In Lettero

A while back, I was reading through the work of Samantha over at Jill of All Trades, when I came across her post writing letters to her younger self (which was inspired by a section of Allie Brosh’s book, Hyperbole and a Half). Past me was a bit boring at times, though I figured I would try my best to address younger me in a manner befitting to the stupid shit I’m sure I did at various points in my life. As a point of order, I’d like to note that no time travelers were harmed in the making of this post.

Note: For those of you familiar with my footnoted posts in the past, I’ve changed how they work with this post. Just hover over the footnote link and you’ll see the footnote, rather than having to bounce back and forth.

To Tim, Age 6

Hi. Because you’re a kid, you’re equal parts dumb and daring. Just because you can jump off of the lowest two steps of the stairs at grandma’s house onto carpet does not mean that jumping down an entire flight of stairs onto concrete is a good idea. In addition to not being able to walk right for a few months, your mom is going to make up a story saying your dad abused you, which will then turn a fairly civil divorce into an extremely messy, three-year ordeal with multiple custody changes.

It’s just not worth it[1].


Future Tim

To Tim, Age 11

You know how you didn’t think it seemed right that your first stepmom had both of her kids in her wedding to your dad, but you weren’t allowed to do anything? Yeah. That shit is foreshadowing. She’s a maniacal, freeloading bitch who takes your dad for all he’s worth emotionally and nearly as much as your mom did financially. When she gets out of the car and threatens to leave your dad two weeks after they got married, don’t try to stop her.

On an unrelated note, this is the age you gave up baseball to play basketball. While you’ll think both sports suck as an adult, you were actually really good at baseball. Stick with baseball. It’ll be better than repeatedly screwing up your ankles running track on cinders in high school[2].


Future Tim

To Tim, Age 14

Your stepmom is about to call you a “fucking liberal pussy grass fag” because you give up playing football because you’d rather run cross country. The only thing you were good at was kick returning, so it’s not like you were going to see the field anyway. Besides, the other kid in your grade who also returned kicks breaks his arm on his first kick return in high school, while you get to play trumpet and hang out with your friends.


Future Tim

To Tim, Age 16

Sophomore English sucks[3]. You have a horrible teacher who favors football players without question, and after you question her definition of first-person perspective (which, even looking back 10 years later, is still horribly incorrect), she WILL seek any opportunity to make you feel like a shitty student.

Stick it out. You’re going to get two things out of that class that you won’t get anywhere else. First, you’ll take 15-20 grammar tests in the semester, which are the only thing that keep you afloat GPA wise. These will come in extremely handy when you work to become an author later in life. Oh…and about that author thing. When said teacher tells you that you’re a terrible writer and that you should never attempt to write or go to college, it’ll piss you off enough that you’ll consider dedicating your book to her[4].

Fun fact: you’ll never find motivation quite like someone telling you that you can’t do something.


Future Tim

To Tim, Age 18

Your senior year is going to suck, as is your first semester in college. For that matter, it’s the only year in high school you’re going to hate, while that first semester in college is going to become one of the darkest points in your early life. Allow me to save you some trouble. When your high school sweetheart breaks up with you the first of 5-10 times senior year (none of which were for longer than a week), let her.

You’ll have a better chance of being productive in your first two semesters of college. You likely won’t date a rebound girl who your best friend calls “SEVER”[5] because of how much he wants you to break up with her (and her lack of brains, personality, and fiscal responsibility). Maybe you’ll get to talk to your middle school best friend for longer than five minutes without worrying if she’s jealous. The sweetheart, not the best friend. Said best friend goes away forever when you stop talking to her.

On a semi-related note, you’re really, really going to want to go to Northwestern. You don’t need to go there (after all, your eventual college choice works out pretty well), but at least consider it for longer than three minutes. At least tell someone you’re considering it.


Future Tim

To Tim, Age 19

When you’re in Spain as part of your study abroad program, you barely leave your guest family’s apartment because you’re too busy emailing/Skyping with SEVER. Go see sights. In consecutive weekends, you turn down a trip to Portugal with three guys in your group, a night of drinking with Swedish twins[6] in Granada[7], and a trip to Italy and Slovenia with the aforementioned three guys in your group. At least take advantage of one of the opportunities. It may well be the last time you go to Europe.


Future Tim

To Tim, Age 22-23

You’re about to run through four of the five worst relationships you’ve been in within the span of eight months. They’re all going to suck, but they’re all going to serve a purpose.

The first will teach you that there are some people in the world who will only make you happy if it’s in their best interests. These aren’t the people you’ll want to associate yourself with. Fortunately, the end of this relationship will be part of what spurs you to move to Arizona, which is a short-term setback for a long-term benefit.

The second one will teach you that there are wonderful people in the world who truly can treat you great. Sounds awesome, right? It is briefly, but then you realize that just because someone is a friend doesn’t mean you like each other as relationship partners. It’ll even ruin this friendship. But it will restore your faith that not everyone in the world is a dick.

The third will show you that you are capable of ending a relationship for reasons other than fear. You’ll realize you have standards and want to live up to them.

The last one will show you that just because someone has the same life goals and enjoys the same things as you doesn’t mean they’re a good fit to be with you. Much like your senior year with your high school sweetheart, this one goes on and off for a while. Get out earlier rather than later.[8]

The good news to all of this? There’s something better that comes down the path just months after relationship four ends.


Future Tim

To Tim, Age 24

Keep the cat. Your neighbor is a cockwomble.

Also, just because you lose your job doesn’t mean you’re a failure. If anything, it’s a blessing in disguise. That university you worked for? It shuts down less than a year later and rumor has it that all the employees got screwed while all the investors made off like bandits. You’ll end up working for a company that recognizes that education is just as important as experience when furthering someone’s career. You’re going to go a lot of places with them in a span of two years.

Oh, and that nerdy girl you’re dating? Start saving money for shiny things for her now.[9]


Future Tim


  1. I loved this a lot. Gave us a little more insight into you.

    Also, I think I’m going to take this idea, because it’s an easy blog point, and maybe it will help me to let some stuff out.

    • Tim says:

      Excellent. I’m glad that you liked it. Since this is an old post that I reposted, I’ll be doing a new version of this soon as well. I’ve tentatively got that set to post on the 27th.

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