08/14/2013 06:56 pm ET Updated Oct 14, 2013

4 Ways to Run Your Love Life Like It's An Entrepreneurial Startup


In 2012, Reid Hoffman, founder of LinkedIn, and Ben Casnocha, founder of Comcate, both serial entrepreneurs ('treps for short), published their book The Start-up of You, in which they argue that the key to career success in the 21st century is to manage your career as if it were a start-up business, a "living, breathing, growing start-up of you." Why entrepreneurs and why start-ups? Because, as the book jacket states: "Startups -- and the entrepreneurs who run them -- are nimble. They invest in themselves. They build their professional networks. They take intelligent risks. They make uncertainty and volatility work to their advantage."

I'm going to take things a step further.

For those singles looking to create a healthy, happy, committed relationship, manage your dating and love life as if it were an entrepreneurial start-up.

Many of the concepts that I teach single women in my dating coaching practice (The Love TREP) are based on the spirit and approach of traditional business entrepreneurs. As I've learned, entrepreneurship is about much more than starting a business; it's a particular way of thinking and acting, a life skill that guides and prepares people to navigate uncertain, unknowable situations, and, more importantly, to be comfortable existing in that uncertainty.

And what could be more uncertain and unknowable than your dating life, especially in today's day and age?

I'm a big proponent of learning in the contrary: lessons about one aspect of life drawn from a seemingly unlikely source. (To wit: Fish! A Proven Way to Boost Morale and Improve Results and What Shamu Taught Me About Life, Love, and Marriage: Lessons for People from Animals and Their Trainers -- both bestsellers). In my opinion, people are often more likely to remember concepts and ideas (and be inspired by them) when they learn about them through a completely unrelated topic. are five ways you can start thinking and acting like an entrepreneur in your dating and love life today:

1. Be tenacious

Entrepreneurs need to have desire to do what they do. So do singles. I know it's not the most romantic thought, but I believe if you want to create love, you have to put a stake in the ground and go after it. Meeting someone and finding love has to be a priority for you. You have to be ready to dedicate time to the search. You have to really want it in your life, so much so that the setbacks and rejections and frustrations you will inevitably experience along the way will only serve to fuel your desire, not hamper it. You have to be committed, even when you're not feeling all that confident or have doubts or are scared by the uncertainty of dating, even when you feel lazy or uninspired. That is desire. If you're wishy-washy, skeptical, half-committed, or not prepared to look inside, you're not ready to start your venture.

Consider the mindset of Jackie Summers, a friend and colleague in the world of dating and relationships and also the founder of the Liquortorian, an artisanal liquor company. Profiled in the May 2012 issue of Entrepreneur, Summers, whose love and passion for creating homemade spirits prompted him to start his own company, talks about the importance of desire, although he calls it something slightly different: "We face a host of insurmountable tasks when starting a business. The key to our success is focusing on one insurmountable task each day and surmounting the hell out of it. It's tenacity -- that's what powers the entrepreneurial spirit."

Indeed, desire fuels tenacity, and when you are filled with tenacity you go after what you want and do the work to get there in both business and love. (Lest you be concerned: tenacity and desire are not the same things as desperation and neediness.)

The best way to start your entrepreneurial journey to create love in your life is to figure out if you have desire. If you do, the next step is to ask: "What is my affordable loss?" That is to say, what can you realistically afford to lose by taking the next step should that next step not work out? What can you afford to put on the line? Can you afford heartbreak from time to time? Can you afford to be rejected? Can you afford to be vulnerable? Can you afford to put time, money, and energy into your venture?

I hope the answers are yes!

I want you to believe that the reward of finding a healthy, happy relationship is worth risking all of these things. You have to have some skin in the game if you want to create love in your life and succeed in your venture. By acknowledging what you can afford to lose upfront in the process, you make it easier to risk freely, without hesitation or fear of failure.

2. Be a creative problem solver

'Treps are problem-solvers. They want to roll up their sleeves and get to work, to uncover what's not working in their ventures, and to seek solutions. So as an entrepreneur in your dating life, instead of making excuses for your problems in love, instead of playing the victim, you'll start to feel inspired and empowered to find answers (maybe with the aid of a therapist, a coach, a trusted friend, or self-help books, to name a few -- 'treps understand that mentors are key in their growth), which turn up new possibilities and opportunities.

Truly, the ability to turn problems into opportunities is at the core of entrepreneurial leadership. The best 'treps solve problems through creativity; they are blue-sky thinkers, which I wrote about here. They seek new ideas, fresh solutions to old problems and ongoing issues within their ventures. And then they experiment with their ideas, learn from their experiments, and act again in smarter, more empowered ways.

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Grab the latest issue of Entrepreneur and you will see the desire to solve problems and rid the world of outdated ways of doing or seeing things in every entrepreneur profiled. And you will see how their desire and tenacity fuels them to problem-solve day in, day-out.

So, too, will you need to be a creative problem-solver in your dating life. It's time to roll up your sleeves and get to work. What's been holding you back from creating that healthy, happy relationship you've always wanted? What new ideas or possibilities can you start experimenting with?

3. Be flexible

In a 2002 Inc. survey of Inc. 500 founders, when asked if a formal business plan was drafted before launching their companies, only 40 percent responded "yes," and of those, 65 percent said they had "strayed significantly" from their original business conception, adapting their plans as they went along. My guess is for most of these entrepreneurs their overarching vision remained the same, but they learned not to get stubbornly locked into a very particular idea of how that vision would come to fruition or how their concept would eventually be delivered or experienced. As Naveen Jain writes in an Inc. magazine piece titled, "10 Secrets of Becoming a Successful Entrepreneur," you have to be "flexible but persistent ... and continuously learn and adapt as new information becomes available. At the same time, you have to remain persistent to the cause and mission of your enterprise."

So, too, will you need to hold tight to your overarching vision of creating love in your life, while simultaneously understanding that your ideas of what you want and need in a man and how you go about finding him might evolve as you go out into the dating world and start learning about yourself through experimentation.

4. Be a doer

Most 'treps prefer acting their way into thinking instead of thinking their way into acting. Trouble is we've been conditioned for much of our lives to use the scientific method approach when making decisions (thought, evaluation, and then action toward a predefined goal or objective). That works well sometimes, but a lot of the times in both dating and entrepreneurship, you just need to take action to learn what your next step can or should be.

A former client of mine named Jessica was hesitant about going to a networking event that I had mentioned would be a great place to both make new connections and meet men. She was also nervous about going alone, so I told her I would attend the event with her. An hour or so into mingling, during which Jessica had already met several men who asked for her card, she exposed the real reason she was hesitant -- she felt embarrassed by the fact that she was attending these types of events actively looking for men; her belief was that she shouldn't have to put herself out there in that way (it was an ego thing for her). Moreover, her sister chastised her earlier that evening for going to the event for the sole purpose of meeting men, saying that it was ridiculous to search for dates that way. Instead of hemming and hawing about going to the event and spending time letting her internal voice (and the voices around her) convince her to stay home, Jessica pushed herself to go the event. From that action, she learned that NOBODY cares why you're at a networking event, the only person who can make you feel embarrassed is yourself, and that there were plenty of eligible men who were quite happy she attended that night, whatever her reason. My client gained these insights by taking action.

In the realm of (traditional) entrepreneurship, consider the story of Suzanne Sengelmann and Mary Jo Cooke, vice presidents of new business for Clorox's laundry home care division, to illustrate the concept of acting your way into thinking.

In 2005, as explained in The New Entrepreneurial Leader, Sengelmann and Cooke were tasked with introducing a new Clorox brand to consumers. A "green" line for Clorox, a company that specialized in chemical-laden products, would have been deemed far-fetched if conventional business analytical approaches had been used. But according to authors Danna Greenberg, Kate McKone-Sweet, and H. James Wilson, the entrepreneurial leaders at Clorox had a different worldview of business. "They used an alternative decision-making approach in which they started by taking action, rather than just analysis, to build the new brand." After overcoming various challenges and forming a strategic partnership with the Sierra Club, a well-known environmental activist organization, "Green Works" was brought to market in 2007 and met with resounding success -- it captured 42 percent of the market share within 6 months of launching. The women involved in the success of the product "acted their way into an innovative solution" for Clorox.

Rather than endlessly analyze how to make their way into the market or ruminate on if it was even possible, Sengelmann and Cooke got started by taking action!

To be sure, there is a time for predictive thinking in your dating and love life, but how can you also turn off the voice in your head -- the one that says: "Should I do this? What if I fail? What if I look stupid? What will other people think? What if I get rejected?"--and start acting your way into a new way of thinking?


There you have it: A brief primer on how to start thinking and acting like an entrepreneur in your dating and love life. Now get out there and start taking action!

Many of these ideas have been adapted from my forthcoming book, Skin In the Game: Unleashing Your Inner Entrepreneur to Find Love. Stay tuned!