photo by Mike Foster

You have a hobby you love, and you’re good at it. Good enough to make a living, maybe. You also have a day job you don’t love. Should you quit your job and start a business? Should you turn your hobby into your career?

It’s a fascinating question, and I’ve lived both sides of it: I’ve been both an amateur and a professional musician. And I’ve noticed that most amateurs fail to ask themselves two crucial questions before deciding to turn pro.

One of the things you learn as president is you’re always dealing with probabilities. No issue comes to my desk that is perfectly solvable. No issue comes to my desk where there’s 100% confidence that this is the right thing to do. Because if people were absolutely certain then it would have been decided by someone else. — Barack Obama

I am a certainty freak.

When considering a big purchase, I research exhaustively.

It is not enough to be busy. So are the ants. The question is: What are we busy about? — Henry David Thoreau

It’s not the hours you put in; it’s what you put in the hours that count. . . . Don’t mistake movement for achievement. . . . Some people are busy all day long doing figure eights. They’re not making much forward progress. — Jim Rohn

How do you measure productivity?

This morning at 6:45, I saddled up for a bike ride.

Fall is here, and it’s hard to dress for an hour on the bike. In the summer, it’s simple: wear as little as possible, because you’re going to get hot quick. Cycling in the cooler months is a little trickier, but there are basically two options:

1. Dress warmly so you’re immediately comfortable. After 20 minutes or so, you’ll be sweating profusely and will have to shed a layer (and find somewhere to put it).
2. Underdress slightly. You’ll be cold at first, but cycling generates a lot of heat. 20 minutes into the ride, you’ll be happy as a clam.

It’s not a matter of personal preference. Option 2 is the safer choice. Hypothermia is always a risk in cool weather, and it’s better to be dry and slightly chilly than warm and wet.

When discussing major choice with a college freshman, I’ll sometimes use the following illustration.

Imagine you’re a manager at a midsize company. You gaze out your office window onto a beautiful May morning: the peonies are blooming, the robins are flitting about, and you’re hiring. It’s an entry-level position, and two resumés sit on your desk. Both applicants graduated from the same college last week.

Let’s call them Lisa and Steve.