The big gamble

Not a surprise, yet still a delight. (Image by valentin hintikka)

When I started my first business, I didn’t really think about the implications.

It didn’t feel like much of a commitment. Did I really need an exit plan for teaching music lessons? Nah. I figured I could do it is long as I wanted to, to whatever degree I wanted to.

That’s the nice thing about freelancing. That’s also the nice thing about being young — you don’t really think all the way through the consequences of your actions.

A lot of my other projects have been the same way: Just start and figure out the details later.

The advantage of doing things this way is that you get going and build momentum quickly.

The downside is that you can quit just as easily as you started. A couple of setbacks, and you’re off to chase the next shiny object.

As a student and then a coach of an online course, I learned that most people sign up without considering what it will take to complete it. Thus, hundreds of people start, but only a handful will finish.

To follow through with a course like that, you have to estimate how long it will take and set aside the time. In The Dip, Seth Godin points out that it is wise to think this all the way through before you begin, and even to walk away if you realize that, barring some miracle, you don’t have the resources to make it.

Since our lives are already full, we also need to consider what we will give up or put on hold in order to accommodate a new project. We can’t necessarily squeeze it into the nooks and crannies of our day.

When it comes to a creative project, such changes can be hard to justify. After all, there is no guarantee that our efforts will pay off. So we stand at the water’s edge, wondering whether it’s worth the hassle of getting wet.

I’ve seen countless clients struggle with this decision point, and now I’m there myself. I’m considering writing a book, and I know too much about what the likely outcome will be: Everything exactly the same, except now I’ve written a book. Is it enough to justify the effort?

I know too much about the effort, too. I can estimate how long it will take. It doesn’t sound fun. It honestly doesn’t sound worth it.

And yet, there is something there that I can’t quantify. I will experience a transformation of identity for doing this difficult thing that defies logic. I will be an author. I will join the club of people who wrote a book even though there is little rational reason to write a book.

It’s similar to the club of people who run marathons. You can’t know why you should bother until you do it.

So if I were to write a book, I would become an author. But it feels like a big “if.”

I think that’s because there is no halfway. My career as a music teacher, my work as a content creator — these journeys were incremental. They didn’t feel risky.

A book, on the other hand — I have to go all in or not do it at all.

The big gamble isn’t whether the book will be successful. That’s not even on the table. It is whether I will complete it or not.

This gives me a new level of understanding of why my clients hesitate. When we can’t be assured of success, the endeavor is a daunting one. To the young and carefree, it’s no big deal; to the formerly young and carefree, it’s a bit more fraught.

There are so many things I’ve undertaken without knowing the challenges that lay ahead, yet the journey was intriguing enough to begin. When I have a good sense of what those challenges are, it’s a little less appealing. And yet, maybe I will do it anyway. I won’t really know what it’s like until I try.