I am a city boy. I was born a city boy, and aside from Summer weekends in the South Jersey pine barrens, [1] I was raised a city boy—more specifically a Northeastern-US-city boy. I get nervous when there’s nothing around me taller than six stories. Nature bothers me. It’s nice to visit the “great outdoors,” but after a day or two, I just want artificial light, traffic noise, and to be able to walk somewhere for a slice of pizza. I’m not agoraphobic, but I do prefer close quarters. I value efficiency of space over room to spread out. I like to live high up, and I like to travel underground. I like to be anonymous. I like to be able to walk into a pharmacy, buy a box of prophylactics, and not have to worry about who sees me. Give me the city. Give me the big city. Give me places to go, things to do, people to see, and people to see me. Give me the option to live without a car, to walk to the grocery store, and to have actual weather.

My city, my home, has been Philadelphia for most of my life, but I’ve wanted to live someplace bigger for a while now. My sights have often cast themselves north, to New York City. It was a place, I thought, well suited to me, and ten years ago, I picked Polytechnic University in Brooklyn for college to give it a try. After a few difficult months of rooming issues, I eventually found myself settled in, but my place at the school never really gelled. I took the same Introduction to Pre-Calculus class seven times in three miserable semesters. After earning a 1.2 GPA, I was politely told to vacate the premises and never darken their doorstep again. I was more than happy to. [2] However, this meant I couldn’t stay in the big city any more. I would have needed a place to live, and money to pay for it. I didn’t have either. I had to tuck my tail between my legs, and slouch back home a mass of chagrin and shame.

While I didn’t settle in at the school, I became part of the city. When I left, I left behind dreams, and I left behind a wonderful person as well. Even as my academic life collapsed around me, I had found someone important and special in that city, and I wanted to get back for her, even more than for myself. Love has a tendency to do that to a person. Sure, we are now a two hour bus ride and an hour subway ride from each other—instead of just the hour subway ride it was before I moved home—but that extra two hours made all the difference. Thankfully, we’ve made it work, but it has been hard spending over seven years of our eight and a half year relationship separated by 115 miles. People have been separated by further distances, for longer, but I am not them.

My plan was to re-try college at the Community College of Philadelphia, pick up an Associate’s, enroll in a school in New York City, and try again. I got two out of the three, then ended up having to get my Bachelor’s in Philadelphia as well. [3] “Fine,” I told myself, “I’ll finish my education here and get a job up there.” No luck. I ended up taking a miserable job here, and got stuck for a time. I have a lot to say about that job, but that’s for another time. Still, with money coming in, I decide to live on my own and made the move to West Philadelphia. My new plan was to make a go of the crappy job for a year, and if I didn’t like it, start looking for work in New York. One big reason I took the job in the first place was that they had an New York office, and I thought I might be able to transfer up there. Turned out their New York office was just the second apartment of one of the owners, which says a lot about the place.

Fourteen months later, I was fired. If I were more clever, I would have seen that as my time to move, but I thought it would be smarter to stay local, collect my unemployment, and look for work in two places at once. Thus, I spent a year in the wilderness. I was saved by a low-paying, mind-numbing government job, but it was something. That was a year ago, and in that year I’ve struggled to find some direction in my life. All I know for sure is what I don’t want to do, and among the things I don’t want to do is stagnate. I don’t want to sit in the little fabric-covered box I sit in for eight hours a day, doing the exact same things, over and over again, until I’m 67 and can retire. That path leads to ruin.

This move is a chance to shake everything up. I will be leaving behind my home town, my apartment, my family and the social life I have slowly fallen into here. They’ll only be 115 miles away, not out of reach. It will be a goodbye, not a farewell. Still, it’s scary. Sometimes I wonder why I’m so willing to put everything I’ve built aside and try something new. Maybe it’s insanity, maybe it’s Saturn’s return. Maybe it’s both. Once again, I don’t know what I want, but I know what I don’t want. I certainly don’t want ten times more of what I have now. For God’s sake, I am ready, at least, to be scared shitless and stop doing what I am expected to do, and go do something new and different. What, specifically? Hell if I know. But I will be doing it, in a new, and different place.

Just… not quite yet.

Let’s face it. I talk a big game in the last few paragraphs, but I am in a holding pattern for another few months. My lease expires in August, so the current plan is to move to New York City by August 31st. September 1st, at the latest. In the meantime, that leaves six months to make things happen: finding a job is probably the biggest concern, but I won’t let the lack of one keep me from making the jump this time. Things will happen. I am not going to die. Even still, I am done with putting it off. I am done with pissing around. The reason I am still here, and not there, is my fear. I’ve clung to my city, and my apartment, and my two sub-par jobs, because the idea of giving them up is scary as hell. Absolute brown trousers time. But, if I want to get what I want—even if I don’t know what I want—the only way out is through.

Wish me luck.

Or, if you live in New York City, offer me a job.

Until recently, I did not know how to dress myself. Well, I exaggerate. I knew what clothes were, how to put them on, and could arrange my clothing as to go outside clad in a manner that was mostly weather appropriate and in tune with local decency laws, but that still left a lot of leeway. I don’t know why I never learned how to dress myself properly. It may have been the stringent uniforms of my early Catholic School education days that left me with a distaste for ties, dress shirts, and canary yellow that I’ve only recently gotten over—save for the canary yellow part. It might also have been the adolescent infatuation I had with the “goth” thing which lead to me wearing all black in a vain attempt to be rebellious and threatening. It could also be the transition from that into an equally apathetic college wardrobe of all black because I was lazy. I don’t know.

I do know that awareness of “proper dress” came to me about the time I was about to graduate college. Facing down the idea of job interviews and life as a working man, I realized that something had to change in my appearance. I posted a question on Ask MetaFilter asking for advice on dressing like an adult, but the answers lacked some of the more concrete details… So, as I graduated college, I went from being a long-haired, bearded, chubby dork who wore monochrome to a clueless, short-haired, clean-shaven dork, who wore bad outfits, cheap clothing and a rather pretentious, cheap black felt hat. Still, I think I was more ahead of the game than some of my peers who even now somehow manage sartorial disasters that blow my mind, or just look like schlubs, even today.

It was during my period of semi-unemployment that dressing correctly really came to my attention, thanks in part to the great blog Put This On, which taught me the basic rudiments of classic men’s style. With my limited income and access to some thrift stores and eBay, I began to toss out the ugly sateen shirts and beat-up cheap shoes that I had worn to my office job. Sure, I’d dressed well enough to get the job, but that job probably would have hired me even if I had come in with only the barest minimum of interview-appropriate attire. I needed to step up my game, not just for the job hunt, but for myself.

Fear of a White Shirt

For many years, the only whites in my wardrobe were my undershirts. No other white garments even existed in my wardrobe. No white socks, no white underpants, nothing. I wore a lot of black and gray, some reds and blues, and the occasional spot of brown when I felt flashy. I remember the first non black or gray item of clothing I picked out for myself: a short-sleeved brown button-down shirt. I still have it, but not for long. The majority of shirts in my wardrobe were polyester blends, ill-fitting, and often in dark shades. It lead to a bit of teasing at my old job whenever I sauntered in wearing a bright red shirt. [1] I decided to invest in something white, just as a first step. I secured a lovely Oxford Cloth Button Down—OCBD, in the style parlance—at my local thrift store. It was as good a fit as one can get from off the rack, and looked good paired with dark denim. It was a start. Until then, my “best” shirt was a garish blue number with French Cuffs. [2] Not long after I got the first of my OCBDs, I got a full weeks worth, some with pointed collars, some button-down, and explored a new world to me: patterns.

Pattern Recognition

I never liked strongly patterned clothing. Still don’t. Stripes and things were just too darn complicated for me. Keep in mind, my idea of varying my wardrobe until about a year prior was wearing gray shirts or blue jeans instead of black ones. As I’ve grown my wardrobe, I’ve started to get an idea of what goes with what, both in terms of color and in terms of pattern. One help has been the BeSpeak app for the iPhone. It gives suggestions based on items in your wardrobe and tips on what patterns and colors suit you. It mostly focuses on suits and ties, but it is still a great resource. I now wear striped shirts and patterned ties, and thanks to BeSpeak, can even match them properly.

Suiting Up

Early on, I had made the mistake of thinking I could fake a suit. I had purchased a nice enough gray blazer, and it matched well enough with a particular pair of gray slacks I had, but it wasn’t enough. I think people could tell that I was trying to fake it. One of the most important purchases I made, early in this project, was a lovely, gray herringbone wool Hickey Freeman suit. It was a bit long at the sleeves and legs, but it was perfect interview wear. I kept promising myself that I would get it altered, and eventually I did—over a year after the fact. [3] Now that I have it back, I only wish I had done it earlier—the fit is so improved it’s insane. I look good, and I feel good in it. After alterations, the gray suit cost me a mere $80, and looks incredible. It feels great to wear a real suit, and to look good doing it. Now, I just need to get the three-piece navy pinstripe suit I found to my tailor, and I’ll really be set.

Shoes and Perish

Douglas Adams wrote an amazing thing about cheap shoes—the Shoe Event Horizon—which states that as shoe demand increases, quality diminishes, causing people to buy more shoes of lesser quality, until at last the economy collapses. I didn’t have $200+ to spend on high quality shoes, but there’s a wonderful resale market on eBay for them. I picked up a pair of $250 Allan Edmonds shoes for $80, and with care, polishing, shoe trees, and occasional resoling, they’ll last me for life. I’ve bought a few other nice pairs of shoes this way, too. The only shoes I’ve bought new were a pair of city boots that, though not exactly fashionable, are at least well made and good for the cold, wet, urban winter. Now I have shoes for almost every occasion I would need, and don’t have to pray someone doesn’t realize I’m wearing boots.

Putting it all Together

I’m far from a fashion plate, and I certainly am not trying to be. I do, however, have the ability to dress myself now, in a way that is attractive, appropriate and functional for home, work, and play. I’ll never forget visiting my parents and the look of surprise on my father’s face when I appeared with a striped Oxford Cloth Button Down, a brown sweater, and looking quite nice. I look better, and I feel better, and that’s a huge boost to my self-esteem—as long as I don’t have to wear canary yellow.

On a recent episode of Back to Work, Merlin bemoaned the struggles of using Apple’s new iCloud service. In short, iCloud fails to let Merlin have everything everywhere. He contrasts this with Dropbox, which–while lacking in Apple-like integration–does just that. Merlin’s iCloud woes echo a struggle I have in my own system, which is making sure that what I want is where I am, whether I’m at my computer, or on my iPhone. This isn’t nearly as complicated as Merlin’s struggles. I have only two devices after all.[1]

A long time ago, I wrote about having a hole in my software library, and the hacked together system I had developed to work around it. I still use that system, more or less, but I’ve run into a few holes that drive me bonkers now and then–and it all has to do with my task management system. For the longest time, I’ve used Things, which is a lovely, easy-to-use application. There’s an iPhone version as well, which is pretty solid and elegantly designed. Both work well on their own, but getting them to work together is a pain. It’s one of the few multi-platform applications I use that has no cloud-based synchronization.[2] To keep all my data from Things in concert across my Mac and my iPhone, I have to launch Things on my iPhone, while connected to my home Wi-Fi network, and let it sync with the desktop application.[3]

Look, despite what the folks at Cultured Code say about it, synchronization of something like this is a solved problem. Sync is hard, yes, but that doesn’t mean you need to re-invent the wheel when you’re doing something as low entropy as this. Case in point: Wunderlist. Wunderlist is not as nice, or as Mac-like as Things, but it does do one thing very well that Things does not: cloud sync. I can add something to the Wunderlist iPhone app, and it just appears, like magic, on the desktop app. They’ve got a solid web-based infrastructure for this, and it works out of the box. Also, Wunderlist is freeware, which is a nice plus compared to the expense of the more heavy-duty task management applications out there.

Wunderlist falls down for me in that it does not support repeating tasks. When David Allen suggests having a mind like water, I don’t think he meant it in the way my mind is. Without something popping up in my view to remind me about, say, watering the basil plant on my windowsill, I would no longer have access to fresh basil. I spent a couple days trying to kludge some form of reoccuring tasks using iCal and Wunderlist’s ability to add tasks by e-mail, only to throw my hands up in frustration after needing to break out Automator and Mail.app to do it–and finding even that didn’t work properly.

Here, someone would suggest using OmniFocus. I have tried. Lord, how I have tried. I tried it for the first time when it was Kinkless GTD, consisting of a bunch of scripts and things for OmniOutliner. I tried it again when it was in Public Beta. I tried it one last time before I wrote the first draft of this essay. All I can say about OmniFocus is that while it may work for certain people whose brains function in a certain way, I simply cannot wrap my head around it. We’re talking about an application for managing tasks. This is the sort of thing that could be done with a pencil and paper. After using OmniFocus for ten minutes, I felt so overwhelmed that I was ready to go back to a pencil and paper–even going so far as to check if the 2012 Moleskine Weekly Planners were on sale yet.[4]

So, I’m back to using Things. I stick with it, though I am well aware of other options like The Hit List, Remember the Milk, and a dozen or so other pretenders to the throne. Truth is, the minor inconvience of having to launch Things on my iPhone every morning and every evening to keep my world in sync is nothing compared to the sheer pain in the keister of switching systems now.

What I would like is something that combines the ease of use and design sense of Things with the power and flexibility of OmniFocus, has an iPhone app, some form of cloud-based sync, and a price point that won’t make me feel like I’m throwing away the $60 I’ve already spent on Things for the Mac and iPhone. There’s got to be an app developer out there who can do that.

An artistic dilemma–I would rather make fewer things that are awesome than make more things that are mediocre.

The trick, I think, is that to make more awesome things, one has to produce a lot of mediocre, if not downright shitty stuff before then. Nobody sits down at a keyboard, opens up a new file, says “I am going to write the greatest story that has ever been written by anyone,” and succeeds. Anyone who tries will likely end up paralyzed by fear. Art is as much about destruction as it is creation. This ranges from knowing that you really, really, really need to cut out that epic seventy page monologue because it slows the story down to a grinding halt, to cutting a single good paragraph out of your free-writing because you know–simply know–that it’s the only one that you can actually make something with.

A couple of years ago, my Internet Hero, Merlin Mann, wrote a profound piece called “Better”. I read it when it was originally posted, but a key point Merlin was making only hit me about ten minutes before I started writing the first draft of this piece. I thought it was more about focus, but it’s more about effort. It’s not the same point as I make in the above “artistic dilemma,” but it is related: how can I make better things? How do I become better? The perfect may be the enemy of the good, as Voltaire claims, but how can one reach perfect without at least churning out a lot of good, mediocre, or downright awful things? More to the point… how does one even know the difference?

I remember as a kid watching an episode of The Galloping Gourmet, wherein Graham Kerr, in an attempt to complete a full meal in the time alloted for a 30 minute program, ran out of space on the stove top and was forced to make pans share burners. When I look at my own set of projects, whether its state is active, stuck, not-yet-begun, or simply pie-in-the-sky, I’m left with a crippling sense of fear. “Good lord, I work two jobs just to barely stay in debt,” I shout, “and I expect myself to do all this other stuff in the limited amount of free time available to me, maintain the rudiments of a social life, and get the occasional good night’s sleep–and I want to do them even better than I do now? What is wrong with me?”

Then you come across things like The Cult of Done Mainfesto, where the point is that one should stop worrying about perfection and just get whatever project you’re on the hell done already and move on to the next thing. There’s different states of “done” in the worldview of this manifesto, and I’ll happily agree with it on a couple of points, namely: “11. Destruction is a variant of done.” and “13. Done is the engine of more.” Everything else, though, runs contrary to that aching desire to do better work. At the minimum, to do better work, I have to go through an editing stage.

Writing, like any other creative endeavor, is an iterative process. You pour the contents of your heart and mind on to the page, then you get a mop and clean it up, keeping the important bits. Part of why I don’t post on this site every week on the nose is that I’d rather what gets posted here be something really meaningful to me. ¹ It takes time, it takes effort, and it takes editing. Every morning, Ernest Hemingway wrote exactly 500 words per day, stopping in the middle of a sentence if he had to once his 500 words were up. The next day, he revised the 500 previous words, and wrote another 500. Lather, rinse, repeat. It worked, and he made some amazing works of literature. Hemingway had focus, he knew to throw down, stick to this project and only this project, and not keep his attention flitting between the pans on the stove top.

Some people can handle the stress of having a whole bunch of projects and things to do, and some people end up gibbering in the corner the minute a second task lands in their inbox before the first is done. I’m not the latter, but I envy the former–lucky bastards, with their ability to focus on all the things they possibly want to accomplish. For the rest of us, it looks like we face a serious quandary. Do you cull the weak projects from the herd (Point 11, Cult of Done Manifesto) or do you keep squeezing out crap in the hopes that something sticks to the wall? What good is being done with something if you can’t look at it and say that, “Yes, that was worth the effort. That was me doing my best. Now, let me try to do even better.”

Lately, I’ve been reading The Young Man’s Guide
by William Alcott, a 174 year old book aiming to teach young men “to be of the greatest possible usefulness.” The majority of its teachings hold up, even in the 21st Century. If there’s a regular theme in The Young Man’s Guide, it’s an attack on idleness. The emphasis is repeatedly on not wasting one’s time with trifles like sleeping late, eating and drinking to excess, and excessive time spent at leisure. ² One needs to just do the work–and do it well–and they shall reap rewards. What would a modern-day William Alcott say about The Cult of Done Manifesto?

I don’t have the answers to any of the questions I’m raising here. The last six essays on this site have revolved around the same basic ideas: getting the work done, getting better, and getting better at getting the work done. I would like to close the book on that, at least for now, but it’s the biggest thing on my mind. What matters is doing the thing that inspires me, that makes me happy, that leaves me with a sense of pride, and that’s writing good stuff. I can’t short-circuit the process behind it. I’ve tried and gotten nowhere fast.

Until recently, I described myself online and in person as merely an “aspiring writer.” Oh, sure, I wrote–intermittently–but I applied the epithet “aspiring” to my title as I had yet to actually make it as a writer. After all, I hadn’t published a novel, sold a story ¹, or landed a gig writing for pay in any form. Until something along those lines happened, I felt unfit to actually call myself a writer, no matter how much or how little I wrote. Dropping the qualifier has gone a long way to make sure I actually live up to the title I assign myself.

There’s an interview with Kevin Smith, of Clerks fame, that says much the same thing.

See, I had this little experience with my sister. She was like, “What do you want to be?” I want to be a filmmaker. She’s like “Be a filmmaker.” And I was like oh, yeah, right. And she was like “No. In your mind become a filmmaker. You’re a filmmaker from this day forward. Do everything as a filmmaker would do.”

And it’s true. It works.

It’s the commitment–and thus the accomplishment–that made him a filmmaker. If Clerks didn’t succeed, if Kevin Smith had made, say Birdemic, instead of a cultural touchstone for a generation, he could still call himself a filmmaker–he made a film, after all. I commit myself to writing, ergo I am a writer. No matter how good my work is, no matter how many or how few read my work, it’s still writing. If I do everything a writer does, I’ll be a writer.

Here’s the tricky bit. You can call yourself something while you’re doing it, but once you stop, you have to apply a new qualifier to your title: “former.” All the best writers, so they say, write every goddamn day. I can’t say that I do that currently, but it’s a good point to make. When you do a thing each day, when you finish, and move on to the next thing, you get better, and you get to keep that badge. I mean, for God’s sake, you don’t need permission to be awesome. Start, finish, and start again. It works this way in any sort of art or practice–and make no mistake, writing is a practice. It’s a practice that I am still getting the hang of actually practicing regularly, though.

Natalie Goldberg in her excellent book, Writing Down the Bones compares writing to the practice of Zen meditation. She does both, daily, come what may. I wish I had that level of dedication to the craft. Some days I am a writer, some days I am not. Fortunately, the days I am a writer are becoming more and more frequent. I’ve been trying my damnedest to find the time to write–and use it properly. It’s not just Natalie Goldberg saying this; every book on writing, every book on art and creativity, makes the same point over and over again: Work on your art every day.

I’m not trying to put down the idea of aspirations. Aspirations are fine things: they guide us and give us something to work toward–but, you do have to work toward them. No amount of The Secret type positive thinking/law of attraction/affirmation bullshit will make a finished manuscript fall into your lap. As the aphorism says, “Wish in one hand and shit in the other, and see which piles up first.” Now, I’m done with wishing. ² If I want a finished manuscript in my lap, I’m going to have to write it. I am going to write it, because that’s what I do. I am a writer.