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The Intrepid Guide to City Living

As of this writing, I’ve lived in the Chicago Loop for five months. Below are a few observations and lessons for how to properly interact with the city.

How did I come up with them? Well, some are just common sense and a simple matter of being aware of the world around you. But frankly, I’ve evolved in how I interact with the city in the five months I’ve lived here, and I wanted to share the lessons I’ve learned — all to help us better go with the urban flow.

Yeah, these are direct experiences of mine from living in Chicago, but they apply to most major urban centers.

Enjoy. Here we go!

The Intrepid Guide to City Living:

1. When you are waiting to get into an elevator, be sure it empties out before you attempt to get in. Yes, it’s ok to wait an extra second to be sure. And don’t stand immediately in front of the door. How in the heck are we supposed to get out? This same principle applies to allowing passengers to get off the train as well.

1.5. And gentlemen, speaking of elevators: Let the ladies out first, will ya?

2. When walking on the sidewalk, don’t stop suddenly to check your damn phone. There are people walking behind you…people hustling to get somewhere.

3. When you are done eating at a restaurant and preparing to leave, please push your chair back into the table. Be mindful of both the staff and your fellow patrons.

4. When you are walking down the sidewalk, be aware that actual people might be coming out of a building, so that you don’t plow into them. But also, if you are person walking out of building, be aware that people might be coming down the sidewalk, so proceed with a little caution.

5. Pedestrian sidewalks aren’t for biking.

6. And if you are biking in the city, wear a helmet. Those cabbies and delivery trucks might not stop for you.

7. That bar stool next to you isn’t a briefcase/backpack/purse/handbag storage unit.

8. If it is 5 degrees outside, use the revolving door (if there is one). Keeps everyone inside a lot warmer. And in the summer, using the revolving door keeps the cool air inside.

9. If it is raining and you are using an umbrella, be aware of the pedestrians around you, and don’t thoughtlessly poke them in the eye with your umbrella spokes.

10. If you are walking on the sidewalk and approaching a slower person, don’t just mindlessly veer around them. There is probably a faster walker already in that lane. Pay attention. I’ve had dozens of people walk right into me.

11. It’s a train. When it speeds up, or slows down, you need to be ready, and not lose your balance and fall into my ass. Please recognize that something this big needs power to accelerate, and something this big will lurch when it slows down…

12. Thousands of people use various trails to run, bike, or speed walk to get their exercise. So, please don’t walk with your group of five people AND BLOCK THE ENTIRE WIDTH OF THE TRAIL for those that want to pass.

13. If you flick your cigarette butt onto the sidewalk, you are an asshole.

14. It’s ok to stop and look up at a beautiful building. Just be aware of the people moving around you.

15. If you eat at a chain restaurant when you visit a big city, you are simply wasting your life away.

16. Why aren’t you acknowledging the doorman in a building? Don’t you realize how much they can help you if you need something? And learn to appreciate a good one!

17. If you aren’t going to actually walk up the escalator steps, please step to the right so that more active humans can get by you.

18. Don’t stop at the very top of a moving escalator to check your phone.

19. If you are deathly afraid of dogs, why in the hell are you living in a dog-friendly apartment building?

20. When you sit at a bar to grab some food and drink, don’t mindlessly occupy seats that then make the seats around you useless and unusable for other parties. For instance, if you are a solo, sit at the end, and not in the middle of five bar stools.

21. When you and a group of people are riding on a bus or train, be mindful of the people around you, and know that your loud talking, phone call conversations, music, and yes, singing, is disruptive to the people around you.

22. If the elevator door opens for you, and you are standing there oblivious looking at your phone and NOT getting into the car, I am going to press the “DOOR CLOSE” button promptly.

23. Why in the hell are you walking in the bike lane?

24. If a vehicle stops and the driver signals you to cross in front of them, make some attempt to speed up and acknowledge their kind gesture. Why do we feel the need to ignore these drivers?

25. When you make a meal reservation, get there on time for Chrissakes.

26. Going to use a coffee shop? Cool, just don’t occupy a four-top table if you are a solo, especially if smaller tables or counters are readily available.

27. Public transportation in Chicago, otherwise known as the CTA, is AMAZING, and life changing. If you are going to thrive and relish life in the big city, you need to fully embrace public transportation. Like Al Pacino says in Devil’s Advocate, public transportation is the best way to get to keep a finger on the pulse of a city.

28. If you live in a high rise building like I do, you probably have a trash chute. The concept isn’t hard: Don’t put anything into the opening that won’t fit down the chute. Why is this idea so hard to understand?

29. During wintertime, especially in a chilly city like Chicago, you have to wear big thick winter coats, with knit hats, scarves, etc. But it’s the big, thick coats that are a big deal, and very cumbersome. So here’s the deal: when a restaurant offers coat check, please please please use it. Don’t drape your gigantic coat over your chair. It looks unprofessional, people trip over them, step on them, and they are generally just a big nuisance. Utilizing the coat check is just the savvy thing to do.

30. To be a good citizen of the big city, you need cash. Especially singles. It’s just a smart move to have a bunch for when you need to tip people who help you out.

Writer’s note: I will update this list as I uncover new lessons to share! And email me here if you have a suggestion of your own…


Todd Schnick

Todd Schnick

Editor-In-Chief at
Founder and Editor-In-Chief of intrepid.MEDIA, Todd Schnick is a media + business strategist and talk show host + producer. He is a former marketing strategist, national political operative, and lobbyist. Todd has published five books, writes a business + lifestyle column, is a distance runner, and lives in Chicago with his wife Stephanie + family.
Todd Schnick

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