It was a haze. I remember reading The Conscience of a Hacker (aka The Hacker’s Manifesto), Neal Stephenson’s Snow Crash, and reams of J. R. R. Tolkien, falling asleep midchapter and getting the characters and action confused, until I was dreaming that Gollum was by my bedside and whining, “Master, Master, information wants to be free.”
While I was resigned to all the fever dreams sleep brought me, the thought of having to catch up on my schoolwork was the true nightmare. After I’d missed approximately four months of class, I got a letter in the mail from Arundel High informing me that I’d have to repeat my sophomore year. I’d say I was shocked, but the moment I read the letter, I realized that I’d known this was inevitable and had been dreading it for weeks. The prospect of returning to school, let alone of repeating two semesters, was unimaginable to me, and I was ready to do whatever it took to avoid it.
Just at the point when my glandular disease had developed into a full-on depression, receiving the school news shook me out of my slump. Suddenly I was upright and getting dressed in something other than pajamas. Suddenly I was online and on the phone, searching for the system’s edges, searching for a hack. After a bit of research, and a lot of form-filling, my solution landed in the mailbox: I’d gotten myself accepted to college. Apparently, you don’t need a high school diploma to apply.
Anne Arundel Community College was a local institution, certainly not as venerable as my sister’s school, but it would do the trick. All that mattered was that it was accredited. I took the offer of admission to my high school administrators, who, with a curious and barely concealed mixture of resignation and glee, agreed to let me enroll. I’d attend college classes two days a week, which was just about the most that I could manage to stay upright and functional. By taking classes above my grade level, I wouldn’t have to suffer through the year I’d missed. I’d just skip it.
AACC was about twenty-five minutes away, and the first few times I drove myself were perilous—I was a newly licensed driver who could barely stay awake at the wheel. I’d go to class and then come directly home to sleep. I was the youngest person in all my classes, and might even have been the youngest person at the school, alternately a mascot-like object of novelty and a discomfiting presence. This, along with the fact that I was still recovering, meant that I didn’t hang out much. Also, because AACC was a commuter school, it had no active campus life. The anonymity of the school suited me fine, though, as did my classes, most of which were distinctly more interesting than anything I’d napped through at Arundel High.
* * *
BEFORE I GO any further and leave high school forever, I should note that I still owe that English class assignment, the one marked Incomplete. My autobiographical statement. The older I get, the heavier it weighs on me, and yet writing it hasn’t gotten any easier.
The fact is, no one with a biography like mine ever comes comfortably to autobiography. It’s hard to have spent so much of my life trying to avoid identification, only to turn around completely and share “personal disclosures” in a book. The Intelligence Community tries to inculcate in its workers a baseline anonymity, a sort of blank-page personality upon which to inscribe secrecy and the art of imposture. You train yourself to be inconspicuous, to look and sound like others. You live in the most ordinary house, you drive the most ordinary car, you wear the same ordinary clothes as everyone else. The difference is, you do it on purpose: normalcy, the ordinary, is your cover. This is the perverse reward of a self-denying career that brings no public glory: the private glory comes not during work, but after, when you can go back out among other people again and successfully convince them that you’re one of them.
Though there are a score of more popular and surely more accurate psychological terms for this type of identity split, I tend to think of it as human encryption. As in any process of encryption, the original material—your core identity—still exists, but only in a locked and scrambled form. The equation that enables this ciphering is a simple proportion: the more you know about others, the less you know about yourself. After a time, you might forget your likes and even your dislikes. You can lose your politics, along with any and all respect for the political process that you might have had. Everything gets subsumed by the job, which begins with a denial of character and ends with a denial of conscience. “Mission First.”
Some version of the above served me for years as an explanation of my dedication to privacy, and my inability or unwillingness to get personal. It’s only now, when I’ve been out of the IC almost as long as I was in it, that I realize: it isn’t nearly enough. After all, I was hardly a spy—I wasn’t even shaving—when I failed to turn in my English class assignment. Instead, I was a kid who’d been practicing spycraft for a while already—partly through my online experiments with game-playing identities, but more than anything through dealing with the silence and lies that followed my parents’ divorce.
With that rupture, we became a family of secret-keepers, experts at subterfuge and hiding. My parents kept secrets from each other, and from me and my sister. My sister and I would eventually keep our own secrets, too, when one of us was staying with our father for the weekend and the other was staying with our mother. One of the most difficult trials that a child of divorce has to face is being interrogated by one parent about the new life of the other.
My mother would be gone for stretches, back on the dating scene. My father tried his best to fill the void, but, at times, he would become enraged by the protracted and expensive divorce process. Whenever that happened, it would seem to me as if our roles had reversed. I had to be assertive and stand up to him, to reason with him.
It’s painful to write this, though not so much because the events of this period are painful to recall as because they’re in no way indicative of my parents’ fundamental decency—or of how, out of love for their children, they were eventually able to bury their differences, reconcile with respect, and flourish separately in peace.
This kind of change is constant, common, and human. But an autobiographical statement is static, the fixed document of a person in flux. This is why the best account that someone can ever give of themselves is not a statement but a pledge—a pledge to the principles they value, and to the vision of the person they hope to become.
I’d enrolled in community college to save myself time after a setback, not because I intended to continue with my higher education. But I made a pledge to myself that I’d at least complete my high school degree. It was a weekend when I finally kept that promise, driving out to a public school near Baltimore to take the last test I’d ever take for the state of Maryland: the exam for the General Education Development (GED) degree, which the US government recognizes as the standard equivalent to a high school diploma.
I remember leaving the exam feeling lighter than ever, having satisfied the two years of schooling that I still owed to the state just by taking a two-day exam. It felt like a hack, but it was more than that. It was me staying true to my word.
7
9/11
From the age of sixteen, I was pretty much living on my own. With my mother throwing herself into her work, I often had her condo to myself. I set my own schedule, cooked my own meals, and did my own laundry. I was responsible for everything but paying the bills.
I had a 1992 white Honda Civic and drove it all over the state, listening to the indie alternative 99.1 WHFS—“Now Hear This” was one of its catchphrases—because that’s what everybody else did. I wasn’t very good at being normal, but I was trying.
My life became a circuit, tracing a route between my home, my college, and my friends, particularly a new group that I met in Japanese class. I’m not quite sure how long it took us to realize that we’d become a clique, but by the second semester we attended class as much to see each other as to learn the language. This, by the way, is the best way to “seem normal”: surround yourself with people just as weird, if not weirder, than you are. Most of these friends were aspiring artists and graph
ic designers obsessed with then controversial anime, or Japanese animation. As our friendships deepened, so, too, did my familiarity with anime genres, until I could rattle off relatively informed opinions about a new library of shared experiences with titles like Grave of the Fireflies, Revolutionary Girl Utena, Neon Genesis Evangelion, Cowboy Bebop, The Vision of Escaflowne, Rurouni Kenshin, Nausicaa of the Valley of the Wind, Trigun, The Slayers, and my personal favorite, Ghost in the Shell.
One of these new friends—I’ll call her Mae—was an older woman, much older, at a comfortably adult twenty-five. She was something of an idol to the rest of us, as a published artist and avid cosplayer. She was my Japanese conversation partner and, I was impressed to find out, also ran a successful Web-design business that I’ll call Squirrelling Industries, after the pet sugar gliders she occasionally carried around in a purple felt Crown Royal bag.
That’s the story of how I became a freelancer: I started working as a Web designer for the girl I met in class. She, or I guess her business, hired me under the table at the then lavish rate of $30/hour in cash. The trick was how many hours I’d actually get paid for.
Of course, Mae could’ve paid me in smiles—because I was smitten, just totally in love with her. And though I didn’t do a particularly good job of concealing that, I’m not sure that Mae minded, because I never missed a deadline or even the slightest opportunity to do a favor for her. Also, I was a quick learner. In a company of two, you’ve got to be able to do everything. Though I could, and did, conduct my Squirrelling Industries business anywhere—that, after all, is the point of working online—she preferred that I come into the office, by which I mean her house, a two-story town house that she shared with her husband, a neat and clever man whom I’ll call Norm.
Yes, Mae was married. What’s more, the town house that she and Norm lived in was located on base at the southwestern edge of Fort Meade, where Norm worked as an air force linguist assigned to the NSA. I can’t tell you if it’s legal to run a business out of your home if your home is federal property on a military installation, but as a teenager infatuated with a married woman who was also my boss, I wasn’t exactly going to be a stickler for propriety.
It’s nearly inconceivable now, but at the time Fort Meade was almost entirely accessible to anyone. It wasn’t all bollards and barricades and checkpoints trapped in barbed wire. I could just drive onto the army base housing the world’s most secretive intelligence agency in my ’92 Civic, windows down, radio up, without having to stop at a gate and show ID. It seemed like every other weekend or so a quarter of my Japanese class would congregate in Mae’s little house behind NSA headquarters to watch anime and create comics. That’s just the way it was, in those bygone days when “It’s a free country, isn’t it?” was a phrase you heard in every schoolyard and sitcom.
On workdays I’d show up at Mae’s in the morning, pulling into her cul-de-sac after Norm left for the NSA, and I’d stay through the day, until just before he returned. On the occasions that Norm and I happened to overlap during the two years or so I spent working for his wife, he was, all things considered, kind and generous to me. At first, I assumed that he was oblivious to my infatuation, or had such a low opinion of my chances as a seducer that he didn’t mind leaving me alone with his wife. But one day, when we happened to pass each other—him going, me coming—he politely mentioned that he kept a gun on the nightstand.
Squirrelling Industries, which was really just Mae and me, was pretty typical of basement start-ups circa the dot-com boom, small enterprises competing for scraps before everything went bust. How it worked was that a large company—a carmaker, for instance—would hire a major ad agency or PR firm to build their website and just generally spiff up their Internet presence. The large company would know nothing about building websites, and the ad agency or PR firm would know only slightly more—just enough to post a job description seeking a Web designer at one of the then proliferating freelance work portals.
Mom-and-pop operations—or, in this case, older-married-woman/young-single-man operations—would then bid for the jobs, and the competition was so intense that the quotes would be driven ridiculously low. Factor in the cut that the winning contractor would have to pay to the work portal, and the money was barely enough for an adult to survive on, let alone a family. On top of the lack of financial reward, there was also a humiliating lack of credit: the freelancers could rarely mention what projects they’d done, because the ad agency or PR firm would claim to have developed it all in-house.
I got to know a lot about the world, particularly the business world, with Mae as my boss. She was strikingly canny, working twice as hard as her peers to make it in what was then a fairly macho industry, where every other client was out to screw you for free labor. This culture of casual exploitation incentivized freelancers to find ways to hack around the system, and Mae had a talent for managing her relationships in such a way as to bypass the work portals. She tried to cut out the middlemen and third parties and deal directly with the largest clients possible. She was wonderful at this, particularly after my help on the technical side allowed her to focus exclusively on the business and art. She parlayed her illustration skills into logo design and offered basic branding services. As for my work, the methods and coding were simple enough for me to pick up on the fly, and although they could be brutally repetitive, I wasn’t complaining. I took to even the most menial Notepad++ job with pleasure. It’s amazing what you do for love, especially when it’s unrequited.
I can’t help but wonder whether Mae was fully aware of my feelings for her all along, and simply leveraged them to her best advantage. But if I was a victim, I was a willing one, and my time under her left me better off.
Still, about a year into my tenure with Squirrelling Industries, I realized I had to plan for my future. Professional industry certifications for the IT sector were becoming hard to ignore. Most job listings and contracts for advanced work were beginning to require that applicants be officially accredited by major tech companies like IBM and Cisco in the use and service of their products. At least, that was the gist of a radio commercial that I kept hearing. One day, coming home from my commute after hearing the commercial for what must have been the hundredth time, I found myself dialing the 1-800 number and signing up for the Microsoft certification course that was being offered by the Computer Career Institute at Johns Hopkins University. The entire operation, from its embarrassingly high cost to its location at a “satellite campus” instead of at the main university, had the faint whiff of a scam, but I didn’t care. It was a nakedly transactional affair—one that would allow Microsoft to impose a tax on the massively rising demand for IT folks, HR managers to pretend that an expensive piece of paper could distinguish bona fide pros from filthy charlatans, and nobodies like me to put the magic words “Johns Hopkins” on their résumé and jump to the front of the hiring line.
The certification credentials were being adopted as industry standard almost as quickly as the industry could invent them. An “A+ Certification” meant that you were able to service and repair computers. A “Net+ Certification” meant that you were able to handle some basic networking. But these were just ways to become the guy who worked the Help Desk. The best pieces of paper were grouped under the rubric of the Microsoft Certified Professional series. There was the entry-level MCP, the Microsoft Certified Professional; the more accomplished MCSA, the Microsoft Certified Systems Administrator; and the top piece of printed-out technical credibility, the MCSE, Microsoft Certified Systems Engineer. This was the brass ring, the guaranteed meal ticket. At the lowest of the low end, an MCSE’s starting salary was $40,000 per year, a sum that—at the turn of the millennium and the age of seventeen—I found astonishing. But why not? Microsoft was trading above $100 per share, and Bill Gates had just been named the richest man in the world.
In terms of technical know-how, the MCSE wasn’t the easiest to get, but it also didn’t require what most self-respecting hackers would conside
r unicorn genius either. In terms of time and money, the commitment was considerable. I had to take seven separate tests, which cost $150 each, and pay something like $18,000 in tuition to Hopkins for the full battery of prep classes, which—true to form—I didn’t finish, opting to go straight to the testing after I felt I’d had enough. Unfortunately, Hopkins didn’t give refunds.
With payments looming on my tuition loan, I now had a more practical reason to spend time with Mae: money. I asked her to give me more hours. She agreed, and asked me to start coming in at 9:00 a.m. It was an egregiously early hour, especially for a freelancer, which was why I was running late one Tuesday morning.
I was speeding down Route 32 under a beautiful Microsoft-blue sky, trying not to get caught by any speed traps. With a little luck, I’d roll into Mae’s sometime before 9:30, and—with my window down and my hand riding the wind—it felt like a lucky day. I had the talk radio cranked and was waiting for the news to switch to the traffic.
Just as I was about to take the Canine Road shortcut into Fort Meade, an update broke through about a plane crash in New York City.
Mae came to the door and I followed her up the stairs from the dim entryway to the cramped office next to her bedroom. There wasn’t much to it: just our two desks side by side, a drawing table for her art, and a cage for her squirrels. Though I was slightly distracted by the news, we had work to do. I forced myself to focus on the task at hand. I was just opening the project’s files in a simple text editor—we wrote the code for websites by hand—when the phone rang.
Mae picked up. “What? Really?”
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