This is a post from a member of the Freelancers Union community. If you’re interested in sharing your expertise, your story, or some advice you think will help a fellow freelancer out, feel free to send your blog post to us here.

A few weeks ago, my son Evan graduated from Rhodes College in Memphis, Tennessee (school motto: We’ve never heard of you either).

In addition to his academic work, key accomplishments include fronting a (now defunct) band, co-founding a nonprofit newspaper for the homeless and launching a (recently venture-funded) business.

He’s had a great run and, needless to say, we are quite proud.

But I have to tell you, the one thing about his college career that I expect to remember the longest, is that every week, during the winter, he drove south into Mississippi, to play intramural ice hockey.

That’s right, ice hockey in Mississippi. If there’s an oxymoron hall of fame somewhere, “Mississippi Ice Hockey” has got a prominent display in the lobby.

The cost per season? Thirty dollars. And last year, when Evan began playing, he asked if I could pick up the tab.

It’s not a lot of money. But just handing over $30 seemed kind of dull. So I said, as I sometimes do, “Care to make it interesting?”

Then I proposed a simple metric: Instead of $30 up front, I’d pay him $2 for every goal he scored during the season.

He liked the concept, but not the number.

So after much negotiation and assurances from Evan that he wasn’t that good, we agreed on $7 per goal. And while I don’t mean to suggest that my own son bamboozled me, the season’s not even over and I’m already $42 in the hole.

But you know what, that’s what makes it fun. It’s not about the $30 or $42 or whatever. It’s about rolling the dice and seeing what happens.

To me, that’s much of what starting a business is all about: Getting in the game.

You launch a product… big success. You hold a webinar… nobody shows up. You send a proposal… the prospect disappears. You answer the phone… somebody wants to hire you out of the blue.

And on and on it goes, with every day bringing its own mix of ups and downs and in-betweens. You never know which will come when, but it sure is interesting.

A couple of years ago, I was a guest speaker on a panel, in front of a roomful of solo professionals. Someone raised her hand and asked how long it took for me to “become successful.”

The implication in her question was that there was some place you could reach where the ups and downs and risks would all go away.
I told her that I have just as much uncertainty in my professional life today as I had 12 years ago. The only difference is that today, I don’t worry about it anymore.

Because I finally realized that the uncertainty never goes away, and the daily ups and downs are a lot of what keeps it interesting.

Michael Katz is Founder and Chief Penguin of Blue Penguin Development. He specializes in helping service professionals stay top of mind by positioning themselves as “likeable experts.” Sign up for his free newsletter, The Likeable Expert Gazette, here.