08/20/2013 01:40 pm ET Updated Oct 20, 2013

3 Questions to Ask Before Making a Big Decision

How do you know which path to take when more than one looks appealing? You don't. But these three questions might help.

1. Are you running to something or away from something?

This is from a favorite professor who knew many of his engineering students -- including me -- wanted to chuck that course of study in favor of something more fun, less rigorous. He reassured us it was okay to do that, with one caveat: that we could live with the answer to his question. Some of us -- including me -- had chosen engineering for all the wrong reasons: respect; the promise of good, if not great money when we graduated; and the so-called proof we weren't stupid.

I hadn't lived long enough to trust my instincts about what kind of work I'm suited to. I couldn't have told you then what I know now, that I'm happiest when I'm writing or in a radio studio.

Thanks to my professor, I got my engineering degree. I finished what I started, and that felt good. The degree bestowed on me three things. Respect for myself, for having grit. Good money, mostly to put aside and fuel other dreams. And the so-called proof I wasn't stupid, if only because I knew great advice when I heard it. Which I have come to think of this way, "If you don't know where you're going, you may as well hang out where you are."

2. If your life flashed before your eyes, would it hold your interest?

This question, from Callings author Gregg Levoy, has helped me summon the courage to make big changes even when getting divorced or being fired didn't force me to. It's easy to coast along, thinking this is as good as your life will ever be. Or is it? It depends on whether you pay attention to that nagging feeling the old woman you'll be someday will have, as she looks back on her life and wonders why she didn't take more chances.

We write our life stories with every decision. What's the point of boring ourselves... to death?

3. What will you be doing at, say, 10 o'clock on a Tuesday?

Many choices look good on paper -- this job, that man, the sprawling house -- but don't feel so good as you're living them.

My friend Brian Kurth from puts it like this: "Isn't being an innkeeper just the most romantic-sounding thing? Until you're scrubbing toilets! Owning a bakery sounds pretty dreamy, too -- until you realize you'll be getting up at 3 o'clock in the morning for the rest of your life."

The guy who sold me my first car owned a boat. We dated for the few weeks after I'd finished college but before I started working, and we spent most of that time at his cabin -- cleaning his boat. I thought, "No, thanks." I wasn't interested in toys that cost so much to maintain, or in men who considered that recreation.

I live in a town so small I usually don't need my turn signal, to borrow an expression from someone else, because people already know where I'm going. Thanks to the stereotypical renovation straight out of hell, I live and work in a house that isn't equipped with a television, a functioning kitchen, or even a couch. When I married my husband I put "pros" and "cons" in a chart in my head, and the "pros" column (sorry, honey) was anemic. Except for one item. I could imagine talking to this person for the rest of my life and never getting bored. Never. And except for a few longer answers to questions when I only had time for the short version (sorry, again), I haven't been.

What would I be doing at 10 o'clock on a Tuesday? Talking with Darrell about work, probably.

Sign me up!

I make mistakes. I make decisions that leave me wistful for what might have been. But the more I pay attention to the answers to these three questions, the less time those detours take -- and the faster I get on down the road.

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