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Sketched this idea out this morning and whipped it up during lunch as some practice with Illustrator. This came out of the thought of what if Monday the 13th was treated as an overly lucky day? Much in the same way we make out Friday the 13th into an unlucky day:


Despite repeated admonitions that I could be whatever I wanted to be, I never determined that to actually be true. Surely, they were talking to the other kids, not me.

When I was smaller and more imaginative, I used to dream of being an astronaut. I’m not even sure why, I didn’t have a telescope and I didn’t love flying, I think it was just the vastness of the sky that did it for me. That and all the science fiction, I’m sure that had something to do with it. And then, at some point in elementary school, a teacher stated clearly that astronauts had to have perfect vision. Suddenly, the dorky glasses on my face went from the thing that gave me sight into a horrifying defect. I kept my mouth shut about the astronaut thing and slowly let that dream die. After all, there could only be a few astronauts traipsing throughout the universe, and they needed perfect vision.

There were other career ideas along the way: poet, rock star, novelist, videogame designer, artist, computer programmer, carpenter… Each were killed off for one reason or another. Money, talent, or resources; nothing all that compelling in retrospect. Nowhere in my life plan did “Work in Business” show up. In fact, for a while I explicitly derided that as a potential future (mostly in college, when you can get away with those things). I’ve always thought the pursuit of money for money’s sake was silly—yet, here I find myself in a job with that as a sole reason I show up every morning.

Sometimes I play this little game with myself where I ask what amount of money would it take to satisfy me in my current situation. By the time I get to the point where I’d call it worth it, it’s worth it because I could pay someone else to do my job for me. However, I don’t play the reverse of that game as much as I should: what if I was doing what I loved? What’s the least I could get paid and still be satisfied? That number is much much lower.

That game leads me to thinking about Solomon from the hit book, The Bible. When asked by God what gift he wanted, he asked for wisdom and knowledge. God ended up giving him that and all the other things he didn’t ask for. Then later on in life Solmon wrote down his ruminations on what it is that’s important in life. His conclusion after tasting of every fruit off the vine of decadent living was that one should merely enjoy their life. To enjoy their work, enjoy their food and drink, enjoy those around them. To live well, Solomon concluded, is to find happiness in life and to know that death—while unavoidable—should do little to distract us from the industry of happiness.

I’m coming to the conclusion that despite some basic commitments to one’s family, faith and friends, at some point you need to start extricating yourself from situations that are impeding you from being happy and fulfilled and putting yourself in one’s that do make you happy and fulfilled. So then, I’m left with the following: my job situation is not right for me. It’s leading to stress and making me into someone who is unhappy and dissatisfied. Perhaps exploring the stars isn’t in my future and never was, but I’m finally ready to admit that perhaps I was wrong to lay some of the other dreams to rest.

Possible futures I’m bandying about. In rough order of attractiveness:

  1. Find another job similar to what I have right now with a smaller company. The hope here would be to find a more agile and open team to work with. I want leeway to experiment experiment and have power to make actual decisions.
  2. Freelance copywriting and content strategy.
  3. Devote myself to learning how to program and look for a job where I can support myself while I’m getting caught up.
  4. Devote myself to learning design and look for a job where I can support myself while I’m getting caught up.
  5. Grad school for Design (assuming funding can be secured).
  6. Grad school for a BFA (assuming funding can be secured).
  7. Apprentice—or just work with—a carpenter of fine furniture.
  8. Apprentice—or just work with—a luthier (string instrument maker).
  9. Professional photography: combination of assisting, selling photos and portrait work.

Or some combination of the above.

Two days ago I met my girlfriend’s grandfather for the first and last time. He passed away early this morning after a tough last few weeks.

He was very very ready to go and made that abundantly clear to us many times while we were there. Near the end he was having an extremely difficult time talking, but that didn’t stop him from graciously chatting with us through the pain and cracking jokes while doing so. Best of all, to me, he told us that one of his regrets was that he had never grown a ponytail.

I’ve been thinking about that last little humorous confession of his pretty much since he uttered it, mainly in terms of this question, “What are the things I’ll regret not having done on my deathbed?” There’s a big overwhelming list that starts swimming through my head at that thought and few—if any—are related to what it is I do for my day job these days.

To be morbid for a minute or two: if I were to take ill right now the only thing I’d be thankful for related to my job is that I have insurance. Not that I got the opportunity to do this or that, but simply that I wouldn’t be putting anyone else in a financially tough spot. The primary reason I’m at my job is because it’s a security blanket. Aside from working with cool people I’m there because it’s a steady income and let’s me go to the doctor without thinking too hard about if I can afford it.

I don’t want to get to the end and wish that I’d spent my time doing something else. Perhaps I’m just whining and not seeing why my current scenario is actually pretty great. Maybe I’ll come back to something like it in a few years after trying something else, but maybe I won’t.

Isn’t that enough reason to give it a shot? To grow the ponytail? Maybe you just laugh and cut it off and move on with life. But maybe you just found something that finally makes you like the way your head is shaped.

This is a continuation of a series of posts on my Job Search. I’m blogging as a cathartic exercise and as a way of being intentional about the process. Here’s Canto 1.

Back in the day, I was hired to be a blogger. The job title was “Content manager,” but this was three years ago when that more or less meant “Blog like crazy.” This was before companies were spewing money at chasing every social media whim, so the fact that we had consistent blogs put us way ahed of the curve. I loved it and it was putting my English degree to fantastic use.

Over the past few years though I’ve seen the responsibilities of the job shift drastically. I took a minute to chart it out just for kicks. The main thing to keep in mind is that the dark blue line is the “Blogging” one. Watch it go down over time as other things go up:

Note the dark blue line

The first major upheaval happened when, as part of an ill-fated restructuring, I was told to either walk or to take the newly minted job of “Online Advertising Coordinator.” A coworker graciously went to bat for me and ended up splitting those responsibilities, with me taking the lead on the Online Ad part of it and he the blogging front.

(Later, it’d turn out that the almost firing was largely a political move related to the death throes of the company, the Ad responsibilities never quite ended up taking all that much time; however, it was a taste of what to expect in the coming years.)

When I took the job with The Corp I signed on as a Content Manager again. However, due to the circumstances everyone who went to the Corp more or less ended up having open ended job descriptions. If you knew how to do something, that was in your job description. If something needed doing, you did it.

Looking back, I don’t think The Corp had an inkling of how best to use us. They hired us because it was cheaper to hire us than 1. Risk losing the deal for the properties we were attached to over feelings and emotions 2. Hiring contractors to figure out what the heck was going on with our sites and do the minimal tasks needed to keep them going.

So, because of that environment we all ended up taking on more duties. For some of us it was just working too long hours, for others it meant doing things you’d never done before and pretending you were a professional:


Our designer jumped shipped before we went to The Corp and rather than hiring a new one I became our defacto team designer for all the low level stuff. We thankfully still contracted out the real hard work. Practically, this meant banner ads and mockups galore and any small tweaks that needed doing. Recently it’s been newsletters as well (see below).

On the whole, I actually enjoy this, but I find it constantly amusing that I was even given the opportunity. Two jobs before this job I’d used photoshop to resize and do minor editing of photos, now I was designing things that hundreds of thousands of people were seeing. Trial by fire and all that.


Like the proverbial frog in boiling water, this shift happened slowly. About 10% of what I do is help out with support tickets now, up from 0% two years ago.


This is the biggest change. I signed on as someone who was an ideas writer. The advertising and marketting stuff was left to other people or very rarely handed to me to do. At The Corp I’ve had to draft things that I’d consider one step above press releases, which are themselves the most soul-sucking sort of writing ever invented. No one likes writing them, no one likes reading them.


Anyone who has ever done an email newsletter can tell you that it is the absolute worse thing ever. Email clients are finicky with HTML and CSS (ha!), there are crazy restrictions, and even if you do your best to do it “right” you’re more or less teetering on the edge of being a spammer. Plus, it’s an industry that preys on people who don’t quite get technology. There are a million better ways to get content than through a newsletter, yet, people sign up for them. So, I dutifully copy and paste content that would be better served as an RSS feed or in a blog. About 30% of my time is spent doing this these days.


While I don’t think that any of these duties fall outside of what my role might be required to do, I take umbrage at how they were added on: mainly as a result of managerial changes above me. Looking back on it now there’s a sense that I had little to no control over how this job evolved, or even recognition from above me that it has drastically changed. I’m willing to shoulder much—if not all—of the blame though, since I’ve done a poor job of defining what it is I want from this “career.” Which, of course, is a topic for another time.

About a week or two ago I decided that it was time for me to move on from my current job to something else. Or to put it another way: it’s quitting time.

I have a lot of reasons; many of them are good, some are petty, but the main one is that at the end of the day I’m not all that happy with what it is I just did. And as I’ve thought through what this burgeoning job search is going to be, it’s become clear that I want this process to be more thorough than the last one. Hence, the blogging thing. Hopefully documentation will lead to organization.

As a sidenote: I’m not a fan of bloggers pronouncing series posts, because 90% of the time there’s only one post in the series. So, no promises on thoroughness.

If I was being honest—and that’s one of my goals in all of this—I’d have to admit that I more or less took the path of least resistance during my last “job search.” The company I had been working for was shuttering and selling off its properties to various other players. I got offers to two of those players who were gobbling up our websites. Both offered me the same pay and benefits (after negotiations, that is). One was a for-profit corporate gig (henceforth referred to as The Corp), the other a non-profit.

The non-profit one was with a bunch of fun and interesting people and meant that’d I’d get to spend all of my time working with our smallest site that—at the time—I was passionate about. It was also 200 miles away, which in the end was the reason I said no.

I ended up taking The Corp gig, which meant working with the lion’s share of the people from my previous company. The new corporation had given almost all of us offers and almost all of us took them. Plus, I’d get to stay with the high profile, high traffic sites. Also, no moving. Also, also, it was a corporate business-y job and I’d decided I needed to try that at least once in my life.

From day 1 it was stifling. I was coming off of a non-profit where lunches were spent playing videogames with each other in the breakroom, and where the IT guys response to my question during the first week of “Do I need approval to install this software?” was “What? I don’t care, it’s your machine.”

The first day at the corporation we were all in ties—the first time I’d seen most of these guys in anything other than jeans and sweatshirts. Half of us had had to go out and buy suits specifically for our interviews there, and here we were doing our best impersonations of capital ‘P’ Professionalism. It was laughable. When we got our machines—mostly shiny new MacBook Pros—we were told that getting administrative access was a privilege that few in the company had, so don’t abuse it.

From that day on there was an underlying sense that none of us really wanted to be there. We’d all taken the jobs for various reasons, most of us for the same one: it was an “easy” transition and we all had bills to pay. We were lumped into a previous department with a manager who was too busy and had too little power to make real decisions, and the guy above him was uncommunicative unless he had a specific thing he wanted from us. We spent a lot of time sitting around waiting for marching orders and doing “maintenance mode” tasks.

(That last bit, the “Maintenance mode” thing, would prove to be the phrase that defined the first 8 months of life at The Corp and—to a lesser extent—every month there after. It also defined the last 6 months at the previous non-profit, but that’s another post in itself.)

At the end of the day I’d head home and try to think of other things other than the mounting anxiety that maybe this job was terrible and that maybe there was a reason I was feeling a growing sense of spiritual angst about the job, but dwelling on thoughts like that just lead to being depressed. Besides, I only had a few hours before bedtime where I’d have to get up and do it all over again. Plus, there were people who truly loved working for The Corp, maybe I’d just gotten too used to how things were at the non-profit? Maybe another day, another week, another month there would confirm something I’d been missing.

More later.

-Break your design down into modular pieces
-Make every element of those pieces easily editable. Vector graphics and scalable fonts are your friends
-You are still in the prototype stage until you find yourself reaching for your wallet to pay someone to do a large print run. Don’t obsess over inconsequential tweaks…yet
-That said, obsess over details that make the game easier to understand to a new player
-Iconography should be designed as such so that as the rules are read the pretty pictures on the board become clear. Think of it like the relationship between a dictionary and a vocbulary. Once you learn the vocabulary, you don’t need the dictionary except in special circumstances.
-To put it another way: it should not be like a map and a location. In that analogy when you are confused the location just tells you where to look on the map for more information. Rule books are annoying and boring to everyone except the person reading them.
-Speaking or rules: If you did your job well, the rules rarely if ever come out of the box after the first few rounds.
-And speaking of rules some more: a good rulebook should include a script for people to read who are bad at explaining rules
-Color is important
-Texture too
-Quality of the actual prototype goes a long way toward engaging players. To put it in human terms: your friends deserve better
-Every piece should have a place, every place should have a piece.

Working on an argyle design for a project I have in the works:

Over the past few weeks I’ve started sketching half-formed ideas for fonts in my notebook (see below for a few hackneyed rough draft attempts). It’s probably a truism of every art, but I’ve noticed that the more time I spend thinking about fonts, the more important they seem. (Watch the excellent documentary, Helvetica, if you need a primer on how seriously people take fonts.)

For good reason though, intentionally chosen fonts convey messages to readers. However, most of those messages are completely hidden from the majority of the populace.

For most people, Comic Sans just means you’re being casual. Helvetica is what you use when you need to be professional. They couldn’t tell you what either of them are called though, nor would they care. They don’t care about serifs. They’re not going to read all the blog posts you’ve read about Comic Sans being horrifying. They’re not going to get or retell any of your lame jokes about Papyrus.

Sadly, they wouldn’t even find Hipster Arial hilarious.

I think typography is ultimately an invisible art forms. They’re unnoticeable to a layperson unless they’re done poorly. It’s only going to be the other font-nerds who are going to appreciate your tasteful curlicues and careful kerning.

There are a few responses to this dilemma. I’m not ready to say one is right, probably–like most things–it’s a combination of them all: Educate the masses on fonts, continue to make well-reasoned typographical choices in your design, or start spending a lot less time worrying about which font is the “right” one for the job.

Untitled font-sketches. All errors and obvious oversights are left in for educational purposes (winky face):

Took a walk today in the woodsy area behind my apartment complex. Turns out it’s full of birds (and a squirrel).