26 Ways To Do The Unexpected (and Not Die*)

Jacob Derry
The Awesome Initiative
3 min readJun 6, 2016

The asterisk is there because I can’t guarantee that you won’t die from doing any of these things I’m about to suggest…

But you probably won’t.

credit: Luca Upper

Too often people run away from doing the unexpected, the absurd, the creative; they think they’re going to die.

Or they believe the opposite: that doing the unexpected won’t make any difference. Even worse is the limiting belief that he or she can’t do the unexpected, can’t make art, can’t be significant in this world.

I don’t think any of these positions are true. Pablo Picasso is quoted saying, “Every child is an artist. The problem is how to remain an artist once we grow up.”

That means at your core, you are an artist. That guy or girl sitting across from you is an artist. Your mom is an artist. Your uncle. Your mail carrier. Your dentist. The librarian. They’re all artists too, whether they realize it or not.

But wait…how do you get back to being an artist if you lost your way?

You start doing the unexpected.

  1. Look up today’s national day on a national day calendar and find a way to celebrate — June 1st was National Go Barefoot Day and June 4th was National Cheese Day!
  2. Brush your teeth with your non-dominant hand — this is difficult
  3. Recall the last dream you had — what about it felt real? what about it felt unreal?
  4. Let a friend or roommate pick out your outfit for the day
  5. Go the whole day without using the word “like” — this can also be difficult
  6. Mismatch your socks (on purpose!)
  7. Hit shuffle on your music playlist and dance to whatever song comes on first — I do this most days
  8. Come up with one question you want to ask every person you encounter today
  9. Change the background image on your phone to an image that represents where you want to be in 5 years
  10. Take a different route to work
  11. Take a different mode of transportation to work
  12. Sit when you would normally stand and stand when you would normally sit
  13. Play a silly game with someone — thumb war or rock, papers, scissors?
  14. Go to a music concert featuring artists you’ve never heard of or a music genre you don’t even prefer — this past week, I listened to hip-hop and R&B in Detroit and then folk punk music with angry lyrics in Flint
  15. Make a new game with your own rules
  16. Write a story using less than 10 words — mine: rematch between Tortoise and Hare. Both win; Hare dissatisfied.
  17. Go out to eat for lunch but do it by yourself and don’t look at your phone
  18. Daydream or doodle when you get bored
  19. Start a conversation with someone in a public restroom
  20. Recall something you learned in the past week and connect it to something else that you learned over a year ago
  21. Choose five random ingredients you have and make a meal out of it — I recently made a pizza burrito type thing using tortillas, chicken, pasta sauce, spinach, and cheese
  22. Make up lyrics to a rap song while you cook
  23. Start noticing what you notice — last week I noticed how grocery stores are really thoughtful and strategic with their store layout and what products they put where
  24. Jump off a bridge into water — make sure it’s safe first; I’ve done this twice in the past week…it’s a thrill
  25. Scavenge your house for materials and build something out of whatever you can find
  26. Come up with a list of 10 more unexpected things to do and send it to me

These things are absurd, but they’re also fun and create all sorts of new possibilities. If you actually did all these things, what would happen? What could you learn? Who could you meet? What could you create?

Doing the unexpected is about creating new possibilities and getting back to being an artist.

Of course, I can’t tell you how to live your life, but I can show you how I try to live mine.

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Jacob Derry
The Awesome Initiative

curious listener, inspired writer, and follower of Jesus