Dear Over-Planners: You Suck and Everyone Hates You – My Take

Many of the most memorable nights of my life were nights that were unplanned, nights that diverged from their original plan, or nights that were loosely planned the day-of. There’s a beauty in that sort of spontaneity. Now, I know what you’re thinking, I sound like a girl on hinge whose profile reads, “I just want to find someone unique and adventurous,” and acts like a game show host by messaging you and saying, “what’s the most spontaneous thing you’ve ever done?” To those girls I say, first of all I’m glad to see the recent breakup is going well, and second of all, that time I responded to your message saying, “there was this one time I was traveling on a train from Budapest to Vienna, and I met a French girl named Céline, and convinced her to get off the train and spend the whole day/night together,” I was lying, and actually just seeing how long I could recite the plot of Before Sunrise before you caught on. You never did. But alas, this isn’t a blog about my Hinge conversations, although that would be a fairly interesting one. No, this is a blog about the over-planners of the world, and why they need to cut it out with their bullshit.

Here’s a great thing about being young, we have this freedom to basically improvise our way though life. But, at some point that shit stops, and we have to start taking things more seriously. So, why not enjoy the freedom while we can. If you’re a real adult, like you have a family and understand taxes and all that shit, then this blog is not aimed at you. Because if you’re a 44 year old suburban dad, I can understand and appreciate why you might be an over-planner. Your life is without joy, your best days are behind you, you’re working a job you hate to support a group of ungrateful kids. I get that your upcoming Disneyland vacation may be the death of you, which is why you over-plan and attempt to have that trip structured out from start to finish, it’s a survival technique. But, if you’re around my age and you’re over-planning every aspect of your life: Stop it. Learn to embrace the chaos of life, and of your twenties.

My issue with over-planners is this, they spend so much time trying to make sure things are going to be fun, they end up ruining the actual fun. No one has ever woken up on a Sunday morning and said, “Last night was fucking incredible, it was so perfectly structured and well-planned-out, best night of my life!” Because true fun is not born out of schedules and rigid guidelines. It is born out of impulse decisions, spontaneous actions, and often times a fair amount of alcohol. Like I said to start this blog, the most memorable nights of my life were not ones in which I followed a plan. But, for some reason, some people my age really like to over-plan. They are the same people who start to act like they’re middle-aged around the time they turn 20, and look down on their college classmates for being “so immature.” We call these people: assholes. Over-planners are the type of people to invite friends over to their shitty apartment on a Saturday night, and have a cheese plate set out on the table when you arrive. I’m a firm believer that there should be no cheese plate at any function I attend until I’m at least 30 years old. The problem is though, I’ll show up to this shitty apartment with a half-full 30 rack of Bud Lights because ya know, we’re 23, and feel like an asshole when I walk through the door and see candles being lit, and a pre-heated oven. If you’re under the age of 25, and you invite friends over to drink, and you have a pre-heated oven for like … real food, and not a DiGiorno’s frozen pizza, then I don’t want to be friends with you. And fuck your cheese plate. I don’t care if you consider charcuterie boards a hobby, you’re boring and everyone hates you.

The problem with people who over-plan a party, a night out, or a weekend away is they usually will get so stressed during the planning process that regardless of how much fun the event turns out to be, it wasn’t worth it. Your night is essentially ruined before it even starts. Don’t worry about what time you’re going to go out, what bars you’re going to go to, or what time you’re going to get home. Instead, just find some friends, have some drinks, and let the night take you where it may. Also, over-planning puts way too much pressure on the thing you’re actually planning. You get so worked up in your own head trying to make sure you have the perfect plan, that the night will never live up to your unreasonably high expectations. But, if you go in with low expectations and no plan then you can’t be disappointed no matter what happens. It’s the same concept I try to explain to all my dates, I will always impress you, just as long as you come in with wildly low expectations.

Nine times out of ten your over-planning friend is also your friend who needs to know every piece of information and consider every single detail of a plan before agreeing to it. You know which friend I’m talking about, the one who responds to your “We’re going out this Friday” text with a million questions such as, “Who’s gonna be there?” “Where are we going?” “How are we getting there?” “Does someone need to drive?” “Which bars are we gonna go to?” “What time?” “How are we gonna get home?” “Are there going to be any covers?” I think we as a society have collectively agreed we all hate these people, but for some reason they continue to act this way all the time. Don’t be this friend. Which would you rather be, the friend who gets a “let’s get drinks tonight” text at work on a Tuesday afternoon and responds, “I don’t know. I don’t really want to drink on a Tuesday. Plus, I’ll probably be tired after work. If we do go I’d probably want to go home and change clothes first, so we would most likely miss most of happy hour anyways, so it’s not even worth it. And I mean are they gonna have food at the bar, because I’ll probably be hungry. Also, neither of us will want to drive, and I don’t think I wanna pay for an Uber tonight. So, I’m probably just gonna stay home” or the friend who responds with a simple “I’m down, let’s do it.”

Another type of friend archetype that overlaps with the over-planning friend is the friend who’s always bragging about all the techniques they use to save money. I understand that most of us are young and broke, and should be budgeting our money as much as possible. I’m not judging people for being frugal, financially responsible, or people who say no to things because they want to save money. I understand all of that. Instead, I’m talking about your friend who constantly tells you about the weird website they found online, and used to buy a knockoff Bose speaker that they swear is the same quality as the real one. I’m sorry, but sometimes risking your credit card information on some sketchy foreign website, and waiting four and a half weeks for a pair of Beats By Dre headphones to get shipped over from China is not worth the $40 you’re saving, especially when you could just go to the nearest Target and buy them there. This friend also has a technique for sneaking their own snacks into a movie theater, and always sounds just a little bit too proud when they explain it to you. Ya know the friend I’m talking about, right? The one who wears a winter jacket to the theater in May just to sneak in a Ziploc bag full of microwavable popcorn from home. Congrats pal, you already spent $18 for a ticket, but you’re really gaming the system and sticking it to the man by saving that $4.99 for a small popcorn. Now, I’m not trying to advocate for people being financially irresponsible, although it can be a ton of fun. And, I know that these money-saving techniques I’m talking about are, on their face, not necessarily bad things. However, if you frequently participate in them, and are very proud of yourself for doing so, then it is fair to assume you’re probably not that fun of a person in other aspects of your life.

When I look at the over-planners of the world, I see a bunch of constantly stressed out people who are not living life to the fullest. People who have an actual answer to the question “Where do you see yourself in five years?” and not just a bullshit one that you use during job interviews, are probably not enjoying their life in the present as much as they could, or should, be. That is really the point I wanted to get across in this blog. That a fun life requires a little bit of improvisation and going with the flow. It is important to not worry so much about everything going perfectly all the time, and instead just give yourself over to the chaos.

Or, this whole thing was just a 1600-word defense of my irresponsible, naive, and childish outlook on life.





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