Being an entrepreneur isn’t easy: Your path is filled with ups and downs, existential crises, self-doubt and more than a few evenings crying into a pillow. But, we do it. And we love it.

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Still, it can't be denied that entrepreneurship is a lonely road. And, it's made even more lonely when you are single and an entrepreneur. As podcaster Gwen Elliot has shared, “I would love to have someone to confide in, lean on and share all the great things and the challenges of building a business at the end of the night with. Right now, I'm just hanging out with myself, a journal and some great music.”

Building a business is a full-time job. Sometimes it’s two or three full-time jobs. And as a single entrepreneur, you're also trying meet the love of your life. That's another full-time gig! Yet, both are worthy pursuits, even if both are roller-coasters of hope and heartbreak.

So, how do single entrepreneurs maintain their sanity -- or at least some sense of balance? Well, your business know-how can help you with your personal pursuits. So, to illustrate, let’s start with “target market.”

The target market

When you’re an entrepreneur, your dating pool shrinks. It’s not like a regular job at a company where you can date your co-workers. As an entrepreneur, you’re employing them -- no dating allowed. In other cases, you don’t even go to an office to run your business. You work from home. So, your water cooler chit-chat is just between you and the dog.

This means that you have to force yourself to have more of a life than just work. Geez.

Often, single entrepreneurs discover that they need to get a bit more strategic with their social lives. You probably have a number of daily or weekly activities that you do alone: going to the gym, hiking, writing, etc. If you’re wanting to meet more people and not get stuck swiping left or right on your phone all day, consider stretching out of your comfort zone.

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How can you turn those solitary activities into social situations that might trigger a spark? Well, let's see:

  • If you like to work out at the gym, take a class once or twice a week. But, make it a point to smile and say hi to a person each time.
  • Or, join a hiking meet-up group and enjoy conversations during the trek.
  • Do you write for your business? Branch out and join a creative writing group.

There are even social groups designed specifically for professionals. One example is Ivy.com. Billed as “the social university,” Ivy.com has locations around the country. Events are geared toward socializing with like-minded professionals at fun and elite events. Keep in mind, however, that you don’t have to view these activities and groups as your dating pool.

Nor do you have to be on the hunt every time you go out. Simply focus on building friendships and expanding your social network so that with all those new connections, you'll increase your chances of finally meeting that special someone who makes you not want to work until 2 a.m.


Of course, the other frustration with mixing dating and entrepreneurship is time. Dating takes time.

There are two ways you can approach this challenge. First, you could hire a matchmaker. Outsourcing your love life is possible -- up to a point. Second, you could look at this process the same way you would your sales cycle: Let’s say that in your business, you need 10 warm leads to land a deal. So, why would you approach a date thinking, “This had better be the one”?

You’ll probably need 10 dates, minimum, before you meet someone worthy of date #2. So, ease up on the pressure and enjoy the process.

You can also save yourself a lot of time if you know whom you’re looking for. In your business, you set clear goals to achieve. That level of clarity should apply to your romantic pursuits, as well.

A dating 'business plan'

A mentor of mine had me write out a very extensive description -- in strenous detail -- of who my ideal man would be. Next, I had to write another description of who I believed I needed to be, in order to attract that kind of man.

This exercise was nothing more than a business analysis, but it pointed toward myself. If you do one, too, you will achieve a clear picture of what your goal is (your ideal partner). The next step is to review the resources available (your fine points, your social circles, the meetups in your city, etc.) and find the gaps that need to be filled in order to achieve the desired goal.

Single entrepreneurship requires higher levels of emotional fortitude. But, in a way, it's a great training ground for dating. After all, your business is already the fickle lover you can learn from: Every day you have to face your demons, put in the hustle, pick yourself up when you fall and push through. Right?

Not that being a single entrepreneur is all down side. Entrepreneurs do more introspection than most others; and that's a good thing. And, as you grow your business, you're likely building a level of self-awareness that others may never achieve.

Andrea Shillington, founder of Brands for the Heart, put it perfectly. “In the past three years of being single," she said, "I've found that what I'm looking for in a partner has shifted significantly as a result of the growth I've done, personally and professionally. In other words, being single as an entrepreneur can be a richly rewarding experience.”

Related: Dating an Entrepreneur Can Be Extremely Exciting or Completely Insane

Well, yes and no. Because, in my mind, if you’re a single entrepreneur, you deserve a medal. Or at the very least, some Ben and Jerry’s.