1. Working a crappy job in LA or NYC
If you look back on your life and say, “Man, I’ve had it so easy the entire time!” you’re doing it wrong. Slaving away at an unpaid internship for the Metropolitan Museum of Art, or getting barked at by an overstressed celebrity assistant while PAing on the set of some webisode builds character, experience, and helps you really understand what kind of life you want to lead. These are some of the toughest cities to break into, but once you figure out your place in them, you’re able to make it anywhere.
2. The great American road trip
How many times in your life can take a solid three-month (or more) span to do something as insanely cool as road tripping across the USA? Whether it’s with a group of homies packed into a VW van, camping your way from Sacramento to Maine, or just yourself and a shitty Honda Civic getting a tan through the sunshine states of Route 66, you’re going to have the time of your life, and tons of selfies to prove it.
3. Offering your time to restore homes lost to destruction
It’s cool anytime you volunteer, but I always try to remember that sometimes, the best way to give back is by doing so in my own community. We often forget that places like New Orleans and Joplin, Missouri, are still experiencing the effects of Katrina and tornadoes. Having the time and the energy in your 20s to help build houses for a week is something that will stick with you for the rest of your life.
4. A weekend in Las Vegas
Let’s be clear: there’s nothing glamorous about a trip to Las Vegas. Even the most luxurious experience has a thin layer of sleeze and slime to it, because that’s all Vegas has ever been really. But like, you have to attempt the series of events portrayed in The Hangover. Gambling is also a lot more fun at this age; since you don’t have as much money saved up in the bank, you won’t lose as hard at the tables as opposed to being in your 40s and gambling your mortgage into the hands of a seasoned cardshark.
5. Taking an overnight bus
I was super poor in my early 20s, and I couldn’t afford to spend two full paychecks on a plane ticket. I got to know the American bus system really well, and how to work it – how Megabus has the most reliable wifi, how BoltBus has the best drivers, how the Chinatown bus gets me to Washington DC in three hours, and how Greyhound is probably the worst excuse for a public transportation system ever. It’s also a way to save on lodging. The older you get, the higher your standards will be, so nut up and pay $30 to sit on a bus for 12 hours.
6. Hiking the Appalachian Trail
Even dealing with lean-tos, Luna bars, running out of toilet paper, figuring out where you’ll shower, and where you’ll score some free booze or weed for part of the trail will change the way you tackle life issues in the future.
7. Coachella / Lollapalooza / insert-music-festival-here
The appeal of dancing in mud, dropping acid like its candy, waking up in a stranger’s tent, donning a crown of roses and strands of pony beads, while pretending to care about the festival lineup, will most likely wear off the older you get. But as 20somethings, our stamina and curiosity allows us to exist on sheer YOLO mentality alone. Nothing has ever been as epic as Woodstock once was, but we can make new memories at Sasquatch, the Electric Zoo, and Bonaroo.
8. Snowboarding in the Rockies
I took my first snowboard lesson at Snowbasin, and while I fell more than I glided, it didn’t keep me from experiencing the unique ‘snow culture’ that is found in Salt Lake City. It’s crazy to exist in an atmosphere where skiing and snowboarding is such a huge part of life — not merely a recreational activity for stoners and rich white kids from the suburbs. Having no other responsibilities but hitting up the slopes post-workday must be a dream.
9. New Year’s Eve in Times Square
As a New Yorker, it’s one of those things where you have to experience it at least once in your life. But once is enough when you realize the hassle that comes with standing in the cold for so long and not being able to pee for nine hours. I find that the older I get, the earlier I seem to turn in on December 31, so doing the whole Times Square New Year’s Eve Ball Drop confetti bath is way more manageable as a youngster who can pound back six Bud Lights and still stand up straight.
Be it Disneyland, or Disneyworld, you’ve got to “be a part of the magic” somewhere between being a kid, and having your own kids. Disney is the land of nostalgia, a perpetual safe place where everyone becomes Peter Pan for a little while. You’d be surprised at how much fun and not cheesy even a quick weekend trip can be, especially when one of those days involves completing the “Round the World” drinking challenge at Epcot — pretty much the only place in Disney where alcohol is readily available.
11. Withstanding the cold in the Midwest
I almost moved to Chicago, but I was too big of a baby to deal with wind chills less than 10°F. That’s not even as cold as it can get in the US though; my friend who lives in Wisconsin got off from school because temperatures in the area fell to -35°F. In some ways, the colder cities bring communities closer together; there’s always a warm bar to duck into, or an underground system that gets you where you need to be without frostbite. Save Boca Raton and Scottsdale for when you’re too old to shovel your own walkway.
12. Paying $20 to watch a baseball game
Sitting behind home plate at a Yankees game will come when you’re making enough money to actually splurge; in your twenties, the view from the cheap seats is still awesome. I love seeing a ball game in cities where the team isn’t World Series material — it’s usually an inexpensive and fun activity. I don’t even remember what team the Arizona Diamondbacks played against in their trippy indoor stadium, my $1 hot dog, $4 beer, and group of rowdy friends were all that really mattered.
13. Mardi Gras in New Orleans
Quite possibly the biggest shitshow in America, going balls out for Mardi Gras means peeing on a statue, gorging yourself with beignets at 3am, and showing them titties before they get all floppy and stuff. You’ve got to wake up on a balcony with a ton of plastic beads wondering, “Where the fuck is my underwear?” and noticing your friend has decided to wear them instead, while stuffing his face full of dirty rice. When you’re older you can really learn about what Mardi Gras means to the people of New Orleans, and appreciate the artistic / community value in it. But when you’re in your 20s, it’s okay not to care so much.
14. Discovering yourself in Portland, Austin, Nashville or San Francisco
These cities are continuously listed as the best places for young people to live. Hunkering down in, or even just visiting, a place where the majority of the neighborhood shares your values, interests, and age, is super empowering. Find your true love at a vegan coffeeshop in Denver, or start writing your first novel in a studio apartment somewhere in Seattle.
15. Eating your way through the Southeastern United States
The best regional cuisine I’ve ever had comes from South Carolina. It’s one of the few places in the country where home cooking is preferred to dining out, so much so that even the restaurants you come across in Savannah, Georgia, or Durham, North Carolina, will often tout Granny’s secret shrimp ‘n grits recipe as their bestseller. It’s important to devour as many varieties of BBQ as you possibly can, before gout sets in.
16. Camping under the stars in Arizona
Getting to see the Grand Canyon in person is life changing; getting to spend the night there, among the nature of the desert, so far from headlights, skyscrapers and fast-food chains, is a whole other level. Really, taking advantage of camping in any of the national parks across America is something worth trying in your 20s. These places will become your go-to family vacation spots, or places you return to year after year if only to measure your own self growth in between.
17. Celebrating the 4th of July in Philadelphia
Independence Day celebrations become a series of over-grilled hot dogs and ambrosia salads as you go through life. As one of the only summer holidays not shared by anyone else in the world, experiencing the 4th of July where it all began is one of the coolest things you’ll ever do in your 20s. Philadelphia is a severely underrated city, and the community spirit is alive and well. Fishtown and Kensington are also revamping into ecospheres of diversity, food culture, and artist lofts, providing the young working class with seriously cool things to do every day.
18. Hash brownies from a medical marijuana dispensary
Buying cheap weed in Europe just isn’t as exciting as purchasing bud for a reason you completely made up. “I don’t sleep well, here’s my medical marijuana card — I’ll take seven space cakes, six cannabis lollipops, and a smoothie full of weed.” Maybe it’s not as strong as the stuff you buy on the side, but it’s legal, tasty, and something to do when you’re bored.
19. Working in the service industry
I learned so much about life from hostessing at restaurants in the USA. We’re one of the only countries whose waiters work almost entirely off of tips, and that definitely makes a difference in the way we treat customers, and are treated by them as well. The people skills you obtain from working in hotels, car rental companies, tourism offices, or clothing shops, steel you for future encounters with assholes. Plus you gain insight into the hard work that built up this country in the first place, and you probably treat people a little better as a result.
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