Questions to Ask When Pondering a Big Life Choice


What’s the worst thing that can happen?

What’s the best thing that can happen?

How do I feel about this choice?

What doors will close if I pursue this choice?

Why am I hesitant or indecisive over making this choice?

If I don’t make this choice, will I always regret it?


A few other ideas:

…and feel free to add some of your own.


Image: Martin

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  • Angela says:

    I’m asking myself variations all these questions at the moment in figuring out what next. And once I have the idea or plan, my favorite is “Will I regret not doing this?” All are asked with the goal of getting really quiet and listening to what really matters to me most. Currently, in progress! Thanks for the timely reminder 🙂

  • Lindsay says:

    Six months from now, am I more likely to be wondering wistfully what would have happened if I’d made the change, or if I hadn’t?

    If someone set two options in front of me that were both brand new, the opportunity in front of me and my current reality, which would I choose then?

    Regarding purchases: If this thing and the equivalent amount of cash were each sitting on a chair, which would I rather have?

  • Pat Dowling says:

    If I were in front of my significant other and/or my children, would I make the same choice?
    at that moment, a week from now, months from now – always.

  • Sandi says:

    After asking “what is the worst that can happen?” be sure to ask yourself “can I live with the consequences if that occurs?”

    Often we cannot make a decision because we are afraid of supposedly dreadful consequences that are about as likely to happen as winning the jackpot in the lotto. Once we figure out specifically what these so-called tragedies are, we can look at them objectively and come to terms with them. In most cases, the worst thing that could happen isn’t that bad at all.

    Since we’re here on Chris’ page, we all know about his quest to visit every country in the world so I will use it as an example. Suppose that Chris wanted to travel to Borneo and he was surrounded by naysayers (which is often the case with that little voice inside your head). The worst case scenario for him might have been things like: get eaten by cannibals, plane crash, luggage stolen, passport stolen and so forth. Admittedly, those are some really bad things! But now that he knows, he can begin to determine how much he wants to do it and how unlikely any of these negative outcomes really are.

    In our regular humdrum existence we are not likely to encounter any headhunters or cannibals. What we are likely to encounter is our ego. Fear of appearing foolish or otherwise losing face is probably responsible for more regret than any other single problem, real or imagined. So the next time that you hesitate to act when you really want to do something, make sure that your ego isn’t to blame because real life cannibals are pretty rare.

  • Luke Ciciliano says:

    Completely agree with you Sandi that people err by basing their decision on “bad consequences” that are unlikely to happen. One thing I would add to the list is “does this choice have to be made right now?” Too many people make major decisions impulsively, or when their life is in a big state of change, and don’t make the most informed or rational choice as a result.

    A good rule of thumb is that if a choice doesn’t have to be made immediately then take a timeout and do something unrelated before sitting down and weighing all of one’s options.

  • Charlene says:

    What choices are most aligned with my values. Change and transition is uncomfortable for most. If we make our choices based on what we value, then we can hold on to that in the middle of the fear that comes with change. I’ve made many big changes over the past few years and each time I hold on to the belief that “with change comes opportunity”. I’m much more comfortable with change now:)

  • Lise says:

    This is the key factor for me in making a major life decision:

    Am I making the decision for positive reasons (as the best possible move for myself and my loved ones) or for negative reasons (as a way to escape or not deal with my current situation)?

    If I realize that it is for the latter, negative reasons, I have work to do in my current situation rather than to immediately make a change. I may still make the change, but it won’t be to escape something bad but rather to move towards something better. This also helps me to avoid hasty, ill-thought-out moves.

  • Ana says:

    I like the one from Harry Potter (kind of) – which choice is right and which one is easy? Am I only doing this because it’s easier? Or does it feel right?

  • Rhoda says:

    I agree with Luke: Am I making this choice impulsively? If yes, can I make this choice at another period in time?

    How will this choice affect the other people in my life? How do I feel about its possible effects on them?

    In the future, will I be glad that I did this?

  • Christine Smith says:

    Follow your heart and situations will evolve exactly as they should.

  • Lash says:

    Thanks for opening up this very useful & important topic. It’s so easy, in the moment of decision-making, to not take the bigger picture – of your life, your goals, the consequences – into account and just make a decision based on immediate concerns or even feelings.

    Asking ” Will I regret this later?” is an excellent way to see how important the decision/choice is in your long term life.

    Another important question is “Does this choice/path fit into my life goals, priorities and values?” If it doesn’t that’s a clear indication to not follow through and/or make a different choice.

    Thanks again for opening up this topic. Good one!

    cheers, Lash

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