The “What If?” Game

By Troy Headrick

I was lucky to have been reared by interesting and intelligent people who taught me much about life during my earliest years.

My maternal grandfather, a man I called “Pawpaw” when I was just a wee thing, was a rancher, and because I spent years living with my grandparents, I acquired much knowledge about the great outdoors, the nature of work, tending to animals and such.

Often, Pawpaw would take me out to the pasture where his cows, sheep, horses, and goats lived so we could check on his livestock.  The landscape was rugged, and we usually traveled in his pickup.  Because the terrain is so rough and the potential to damage vehicles is so great while traveling in such places, ranchers move through wild pastureland by creating trails which are demarcated by well-worn tire tracks.  Thus, they enter pastures, move through them, and exit by following the same rutted paths each time. 

Unfortunately, many people also live their thinking lives in this way.  They have well-established conventional routes of thought which they are reluctant to deviate from.  They think the same thoughts in the same way and at the same time because they have always thought the same thoughts in the same way at the same time.  By doing so, they are really stuck in “thinking ruts,” for lack of a better term.  I know this is true because I see it happening all around me.  Plus, I’m guilty of doing this myself.

When I find myself practicing inside-the-box thinking, especially when trying to solve a problem, I like to play a little game I call “What If?”  Like all games, this one has rules.  Actually, it has only one rule:  There are no rules.

The game works like this.  I have a problem I’m trying to solve.  Rather than reaching for a ready-made solution—perhaps the same solution I’ve always used when faced with such a difficulty; recall those well-worn tire ruts I talked about earlier—I say, “What if, instead of the old solution I’ve always used, I did X, Y, and Z instead?”

Because there are no rules to this game, any solution is worth considering; nothing is taken off the table prematurely.  No solution is considered too unorthodox to be examined. 

This game works especially well in the following situations:  One is facing a familiar problem, but the old, time-honored solution now seems inadequate or now longer works, or one is facing a brand-new problem that is especially vexing, or one is feeling that old ways of thinking are generally unfulfilling and said thinker desires to radically reinvent the self. 

“What If?” helps develop breadth and depth of thinking.  As no solution is viewed as too outlandish to consider, one generates a whole bunch of possible approaches—one broadly looks at lots of possibilities.  Plus, each possible path is then “gamed out.”  For example, imagine that I’m playing “What If?” and I say, what if I quit my job, pulled up stakes, and moved to Timbuktu rather than living the way I am now?  In the process of gaming out that possible action, I’d have to think about the ways I might make a living in Timbuktu, how much it costs to live there, what the place is like, and whether it even allows migrants in.  Gaming all this out is going to help me develop a depth of knowledge about Timbuktu and what it’s going to take to pull all this off.

I’m in a period right now where I’m actively playing “What If?”  There are lots of fun games that one might play.  Few provide as much excitement as “What If?”

I look forward to reading your comments.

Troy Headrick’s personal blog can be found here.

50 thoughts on “The “What If?” Game

  1. “What If” living in Timbuktu ? I had similar thoughts and what I realized was something that Life teaches to many in a hard way –

    Irrespective of whether one is rich or poor,
    irrespective of the facilities or difficulties,
    irrespective of being a scholar or mediocre,
    irrespective of opportunities or failures,
    irrespective of all differences and diversities that Life has,
    everyone does live a life, in his/her own way. It is only a matter of scaling one’s necessities in the graph of livelihood versus happiness.

  2. As I said earlier once, you were lucky to have “Pawpaw”. (I actually paused and imagined for a while, how a little one would call “Pawpaw” ! I used to call people with strange names too, so I know the feel. 😅)

    I love animals and birds, and sometimes I do feel sad why I could not get close to them in my childhood. So yes, you were lucky to have such a great teacher, “Pawpaw”. 💚

    1. In some parts of the American South, the area I grew up in, “PawPaw” is a fairly common name for grandfathers. It is a cute-sounding name, though, isn’t it? Where, may I ask, do you live? Where did you grow up?

      1. Certainly cute – both saying and hearing it. I used to call my father, “Papa” (how quickly a tense can flip from present to past !) and sometimes “Popsoo” or even “Poopoo” ! 😄 I have been an introvert as well as reticent since childhood, hence my free time kept me very much close to family. Later with involvement in information security, especially over the web, I try not to come into limelight, which is also in alignment with exactly what I’d like – others to read my words, not because of me (or reject because of me), but read because of the thoughts expressed by those words (or reject if not applicable). After all, words have their own existence, for “words live longer than humans” – a concept introduced to me in childhood by my father. However, I was not fortunate enough to meet my grandfather, neither maternal nor paternal. So, having a writer’s view of fiction, I can only imagine the “grand” bond (pun intended). 🧙‍♂️ You can find 16 short stories and poems in my blog, under category – Dreams !

      2. I always feel wiser after reading your comments. I knew all my grandparents even though my paternal grandmother died of cancer when I was just a little boy. My other grandmother, my mother’s mother, died not long ago at the age of 103. All are gone now. And my parents are ageing too. I guess we all disappear, don’t we? I work every day to get used to the idea of my own demise. I will check out your stories and poems. Thanks so much for your comments.

      3. “Cancer” – so common a word, and often a common cause ! …

        Pondering one’s own way of “departing” this material world is also a common thought among introspective minds. I might not fear my demise but my brain gets awestruck by the concept of oblivion – “Can we see the unseeable ?” – I recall, I shared that childhood strange experience here (yes, that 3yrs aged brain remembers) –

        Initially, a child does not understand the concept but tries to feel the unfelt, see the unseen … I’m glad to share with grownups, how a child’s thoughts work !
        Thank you for thought-provoking posts as well as comments.

  3. We often associate “What if” thoughts with worry and anxiety, so it’s very refreshing to harness the idea of reclaiming “What ifs” and putting them to positive use. The possibilities are endless! 🙂

    1. I can’t tell you how many times the “What If?” game has gotten me unstuck in my thinking. It’s so easy to do things as they’ve always been done or as we’ve learned to do them. I’ve often thought about the phrase “conventional wisdom.” Often, in conventional wisdom, there is more convention than there is wisdom. Thanks so much for your comment. Are you a life coach or are you a counselor of some kind?

  4. I still do that from time to time. I can’t help but wondering what if I had taken the study major I knew I liked since the first place… I may already have known the answer, but in my head, I would have had to trade away some things I now have

    Still thinking whether it’s a good thing to give away some things for the one I could have had or not…

    1. The game I describe here is more about looking forward than backward. You are right to note that with every loss there is some form of gain. Life is complex and we make the best decision we can given the entire context of the decision-making process. If you ever find yourself stuck in your thinking, try my game or find some other way to get beyond what appears to be the obvious. Thanks for your comment.

  5. “What if” is the best game or is this “gaming theory”? Either way, so good to recognize when it’s needed. It’s just too darn easy to stay in the “ruts.” Kind of feeling that way myself these days.

    1. I call it a game, but it’s really a problem-solving tool or a way if reimagining the future. It’s a form of brainstorming. Since I coach and teach creative/critical thinking, I teach people to ask questions–creative questions that hold the potential for opening doors to new ways of living. Thanks for asking and thanks for participating in this interesting conversation.

      1. Yeah, that’s the word popped up in my mind when I read the post, except that it’s a group activity. Truly, a case of individual brainstorming !

  6. If I understood well, your “what if ” game is future oriented? Like you are planning out something? Is there a “then” to follow in thoughts or actions?
    I know people that play that game thinking about the past and it messes them up, seriously…. two sides of a same coin…

    “Because there are no rules to this game, any solution is worth considering; nothing is taken off the table prematurely. No solution is considered too unorthodox to be examined. ”
    This is a foundation of problem solving 🙂 Nothing is off the table until you made your choice. I encourage my clients to take any road but the known one, as the outcome/ solution on that one is the same one as always. And then (the difficult part) stick to your new solution and add an action.

    1. Yes. This game is really a problem-solving tool, a form of brainstorming–so it’s intended to be used to think about the future and not look at the past. It’s about gathering a bunch of possibilities together and then doing research or thinking about each possibility. After learning more, a person can then rationally chose which path to take. As you probably know, most people don’t make choices; choices are made for them. They act according to convention; they do what others tell them to do. It’s often hard for them to even imagine that they have choices. This game also helps people learn about the importance of evidence and how to gather and use it. If they can look at a bunch of possible outcomes and then gather information about each possibility, they can see which path to take based upon where the evidence is pointing.

      1. Surprising, sad and very true: many people do not even know there are choices. The method you describe is indeed palpable problem solving and shows you various paths. Knowing that people do not even realise there are other options than the one they always do as they were told (and taught in their childhood), I even encourage them to test more than one and see what happens.

      2. I like your idea about having clients “test” ideas. I strongly believe in living “experimentally,” especially if one wants to have an uncommon life, if one desires “transformation.”

  7. Interesting. I think I have often lived my life, asking the “What if?” AFTER I’ve made the brainstorming jump. I summarize my life motto, “I jump off the cliff, then ask, ‘Where we going?'”

    I’ll have to try asking the “What if?” first!

    Ric d. Stark

    1. I’m curious how your approach has worked. It certainly adds spontaneity! Sometimes, some of us need to demonstrate the kind of courage you have demonstrated. I certainly do not believe that “one size fits all” when it comes to living. Thanks so much for your comment.

      1. As far as I have encountered and understood such people, such spontaneity is not only about courage, but a strange confidence in oneself – in fact, practically the brain has already figured out a meta-solution, as ways to improvise the plan on the fly. These are “quick brains” or hyperactive but are also prone to “checkmate” if ever overconfident. To some of us, it’s magic how they work !

      2. Spontaneity, for sure. Courage, yes. Confidence–bred into my core by the heritage of those Iowa farmers, who always know that in the end, the crops will yield their harvest. Over-confidence? I think my father’s ever-present criticism and need for control (of his world, which included me) resulted in a balance for that one.

        On the whole, my” jump-first, ask later” attitude has made life interesting. I.e., I had no idea that one winter vacation to Hawai’i in 1986 would lead to such a colorful second half of my life. Wouldn’t trade this one for anything.

        But I’ve paid for “spontaneity”–many times. With bruises and even some broken bones (metaphor here!) at the bottom of my leaps.

        I’ll close with this. One of my oft-repeated slogans: “They will never write on my gravestone, ‘If only…'”

        Ric d. Stark

      3. Some of the best decisions of my life came spontaneously after an accidental discovery of one sort or another. Sometimes, we pause a bit too much and for too long. Such pauses can lead to inaction or stagnation. I’ve often thought about what I’d like to be carved into my tombstone. “He lived an uncommon life” would be quite nice. Thanks for sharing your story.

  8. It’s difficult without specific situations- picking up stakes and moving is abandoning something and I might be bringing the problem with me

    1. You bring up an excellent point. We often think that running away might help, and, I suppose, it can. But if we are the problem, then we just carry the problem with us, right? I suppose you’ve just made a very powerful argument in favor of being self-evaluative and self-critical. Thanks.

  9. My “what if?” Thinking turns to sleepless nights of scenarios. Can you care too much? Sometimes I wish I didn’t care as much about things and a lot more what is would be pleasant.

    1. Can we care too much? That’s an interesting question. How would you answer it? And, if it is a problem, how does one address it? All food for thought. My knee-jerk reaction is we can care too much. And we can care too much about the wrong sorts of things. Thanks for making me think more about all this.

    1. Your husband sounds like a wise person. There is always a solution. Sometimes we just have to open our eyes a bit wider to take it in. Thanks for the comment.

  10. What if I apply to a job abroad again? I have this kind of thoughts every day. So, I start to draw possible situations to find out how I can make that statement happens. And I will, sooner than later.

    1. I really am drawn to your comment. I think you’re pointing at something that’s very intriguing and important. By beginning to think about the things we want to change in our lives, we create a kind of momentum toward change. This is very similar to the self-fulfilling prophecy. Cool. We start change by thinkng about change. Thanks for leaving such an intelligent comment.

  11. Quite often I need to come up with solutions that are of the unconventional type because of my disability. Habits and routines are a way of life for me because of the limitations I have, but I keep a lookout for when one of these habits or routines no longer work in my life or an alternate maneuver would work better for me. The roads through the pastures end up changing sporadically.

    Although all of the years, while I was a kid, were spent in a large city, almost every summer vacation was spent on a cousin’s ranch where my brother and I helped with the chores that go along with a cattle spread. The only thing I didn’t like about those weeks each summer were the mosquitoes. I continuously smelled of Off until Labor Day weekend each year.

    1. Necessity is the mother of invention. Lots of truth there. I think it’s important that we do something akin to regularly auditing our beliefs and practices. Those that seem outdated or like relics of a past that no longer exists should be discarded. It sounds like you had an interesting life growing up. I think moving between very different environments (the way you did) is really healthy, both physically and psychologically. Thanks for sharing your story.

  12. My biggest fear is getting to the end of life with that question still in mind. When making any major life decision I often think it’s best to map out the worst case scenario and compare that to a more realistic outcome – often the worst case is less scary than people imagine and the realistic outcome very achievable. Nice post Troy 🙏

    1. Hi, AP2. You don’t strike me as the sort of person who’s going to make it the end of life with a long list of regrets that came as a result of not taking chances or from being too inactive. I totally agree that we often psyche ourselves out. We also overestimate the difficult of some tasks. By breaking what seems to be enormous task down into its component parts/steps, we often end up discovering that it was no big deal after all. It’s funny how many tricks our minds can play on us. Thanks for your comment.

  13. I regularly use this “what if” scenario in mind as I’m mulling over things as well. This fear setting (I believe our first conversation ever was about this topic!) has really helped me put my fears into perspective and realize they are manageable. Also, I use the “and so?” scenario which acts as a litmus test for anxious thoughts. You and I ask a lot of questions which is the lifelong learner in both of us 🙂

    1. Hi. I’d like to hear more about the “and so?” technique you use. How does it work? When do you use and what are the usual results. Thanks for helping me see that there’s a potential follow-up to “What if?”

      1. When I was having paranoia and anxious, this kind of logic is staggering. I relearn how to get know better about it.

  14. One of the most mindblowing responses I ever heard when I said “We need to think outside the box”, was also devilishly simple: What box?

    I find I play the “What if?” game a lot when writing my short stories and novels. Trying to inhabit each character and the different choices they might make is a fun experience, and helps me understand different choices I make in this real world we live in.

    Thank you for sharing this thought provoking post. I am still working on the manuscript of my book, and will let you know when it’s at a point where I’m looking to submit to different editors or publishers for feedback on the viability of this story as a book for publishing. (If not, I’ll keep working at it and dive down the self-publishing route but will still need that all important editing help!)

    How goes your website and the work?

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