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1. Get lost in a city at night and take pictures with your shadow.

2. Figure out which vendor’s got the best hot dogs in the city.

3. Spend an entire day in a museum. While you are there, you can:

   1. Try, hopelessly, to craft a half-decent sketch of a sculpture or painting that you like.

   2. Pretend you are an art connoisseur and educate the “less fortunate” about overlooked “tidbits” of art history.

   3. Snoop in on a museum tour.

   4. Make a list of your top ten favorite installments.

   5. Make an offer on one of the more prolific pieces in the place, and refuse to budge.

4. See if you like ballet?

5. Number four was condescending. Let’s really see if you like ballet. Try The Nutcracker.

6. Spice a dish with a smattering of herbs and seasonings you’ve never heard of.

7. Buy a fish from a fish market, name it, and then ask people around the city if they would like for you to take a picture of them with… we’ll call her Gezebel.

8. Play chess in a park with one of those grimy-looking hoodlums who happen to be very good at chess for whatever reason.

9. Find a scenic place to rollerblade.

10. Pretend you are in an indie movie. Improvise the curation of a playlist as you move through the city. There should be heartbreak, loss, hope, joy, and perhaps even peace and serenity. 

11. While nobody is looking, tag an edifice with your name (or something of relational correspondence) so that, many years later, you can return to it with somebody you really care about and discuss that era of your life.

12. Visit an animal shelter, and rename all of the animals in there. 

13. Get day-drunk and make out with somebody who is out of your league under the sun.

14. Go to a jazz bar and act like you belong there.

15. Make an outstanding bouquet of flowers and put it in a vase in your home.

16. Figure out what your favorite color is. Not red or blue or orange. Find the exact hue. (And stick to it, especially when people ask you that inane question). 

17. Dress up and attend a denomination of a religion you do not ascribe to.

18. Lay on the grass, turn your phone off, and decipher the figures in passing clouds. 

19. Craft your own dad joke. Start with a noun.

20. Inform your fellow train riders you are a research assistant at an important institute in the area. Then proceed to ask them how many peaches they think they can feasibly consume in under an hour. Gather as many details as possible by asking “why-based” follow-up questions.

21. Spend too much money at an arcade. When you are finished, and before you leave, give your tickets to a kid who looks like he or she could use them.

22. Volunteer at a children’s hospital. 

23. Volunteer at a nursing home.

24. Tell your friends you are getting a new tattoo, and that you drew the design yourself. You should draw the tattoo design as stupidly and badly as your hand will allow you to. Then, show your friends the tattoo design and relate to them how excited you are to get this tattoo on your back. In the case that some of your friends do not provide push back, you now know who you ought to avoid seeking counsel from in the future.

25. Read a book by a body of water.

26. Light a fire on a cold day and find something fuzzy to nap on. 

27. Buy a coffee for a homeless person in exchange for a story. 

28. Find your forever favorite diner, and figure out what “the usual” is going to be.

29. Determine your favorite “sunset hour” song. Play it when you feel down as you imagine having the sun on your face.

30. Throw clay. A nice glaze and a trip to the kiln can cover up practically any mistake. And there is a lesson in that, I believe.

31. Buy a work of art from somebody who is not very good at art, and then encourage them to keep going. 

32. Watch a movie that brings you to tears with the person who can always make you laugh.

33. Pretend you are an author and that the world around you is filled with a universe of characters who are just waiting to be tapped into for your next great plot. Investigate these characters and allow them to reveal to you their backstories.

34. Relive your childhood with some cosmic bowling, bad bar pizza, and a little ice cream afterwards.

35. Call a family member and ask them to tell you a story about yourself that you may not know or remember.

36. Purchase your favorite children’s picture books and place them near the toilet. Replace one of your long scrolls on the phone with a read, every so often. 

37. Build a scrapbook full of photos of beautiful vistas or “strangers of Chicago” or “dogs that make you smile”; whatever.

38. Build a fort in your living room and sleep in it.

39. Buy a NOW CD, hop in the car, and reminisce. 

40. Go ice skating with someone you want to hold hands with. Hot chocolate afterwards comes highly recommended.

41. Nerd out and play a vintage computer game. 

42. Design your own t-shirt, complete with your very own personal logo. Tell nobody what it is, if prompted.