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30 Questions To Ask Yourself As You Approach 30

30 Questions To Ask Yourself As You Approach 30

1. How many days a week are you hungover and is that something you want to change?
Does a two-day hangover count as one day or two? Asking because every single one of my hangovers seem to last two days.

2. Do you have enough money saved in the bank that you could feasibly lose your job and survive long enough to find a new one?
If by “enough money” you mean, “Do you blur your eyes when checking your bank account for fear of what you’ll see? Because if so, yes.

3. Are you as far along in your life as you thought you’d be when you turned 20?
I spent my 21st birthday taking a shower on-stage with two strippers in Canada. I hope to spend my 30th birthday passing out at 10:30 after drinking an overpriced bottle of red that accompanies a Wagyu steak that my girlfriend buys for me. Does that make me mature or sad?

4. What do you want to accomplish in the next ten years that you didn’t accomplish in the last ten years?
My idea of “planning ahead” is making a note on my phone that acts as a grocery list that I end up throwing out the window after seeing how much avocados cost. I’ll be happy to make it to 40 let alone 35.

5. What’s the biggest difference you see in yourself now versus five years ago? Ten years ago?
What does it say that LCD Soundsystem’s lyric, “You spent the first five years trying to get with the plan, and the next five years trying to be with your friends again” rings way too true with me? Is that a bad thing?

6. After turning 30, what’s the next big step you want to take in life?
I’d say buying a dog to prove to everyone that I can take care of something that isn’t myself, but my girlfriend schedules my doctor’s appointments for me so I’m not even sure that’s a good idea at this point.

7. Do you consider the first thirty years of your life to be a success?
I considered moving out of my parent’s house to be a milestone so I’m not entirely sure that anything about my life can be considered “successful.”

8. If you died tomorrow, what would be your biggest regret?
I made a grammatical mistake in my last Instagram caption and didn’t see it until about forty minutes after posting. Still not sure my heartbeat has gone back to its original pace.

9. What three things matter most to you in your life right at this very moment?
The most mature thing I’ve done is limit myself to one episode of Black Mirror a night, so that’s huge for me. As for the other two, I have a nice bottle of cabernet sitting at my house that I managed to not drink this weekend and the chip on my windshield turned out to be a dead bug so everything is going pretty incredible for me.

10. What attributes about yourself do you want to remain unchanged as you enter your thirties?
Up until Snapchat changed their format, I was really good at exiting out of people’s stories before it advanced to the next person. I’m still pretty good at that on Instagram stories, so I guess that.

11. What’s your biggest fear as you enter the next phase of your life?
That my genes will take a turn for the worse and my hair will immediately begin to fall out. I’ve always been under the persuasion that you can get through life being either bald or fat, but never both. And if I’ve learned anything, it’s a hell of a lot easier to cure fatness than baldness. Or at least maintain being fat vs. maintain having hair.

12. Is there anything you feel pressure to do in your life that you haven’t already done?
My girlfriend has an app on her phone that allows you to test out fake engagement rings on your hand. What do you fucking think?

13. Based on what you’ve seen in the first thirty years of your life, what do you want to see in the next thirty years of your life?
I, for the life of me, cannot figure out why Apple hasn’t allowed us to leave FaceTime voicemails. Like, when I get home from the bar, is it a crime that I want to keep the party going by having a couple coldies with my boys who live across the country? Or, at the very least, be able to at least show them that’s what I was trying to do.

14. If you were forced to make a resolution on your thirtieth birthday, what would it be?
I would pledge to limit my drinking to one night a week. Unless there’s a game on. Or if people from work wanted to go out. Or if one of my friends was having a hard time. Or if of the weather sucked. Or if the weather was REALLY nice. Or if I just, like, wanted a drink.

15. Looking at your life thirty years in, what do you think your parents would have to say about you?
“You either need to pay me for your share of last month’s phone bill or get the hell off of our family plan.” – My Mom, Probably

16. Was there one defining moment of your twenties that you’ll cherish as you enter the next decade?
St. Patrick’s Day, 2010. I woke up with a receipt for $250 worth of shots that I don’t remember buying. What I took from that is that you always have to risk credit card fraud by calling and explaining that it was, under no circumstances, not you who bought those shots and your card was stolen. Even if that card is sitting on your bedside table next to a full (but opened) beer.

17. Did you think you’d be further along at 30 than you actually are?
I cooked chicken in a crockpot last week and have eaten it for every meal over the last four days running. Does it sound like that’s where I want to be in life?

18. Health or wealth: what do you value more?
I’m poor and am considering having to train for a 5-mile race on Thanksgiving day because I’ve worked out twice in the last calendar year. Assuming that I value either of those things would be downright foolish.

19. What do other people value most about you?
I’m pretty sure all my friends hate me but know it’s too aggressive of a move to kick me out of the group text and/or stop inviting me to our regular bar rotation for fear that I’ll just show up and make things weird.

20. Do you put others before yourself, or the other way around?
Let’s put it this way – if all of my friends jumped off a bridge, I’d jump off with them because peer pressure is my sole reason for doing anything in life. I’m both self-serving and squad-serving at the same time.

21. At the end of the day, what motivates you?
I’d say my loved ones, but if I were hooked up to a lie detector test I’d probably have to say, “Buying Yeezy Boost 350s and athletic clothing that costs more than business casual clothing.” But I’m not, so it would definitely be my loved ones.

22. What hesitations or fears are holding you back from being the person you want to be?
I live every day in fear of everyone that surrounds me realizing that I’m human trash. As long as I don’t outkick my coverage in my personal or professional life, I should be able to maintain this until I’m (hopefully) forced into early retirement.

23. What’s something you’ve always wanted to admit to yourself but haven’t been able to muster up?
As much as I want to look good in joggers, I know they just make me look like I’m an overweight dude who was too lazy to put on real pants in the morning.

24. What’s one habit that you know kicking would increase your quality of life greatly?
You know when you get up in the morning and you really have to pee? But then you just sit there in bed and think for twenty minutes, “Man, I really have to pee”? Yeah, I want to be the type of person who gets up and pees. Imagine being that person, man.

25. What do you say “no” to that would inevitably turn you into a better person?
Uh, a benefit of my job is a $10/month gym membership that I essentially don’t use because being able to buy two-thirds of one craft cocktail is obviously more important to me at this point in my life.

26. What steps are you willing to take to be the person you want others to see you as?
I would literally have to get plastic surgery to turn my chin from Lena Dunham-esque to Ryan Gosling-esque. And can I change my answer about what I need to admit to myself? Because having the same jawline as Lena Dunham is definitely the answer to that now.

27. What is one habit that you could incorporate into your daily routine that would benefit you in the long-term?
I buy vitamin gummies because I like the way they taste, not for their health benefits. If I could limit myself to not eating ten of them at a time, I have to feel like that’s going to help me in the coming years.

28. If you could say one thing to someone from the past that you didn’t say in the moment, what would it be?
“No, thanks, I don’t need a shot right now, I’m pretty buzzed.” – Me, to every single person that’s ever offered me a shot.

29. Ideally, how many years do you want to live in order to know you led a fulfilling life?
If I’m too old to bend over and pick up the gimme that my elderly buddy on the golf course gave me, take me out back and mercy kill me.

30. Are you happy?
You’re asking the same person who just admitted to himself that he has a Lena Dunham chin. Does this look like happiness to you?

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Will deFries

Will deFries (@WilldeFries) is the world's foremost authority on Sunday Scaries. Writer, Editor, and Content Manager at Post Grad Problems. Email me at will@grandex.co.

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