How to Overcome Any Challenge

How can one overcome any challenge?

The uh… challenge of life challenges is that they aren’t always straightforward. For example, getting over the death of a loved one isn’t a 123-step process. It’s complicated. Difficult challenges are the ones that we need help with, so how can we help ourselves deal with those?

Adaptability: The Secret Ingredient of Success

If I had to select what I believed was the most underrated trait for humans, it might be adaptability. In an ever-changing world and life, if you can’t adapt, you will struggle. Difficult challenges elevate the adaptable and sink the rest.

There’s the story of Marcus Luttrell, the sole survivor of a disastrous Navy Seal mission in Afghanistan. He suddenly found himself alone and severely injured in enemy territory. His Navy Seal training enabled him to adapt to a seemingly-insurmountable challenge and survive to tell the story. Within that example is the first lesson for overcoming any challenge—training your adaptability.

How to Overcome a Challenge: Train to Be Adaptable

I just looked over my left shoulder, and there was no drill sergeant behind me. It’s very quiet in my apartment. In other words, I am not being trained unless I willingly do it myself! This is the situation for most of us, and the default response is to not train yourself. But say that you wanted to be more adaptable to the challenges life presents you. What would you even do to train for better adaptability? Here are some ideas…

Create high-pressure challenges for yourself: Try to write a certain number of words in a limited amount of time. Try to read a page in a book in a limited amount of time. Time limits are a good form of artificial pressure.

Take improv classes: Improvisation is the manifestation of adaptability in art form. You’re forced to create “mini solutions” to the recurring problem of not having a script!

Try an escape room: Escape rooms are a growing form of entertainment. You and a few other people get locked in a room and must use your wits to get out of the room before time runs out. It’s a great way to train your adaptability and problem solving muscles!

Constraint Is a Great Training Tool

For creative work, use constraints. Michael Michalko, in his book Thinkertoys, teaches that creativity is enhanced by limiting your options. For example, if you tell someone to “make a movie” compared to “make a 3-minute comedy short involving ranch dressing”, the latter will likely end up being far more creative.

In addition to bolstering creativity, constraints mimic real life challenges. I can’t fly. I have the flexibility of styrofoam. These constraints don’t make me worthless, they force me to take a different approach. I have to walk places and fly in planes to get around. Because I’m inflexible, I can’t touch my toes or do a split, but I can still make banana splits. Problem solved. (Or, you know, I guess I could train to be more flexible…)

Start a new hobby: Any new hobby will bring several new skill challenges that will force you to learn and adapt to them. The more you do this sort of thing, the more you’ll see your potential to overcome life’s bigger challenges. 

How to Overcome Any Challenge: Challenge Your Assumptions 

The second way to become more adaptable is to challenge your assumptions. The entire reason that some people aren’t adaptable is because they are too easily locked into one way of thinking.

Long distance transportation was transformed because the Wright brothers dared to think outside of the constraints of ground travel. Ironically, the next step forward might be because someone thinks outside the constraints of air travel (such as Musk’s hyperloop idea). I have my dream career now because I (eventually) thought outside of the college -> degree -> job system. 

This is interesting when juxtaposed against the above recommendation to use constraints in your creative work. Here’s the difference—you place constraints on creative work to provoke action. In life, many of the constraints we create are specifically to prevent action. For example, “I can’t play sports because I’m not athletic” is more of an (untrue) excuse to do nothing than a creative restraint like trying to draw with a blindfold on or riding a bike without using the handlebars. When you use or notice constraints in your life, make sure they’re action-generating. If a constraint prevents action, you need to question it!

Many assumptions are wrong. Challenge them aggressively and see which ones hold up.


Life challenges are diverse and often unexpected. That means we need to be prepared for anything. Well, you can’t specifically prepare for everything, so we need to prepare our adaptability skills and be ready to challenge assumptions that might prevent us from overcoming a challenge.

Just think about the (very reasonable) assumptions that have already been shattered…

  • A blind man climbed Mount Everest
  • An average plane weighs about 175,000 pounds on takeoff and it can fly through the air
  • The internet exists and it is insane
  • I’m using a computer, an insanely intricate piece of technology powered by electricity? What is that, a lightning bolt in a cage? HOW IS THIS POSSIBLE?!

Before these things happened or existed, we would laugh at anyone who suggested them. Our assumptions were wrong! But the crazy thing is that we believe much tamer assumptions like, “I can’t get in shape” or “I’m not creative enough” or “I’ll never recover from this setback.” These challenges can be overcome, and the best way to start that process is by challenging any thought which suggests otherwise.

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