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?

IMG_0057Case 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:

  1. What am I waiting for?
  2. What would I do if I wasn’t scared?
  3. What steps would make things easier?
  4. What would I do if I had all the time and money in the world?
  5. 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 help 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?

All the Money in the World–Five Useful Questions for Making Decisions

37cee-p1020775See, I knew that title would get you to read.

This is week four of talking about Gretchen Rubin’s questions to ask when you have a decision to make that look a little . . . iffy. Scary. Risky. Un-com-fort-a-ble. How can we make better decisions in 2017? Especially when we’re scared?

Fateful Question #4:

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

Well, at least this one is fun to ask. It reminds me of the game I used to play with the kids when I wanted them to stop whining while helping me with chores. “If you had a million dollars, what would you do with it?” The top vote getters at the time were: “Feed all the hungry people in the world” and “buy a giraffe.” We had diverse interests.

So, what does asking this question do for your decision-making capability?

It tells you where you would put all your effort if you could do anything.

If I had all the time and money in the world, would I still write? Yes, I would, and I would fund a giant marketing campaign to get my work actually seen by the Amazon-buying public. That and travel the world, which I could do as a writer since all I need is a laptop, an internet source, and a chai latte.

This tells me I would put all my heart and soul into writing even if it wasn’t a job. I would take the risks of rejection and bad reviews because I wanted to. That’s a powerful statement about what you truly want out of life and are willing to risk for.

This question tells you where you would put all your heart and soul even if it wasn’t a job.

How does it help you make a decision?

If I know what I really want to do, I am freed to start making plans to find a way to do it.

If I ask myself, “Would I still want this if I had all the money and time in the world?” and the answer is, “No, I would fly to Fiji and drink coconut milk and marry a tattoo artist,” perhaps the decision you’re looking at is something you aren’t that attached to. Or you have really unrealistic life goals.


Now, we may still do things we don’t want to immediately do.

Sometimes, we decide to do what we don’t really want to do short term–so that we do get a longer term goal.

Or, we do it to help someone who needs it because that’s what decent people do, even if they don’t want to.

Sometimes, the instant payoff sucks, like getting up with the baby three times during the night and being projectile vomited upon every time, but the long-term is well worth it. (Having said baby become a best friend and the joy of your life. Plus help with the cooking.)

So, there are days we do what we might not do if we had all the time and money in the world, simply because there are other more important goals at work.

But there are other decisions that are tougher. Other choices that would be good to have some guidelines on, guidelines like this one.

Long-term, if you could do the thing you dream of, no obstacles, would you? That gives you something to focus on while making a decision.

Wherever your treasure is, there the desires of your heart will also be. Matthew 6.21

Then back to Question #1—What are you waiting for?

One Small Step — Five Useful Questions for Making Decisions


We’re revisiting some posts on decision making as a good way to start 2017. If you could ask five questions that would make decisions easier, would you use them? I would, and I do. I’ve borrowed the questions from Gretchen Rubin, but the embellishments, for better or worse, are my own.

For the first two questions, see the last two weeks. And now,

Fateful Question #3.

“When I’m reluctant to take a risk or face something uncomfortable”–the next important question to ask is:

What steps would make things easier?

Oh, this one is so important. So often, we don’t tackle a decision because it’s completely overwhelming. Our family has this issue—big time. We have trouble with big, looming “things that must be done” because we know they are enormous, and we don’t know where to start. So that makes them scary.
If you’re like us, you know what happens. Nothing. Nada. Zip. We look at that big scary hairy thing and think, “Yeah, maybe I’ll stalk my friend’s new boyfriend on Facebook for a while and get back to this one.” Except we never do.

Enter question #3–What steps would make things easier?

Ah, manageable, small, steps. I can do that, right? This works in big and small ways.
For instance, you know what happens when you tell your kid, “Clean your room!” He goes to his room, moves two things from the floor to the top of the dresser, then flops down on the bed and plays Xbox. Not because he wants to disobey you (although that may be in the mix, too), but because he has no idea how to approach something as humungous as, “Clean your room.”

Small, manageable tasks.

Pick up your books. Make your bed. Clean the fish tank. See if the fish is still alive. Bring the dishes to the kitchen. Flush the fish.

Say I am staring at a blank page for a proposal I know is due, and it may just be the best-selling NYT-list book that gets me that trip to New Zealand, but I can’t think of anything better than “Publish my book because it’s amazing and — Squirrel! Tree! Monkeys in trees– playing with squirrels! Banana!!!”

Am I going to give the whole thing up and go drown my sorrows at Starbucks?

No. Well, maybe. At least that last part. But I won’t give up. I’ll break it down into steps.

1. Research topic.

2. Look for competing books.

3. Brainstorm chapter outline.

4. Go get Starbucks.

5. Make raspberry truffle brownies.

6. Surf Pinterest for a better brownie recipe.

                 Off. Track.

7. Get back with the program.

What steps would make things easier? For you? Today? To do that big thing that scares you?

  • Make a list.
  • Put it in order.
  • Plan when and how each step will get done.
  • Get what you need to do it.
  • Do it.
  • Celebrate at Starbucks.

Back to Question #1—What are you waiting for?

But I press on to possess that perfection for which Christ Jesus first possessed me. No, dear brothers and sisters, I have not achieved it, but I focus on this one thing: Forgetting the past and looking forward to what lies ahead, I press on to reach the end of the race and receive the heavenly prize for which God, through Christ Jesus, is calling us. Philippians 3.12-14

the Amalfi Coast and Swiss bank accounts–Five Useful Questions for Making Decisions



As promised last week, this week we are asking Fateful Question #2.

What do you mean you didn’t read last week? What’s with that? Get thee henceforth to the archives and read it. Or you just won’t understand.

In Happier at Home,  Gretchen Rubin writes about the five questions she asks herself “when I’m reluctant to take a risk or face something uncomfortable.” We’re exploring these questions for the new year.

Fateful Question #2 is:

What would I do if I wasn’t scared?

For instance . . .

If I wasn’t scared of cliffs, I’d drive the Amalfi Coast. (Oh, and if I had a Swiss bank account. But no matter; we’re dreaming, right?)

If I wasn’t scared of spiders I’d buy a tarantula and call it Fluffy and feed it and read it bedtime stories. OK, probably not, because scared or not, I still prefer pets that sit on my lap and cuddle and purr rather than stare at me with six billion eyes (give or take).

If I wasn’t scared of extreme political wackos I would . . . wait. That is a perfectly justifiable fear. Never mind. Step away from those people . . . slowly.

But the question matters.

What would I do if I wasn’t scared? It matters because

if we can pinpoint what scares us about a decision

+ if we know what we would do without that fear in the picture,

= then we could see clearly what we really want to do.

If, barring fear of cliffs, I would drive the Amalfi Coast, then I know I really want to find a way to make that happen.

If I thought spiders were simply misunderstood cute little things with too many legs, would I then feel the burning need to buy a tarantula? Only if I needed to feed a Komodo Dragon. So, taking fear out of the equation, I know I still do not ever want a tarantula. Ever.

So, I’ve figured out what I would do if I was not scared in both these situations.


But, Big Decisions

These, obviously, are not big decisions. The big ones matter much more. Should I change jobs? Should I volunteer overseas? Should I write a book? What should I major in? Ask yourself—what would I do if I took fear out of the picture? Major in something I love? Get my passport? Change careers? Commit my heart and my time to a person or a cause?

Answering ‘yes’ doesn’t mean you need to do it. This is only one of the Fateful Questions. But what it will do is help you see what you really, really want. Do you really want to go overseas? Maybe this position still isn’t the answer, but at least you know the direction you’ll probably turn, because you’ve clarified what you love.

What would I do if I wasn’t scared?

I know for me, right now, the answer is write things that scare me and pastor this church like it’s the most important place in the world, because it is. Even when I don’t feel capable. Even when the risks I know God wants me to take there are not understood. Even whenI’m deeply afraid of letting people see my work and my “real me.” Even when I’m afraid I’m doing a mediocre job and the thought of being “just mediocre” terrifies me. Even when . . . anything. Because it’s what I’m called to do, and I’ll do it scared or not.

275bd-img_4545What would you do if you weren’t scared?

The Lord is my light and my salvation—
    so why should I be afraid?
The Lord is my fortress, protecting me from danger,
    so why should I tremble? Psalm 27.1
Next week—Fateful Question #3.

Finding Legos on the Floor–Five Useful Questions for Making Decisions


2017! When I was a kid, I thought I would not even live to 2000–I would be SOOOO old by then. And look, here is 2017, and I’m feeling pretty good.

2016 brought a daughter married, school started, a new job, a trip to Spain, and a CUBS WORLD SERIES WIN. Among other things.

We won’t talk about the other things it brought. We . . . just . . . won’t.

So to begin 2017, I’m going to rerun some posts from a few years ago on decision making. How do we decide what matters in this new year? How do we make the decision to go for our hopes and dreams or to find new ones? If you could have five questions to ask yourself about your decisions this year, would you use them?

You can, and I think you’ll like them. So, with thanks to Gretchen Rubin, here they are.

“When I’m reluctant to take a risk or face something uncomfortable, I ask myself the Five Fateful Questions that I’ve pulled together over the years to help make difficult choices.” Gretchen Rubin, Happier at Home

Decision Making 2017

Do you, like Ms. Rubin, have difficulty making choices? Me, too.

Having now read both of Gretchen Rubin’s Happiness books, I can verify that she is probably often reluctant to take a risk or face something uncomfortable, so I feel not only rather a kindred spirit with her but also trusting that if her questions work for her, they will work for other people.
If you’ve read any of her books, you know that she diligently researches her topics. Trust me, a lot of digging and delving into history, sociology, psychology, and literature went into her work and thus, her five questions.
So I thought, why not talk about them while we talk about fearing risk or discomfort? I’m up for learning from someone else’s hard work. I used to think I had to do all the work myself and make sure it was right but now, hey, that’s what Google is for. And other authors whose thoughts I can steal borrow with due credit. (
Her first question when facing reluctance?

What am I waiting for?

What is keeping you back? Name the thing. It may be a legitimate need, like downpayment money, or finishing a college degree, or an OK from your parole officer to leave the country.

Name Your Obstacle

But what if the thing you name isn’t a true obstacle? What if it is blocking your way more through imagination and worry than reality? What if it’s just plain old fearful procrastination disguised as . . . waiting?
Sometimes, for us pious types, it’s “waiting on the Lord.” Except . . . it’s not. It’s holy putting-off-a-decision-I-don’t-want-to-make.
 . . . I’m waiting for the kids the be older.
 . . . The bank account to grow larger.
 . . . The person I’m going to marry.
 . . . The person I’ve been dating for eight years finally to decide we’ll get married.
 . . . A house of my own.
Then, I’ll take that step.

Waiting is forever

I have to tell you something. If you’re waiting for those things to happen before you tackle whatever risk is before you, other roadblocks will pop up. Yep, as liberally as dandelions in my rose garden.
Well now that the kids are older, they’re so busy . . .
Now that I have more money, I have more bills . . .
Now that I’m married, I have to live where his job is . . .
Now that that deadbeat guy is out of my life because eight years is quite enough time to sit around waiting for something about as likely as a rain forest in the Sahara . . .
OK, if that last one is you, you can take a pass on this. You’ve been through enough for now.

Don’t Wait on Obstacles that Aren’t Real

You get the idea. Waiting for circumstances to change before you get started on something usually means new circumstances, new challenges, old procrastination. Because the problem is, that obstacle wasn’t really stopping you. Your own desire to avoid the risk did that. After that, finding reasons not to do something becomes as easy as finding Legos on the floor with your bare feet.
The obstacle isn’t really stopping you. Your own desire to avoid the risk is.

What am I waiting for?

What is it? Is it real? Is it your imagination? Your fear? Your intimidation? Name it. Know it. Maybe you have good reason to avoid something—then these questions are made to help determine that. But maybe not.
This is my command—be strong and courageous! Do not be afraid or discouraged. For the Lord your God is with you wherever you go.” Joshua 1.9
Next week—Fateful Question #2.