A Letter To My High School Guidance Counselor

Dear Mrs. Sewards,

I hope this letter finds you well, It’s been over ten years since we last spoke. I’m writing you because I assume you find some satisfaction in hearing about the success of your former students. To say that I’m doing “well” would be a great understatement. I’m doing fantastic. I’ve made a series of responsible decisions and pursued goals that have helped me become the man I am today.

You may not remember this far back, but during one of our three meetings, you told me I was not going to amount to anything, and that I wasn’t “college material.” I remember it really well. In fact, I replayed that moment over and over again in my head for the four years I was in the military, but I’m sure you didn’t mean it like it sounded. You were just doing that tough football coach encouragement thing probably, LOL. I definitely see where you were coming from. I mean, college admissions are incredibly strict these days! (Have you even tried getting into the University of Phoenix? The application form takes at least an entire hour to fill out!)

I’m really glad you talked my parents out of sending me to art school. All I would’ve done there is paint and have sex with super liberal girls. You suggested I join the military, so that’s what I did. I got to spend my most formative years on a ship with other men who often mistook my sensitivity for homosexuality. But what an adventure! I won’t bore you with the details, but let’s just say it was awesome! I received lots of discipline, and now my shirts are always ironed. Always. ALWAYS. If they’re not ironed, I’m afraid my sister will die in a kitchen fire. (Some say that’s an OCD thing, but they don’t know shit about looking squared away!)

And then there was community college. Turns out I was college material! I knew you just said that to push me though. You got a real “tough love” thing going on! What a treat that was. Working at a video store during the day, and attending night classes with elderly folks and single mothers. That’s actually where I met my first real girlfriend! And her kids! We’ve broken up since then but we’re still friends, and now I’ve got my degree, so that’s cool. Still trying to figure out how to put it to use, but that’s proving difficult in this job market. A job market I would’ve hit four years sooner, when it was doing well, had you not talked me into joining the military.

After college I decided to pursue a career in comedy, which has been going incredibly well. I’ve been doing it for almost ten years, and sometimes I get free booze for performing. Two nights ago I drove to New Jersey and did a gig for twenty dollars and a cheeseburger. I also live in New York City now! How crazy is that?! It’s super exciting. I sleep on a borrowed mattress in an apartment that I share with a Mexican family of twelve in a really bad neighborhood. (I say that’s where I sleep, but really it’s just where I go to lay down and cry at the end of the day. Tears of success of course!)

If my living situation doesn’t give you a clear idea of how successful I am, then let me tell you about my financial situation. In the last five years I’ve made over twelve thousand dollars. Ok, pick your jaw up off the floor now! I’m totally serious! I’m swimming in cash. Scrooge McDuck money! And you said I wouldn’t make it. Tell me this, does a guy who’s “not making it” own only two pairs of shoes? No, that’s a man who is living well, Mrs. Sewards. I’m living so well, in fact, that my credit score is almost back in the triple digits!

I hope you are happy to hear from me. And I hope you don’t see this as bragging. Just wanted to let you know that people in your position do make a difference! Hopefully I’ll get on television before you die so you can see me again!

- Jim