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The Grown-Up’s Guide to Lollapalooza

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10 Tips for Having Fun at Music Festivals (Without Wondering if it’s Socially Acceptable to Take a Napping Break)

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As I stood watching the headliner at the Taste of Chicago a few weeks ago, I suddenly realized something was horribly wrong.

The band was great, but – my feet were tired. My back was aching. I was hot and shvitzing; the music was loud and I could barely see the stage; the gosh-darn kids behind me were tossing around a beach ball that could hit me and my friends at any moment and make us spill our drinks.

I was about to tell them to pipe down and get off my lawn when it hit me—I’ve become old.

I don’t know when it happened, but somehow I have recently turned into a boring adult. Gone are the days of PARTY PARTY PARTYYY when I could stand outside for hours in any weather, unfazed, rocking out until my ears were ringing and my throat was hoarse, all in the name of the “experience.”

No, sir, not anymore – I surveyed my closest friends and the verdict is in: these days, when it’s 100 percent humidity outside, all we want to experience is air conditioning.

But alas, despite the undeniable appeal of planting myself on a rocking chair in my living room for the rest of the summer with a Frank Sinatra record and a stack of knitting, I decided that moment at the Taste that I couldn’t give in to my inner grandma just yet. Surely, I thought, there must be a way to partake in these “young folks” events without being curmudgeonly.

And so, just in time for Chicago’s biggest music festival, after weeks of careful research (and even a successful test run at Pitchfork last weekend), I bring you: Jessica’s 10 Tips for Having Fun at Music Festivals (Without Wondering if it’s Socially Acceptable to Take a Napping Break).

Read on, fellow grandparents at heart, and then get this party started! (But please, be a dear and keep it down – Bubbe’s resting.)

1. Dress for success.

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I’m not saying show up in orthopedics and compression stockings (though, hey, I won’t judge), but maybe leave the 5-inch wedges and strappy bikini tops at home this time. Tom’s or Converse sneakers are great trendy-but-durable options. Wear something you’ll be comfortable in for several hours, and be prepared for rapid weather changes. This means loose-fitting, breathable fabrics, flat shoes, a hat, and a lightweight poncho in your bag.

Another tip you might not have considered in college: don’t wear anything you wouldn’t want your boss to see you in. Not only is it possible you could run into coworkers at the event, but also, note that by entering festival grounds you typically give permission for your photo to be used in promotional and media materials. You might not want to show up on the cover of RedEye in your booty shorts. (Or maybe you do – I’m just saying.)

2. Carry a small pharmacy with you.

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Us old folks have ailments, and it’s hard to get your groove on when you have a migraine or can’t quite digest that spicy vendor food like you used to. It’s a good idea to bring small, single-use packages of any common OTC medications you use frequently, like Advil or Tums. Other necessities: water (you’re allowed to bring in two sealed bottles), sunscreen (reapply, reapply, reapply – nothing says “prematurely aging” like wrinkles from too much sun!), hand sanitizer and of course, earplugs.

3. Make a plan.

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Confer with your festival buddies and make a plan of attack for who you want to see, and when and where to meet up if you go separate ways. It will be much easier to have this all laid out in advance than to try and figure it out on the fly when you’re surrounded by a gazillion people and have to yell in each other’s ears to talk (if this isn't already the norm for you). Related: Make sure your cell phone has a full battery before you head out.

4. You don’t have to see ALL THE BANDS!!

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This one is key – and for me at least, was the hardest to wrap my mind around. But when I realized that just because I paid for a three-day pass doesn’t mean I have to see every single band that is playing in order to get my money’s worth, my whole world changed. It’s seriously revolutionary: you can actually have more fun if you do less. Focus on the artists you really want to see, and save your (let’s face it, limited) energy for them. If you’re already pooped out by the time your favorite band comes on at 9 p.m. … what did you really accomplish?

5. You don’t have to go to the ALL THE AFTER PARTIES!!

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See above. We’re old now. We can only handle so many hours of partying per day. I mean, if you get invited to some truly amazing after-party and you want to live it up all night long, go for it, but then do yourself a favor and maybe skip the first couple acts the next day? You will have more fun if you’re well-rested. (It’s true – Bubbe knows best.)

6. You don’t have to power through RAIN OR SHINE!!

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The lesson I’m getting at here is really all about the concept of sunk costs. The beauty of being an old fogey is you don’t have to prove how “hardcore” you are anymore. There’s no reason to power on through lightning and hail just to “get your money’s worth.” If you are having a miserable time, and there’s an option of not having a miserable time by leaving, choose that option! It will be liberating. Also, the Apple store will not replace your iPhone because it “got wet.”

7. You don’t have to drink ALL THE BEER!!

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See No. 2 – our bodies aren’t the machines they once were. It’s not as easy as it used to be to stand outside in the heat all day throwing back the brewskies. The trick is to avoid dehydration, not induce it (remember, beer dehydrates you). Also, you can have beer next weekend when you’re not surrounded by sweaty people in 80-degree weather. Keep in mind that unlike when you went to a music festival in college – this time, you are over 21! (Lots over!) You can drink beer any time you want, you cool adult, you. So take it easy.

That said – you DO have to drink ALL THE WATER!! If the refill lines are too long, just suck it up and buy a new bottle. You have a job now. You can afford it.

8. Bring a towel or blanket, and plan to camp out if you want to get a good view.

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You won’t want to push through the throngs of teeny-boppers vying for a spot. (I know this is hard to accept, but … you are no longer a teeny-bopper.)

9. Or, shift your expectations and don’t bother trying to get a good view.

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Be happy with having ample breathing room in the back. Take it from Patrick Swayze – this is your dance space, and that’s their dance space.

10. Embrace your inner old person and just go with the flow!

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Don’t be embarrassed if the words, “I want to leave early to beat the crowds” tumble out of your mouth, or even if you decide to just skip the whole shebang this year. It’s better to take care of yourself and tend to your needs than to “power through” and spend the whole time kvetching. And after all – isn’t doing whatever you want the best part about being a grown-up, anyway?

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