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Your Twenties Are A Series Of Bad Haircuts

No, it’s not because you never know which one you’re gunna get—although I’ll admit that with haircuts that’s often been case for me.

When it comes to hair, I’ve got war stories that date back to elementary school and the pictures to prove it. It all began when I inadvertently started rocking the never-in-style bowl cut. Then at some point I pulled a Britney Spears and shaved my head. Then I passed through the fan haircut era where I’d drown my hair in thick, gooey gel and then comb it straight forward where it’d erupt into one glorious, rigid semicircle that crowned what later, during my freshman year of high school, Tyler Daily, our superstar freshman sports protege (he started on the football, basketball and baseball team), would call a “huge forehead dude.”

Although I often disdained being a “carrot top” growing up it did save me from one particularly awful trend: bleached tips. I went through a spiked phase in high school and then decided (after establishing myself in all the right social circles first) to just stop getting haircuts altogether. Then in my early twenties I went through an awkward wandering phase where I really didn’t know what to do with my hair. I once got a haircut named after some rapper I didn’t know which I thought was the pinnacle of cool but no one noticed it.

Now it’s always the same: “give me a fade on the side from 2 to 0, long in the front, short in the back, tight around the temples.”

But this isn’t a post about the history of my atrociously negligent sense of hair styles (a full account of that would have to be a much longer post). It’s a history of what my twenties were like…told through a series of bad haircuts. Let’s take a look.

I don’t know exactly when I stepped out of the Garden of Eden and first became self-conscious of my hair but I suspect it was probably around 6th grade when I began dabbling in the hard stuff—gel and hairspray. After that (and through much of high school…ok all of high school) I spent an embarrassing amount of time looking into a mirror. I combed my hair and blow dried it, gelled it and sprayed it, tried to mess it up and then combed it again. If it didn’t look just right I’d take another shower and start the process over. If I was leaving for a party (which despite my hair I was occasionally still invited to in those days) it was never without a glancing look at the mirror on my way out the front door (and then a second look in the reflection of the car window upon completing the long journey from my front door to the driveway…one can never be too sure).

I remember one time, in middle school I think, getting a haircut and the hairdresser asking me if I wanted sideburns or not. What the hell were sideburns? That never came up before. I didn’t think to ask…probably because I was too embarrassed to admit I didn’t know what she was talking about. Does everyone know about sideburns? Instead I casually answered “no, no sideburns.” Embarrassing moment averted. Except up until that point I had always had sideburns and it wasn’t a particularly trendy time at Castro Middle School to not have sideburns. My slightly metrosexual friend noticed immediately and gave me hell about it for a few days which might as well have been forever.

I reflected on the incident. My ignorance of hairstyles had caused me unwanted attention. I had stood out. Next time I would get side burns. That moment marked my loss of innocence as good as any and over the next few years I’d become increasingly self-absorbed with my hair—and as a result, painfully self-conscious of what other’s thought about it.

Monkeys in Orchha, India.
“You call that a haircut?” Monkeys in Orchha , India.

Then the pendulum swung in the other direction—or so it seemed—as I let my hair down…literally. It became pretty cool to pretend I didn’t care what others thought of my hair. So I played the part. Secretly though I was was still blow-drying it to get just the right amount of that “oh what, this? This is what it naturally does” look. By now haircuts had become a cause for dread and concern—like going to the dentist for a cavity. With long hair a bad haircut can look…well…really bad and high school was no place for a bad haircut. It could take weeks for my fragile ego to recover from the stigma of a bad haircut…and it often did.

Once I found a hairdresser who was acceptable (meaning that no one at school laughed at me or even more ideally, noticed) I never deviated from them. In retrospect, the often mediocre performance of my hairdressers probably had much less to do with their actual ability than the fact that I didn’t know shit about how I wanted my hair cut. I’d commonly walk in, sit down on their black swivel chair and immediately defer everything to them. The sheer fact they had a pair of shears in their hand meant that they must know more about my hair than me, or so went my reasoning. Then I would close my eyes and hope. Sometimes, if I was feeling brave, I left them open but I was always too scared to say anything mid-haircut. As a result I held silent witness to more than one atrocious haircut.

One time, in high school, I received a particularly bad haircut from a friend’s mom who at that point had been cutting my hair for a while. It had looked a little too much like my forty-something Spanish II teacher’s hair, which was dyed red and was singlehandedly trying (but not succeeding) to relive the never-having-existed golden days of the never-in-style bowl cut. Ms. Paulsen, who was so obsessed with Sci-Fi that she made our whole class translate Spanish episodes of Stargate, was not someone I was eager to emulate.

And as good friends in high school are apt to do, my friend Kevin immediately coined a new, devastating nickname for me: “Ms. Paulsen.” It stuck.

After that my friend’s mom was dead to me. I was like a young spoiled king who calls his jesters into court to be entertained only to behead any that displease him. Through much of college I’d continue to follow the same strategy of crossing my fingers and hoping someone else would know what I wanted. I’d strategically time my haircuts around school holidays when when I traveled the 400+ miles home which gave myself plenty of time to hide if it turned out they didn’t know either.

Bad hair day.
“You’ve angered the haircut gods!” Artwork on a Tibetan temple in Upper Mustang, Nepal.

Despite my best efforts, I was slowly beginning to wise up to what made a haircut bad. However I still had no clue what made a haircut good, or for that matter, that I couldn’t possibly know this until I knew what I wanted in a haircut in the first place.

Then on my 21st birthday I let my mom persuade me into cutting off my golden locks. She took me to her hairdresser and payed an exorbitant amount for me to get a regular haircut. It was a sly move however as I still mainly associated ability with cost. The haircut turned out not awful, which at the time was still my definition of good. But I was no longer willing to go through the awkward phase required to grow my hair long again—I had crossed the Rubicon. Plus, as a soon-to-be business graduate I had vague ambitions I might get a job. I appreciated how much less maintenance my short hair was requiring and began to wonder why I’d never thought to cut it earlier.

Not quite as self-conscious about my hair as I used to be, I slowly started experimenting. I began to paying attention to hair styles and I’d ask people questions about their hair. I started going to stylists and continued to pay way too much for a basic men’s haircut. It was ok though because I was learning what made a haircut good as opposed to just not bad. I went through a phase where I only let women cut my hair. Then I went through a phase where I only let men cut my hair.

As I grew more and more confident in my own fledgling tastes, I moved on from pricey stylists to reputable barbershops. They were less expensive but often took walk-ins only and sometimes I waited for hours to get a haircut. My barbers varied and I started recognizing each barber’s preferences and nuances. My own sense of style continued to develop. As I became more and more confident and I took bolder, but calculated, risks with my hair. Most of the time it turned out better than it would have been had I not taken the risk, but even if it didn’t it was never catastrophic the way it used to be.

Baby goat in India
“Is it safe to come out?” A baby goat in a village in the Thar Desert, India.

One time my barber suggested a trendy haircut that I later on I found out was named after the rapper, Macklemore. It involved shaving one side of my head while keeping the top long, which at the time had felt pretty edgy for me.

By now, I expected to come out of the barber shop looking better than I had going into it. I hadn’t realized it at the time but the Macklemore was a turning point. As I got up out of the barber’s chair, I had known without anyone telling me so, that I’d just received a bitchin’ cut.

However—and to my dismay—no one, besides my girlfriend and my equally style-conscious roommate, seemed to really care about my spiffy new haircut or appreciate the risks and effort it had taken for me to arrive on what I considered the bleeding edge of style. Here I was at the pinnacle of my haircut career—the high water mark—and no one even cared!

I began pondering my haircut’s insignificance in the larger scheme of life. What was it all about anyway? What did it all mean?

I never got the Macklemore again. Not because I don’t still think it’s a bitchin’ cut (it is), but because after that I no longer cared to keep up the constant effort required to maintain it.

Now, 3 months away from 30, as I walk down the seedy, shifty streets of New Delhi I know exactly what kind of haircut I want. And judging by the current length of my hair, I should have got it a month ago. But who really cares?

Now I walk into the first hole in the wall I see with a chair and a man wielding scissors. My cortisol doesn’t spike when he tells me the price will be $1.50 in halting English. Hair grows back (usually).

He’s on a short leash anyway. I know what cut compliments the profile of my face, what my hair can and won’t do and I know it needs to be low maintenance—no thanks, I don’t need any product. I don’t give it a moments thought as I sit down and say “give me fade on the side from 2 to 0, long in the front, short in the back, tight around the temples.”

I keep my eyes open and watch him closely in the mirror. It’s the first time I’ve looked in a mirror in days. If he strikes me as talented I’ll give him some creative license. If not I’ll hold the reigns tight and keep him in line.

To my surprise I recently arrived at a whole new level of haircuts, one I never knew existed back in my Macklemore days: my younger brother’s girlfriend requested he get the same haircut as me.

And you know what? It looked good on him.

Bitchin’ good.

Came in Thar Desert.
My camel during a tour of the Thar Desert, India.
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Hello. I’m Alasdair.

Hello. I’m Alasdair.

I believe that being aware of who I am and mindful of who I am becoming is the best investment I can make in my life —and that when we focus our efforts within, the rewards naturally flow outward to those we love and through the communities we belong to.