Trying to Make a Tough Decision? Try Asking the Five Fateful Questions.

Every Wednesday is Tip Day.
This Wednesday: the 5 fateful questions to ask yourself if you’re trying to make a tough decision.

When I’m reluctant to take a risk or face something uncomfortable, I ask myself these five questions which, in melodramatic form, I call the “Five Fateful Questions.” They help me think clearly about a situation.

What am I waiting for?
What would I do if I weren’t scared?
What steps would make things easier?
What would I do if I had all the time and money in the world?
What is the worst, and the best, that could happen?

For example, when I considered switching from law to writing, I thought, “I’m moving to New York, the publishing capitol of the country. I have friends who are agents and writers who can give me advice. I have an idea for a book that I’m dying to write, and in fact, I’ve already started writing it. I really want to be a writer. What am I waiting for?” Nothing. I made the switch.

What about you? Do you ask yourself these questions — or do you have a question of your own? I suspect there are more than five fateful questions! Though that phrase does have a nice ring to it. Which ones have I overlooked?

* I’ve said it before, and I’ll say it again: Unclutterer.

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  • Love those questions! I used the same ones when deciding to leave the practice of law many years ago – and, I ‘ve used them many times since to make difficult decisions. A great reminder on the power of asking the right questions.

  • Robin

    I don’t ask myself all those questions, but I do look at the worst and best that can happen; after giving myself plenty of time to ponder, I go with my heart knowing I’m ready to take the “consequences” whatever my decision.

  • Joe

    I think you got the essence of all the questions in these 5 Gretchen.

    In 2008, I sold my business, my house and virtually everything I owned. I bought a sailboat and sailed it 1000 miles down the Mexican Baja. I had never sailed before in my life!

    These were pretty much the 5 fateful questions I asked myself before starting.

    For me anyway, once I’ve kicked the monsters out from under the bed it makes living a joyful and happier life a whole lot easier.

    Thanks for this.

  • Debi Barton

    Sometimes the question “Why not?” can be pretty powerful also 🙂

  • LivewithFlair

    Here are my questions (from a more spiritual perspective) that radically changed my life last year. I actually have a piece called 3 Questions that fleshes out this process. The questions: 1. Will I live the life God asks me to? 2. Will I pursue wealth or godliness? 3. Is knowing Jesus better than anything? For me, reminding myself of my purpose and calling helps remove impure motives and unwise pursuits. What a great post and a great question for us, Gretchen!

    • Karen

      I like these questions. In the book, I did skip right to the Buy Some Happiness chapter. So, I have realized I do like some material things, and some nonmaterial things also cost money, so I need to pursue some money, even to pursue godliness. It’s a quandary. Is that the right word? 🙂

    • TS Alfabet

      I agree Ms. Flair, but I would frame it just a little bit differently. Rather than trying to make decisions based on a formula or set of questions, what if God was someone you could actually relate to in a real and personal way? If so, making big or tough decisions becomes just one more part of that relationship. It isn’t so much what I am pursuing or what I am fearing– God knows those things about me better than I do myself– but learning how to listen, making the decision out of that relationship and then relaxing in that relationship, knowing that God is perfectly OK with us making mistakes and more than able to help us deal with the consequences, good or bad. Just like a parent with a little child learning to walk, God loves our efforts– even the clumsy or misguided ones.

  • Gretchen- This piece is particularly touching to me today because yesterday my dog died at home with me.

    She was fifteen years old and starting to show signs that it was the end, having trouble getting up and going to the bathroom, refusing to go out, panting and having a hard time getting comfortable. I asked myself, and the vet, if it was time to put her to sleep. No one could say for sure. I started to agonize about the decision and did internet research to help me make it.

    Then I realized that if the answer wasn’t clear, then the answer was that it wasn’t the right time. So we waited and she died quickly and peacefully at home a couple of weeks later. I made right decision, and I feel so grateful for that.

    • gretchenrubin

      I’m so sorry to hear about your dog. Hang in there. How comforting that you
      felt that you found the way to make the right choice for her.

      • Thanks, Gretchen. It is interesting how much stress decisions can cause, even when they are much smaller than a life or death one

  • Maggie

    Before making a scary decision (like submitting a pitch to an editor or entering a job interview), I always ask myself two things. First, do I have all my ducks in a row? (Is the pitch as great as I can reasonably make it?) If yes, then what the hell have I got to lose?

  • BerniceWood

    This is perfect timing! I am trying to make a decision to move ahead with something and I believe, after answering these questions, that now is the time!

  • Great questions! I find the “What would I do if I weren’t scared?” question really powerful.

    I just posted about this too, since I’m turning my kife completely around in less than two weeks from now. Check out my latest post “Turn Your Life Around: 11 Great Tips to Make a Confident Decision” if you are interested in reading more about this. 🙂

  • Gerri

    This post is very timely as I too am trying to make a very tough decision about my job. I ask myself all of the questions you have listed and a few more. Others that I feel are very important are:

    * Will this decision put me in a better place financially and/or emotionally?
    * How will the decision I make affect my family?

  • clearlycomposed

    Those questions are fabulous! I have been working with the idea of fear and how it limits us so the part about what would I do if I weren’t scared resonated with me. Another question might be…Can I be okay with being scared and do it anyway? 🙂

  • TJ

    I also like to try the “pretend you’ve made the decision” test. Before making a really tough decision, I’ll pretend I’ve made it one way, and rest on that for a few days. Then, I’ll pretend I’ve made the decision the other way, and rest on that for a few days. It really makes a difference to give it time, for me. Usually, my anxiety level or gut feeling during those “pretending” times will help me figure out which decision will actually work best for me, if after looking at everything logically, the decision could really go either way.

    • gretchenrubin

      This is a great one. I often do this myself. Also, I’ll pretend that it’s
      five years in the future and I’ve been living with the decision.

  • Keeping it simple is so important. I like to narrow the questions down to two or three to avoid getting stuck in the process of answering the questions. There have been times in my life where I have known where I wanted to get to or acheive but still was not moving forward. This question, What am I waiting for? is very powerful question and is complimented by What is holding me back?

    I find that giving myself a timeframe to answering … such as if an answer doesn’t come to me in 30 seconds or less on one of those then I move on. If I have to go searching for reasons then in my eyes they are not bigger enough to hold me back.

  • For me it has always boiled down to one of the questions on your list, and it is one my mom emphasized to me growing up: what’s the worst thing that could happen? Sometimes you need to really push through that line of thinking to uncover your core fears, so keep going with “and then?”. Example — worst outcome, I get an F in a class. And then? I don’t get into the college I want. And then? I can’t get a good job. And then? Maybe it’s that you won’t be able to buy what you need, or maybe it’s that your family will be disappointed. Two very different fears. Identifying the ones that make you tick help unravel things when making big choices.

  • These are great questions. Another way of thinking that helps when making a difficult decision is to remember that most decisions in life are reversible. If we accept a job we don’t like, we can always quit at some point in the future if it isn’t a good fit. If we buy a house that turns out be too small or large or in a neighborhood we don’t like, there is no reason why we can’t sell it eventually. This doesn’t work for every decision, of course, but most decisions don’t result in an irreversible outcome.

  • Hi Gretchen,
    What a powerful post and powerful comments. Thanks to everyone who contributed.

    My husband and I are right up against some really big job/relocation/lifestyle questions and your post and some of the comments really shifted my approach to moving toward a decision.

    “When you are ready to learn the teacher will appear” and all that good stuff:-)

  • Karen

    I have used most of these questions, though not all of them at the same time. Many of the “What would I do if I weren’t scared” questions are taken care of by the “all the time and money in the world” question. I have a decision to make now that I will use these questions to sort through.

  • Aedma

    I’m not sure I like these questions. These are blinders. Maybe you’ll feel good while you’re taking a decision, but the consequences could make you miserable. It’s all well and good to say that you may be preventing yourself from following your dreams, but not every problem can be solved with self-introspection and a leap of faith.

    I just sat down and thought about a major decision I have to make and came up with these answers:

    What am I waiting for? Greater clarity on the ramifications of each choice.

    What would I do if I weren’t scared? Take the path of least resistance.

    What steps would make things easier? Forcing myself to eliminate choices by making decisions before I have enough information to know which choice is better.

    What would I do if I had all the time and money in the world? Move to a tropical island, launch many projects, support my friends and family.

    What is the worst, and the best, that could happen? I could lose my job, family, home, and have to leave the country. Alternatively, I might be happier.

  • Tracey

    Love your new newsletter design! I work nights as a nurse and the lovely shade of blue in the background made me feel quite “happy” in the wee hours of the morn.

    • gretchenrubin

      Terrific! I’m so pleased to hear that you like it.

  • Those are great questions. Helpful to me at the moment too, as I’m facing some big decisions.

    I also like the idea of the commenter below to spend a couple of days “pretending” you made the decision, each way, and then rely on your gut feelings to tell you if you did the right thing for you. The gut always knows!



  • mathews

    Great thoughtful answers for the blinders .But it really helps keep me away from procrastination when i started pretending about my answers. it helped me take action in some areas of my life to better it. i have learnt to become more creative.

  • Julie

    Another way to make difficult decisions is to create some perspective. A female friend who had a hot career as a VP of manufacturing for a cell phone manufacturer was told by her doctor that her heavy workload was the cause of multiple miscarriages. He advised her to take a year off if she wanted to have a baby. She was afraid she would ruin her career if she did. She asked me for advice. I told her to pretend that she was 85 years old and I was her great niece asking her about family history. I said, “So Aunt Abby, tell me the story of your life. When you get to today tell it the first time if you took the time off for the baby, and the second telling is if you don’t.” She got as far as saying “I was born in Iowa to a loving family” when she stopped and had a funny look on her face. “I don’t need to finish the story”, she said. “I know the answer.” She took time off, had a cute little baby girl, consulted part-time for a few years until her daughter got into pre-school. And then returned to work in the corporate world. She found a great job, lost nothing and has a lovely daughter.