I shocked a friend the other day by asking a guy in Central Market about his relationship status.

She started it.

Given that other patrons occupied every seat in the café and he had finished his meal, the man offered us his table. He packed up and left, I told my friend I found him attractive, and she asked if I’d gotten his number.

I replied, “I don’t do stuff like that!”

Yet I saw him a second later, leaving through the front door. He happened to glance back. I thought, “Why not?”

And really, how big was the risk? What could have gone wrong? Even though it came to nothing, I still flattered the guy. (Yes, it did so happen that he was single. And straight.)

In another recent incident, I sent a fan e-mail message to the CEO of a company that offers products I enjoy and admire. Why not? I work hard at my businesses. I love feedback. Why wouldn’t she?

As a result, we scheduled coffee.

I take big risks in business every day—risks that affect financials and people and other businesses. Taking these big risks often “risks me out.” I don’t gamble, for example. I’m not tantalized by daredevilry that might bring about bodily harm.

Yet what about the minor actions that carry very little real risk that I consider doing but don’t—either out of propriety or ego or awkwardness or potential embarrassment?

I should do those things more.

What’s the last risk you took?