Dear Jackson,

August 15, 2009

A lesson about fear, regret, and risk

Filed under: Life lessons — Tags: , , , — aJOHNymous @ 3:58 pm


[This takes a really unexpected and dark turn at one point. It was not my original intention to expose you to some of these things, but now I feel as if I owe it to you because it is me at my most brutally honest. I hope you don’t think less of me after reading this.]


You’re just over a month old now (today [8/15] was your planned due date) and growing bigger and stronger everyday. It’s an incredibly amazing feeling to be able to watch as you make such positive progress and begin to show signs of an individual personality.  Everyone has been telling us that you look so much like me, but I really don’t see it. I see you have your Mom’s chin and your right ear sort of looks like mine, but other than that—I can’t really see past your basic infant exterior. There are moments when you make a particular face that I can just barely make out something vaguely familiar, but they are fleeting. I guess I just need to give it a little more time.

Waiting for those familiar faces to show up has become a new hobby for me. I find myself constantly studying your face and marveling at how small you are as you lie in my arms and make funny noises. One of my favorite things to do is lose myself in thoughts of your future and what you could be like 20 years from now. It’s hard to imagine that the 5 pound baby that I’m holding will someday be talking, walking, going to school, and growing up. It’s even crazier to think that someday you’ll be a 26 year old man with a career and a family. It’s in those thoughts where I begin to wonder about just what kind of man you’ll become and what impact you could make on the world. You could grow up to be a professional athlete, a teacher, an actor, a scientist, a man of God—anything at all.

My only fear is that you’ll repeat the same mistakes I’ve made. Perhaps “mistakes” is the wrong word to use—“missteps” might be more appropriate. I like to think that I live life without regrets. Well, that’s not entirely true. I don’t regret the decisions that I’ve made in life because everything I’ve ever done has led me right here to you. It’s the lack of contemplation of certain decisions that I find myself regretting the most. There are just some decisions in life that I never gave much thought to because they involved a risk (not the life-or-death kind, but the life-altering kind). I’ll put this into even simpler terms: it’s not the things I’ve done that I regret, but the things I did NOT do that keep me awake at night.

The “things I did not do” list is always there [in my mind]; a constant reminder of how I let fear take hold and guide me toward the safe route in life. The worst thing about this list is that everything on it was a genuine opportunity that I was presented with. Pretty much all of them were limited-time opportunities as well. The fact that I can never again have the opportunity to reverse most of these decisions, even if I wanted to, really nags at me everyday. Even worse, I’ve let these nagging thoughts turn me into the cynical pessimist that I am today.

My glass is almost always half empty and everyday I wish I could find a way to make it half full. Since you came into my life, it seems as though it’s gotten worse. Let me clarify: you’ve been the best thing to ever happen to me; it’s the desire to not let you see my ridiculous negativity and have it affect your life that has really fucked me up. For the first time in my life, I have the opportunity to directly affect the life of another human being and shape who he will become for the rest of his life. Knowing how much power I currently wield over your future has only opened my eyes further to how dark I’ve let my mind get. I’ve become selfish with my thoughts and emotions. That’s not fair to you or your mother. All things considered, my life is pretty damned good right about now. I have a great wife, perfect son, steady job, nice home, awesome dog, and a loving family. On paper, it seems like I have it all and indeed, in terms of everything I just listed—I do. Yet I still feel as though I am living an unfulfilled life.

Here’s the brass tacks: I’m working at least 40 hours a week in a company and department many people would love to be in—but I loathe every second of it. I’m a glorified button pusher sitting in a cubicle ruminating over spreadsheets and ridiculous retail copy. I’m everything I never wanted to be when I was a kid. There’s an old saying that goes “I didn’t sell out, I bought in”. Well, I did just that—I bought in to the machine of monotony. I’m a hypocrite with a capital H. Being a corporate wage slave at a job I hate was everything I railed against as a rebellious youth. Yeah, I know—we all grow up sometime, right? We all have to be responsible, get good grades, go to good schools, and be good little worker bees, right? Wrong. We don’t have to. That’s the safe route. Sure, it’ll get you a comfortable lifestyle, but you’ll have to deal with the inner turmoil of leading an unfulfilled life because you were too afraid to take risks.

You know what? This is meandering quite a bit. I’m just going to start from the beginning so you can better understand where I’m coming from; the beginning—in this case—happens to be my senior year of high school. The beginning of my senior year was when I decided which college I’d be attending. It was also when I decided that I couldn’t afford (read: was too afraid to try) my dream.

I love movies. I’m sure by now you already know this about me. I had this dream when I was 17 of driving out to California after graduation, staring up at the giant Hollywood sign, and just smiling. It was to be the kind of epic road trip that they make movies about. You can see now why I wanted to do it so much. I was just a Midwestern kid who dreamed of making movies. Unfortunately at some point, I started to think of the whole idea as silly and clichéd. I began to feel as though people like me were a dime a dozen. You’ve probably heard the story by now, for every million who try, maybe one will get lucky. My first mistake was letting those thoughts of failure enter my head and cloud my judgment. Failure is always a possibility, but when that possibility turns into fear, it becomes truly dangerous to the individual.

My parents always told me to follow my dreams and once they found out what mine were they continued to support me. I was the one who let the financial issue ride the wave of fear that was beginning to drown me. As soon as I let the financial issue become more than it needed to be (to me), many more fears began to rear their heads. I began to have second thoughts about even driving out to California after graduation. I had wanted to go with my best friend Adam, but when he bailed on me to spend the summer with his girlfriend; I began to wonder if it was a trip I’d be willing to do alone. Ultimately, I decided to not go because I was too afraid to go alone. Mind you, this all happened right as my senior year was beginning so I still had the full school year to really let my mind torture itself about all this. Since I had already chickened out from driving out there for the summer, I was able to apply this same fear to moving away and going to school out there as well. At the time, I was able to convince myself and everyone else that my decision to not attend film school in California was a purely financial one. As I got older, I was forced to tell myself to the truth. I mean, come on; I wanted to make movies but I wasn’t willing to go to California (let alone New York or Chicago) to do it? I must have been smoking some amazing weed for that idea to make sense. [Sorry, my digressions can get ridiculous at times.]

There was one other nagging issue that kept me from pursuing a move out of state. To be honest, it’s really just a silly excuse that I used as back-up to the financial issue. I didn’t want leave all of my best friends and have to live with complete strangers. I couldn’t fathom the idea of having to make new friends. Ironically enough, while I was afraid to leave all of them, they’d all leave me within the next year anyway. Adam moved to Pennsylvania and came back a year later, but our relationship never went back to what it was before he left. Jake and Ryan moved to Arizona, and later, Las Vegas. All three of us remained in touch via phone calls and the internet, but it’s not the same when you can’t hang out with each other. I somehow just fell out of touch with everyone else.

So I suppose chickening out of California would be the first major decision affected by my fear of taking risks. I used the same thought process when I decided to go to school in Wisconsin in order to get cheaper tuition for being a resident. So, okay, whatever—there are schools here in Wisconsin that have film programs. I checked out UW-Madison but wasn’t too impressed with what they offered at the time so I didn’t apply there. I checked out a few of the other schools in the UW system and decided that wherever I did go, UW-Parkside would be my safety school. Parkside would allow me to save money by living at home and commuting. Besides, they pretty much accepted anyone so I figured I was a lock.

With a safety school in place I was able to narrow my list of UW schools down to one that I really wanted to attend: UW-Milwaukee. UWM had a burgeoning film studies program and was just over an hour’s drive each way from my parents’ house. I figured I could live on campus and be able to go home pretty much every weekend without hassle. This all added up to a pretty good fit for what I was looking for in a school so I decided to apply for admission to UWM as well as Parkside. A few weeks later I got letters of acceptance from both schools.

I think it was the acceptance letters that really scared me the most. They made the situation actually real. I was going to college in a few months and I would no longer be living at home with my parents and seeing my friends everyday. Life was going to change dramatically. With that realization, I started to get cold feet about my decision once again.

I neglected to mention earlier that though I desired to live in or near a city like Los Angeles, I was actually deathly afraid of cities. Yeah, so you can see how something like this would present a problem when I realized I’d have to live in high-rise dorm in downtown Milwaukee for four years. If I couldn’t take living in the Brew City, there’s no way I’d ever survive in Hollywood. I’d spent the last 18 years living in the open country and driving up and down roads with cornfields on either side. Suddenly I was about to be thrust into the polar opposite of that. No lie—it scared the hell out of me. To this day I’ll never be able to really explain why I let this absolutely ridiculous issue prevent me from attempting to live my dream, but it did. I’m shaking my head in disgust as I write this. Further elaboration on this is unfortunately not necessary because it literally was that quick of a decision for me: fuck the city, I’m going to Parkside and living at home with my parents like a bitch. [Sorry, Jackson. That’s my regretful, self-loathing inner child coming out to say ‘Hi’. He can be a dick sometimes, but he’s usually right.]

So, just like that, with neither a bang nor a whimper, my dream was effectively dead on arrival. Sure, I could have fulfilled all of my general education requirements at Parkside and transferred to UWM at a later date in order to bury myself in film studies. Sure, I COULD have done that; but I never did. I never let it be more than a tiny option nagging at me from somewhere deep inside my brain. Eventually, as I got more an involved at Parkside, that option all but died.

Today I can freely admit that the worst part about going to Parkside became the best part about going to Parkside. After one year there, I fell in love with the school and didn’t want to leave. It was small enough for me to form close relationships with a few professors as well as allow me the opportunities to get involved with on-campus groups and activities like the campus newspaper and radio station. Actually, I take that back; I allowed myself those opportunities. The problem is that the more I enjoyed my time at Parkside, the less likely I was to transfer later on. For that reason, I’ll always look back on my time at Parkside with nothing but fondness, but a small part of me will always be rhetorically asking life’s cruelest question: “What if?”

With all that said, let me bring this letter back to the present. I sit here today, a regretful 26 year old man struggling everyday to not live in the past. It’s incredibly difficult, and like I said much earlier—incredibly selfish. Ruminating over this shit is doing none of us any good and only serving to push me further into a bitter depression. I’m trying my best to be a better man for you and your mother but I fear that I let yesterday invade today far too much. By the time you are old enough to read this, I hope that the author of this letter is a complete and utter stranger to you in every way. This is not how I want to be seen by you. If you’re reading this and feel as though it’s nothing more than verbose elaboration on things you already know, then I have failed as a husband and a father. If that is the case, I am deeply sorry and I hope that you can forgive me someday.

I’ve tried to put all of this into words so many times now that’s almost maddening. I keep hoping for some sort of catharsis or comfort, but I can never find it. Reliving and recounting some of this is actually quite hard because I’m forced to revisit some of the decisions I’ve made in the past with the knowledge I have today. They say hindsight is 20/20 for a reason. I can see everything so clearly today because I have the knowledge of where I’ve been and what I’ve done as a means of comparison. I’ll be honest with you; sometimes I wish I could go back and do it all differently. I’d make the hard decisions that involved the most risk. I’d take the path less travelled and hope for glory. I think that trying and failing is better than never having tried at all. It’s not knowing what could have been that becomes crippling later in life. Living with regret is tough to do; there are no do-overs or mulligans allowed. I hope that you will become a much stronger man than I am. I want you to be fearless about your decisions and do whatever makes you happiest. You owe it yourself to never have a moment where you look back on your life and are forced to ask yourself, “What if?”

So here’s the cheesy part. I’m going to leave you with a paraphrased quote from one of my favorite movies that, interestingly enough, was released the year I was born. It perfectly sums up everything I’ve just gone over and is a fitting conclusion to this letter. Hell, even the name of the movie is eerily appropriate:

“Every now and then say, ‘What the fuck’. ‘What the fuck’ gives you freedom. Freedom brings opportunity. Opportunity makes your future.” 

– Risky Business (1983)

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