I have a few pictures of myself graduating from high school, and on a recent trip back home to Portugal I found them in a box full of other embarrassing mementos. I know, just from looking at those pictures, that I was in good physical condition, and that my hair has never been quite as luxuriously indifferent to the world since I left school.

Keeping grinning, kid.

Most of it is a blur, of course. I don’t really remember much about that day, not on the whole, except that I had very suddenly (the night before) embarked on a wildly terrifying and fun romantic whirlwind with someone I’d just met. And that I drank less champagne than I should have.

I also know I that gave a graduation speech, and that I hadn’t been the popular choice for that task. I like to think I didn’t disappoint the critics in my class: I made no mention of how much fun our class had had together, and I didn’t try to highlight the cohesion of the group, the debt we owed to our teachers, the memories we’d cherish forever.

Instead, I addressed the younger students, tried to imply (without overtly criticizing anyone) that it was worth trying to talk to those in the student body who were usually isolated, and offered some other sound bites that weren’t particularly in keeping with previous graduation speeches at that school.

Yep, I was that kid, the loner on a messianic mission.

The only things I knew were keeping me going at that time were a total faith in my ability to “do better” than I’d done so far, and the incredible relief of seeing the light at the end of what I thought to be a very dark tunnel: the end to five years at an expensively impersonal boarding school.  They were years of feeling utterly alone, and although I didn’t quite want to admit it at the time, a lot of that loneliness had come about through my own social ineptitude and my own glorification of it, the self-serving belief that chosen isolation was better than the nothingness of popularity.

It may not be surprising that it was around that time I read Kierkegaard most obsessively.

While many parents came up to me to congratulate me after the speech, what I remember most is a few unpleasant glares from my classmates as I walked off the podium. They were probably right: I was the school’s best student, and one of its unhappiest. I’d trained myself badly. I would have preferred more friends and less publicly acknowledged brilliance. I’d have tried less hard to stand out because of my achievements if I’d felt like I had a place.

But on that graduation day, smiley and enamored as I was, there was very little inside me that you could call happy. The killer part is that a lot of that unhappiness was a result of my own decisions, and had been innocently encouraged by a school that wanted a truly good student and which, in the end, was much less to blame for my unhappiness than I thought at the time.

I was publicly aggressive. Because I got along with the teachers (yep, I was also that kid), I was often given, hmm, special privileges. Sometimes they let me get away with things I really shouldn’t have been allowed to consider doing at all. That, too, was ultimately counterproductive. It made me feel comfortable not following the rules, and making up for it by being a high achiever. This is a stupid attitude to create in yourself: the idea that as long as you keep on being excellent at a few things, you are exempt from social niceties. You lose friends that way, and eventually you lose all sense of what you actually are: a mortal, flawed, egotistical kid.

When I left school, I spent a year “finding myself” in the world. Technically, I found very little of myself. I discovered ways of being more sociable (tip: ask people questions about themselves before you announce the death of civilization) and I got some travel experience.

But the most valuable part of that year, I think, was the chunk of time I spent living in Turkey. That was truly life-changing, and I wish I’d kept the true lesson of those months in mind later. I moved to Istanbul to live with a friend I’d met while traveling there the previous summer, and I set myself a stupid, helpful, reductive goal:

I would not leave Turkey until I’d spent three months talking to 30 strangers a day.

With the exception of Sundays, when I was allowed to slack off, I had to approach 30 different people every day and talk to them, however briefly: young or old, male or female, hostile or welcoming. It didn’t matter if it was only for ten seconds. It didn’t matter if it went terribly wrong. The only goal was to have a verbal exchange with 30 strangers.

Why? Because I was a wuss. I was afraid of people. I had managed to go my entire life without ever feeling comfortable around people. I’d told myself I was absolutely fascinating, and I’d proved it by being absolutely fascinating to those who bothered to notice, without ever really sitting down to ask myself whether I was okay. The short version is that I wasn’t okay. I was academically “okay”  and I had developed an unapologetically vicious sense of humor; I had a naturally athletic body (though even that deteriorated for a few years) and few obvious nervous tics.

This is Howard Roark, who never cared what anyone thought, ever. And was a fictional character.

The result was that I could be clever and funny and presentable for the first few hours of meeting someone, and beyond that I felt stifled by my own inadequacies. What was there to me, beyond what I already knew and couldn’t communicate? Even if I had interesting things to say, or assumed I did, there was always a hostility to the way I handled social situations, something irrationally aggressive and individualistic, that stopped me from making friends. It was sheer self-defense. And I hadn’t even read Ayn Rand.

Those months in Istanbul were transformative because I had to humiliate myself. I decided to get humble. Realistic. The first couple of weeks were terrifying: I relied on a Turkish phrasebook, which I would use to approach some random old man, some store clerk with nothing else going on. I’d point at a Turkish word and ask them how to pronounce it. They usually looked amused, and helped me out. Then I thanked them and left the scene. That was one. Only twenty-nine more to go.

I knew it would pay off, because it was logical that it should pay off. Talking to thirty strangers a day is scary even when you’re “normal” or well-adjusted. I was no longer able to come across as absolutely fascinating for a few hours, and then crash and burn. I had a few seconds of a stranger’s time, multiplied by thirty. That was it. Many of these people spoke no English. They looked at me as if they thought I was the weird thing they’d seen that day, and I probably was. I had a forehead covered in sweat, I kept grinding my teeth, and there’s also this: I was walking around asking people how to pronounce words in Turkish.

But after the first two weeks, things picked up very, very quickly. It was a dramatic difference. I started making friends. The scary part died down, and it turned fun. Because I didn’t know anyone there except the friend I lived with (who worked at a fashion design office until midnight every weekday, and so couldn’t keep me company), I had to start from scratch. I went from having no sense of what was happening around me to getting the numbers of many new people.

I remember a dude with a ponytail called Ugur in particular, because we both played bass guitar and I met many new people through him. I went on dates, and wrote a lot of songs. An unusually poppy track that I recorded recently features a section that I wrote back then. (It’s the obnoxious “I don’t wanna go home again!” part, which probably isn’t surprising.)

Kierkegaard’s handwriting here spells out the following words: “I should really get a social life.”

What initially took me four or five hours, with a lunch break in between, ended up taking no more than two on a normal day. I knew the most crowded places (my favorite was Taksim, which is worth witnessing for yourself if you ever go, because some vendors will try to sell you your own shoes if they feel cocky; when you sound American, you make an obvious target) and I went out there, talked to my strangers, and left.

Sometimes I cheated: If I talked to someone who was in a group, I counted every single person to whom I addressed at least a word. But that was okay. I was happier.

I have never been quite so sociable since. It’s a shame that, over time, I forgot the biggest lesson: that I was only happier because I’d tried to overcome my own pathologies. I’d admitted to myself that there were things to work on, and then I’d gone out and tried my best. When I left Turkey I felt better than I had ever imagined feeling.

I went to university, and fell prey to many of the traps of undergraduate life: inflated sense of my own understanding of the world, libido, and a tragic forgetfulness when it came to recalling how much happier you can be when you just admit you’re still learning to learn how to live.