10 questions to ask when you’re stuck

If uncertainty were a publicly traded company, I’d be a wealthy man, for I’ve owned my share, sold some, and bought more.

But I’ve never divested. I’m a long time shareholder in Uncertainty Corp. and I expect to be a life-time owner.

10 questions to ask when you're stuck

The ways of Uncertainty Corp. make me nervous though. I’d rather know what it’s up to—to have the future mapped out—but God never promised foreknowledge and understanding, just peace. I take comfort knowing that the apostle Paul, during some very uncertain times in his own life, described himself as “perplexed but not in despair” (2 Corinthians 4:8). If he, with all of his spiritual insight, can be okay with being perplexed, then who am I to demand absolute clarity in my own life? In fact, maybe his confidence in God, rather than in his own understanding kept him from despair.

I can’t make the same claim. There have been plenty of times when I’ve been both perplexed and in despair. When I’ve lost my motivation for work and don’t know what to do about it. When my child has succumbed to a critical health issue and there are no clear answers. When I have a disagreement that seems unresolvable.

Uncertainty Corp. sells a lot of products. And when we put them into the shopping cart of despair, we get stuck.

When we’re stuck, we need good questions to get us going again. I remember reading Barbara Sher’s book, I Can Do Anything If I Only Knew What It Was, during a time in my life when I was perplexed about my career. I found the book very helpful, not for the answers, but for the questions it asked. They helped me stay out of despair and look toward an uncertain future with a sense of ownership for the outcome. I had some decisions to make and her book raised the questions I needed to ask of myself at the time.

Since then, I’ve collected a number of questions I ask myself when I get stuck. Here are ten:

  1. What are all the different ways I can write down the problem I am trying to solve?
  2. Who will evaluate the outcome of my decision and how do I feel about that?
  3. What outcome am I most hopeful for?
  4. What scares the living daylights out of me? What am I resisting most?
  5. Is there any critical information or another’s perspective about the situation that I’m lacking?
  6. Who else may have made a similar decision and how would I imagine them handling it?
  7. What’s the benefit of making the decision now?
  8. In a year from now, if I imagined choosing each of the possible options, which option would I wish I had taken?
  9. Will the option I am contemplating make me more like the person I want to become?
  10. Which option will best serve the ones I love?

Not every perplexing situation we encounter has a ready-made answer just waiting to be discovered if only the right question were asked. It’s never that easy otherwise it wouldn’t be a perplexing situation.

But that’s the way Uncertainty Corp. operates. We can either buy shares and suffer in despair or sell what we can by leaning into perplexity and asking questions of ourselves. As Albert Einstein once put it, “It is not that I’m so smart. But I stay with the questions much longer.”

I’m guessing that he was a minority shareholder.

What’s your favorite question to ask when you’re stuck?


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4 thoughts on “10 questions to ask when you’re stuck

  1. This one hit home for me:

    “In a year from now, if I imagined choosing each of the possible options, which option would I wish I had taken?”

    I appreciate your words Leary. I’ll keep coming back 🙂

  2. Great stuff Leary. I’m adding it to my “resource file” for the benefit of self and others who present this quandary to me! Cheers! Theresa.

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