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How Much Preparing is Too Much Preparing?

The ways not to overthink those important moments, from a big day at work to all-out armageddon

Until very recently, I was a firm believer in the “let’s just fucking wing it” mentality. No matter the size of the presentation or the time I had to prepare for it, I held firm in the belief that my charm and quick wit would save me from any peril that came my way (sometimes it did, sometimes it very much did not).

Major life changes have required me to be more disciplined, though, so now I’m the polar opposite: My days are planned down to 15-minute intervals, and I schedule everything, even new schedule-making. I’ve become so rigid that whenever something unexpected comes up, like my kid getting sick or my phone battery dying, my whole day is screwed. Worse, if I don’t accomplish every item on my to-do list, I inevitably lose sleep over it.

Clearly, there’s a middle ground here that I’m missing, so I turned to a few experts in their respective fields about the fine line between overthinking it, and knowing what the hell you’re talking about, in a few different scenarios. Starting with…

Tomorrow’s Hectic Day at Work

“There’s no perfect plan,” says CEO Amanda O’Reilly, who runs the personal concierge service Balance InStyle. The main thing, she says, is to keep your plans light: “At most, you want three to five things on any day’s to-do list, that way you’re setting realistic goals. Life throws you curveballs, so you have to keep a bit of flexibility in there.”

O’Reilly also shares that you’re probably over-preparing for work if it consumes all of your social life. “If you’re the type of person who constantly cancels on friends because you’re working late, you’re definitely obsessing too much about the future.”

That Big Presentation That’s Coming Up

Paradoxically, life coach and trainer Lindsay Jackson feels that the people who tend to over prepare are the ones who know the least about their topic while doing a presentation. “If someone doesn’t know the material, they’re already stressed, so that anxiety may drive them to over prepare, because they’re not confident in their own knowledge.” As far as Jackson’s concerned, the best approach is to, “Know your material well enough that you don’t have to memorize it verbatim.” Or, if you do know the material and you’re just suffering from performance anxiety, Jackson encourages you to trust your own expertise and experience.

Being overly rigid about timing also can mess you up. “If you’re breaking your presentation down into too many specific time frames, losing your place can be overwhelming,” she says. “It’s a good idea to know approximately how much time you want to spend on each area or topic, but if you sound too scripted or if you cut people off during a discussion, it will prevent you from connecting with your audience.”

The Anxiety-Provoking Job Interview

“During a job interview, you should know the basics about the company you’re interviewing for, like how long they’ve been around, what their mission is, as well as the basic responsibilities of the role you are interviewing for,” says recruiter Holly Oths. This will probably serve you better than trying to anticipate every question they’re going to ask you. “They could be a new-age hiring manager and ask you, ‘What kind of appliance would you be?’” Oths warns.

As long as you meet the minimum requirements of the position, Oths believes, “Your personality counts almost more than your qualifications. The people factor is the toughest part of recruitment — finding which person will fit in with which team can be a real challenge. That’s why you want to come through professional and polished, but you also want your personality to shine through.”

The Upcoming Vacation Where You Want To Do 10,000 Things in One Week

“I don’t know if there is such a thing as over preparing for a vacation, but you can definitely overplan it, overpack it and overthink it,” says Leslie Erickson of Mad Tuscan Travel. “If you put too much in your itinerary, your whole vacation can be a blur and you’ll come home saying, ‘What did I see?’ Planning anything back-to-back is probably doing too much — at most, I tell [clients] to schedule two majors things during the day, and that’s it.”

The Inevitable End of Days

If you’re reading this article in your personal bunker, surrounded by an arsenal of weapons, a decade’s worth of food supplies and your own handwritten “manifesto” for a post-apocalyptic new world order, congratulations: You’ve definitely over prepared. “You’re much more likely to need to move your family to safety in the event of natural disaster rather than a revolution,” shares Rob Moore, director of the Water and Climate Team at the Natural Resources Defense Council. “Remember, you’re preparing for your family’s basic health and safety, not the Zombie Apocalypse,” he says.

In the event of natural disaster, you’ll want to be able to grab a few necessities. “[You need] food, water and any daily medications. You want to take a flashlight, a first-aid kit and a good multi-tool. Paper maps of the local area may also be useful, as well as cash and paper copies of important documents like insurance policies, social security cards, mortgage info, etc., which you may need to file disaster paperwork or go to a hospital.” He also pleads that you bring your pet, and not to abandon them as so many people do.

“You’ll notice offensive and defensive capabilities aren’t on this list,” Moore laughs. In fact, rather than packing knives, guns and other end-of-the-world props, Moore recommends bringing, “Some books, games and puzzles, because disasters aren’t nearly as exciting as the movies make it out to be.”