I guess I should have anticipated the question.

I have written that serial entrepreneurs--people who have started two or more successful companies--are the masters of overcoming uncertainty. They have figured out what to do when you don't know what to do.

And, I added, their approach works in all situations.

"All situations," a friend of mine asked. "Even dating?"

Yep. Even dating, we told our friend, who has been divorced for a while and unhappy with her social life.

Kathy, not her real name, was surprised and skeptical about that response, but we told her she shouldn't be.

After all, if you think about it, trying to find someone with whom to have a relationship is just another example of heading into the unknown.

And the serial entrepreneur's approach to doing that, when it comes to creating his or her companies, will work perfectly well for your love life.

Step 1, in either case, is knowing what you want. The entrepreneur has a desire to build a successful company. Our friend Kathy wants to have a serious relationship.

Step 2: You take a small step toward your desire. The entrepreneur draws on the resources he has on hand--who he is, what he knows, and whom he knows--and begins talking to people about a potential idea. If he's thinking about opening a restaurant, he could show potential customers the menu he has in mind; if he's thinking of creating a new product, he might show a sketch of the prototype.

If you are trying to increase the number of dates you get, you could do exactly the same thing. Kathy could conclude that there is a certain percentage of single guys who want to spend time with a woman who has no immediate expectation of marriage. As for what she knows, Kathy believes her education, training, experience, and expertise make her attractive.

And the question of whom she knows has her excited. She is convinced that telling everyone in her personal, social, and professional networks that she is going to use an entrepreneurial approach to relationships will improve her social life.

It turns out, she was right. The people in her various networks knew lots of guys who might fit her criteria, and they were happy to make introductions.

Step 3: Entrepreneurs don't risk a lot as they go about creating the new ventures, and Kathy doesn't risk a lot either, as she considers all the names her friends and acquaintances have given her. She talks to each man by phone, investing just a small amount of time.

If the conversation goes well, she will suggest coffee. If the face-to-face meeting is promising, she decides she is willing to invest more time (a dinner date, perhaps). At each step of the process, she is deciding whether it's worth taking an additional step.

Her new approach to dating is exactly how entrepreneurs build their companies.

  • They figure out what they want.
  • They take a small step toward it.
  • They pause to see what they learned from taking that step.
  • They build off what they learn.
  • And then they repeat the cycle all over again.

The process continues until the entrepreneurs, or Kathy, have what they want (successful companies, or a successful relationship); decide that it is impossible; or want something else.

The key in either case is taking action. If all you do is think about starting a company, you might end up with a lot of thoughts, but you are never going to have a company unless you do something about it.

It is the same with dating. You can think all you want about how nice it would be to have a relationship. But unless you do something to make it happen, there are going to be a lot of lonely weekends.

Published on: Aug 13, 2014