How Valuable Is Second Guessing?

I’ve been holding onto the following quote for a long time, wondering at how true it is, or isn’t.

when you feel insecure about something you are doing … that vulnerability means that you are doing the right thing and when you watch that … the part when you started second-guessing … that is likely the best part … same goes for writing and photos of yourself.

It’s from Raymi, and you can read the full interview with her here.

Here’s my difficulty: I’ve always admired the people who know exactly what it is they’re about, or what they want to do. And whatever IT is, IT powers (or overpowers) everything else, any other disappointments or losses. IT offers meaning, and there’s no second-guessing as to the meaning of IT.

Raymi refers to second-guessing as something related to vulnerability—and true, it’s necessary to face vulnerabilities or fears in connection to creative work. (Think of The War of Art by Steven Pressfield.)

But does second-guessing always mean vulnerability, though? Sometimes second-guessing is about challenging yourself—to have humility and to realize you need to improve and grow.

How can we distinguish between second-guessing that is valuable, and second-guessing that is wheel spinning?

What’s your take on this?

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About Ben Sobieck

Benjamin Sobieck is a Wattpad Star and 2016 Watty Award winner. He’s best known on Wattpad for Glass Eye: Confessions of a Fake Psychic Detective, the Watty Award–winning sequel Black Eye, and When the Black-Eyed Children Knock & Other Stories. Four of his titles have appeared on Wattpad Top 100 Hot Lists, all at the same time.

10 thoughts on “How Valuable Is Second Guessing?

  1. David Mark Brown

    I guess I would differentiate between second and third guessing. I feel it is a cyclical thing during the creative process. A time of confidence and boldness in the process is necessary, but for the work to progress to the next level, that season is followed by one of doubt and second guessing. A new spark hits and launches one into a new season of boldness and confidence. Even if the process is two steps forward and one step back, it is the fear of having to take the step back in the future that leads to third and fourth guessing and a total failure to progress.

  2. Jason Black

    Useful vs. wheel-spinning. With second-guessing, I think the difference comes in the motivation for the guess.

    Some second-guessing is based in a desire to truly do well, and comes from the mature self-awareness that we’re trying something we haven’t necessarily mastered. It comes from an awareness of the limitations of our own present skill, and the understanding that we are nevertheless attempting to perform beyond those limitations. I think that kind of second-guessing is useful, because it is more likely to make us conscious of our choices in whatever we’re attempting to do. It is likely to remind us to be aware of _why_ we’re making those choices, so we can verify as best we can that we are making good choices. That we are truly doing well.

    The other kind of second-guessing is based in fear of doing poorly. It comes from a lack of confidence in our ability to perform to a sufficient level, and the subsequent worry that we’re going to screw up in some tragically horrible or embarassing way. So ever potential choice becomes laden with the fairly pointless, hand-wringing observation "oh! Can’t do that! It might come out badly!" Well duh. You’re trying something new. Of course it might come out badly. But in this latter case, second-guessing that’s based in fear exists to _prevent_ us from making any creative choices at all, because in that twisted logic if we don’t try it then we haven’t failed.

    Except, of course, that not trying is its own kind of failure.

    So I say yes, second-guess yourself. But only to the extent that you’re double-checking your reasons for your creative choices. And if you feel, based on your current level of expertise in whatever you’re doing, that you do have a good reason then go right ahead and make that choice.

    But as soon as the second-guessing starts telling you not to make any choices, tell it to shut up and forge on ahead anyway. I think, in creative endeavours, it’s better to make _any_ choice (even a random one), than to make no choice out of misguided fear. You may well fail, but you’ll learn something, and in doing so will push yourself forward anyway.

    When you’re walking a path through darkness, the only way to know where the path is, is to occasionally step off it.

  3. Justine Musk

    The second-guessing that Raymi is talking about sounds a lot like fear to me, which is very different from the kind of healthy skepticism you need to maintain in the face of your work.

    And you need both — you need the fear to go toward, and you need the sense of skepticism to help you ensure that you’re traveling correctly!

    Which is why other perspectives — carefully chosen perspectives — are such a necessary source of feedback. Also why I think that the ability to seek out in-depth, tough-love, constructive criticism is the quality that separates the professionals (or future professionals) from the rest. It seems a relatively rare quality, and a relatively small group.

  4. Susan Cushman

    Great question, Jane, and one I’ve thought about a lot. You know that sick feeling you get in your gut when you’ve sent something out that wasn’t quite ready? Or when you’ve exposed someone (or something about yourself) in a memoir piece and have second thoughts? It’s like saying something aloud and then immediately regretting it, wishing you could suck the words back into your mouth.

    David Magee, radio host and author of twelve nonfiction books, was a panelist at the 2010 Creative Nonfiction Conference in Oxford, Mississippi, in November. During the panel, "The Writer’s Life: Off the Page," he said that, in order to be successful, a writer needs 3 things:

    VANITY – 0
    EGO – SOME

    He talked briefly about the difference in vanity and ego, and I think that’s at the heart of the question about second-guessing. Without a healthy degree of ego, we will always second-guess ourselves and never send anything out there. But vanity is a different animal, and it fills us with a false sense of confidence. It can cause us to become complacent and careless with our work. I guess the trick is knowing ourselves well enough to discern the difference, and of course, learning patience along the way.

  5. Colette

    Jane, I want to distinguish between that insecurity or fear because you know you need to try something, stand up to someone, or do the right thing — and you know it’s going to be hard, controversial, or unpleasant. In that case, then — yes– that’s when you know it’s the right thing to do.

    But second-guessing a decision you’ve made or whether you are on the right path, is an entirely different thing altogether. Like you, I have always been in awe of those who know exactly what they want to do — life would be so much simpler. But in my world there are just so many possibilities, and it’s easy to get caught up in them. I rack it up (at least partly) to the ‘perfectionist’ gene — there always seems to be another option, or a way to do it better.

    I think the trick is to not get stuck. When you feel stuck then movement — any movement — is a good thing. As long as you are in motion you will get there eventually.

  6. Erica Rodgers

    As far as writing is concerned, useful second guessing is that nudge, that inner voice, that tells us that something really is wrong with a ms. There are holes in the plot, or other problems, and if we ignore this ‘nudge’ and send it out anyway, rejections will fill the inbox. On the other hand, if your second-guessing comes down to brooding over a single verb in chapter fifteen, then you’re probably spinning your wheels. Send it out already.
    I can also say that in the first case, that hole in my plot won’t be my best writing, no matter how vulnerable I am as I ignore fixing it. 😉

  7. Carol Henderson

    Second guessing can become a debilitating way of life, a paralyzing modus operandi. I have a good friend who is an incredibly creative fabric artist–she has made amazing fabric collage and oilcloth rugs etc. But she is unable to work now. Everything she thinks of doing she second guesses before she even gets into the studio. She can not "play" with materials she’s so busy screaming at herself that her work is no good. Why bother, etc.
    She is doing what I call de-constructing. This happens when we do something–it might be quite successful–produce an essay, teach a writing workshop, create a visual piece–and then we take it apart in our minds. "If I had done that part differently would the result have been better? What about that middle section? Crap. Why did I . . . Taking everything apart in that way is classic anxiety and it can crush creativity. One thing I love about prompt-inspired free-writes in a supportive workshop environment is that, with practice, people can experience writing without those nagging voice piping up and crippling us. We learn to trust the words and images and let them flow. This has helped me so much. As a columnist I used to get stuck on my lede–couldn’t get anywhere until I had that perfect. What could have taken me an hour to write took three days. Talk about second guessing!
    Anyway, a ramble but I’m going to post it before I second guess and delete.

  8. Mark Neumayer

    This is a tough one. As creatives we need to trust our instincts. We need to trust that subconscious voice that is telling us something is wrong. This sort of second-guessing is invaluable.
    But second-guessing can also arise from fear. We worry that what we have done is not good enough and over-edit ourselves, stripping the life and spontaneity out of our work.
    Unfortunately, it takes a combination of experience and being honest with yourself to tell the difference between the two. When the little doubts start tugging on my metaphorical shirt-tails, I try to judge whether I am feeling anxious or uncomfortable. Feeling anxious usually means I am afraid. It is good to ignore the fear and push on. This is what leads to actually accomplishing things. If I am feeling uncomfortable or something feels awkward, it usually means that something is wrong and needs to be fixed.

  9. Gunter

    Jane, Here’s my take.
    Second guessing is valuable in the context of being willing to change your decisions or opinions when you find facts that don’t support them. An admission of error or the realization that we may have made a mistake is a sign of self-confidence rather than self-doubt or insecurity. It demonstrates that person’s quest for the truth, tempered by the knowledge that "truth" itself has a subjective meaning. Insecure people have difficulty accepting the notion that they may be wrong or that they need to improve. They often manifest their unease with personal attacks on those who present a compelling opposing view. They feel vulnerable so they find arguments that bolster their views while outright rejecting all contrary evidence.

    Second-guessing can cause consternation with a well-adjusted person, however, especially when a long standing opinion dear to one’s heart is successfully challenged. There is nothing wrong with this. It means that we have faced the reality of our own falability. Sometimes a change of view is painful.

    Wheel-spinning second-guessing occurs with people who have a difficult time coming to a decision when the considerations and facts make the decision process difficult. It signifies an unwillingness to commit oneself to an idea or theory because it may be wrong. Wheel spinning also is the result of over-analyzing a situation to the point where nothing further is gained. After a while the questions and arguments become circular resulting in a delayed decision or no decision at all.


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