How It Feels to Return to the Internet After a Decade in Prison

A decade is a difficult amount of time to define. For fruit flies and children, it's pretty much forever. If you subtract my first seven years of existence—I mostly remember them as indiscreet bodily functions—ten years is also a third of my life. For the internet, quietly born in 1969, ten years is a lot or a little depending on which years you're talking about. Many of the early ones were uneventful, but the last decade can only be called revolutionary.

It's too bad I missed the whole thing.

The digital realm waits for no man. When I was sentenced to serve 12 years in prison, I knew that the earliest I would be online again was in 123 months. I was released a year ago, after ten years and three months, and my minor in computer studies has done me no good. The 21st century is no longer as fresh as it was in 2003; there's been a sea change that overwhelmed me when I returned to the real world.

The internet was once confined, but while I was inside, it managed a daring escape. Cell phones with mobile computing have brought the web to the dinner table. Social media is a new human interaction zone, which already has its own etiquette, rules, and values. It's taken for granted now that along with a camera and music player, the entire sum of human accomplishment might be found in anyone's pocket.

In prison in upstate New York, I met plenty of slow adapters who never learned to type, use a computer, or—in extreme cases—read. They lost track of the world the moment they were cuffed. Armed with magazine subscriptions to fight the obsolescence I teetered over, I read New York to know what was cool, at least in broad strokes. Music criticism tantalized me with entire styles that I couldn't hear; New York state had built its prisons in rural areas, far from the broadcasters of electroclash and bhangra. Convicts are only allowed cassettes, meaning classic rock, country music, and dated hip-hop are the chief genres available to them. Some of the 12 prisons I visited were in range of college radio stations, which allowed me to catch up a bit, but it was innovations in technology that were hardest to stay abreast of.

I read every issue of Wired and gleaned what I could from new arrivals with Facebook experience. Despite catching sight of a flat-screen television and illicitly fingering a cop's touchscreen, I felt modern life slipping away from me. It didn't help that my peers were the least techno-savvy slice of American society; they would have called themselves Luddites, had they known the term.

I was born in 1978; my cohort was the last American generation not to have a social life dominated by digital tools. I never found a parent-less house party by mobile phone. I never nervously emailed a crush, and I never gossiped about school in chat rooms. BBSes were for nerds, printed schoolwork for kiss-asses, and I used pay phones so much that I liked to think I was buying beer with quarters saved thanks to the trick of making an external connection with a paperclip, thus avoiding the 25-cent fee for a local call. Beepers were used to sell drugs, but when I struck the dealer's pose at 18, I couldn't afford a proper one. My pager had no screen and beeped mysteriously if I was left a voicemail. Raves were advertised with gorgeous flyers, and I knew all of my friends' phone numbers by heart. Still do.

Last February, there was a tablet in the car that took me home. The availability of information has thrilled me ever since. I gorged on the internet, which worked so much better than before! There was no denying that Wikipedia excelled compared with my beloved and leather-bound Britannica. Even my father's 1890s Bruckhaus encyclopedia cannot compete, and there are 130 Teutonically organized volumes of it. Porn is free now, and way more intense. I was so curious about those two girls and a cup when I could only read about them, and now I can never forget what I saw.

I'm smart enough to stay away from the games; enough of my time is eaten by social media as it is. Facebook played an enormous role in reconnecting with friends and networking. An ex-con has no better ally, and with some strategy he can tell his story himself. For a career, like mine, that requires an audience, digital exposure is a gift. Skype let me lecture to a Vancouver university's philosophy department when both the rules of parole and Canadian law forbade it. Every film and television show I missed is available. Every site lets me leave a comment. I even tweet.

But while it may seem that I enjoy these developments, the reality is more complicated. A metaphor is illustrative: In Escape from LA, Snake Plissken is played by Kurt Russell in a dashing eyepatch. He obtains a device that can turn off all the power around the globe, ushering in another Dark Age. Entering the numbers 666 will do the trick, and instead of returning this doomsday button to the president, he presses it.

I'd press it twice just to make sure.

Navigating the web is not my issue. I can vanquish a captcha after only a few attempts, and I do not fear the singularity and resultant apocalypse, whether of AI, nano, environmental, or other variety. But the web is part of everyday life now. Search engines settle every bar bet, yet deny the ice-breaking bar chatter that may have warmed your bed that night. The art of description is replaced with the accuracy of photography and video—more exact, less compelling. Facebook makes sure that no one misses my birthday while eradicating its meaning. The program is the one sending me cards; relying on the feature, my friends have long forgotten the actual date. I prefer a smaller handful to think of me than a wave of wishes from people who deign to press a button. Our information flows in a broader river than ever before, but it's so shallow. Keeping the digital realm largely confined to desktop cages once contained this devolution, but no more.

Becoming a prisoner means an erosion of identity: Numbers are used as names and uniforms replace clothes. Men scrawl mottos on prison walls in a bid for self-expression. Limited minds repetitively vandalize with slurs; inevitably someone is reported performing fellatio, sometimes with illustrations. I contributed, even though I can't draw.

In ironic states of mind I wrote "Yale '96" under the Blood tags and Latin King mementoes. When feeling earnest, I quoted Cicero, Omnia mea mecum porto. It fit so well, as all that was mine I carried with me, up in my noggin. Before prison, my learning made me "well-rounded" with those who liked me, "erudite" in polite conversation, and a "wise-ass know-it-all" behind my back. Inside, where 68 percent of state prison convicts do not have a high school education, I was basically a genius.

However, upon my release, I found that the sum of a lifetime processing information merely made me good at Jeopardy. Conundrums I once impressed girls by solving were easily figured out by smartphones. Arcane vocabulary in obscure tongues, the ability to thank waiters in Latvian, listing Hapsburg dominions—it was all available to anyone who could type. Via handheld devices, the internet reached out and took Omnia mea by giving it away. I'll never forgive it.

Adjusting to life after double-digit sentences was considered challenging enough that I took a class in it, perversely taught by men with 20 years inside. Even though they were the least qualified because of their decades away from society, the job had perks, so old-timers claimed. In the class, I was shown how to balance a checkbook and was warned of reentry difficulties. In prison, men turn their silverware in with great care, as losing a fork can mean 90 days in solitary. We were told anecdotes about released convicts handing their mothers spoons after meals. Crossing the street was supposed to scare me. Crowds and technology were said to be overwhelming. Granted, the cell phone in my pocket on the day I was arrested in 2003 was a black-and-white Hyundai (I think they've given up on that business) and passersby did get closer to me than inmates would, but this was nothing compared with social media. Adjusting habits only required observation, but I had a whole new arena to master.

Ten years of voraciously reading had worked, as much as possible, to keep me from falling behind. Communication with family, watching the right things on television (the news and The Office, rather than videos and sports), listening to radio and asking new arrivals all helped, but I lacked the internet's power. I hadn't been online since Compuserve worked.

It didn't seem like things could have changed much. Before my time in prison the world had laptop computers and cameras and address books and Blackberries already. But what's new is the interpersonal software, and what's shocking is how quickly and totally society has absorbed its presence. Adult social life is no less mediated by digital help. I was once invited to parties and RSVP'd by phone. Event pages perform that function today, but their interactivity makes them much more than the digital version of a preexisting thing. I can see who else was invited, who declined, and whether my friends are welcome. Googling someone is a digital background check, but once again, the information doesn't just flow one way. Expecting to be researched, I groom my image and control its presentation. This is important for those with criminal records—thanks to the press, we usually have less say in the matter. Knowing this, I maintain a website telling my own story, along with a Wikipedia entry. Having seen men serve decades under misspelled names, I know the importance of image control.

Etiquette around things digital has developed in silence, with everyone taking for granted that it's common knowledge. As a result I made several faux pas in the beginning; some of my victims were understanding, knowing about my absence, and some were not. I was taught fast lessons in the propriety of pasting things on people's Facebook walls and posting photographs without permission. I did my best by asking questions when I wasn't sure and managed to present my explosive debacle of 2003 in the best light to those who didn't know. Facebook let me back into the world in a way impossible before it, and I only got blocked by one ex. Of course, she has a felony herself—Google works both ways.

I didn't mind giving up some privacy, especially when living off my pen, to advertise my side of the story. I learned the rules and accepted that my stock of superficial knowledge was just trivia now. But I remember a world without a digital layer with fondness. Perhaps I miss a smaller pond where I was a bigger fish, or merely resent unearned omniscience after learning to count in Turkish. But I know you can't fight the future. How can you go back?

There's a way, actually. I just don't want to.

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