Do You Have Five Years? Five Useful Questions for Decision Making

This is week five, the final, the ultimate, the World Series last game (Oh, they have seven don’t they? Which sport has five? Whatever.) week of talking about Gretchen Rubin’s questions to ask when you have a difficult decision staring you in the face.

Fateful Question #5 (This is it, folks):

If I were looking back at this decision, five years from now, what will I wish I’d done?

I actually do use this one a lot. I use it in parenting. If I say yes or no here, what will it matter in five years?

I use it in ministry. If I choose to go in this direction, what might the cost or gain be in five years?

I’m thinking maybe I need to use it in my eating habits, because imagining my weight gain in five years just might get me to reconsider that brownie making its way into my mouth completely on its own power.

But since I’m a strategist by nature, I use this question to help clarify–what really matters in this decision?

Case in point—Some years ago, Child #2 asked my advice in college choosing. Go to the school seven hours away from home or the one fifteen minutes from home? Mother’s from-the-gut answer: Um, there’s a choice there? Go to the hinterlands of Minnesota or stay here with your loving loopy family where you can do laundry for free and pilfer pantry items at will? Really? Im not seeing the conflict here.

I desperately wanted to give her the answer—Stay. Here. With. Me. Because I did not want to lose my baby.

But I didn’t. Because if I asked, “Five years from now, what will I wish I’d done?” the answer would be, “I’d wish I had let her make her own decision and go where God was leading her to go.” I knew that five years from then, she would be gone anyway, and she had to be going in the right direction for her. So my decision was to keep my mouth shut.

Taking your hands off the wheel is a scary decision. Asking yourself, “Five years from now, what will I wish I’d done?” helps lessen the scary factor, because it forces you to examine the long-term outcome and gain some perspective on the decision.


Such a key word. Paralyzing decisions become less so when we stop focusing on the wall in front of us and look farther out, envisioning where we want to be if we decide to scale it. Or where we could still be if we don’t. That’s the alternative. Sometimes you may envision the future of a choice and realize, “You know, I think I don’t really want to go there.” Or, “Hey, I’m pretty sure I don’t want to still be here.” Good or bad, you’ve gained perspective.

Finally, five questions to ask yourself when faced with a risky or uncomfortable decision:

What am I waiting for?

What would I do if I wasn’t scared?

What steps would make things easier?

What would I do if I had all the time and money in the world?

If I were looking back at this decision, five years from now, what will I wish I’d done?

I think I may have one more of my own to add. Next week. Sorry—that’s a teaser designed to get you to come back. That’s how this whole gig works, dontcha know. (Why yes, I do have Wisconsin roots, why do you ask?)

Whatever you’re feeling fearful or paralyzed about right now, I hope they help you figure out whether it’s a yes or a no on that decision. Either way, make the decision. What are you waiting for?

By Jill Richardson at

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