Destroy Challenges By Asking These 9 Questions

A problem doesn’t have to be huge to feel overwhelming. Sometimes it’s the small, but persistent challenges that wear on us the most.

And in worst-case scenarios, we’re assailed not just by the problem itself, but by the attendant problems springing from our fear and paralysis.

But regardless of size or seriousness, twisty problems can often be unknotted simply by asking the right questions, much like a doctor assessing a patient’s presenting symptoms.

Below is my own trusted (though certainly non-exhaustive) battery of questions I’ve developed that can help you quickly move from a place of ‘emotional reaction’ to ‘analytical action.’

T. Harv Eker once said, “No thought lives in your head rent-free.”

So what’s the thought – the worry, the problem – you need to evict?  I challenge you to take the thing that’s weighing on you most right now and run it through this process…

  • Is something broken here? If so, what is it that needs to be fixed?
  • Is something just sub-optimal? If so, what’s the sticking point?
  • Is this actually several smaller problems that look like one big problem?
  • Can I adjust my goal?
  • Can I adjust my timeline?
  • Can I bring in additional manpower or womanpower?
  • Is there a skill I can acquire to resolve this?
  • Do I need to bring in a subject matter expert to assist?
  • Is my goal detachable from my intent? In other words, is what I’m calling the ‘goal’ really the goal?   Is there a non-problematic action – an alternate route – that can get me where I’m going?
  • Does this actually matter?

Have your own questions to add?  Let us know in Comments.

– Matthew Porter

Matthew Porter writes about decoding success, creative leadership, marketing, and productivity.

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P.S. For more on this idea of how to destroy challenges simply by asking the right questions and taking the next step, check out Chris Hadfield’s An Astronaut’s Guide to Life on Earth.  In it, he discusses how to think like an astronaut — and it’s pretty cool.


  1. DurstNovember 20, 2018

    I think ‘Does this actully matter’ should go first.

  2. […] PS:  Facing some major obstacles?  Try asking yourself these nine questions. […]

  3. Matthew PorterApril 15, 2019

    I think you’re right. Asking that can save a LOT of time and heartache.

  4. Dear "Loser Kids"... -August 6, 2019

    […] Matthew Porter writes about decoding success, creative leadership, marketing, and productivity. […]

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