Nearly a year ago I boldly blindly decided to start writing a newsletter. My intention was simple - one newsletter a week, every Wednesday, written about whatever was on my mind that given Hump Day. Judged by that simplistic metric it has been an overwhelming success. I have successfully published an essay for nearly 52 weeks in a row and what I’ve written has certainly been whatever was dancing around my scattered mind. I’m batting at 100% efficiency with this goal of mine. A real Magna Cum Laude performance.
Writing a weekly newsletter for one year was never the implicit goal, however. We never do things just for the sake of doing them. That would be madness. We spend our time on things in exchange for anticipated outcomes. And, for me, my desired outcome was to improve my ability to write. To go from a mediocre writer to someone who could hold their own in a literary circle. What is a “literary circle”, you ask? I have no idea but thinking of it brings to mind images of old fashioned tobacco pipes and an idealized form of crippling alcoholism that contributes to the creative process.
And how have I done with that goal? Well, I still do not own a tobacco pipe and the only creative thing I’ve done over the past year while inebriated was bring my own screw-top Coors lite to the bar with me so that I could refill it and have a spill-proof receptacle on the dance floor (a decision I still stand by). But surely my ability as a writer would have more weight in a literary circle anyway. And to that end I can definitively say that I would still be out-of-place.
Over the course of the last year I’ve gone from literary mediocrity to slightly less mediocre literary mediocrity (mediocre+?). That may even be generous. In fact, I’d venture that many of my earliest newsletters were subjectively more engrossing than any of the previous five weekly offerings. Does this mean I’ve regressed? Probably not. But it does highlight something I think is really important to talk about:
Writing is fucking hard.
Stringing the English language together in a way that conveys emotion, or meaning, and captures the attention of your reader in a way that justifies the precious minutes of their time they spend staring at your stupid little letters is no small fish.
Writing, perhaps more than any other skill I can think of, is something that people overestimate their ability in. Most people have been writing since they began learning their ABCs and practicing them in crayon on their kitchen cabinets (sorry mom). Someone who got an A on all of their English 201 essays will always think of themselves as Edward Allen Poe even though they haven’t written anything more emotionally complex than a passive aggressive “per my last email…” since they picked up their Diploma. It isn’t until we stare at a blank page that the daunting nature of the task becomes clear. It isn’t until that very moment that we are no longer able to hide from the anxieties and feelings of inferiority that are so easy to ignore when we avoid creating anything at all. Pretending you have a New York Times Best Seller living between your ears is so much nicer than trying to puke that best seller into a Word document. K-Fucked radio, as Anne Lamott, writer of Bird by Bird calls it, turns up to 11 the moment we face our reflection in the form of a blinking cursor on a blank white sea.
The goal is to be able to write in a way that your unique voice shines through. So that someone can read what you’ve written and hear you narrating it for them in their minds. It’s as if you’re sitting next to them, arm around their shoulder, bearing your soul to them in the best pep talk they’ve ever heard.
The reality for most of us is that our writing doesn’t sound like the best version of us. It sounds like the version of us that shows up when we’re having dinner with our significant other’s parents for the first time and we’re not sure what to do with our hands when they ask us to say Grace with them. We’re all elbows and left feet. All yes ma’ams and thank you sirs. We write as if our readers are about to ask us our intentions with their son or daughter. As if we’re trying too hard not to rest our elbows on the table because we heard somewhere sometime that it’s considered rude.
I’ve spent so many Wednesday mornings staring down a 100-word paragraph that in my head was a masterpiece but somehow came out as something that makes me want to light myself on fire. Speaking of Wednesday mornings, that’s typically the moment I decide its time to write that week’s newsletter. Hours before I need to send it to you all. I had a full 7 days, 168 hours to put something together but I avoided it until the last moment because I CAN IGNORE MY FLAWS UNTIL I START WRITING IT.
Writing is fucking hard. I knew this going in and I’m still struck by how acutely I feel the pain of it some weeks. And yet, I’m still glad I started this newsletter. Because understanding that personal writing is difficult and experiencing that personal writing difficult are two entirely separate things. In fact, they’re so different they don’t even exist in the same realm. No amount of “understanding” that writing is difficult can be traded for even a crumb of experience. There isn’t an exchange rate. Experience doesn’t give a shit about your understanding.
If I were given the opportunity to put something on a billboard that the entire world could see - ignoring the fact that a billboard that large would probably have significant ecological consequences - I would write something like “The only way to understand yourself is to experience yourself” or something philosophical like that. Prime material for one of those InspoGram accounts.
But, corniness aside, it’s a belief of mine that guides me more than perhaps any other idea I hold. We cannot think our way into living our best lives. We can’t decide what our passions are by writing things in our journals. We have to go out into the world and try things and dedicate ourselves to projects. We have to spend hours immersing ourselves in failures, and successes, and confusion, and Youtube videos from 2013 with less than 100 total views trying to find the answer to something we can’t even articulate the question to.
Over the last year I have spent hundreds of hours writing and rewriting newsletter posts. I’ve had whole days ruined when something I thought was my best work so far was left underappreciated. I spent hours stressing about topics, and I’ve filled up my iNotes with pages of shower thoughts that rarely make it into a newsletter. I have stared at my reflection in the blank page.
And I have learned I don’t care to be a writer. After I finish my 52 weeks, my work will mostly be done here. And I’m okay with that.
Over the course of this year I have not improved much as a writer. But what I got instead is a year of experiencing myself. I gained more through painstakingly writing 800 or so words a week than I could have ever gotten out of a lifetime of telling myself I could totally write a newsletter if I wanted to.
And this isn’t to say I couldn’t have improved if I want to. I could have dedicated myself completely to the craft. I could have studied the masters, and joined a community, and relentlessly sought constructive criticism. If I had done that then at this point I would still probably be shite. But I’d be less shite. The fact of the matter is that mastering a skill is impossibly slow and we vastly overestimate our ability to learn. We want to be great Now, but the greats in any field are those that have spent their lives dedicated to that sole purpose. It’s a natural law of life that you can be great at something if you want, but it will almost certainly be at the expense of nearly everything else. Greatness can come to you, but it won’t come anytime soon. As my good friend Billy Gates once said “Most people overestimate what they can do in one year and underestimate what they can do in ten years.”.
And I certainly am not going to spend the next 10 years being a writer. I’m quite content with that knowledge. What I will almost certainly do is spend the next 10 years mastering fine woodworking. Ten years from now I’ll be making some beautiful ass furniture. Because when I throw myself into that frustration I feel alive. But one year ago I had no idea that part of me existed. None of the hundreds of self-discovering journal entries I’ve written since I was fourteen mention being a master carpenter as a life goal, and yet, there it is. I had to try something and experience it for myself to learn it.
So here it is folks.
You should start a newsletter.
Or learn how to mountain bike
Or try coding
Or learn an instrument
Or start breeding ferrets
Or whatever it is that you’ve thought to yourself “hey that might be cool” because it certainly will not be cool if you just never do it.
And it’s going to be difficult, and incredibly frustrating, and you’re not going to want to hang out with your friends on the weekends anymore because you’ve almost nailed the refrain to ‘God’s Plan’ on the Tuba and going to the bar will interrupt your flow.
Listen, over the last year you may have hated every single newsletter I wrote. I certainly did. Maybe you’re just here because you enjoy reading it line by line to your significant other and laughing at how cringe it is. That’s fine. But I fucking did it. I did it and that’s pretty damn cool, don’t you think?
You are amazing and you did it dude! I think it’s the coolest. I loved reading your thoughts each week and gaining some different perspectives from you. You’ve inspired me in some of your newsletters and in some of my own writing too. Proud of you always! Can’t wait to buy a dining room table from you one day. Love, Soup