't wait for it to fall into your lap," admonished Orna with regard to companionship. "Go out and pursue it. It won't fall into your lap. Trust me." When I tried to track to down Orna to see if his idea ever helped him find dates, I came across his Facebook page. Relationship status: Married. It could be that he falsely changed his status or it could be that his blue-sky thinking was the catalyst for creating love in his life. Mr. Orna, if you're out there and read this, drop me a line and let me know!

And let's not forget Lisa Linehan. OK, while I might have poked fun at her on an old radio show I hosted, I've come around to thinking she's kind of awesome. In 2010 she created a song titled "I want to get married" and posted it to YouTube, kicking off an initiative she called "Project Husband." Her video (which, apparently, didn't sit well with Dr. Phil and a couple of guest matchmakers -- but listen to this guy who agrees with me and the premise of experimentation: "It took Edison more than 240 tries to come up with the incandescent light bulb") netted her 56,000 views and more than 80 dates. Clever, entrepreneurial-thinking bridal businesses donated a wedding cake, ring and dress to Linehan; unfortunately, she didn't end up making a love connection. While there's possibly some internal work that needs to be done on Linehan's part (and perhaps a new way of looking at the soul mate meme, which, frankly, can be burdensome for singles), she did create an incredible opportunity for herself to meet new people, one of whom she dated for five months. A year after her project ended, her ring finger bare, Linehan did what any entrepreneurial thinker would do and turned her failure into an opportunity... for someone else: A wedding giveaway! The donated wedding items would all go to one lucky couple. Linehan selected the winning duo out of the many applicants who uploaded their pictures and love stories onto her Project Husband site.

When it comes to your love life, are you engaging in blue-sky thinking and curiosity-led dating, or are you stuck in prediction, status-quo mode, attending the same tired bars? How can you make blue-sky thinking work for you? Organize a ladies night and brainstorm with your friends. Think as big as you can. Imagine that there are no barriers whatsoever in your way, that anything is possible. Whatever resource you need is available to you (time, money, personality traits, networks, abilities, and the like). Move beyond your assumptions and limiting beliefs of what is possible. What ideas can you come up with?

Lest you be concerned: I'm not saying that you have to record a song on YouTube or strap a sign around your neck or start a personal website aimed at meeting people -- those are ideas that worked for other people but they won't work for most. But maybe there are new ideas and possibilities that you can explore, ideas that seem a little nutty to you because of the limits you've placed on yourself, ideas that make you step outside of or expand your comfort zone. Those ideas could be anything from joining a niche online dating site to going out to an event by yourself to joining a co-ed sports league as a free agent, and so on and so forth. You can also extend blue-sky thinking to new ways of communicating with men, new ways of risking with men, and news ways of thinking about yourself, but that's an article for another day.

We live in an exceedingly uncertain, unpredictable dating world, and when the future is unknowable, when you can't predict it, you have to start creating it. The entrepreneurial way, in many regards, is a great way to live your dating life, because it offers a framework for you to work through uncertainty: taking action and experimenting, engaging in reflective thought and then acting again in smarter, more empowered, more creative ways -- all of which leads to increased self-awareness and confidence.

Blue-sky thinking is one example of how to date entrepreneurially; it demands that we ask the tough questions about why we can't do x, y and z and encourages us to push past those boundaries we've erected for x, y and z reasons. As Martyn Perks, a blogger for the Independent, so eloquently puts it, blue-sky thinking "can reveal the barriers, hindrances, hurdles and naysayers which might be the real reason as to why so many good ideas never come to fruition. Challenging those limits is an important first step to putting the future back within our grasp."