5 Mistakes Every Graduate Should Make

This time of year, everyone’s dolling out advice to graduates. I truly enjoy a good college speech (the one by George Saunders to the students of Syracuse University and the one by David Foster Wallace to Kenyon College come to mind as examples of oratorical awesomeness), but, perhaps unsurprisingly, I’ve never been asked to give one. Like many, however, I have a few thoughts for young adults emerging from the cocoon of semi-structured days punctuated by impromptu Frisbee games. And whether the Internet likes it or not, I’m sharing my two cents.

To start, I’d like you to think about the army of the Unsullied in Game of Thrones. Since the Unsullied’s original masters believed that those unencumbered by sexual impulses would make better warriors, they castrated the young boys they conscripted before training them as slave-soldiers. Sounds like a pretty terrible lot, right? But when Grey Worm, the man appointed to lead the Unsullied from among their ranks, is asked about his bad luck, he expresses that if he had not been enslaved, he would not have been freed, eventually, by Khaleesi, a woman he respects and admires; he would not have been chosen to be commander of the Unsullied, a position that brings him honor; and he would not have had the good fortune of meeting Khaleesi’s right-hand woman, the beautiful Missandei.

Grey Worm’s reasoning is powerful, and not just because he manages to maintain a positive outlook in spite of experiencing castration and slavery. The underlying message behind his philosophy is that you can’t ask “what if?” without upending everything else within a continuum. So when you let yourself think: What if I’d just prepared a little better and nailed that interview? because you weren’t offered a certain job, you also have to consider that studying harder may have altered every other forthcoming event, including all the good stuff, like taking a long walk to unwind and bumping into a smart, attractive guy or girl with whom you fall madly in love.

Rather than entertaining regret and invoking the counterproductive what-if line of thinking, it makes sense to extract a nugget of wisdom from every experience, especially the most upsetting ones. That way, you can modify your future behavior as necessary instead of ruminating over the past. By choosing to learn from failure, you effectively strip it of its negative connotation. As Ryan Holiday demonstrates in The Obstacle Is The Way , many of the most valuable life lessons are gleaned from missteps.

In short, it’s not such a bad idea to fuck up! Here are just 5 “mistakes” worth making.

1. Have a one-night stand

No-strings-attached sex has a pretty bad reputation, but there are things you can gain from it besides a guilt complex or an STD. To be clear, casual sex doesn’t have to mean unsafe sex. So use protection, but be reckless with your feelings and embrace the moment by sleeping with a stranger while you’re still young.

Why? Because as you age, the truth is that it won’t be as easy to orchestrate a one-night stand. Things like children and responsibilities and wrinkles tend to get in the way. Plus, if you end up feeling sad about the whole thing, you can rest assured that you’re not the type who should partake in carefree hookups instead of wondering whether you’ve missed out for the rest of your less-likely-to-get-laid life.

2. Party your face off at the least appropriate time

While working as a bond trader right out of college, I typically went to bed around 9pm so I could be on my “A-game” by 6:15am the following day, by which time I was expected to be at my desk. Unless entertaining clients, I rarely went out during the week. But one early summer night during my third year, I met up with a childhood friend for drinks at an outdoor bar and we ended up dancing until 4am. By some miracle, I woke up—fully clothed atop the covers, of course—in time for work. My hangover was wretched, and throughout the next 12 grueling hours I was barely able to perform my duties.

But guess what? I lived! And the bank that employed me managed to scrape by, too. I’m not applauding consistent irresponsible behavior, but I’d argue that you’re doing yourself a disservice if you behave responsibly all the time.

3. Splurge

Around age 16, my sister was in a car accident that left her with minor facial wounds caused by shards of windshield glass. The at-fault driver’s insurance company ended up awarding her a settlement fee of about $2,000, which was a lot of money for her at the time. But she didn’t labor over what to do with the extra cash for more than a minute. As soon as the received the check, she called up her best male friend and invited him to join her for dinner at Le Cirque, a pricy New York City restaurant.

My sister spent almost the entire sum in one sitting, but she had the time of her life dressing up and indulging in exquisite French food within ridiculously elegant surroundings. I remember being incredibly impressed by this as her younger sibling. Yes, credit card debt is paralyzing. Yes, saving is wise. But sometimes, you need to fuck the rules, waste some money, and make a memory.

4. Volunteer to do something you’re totally unqualified for

It’s not usually a good idea to misrepresent your skillset. But once in a while, consider raising your hand when the boss asks who can take on a task requiring talents you don’t have. By cornering yourself, you might just end up more motivated than ever to expand your expertise. No matter what, you’ll end up acquiring a new skill, even if that skill is learning how to humbly admit defeat.

5. Date the wrong person

Sometimes, it’s unequivocally clear from minute one of meeting someone that they would make a poor romantic match for you. But while there’s something to be said about instincts, there’s also something to be said about questioning your kneejerk reactions. Operating on autopilot without performing crash testing once in a while is super dangerous. So I would encourage you to date someone you suspect is entirely wrong for you at least once, no matter how much of an asshole or a narcissist you suspect they are.

Doing so will serve to illuminate one of two truths: 1.) you were right, or 2.) you were wrong. If your initial impression proves accurate, your gut gets a gold star and you can trust it wholeheartedly moving forward. If you were wrong, you just saved yourself from holding onto assumptions that may have deprived you of the ultimate reward: love!