Lifehacking Your Looks

By Jonathan Roseland


From How to Be Cross Eyed: Thriving Despite Your Physical Imperfection — a mémoire and lifehacking manifesto

The Central American country that you most associate with surfing, beautiful natural parks, exotic wildlife, lackadaisical Latin lifestyle, coconuts, paradisiacal islands, and beach parties with girls in bikinis is probably Costa Rica. But, trust me, you don’t want to go to Costa Rica…

The country does have tremendous natural beauty in some of its parks and beaches but everywhere that Costa Ricans live they abuse the environment. You’ll see fields full of burning trash, beaches strewn with washed-up plastic, and trash bags piling up next to waterfalls.

It’s quite dangerous; lots of petty crime, mugging, corrupt police, etc. If you venture at all out of the tourist zones, you need to watch your back.

It’s not populated by the beautiful Latina women of your fantasies. More like the hobbit women from the shire speaking a mumbling dialect of Spanish.

The food is terrible. Just fried crap and junk food. No spice or flavor. A fancy dinner is rice and chicken. The national drink is rum and coke. The popular local beers taste like fermented pond water that a kid peed in.

American tourists have been flooding into Costa Rica for 50 years, so you’re just another gringo there to be funneled through their economy that relies fundamentally on ripping off tourists. No special treatment. Nobody asks if you like their country. Nobody is excited to meet an exotic foreigner and practice their English.

It’s also a terrible value for your tourism buck; Costa Rica has one of those stupid economies where the local people make a tiny pittance but the cost of things is quite high. You’ll often find yourself paying similar prices for foods, goods, and services that you do in North America.

I recommend going to Nicaragua or Panama instead

This brings me to an illustrative anecdote…

I had escaped Costa Rica and was hanging out in the surf mecca of San Juan Del Sur, Nicaragua.

Which is an idyllic village, everything was cheap as hell there so I let my hedonistic side out. Spending a few hours a day working on my laptop, but most of my time lounging by the pool or beach. I explored the mountains around the village which overlooked the bay. And during the nights I would get dinner with newly made acquaintances at the beachfront restaurants and then hit up the open-air discos or tiki bars sometimes until the sun peaked above the blue horizon of the Pacific. This was the carefree Latin lifestyle I came for!

I ended up meeting this Dutch girl about my age who was also cross eyed. One night sitting across from her in a mojito bar I realized that her crossed eye just barely detracted from her attractiveness. But she was a well-put-together young lady. She was quite fit, had a stylish haircut, and wore fashionable, yet casual feminine clothing that complimented her slender figure as opposed to the sporty, hippie, or hipster look that you encounter so much along the gringo trail in that part of the world.

She also had a decent personality, a sense of humor, and could hold a conversation. If she was like some of the slovenly and unkempt lady travelers I’ve met, who seemingly always had a beer in one hand and their smartphone in the other, her crossed eye would be a distinctively ugly feature.

I realized that because she had some style and swagger, her crossed eye gave her more personality than it detracted from her attractiveness. I realized that the same must be true for me.

Lifehack Your Looks

Since nature disadvantaged you with a physical imperfection, it’s incumbent on you to do everything in your power to maximize and improve your appearance with…

  • Fashionable clothing
  • Tailoring and styling of your look
  • Grooming and hygiene
  • Posture and body language
  • Exercise and weight training

Inner Beauty?

Inner beauty

There is this myth of inner beauty; that we will be loved and wanted for our individual inner beauty. This could not be further from the truth; you’ll be accepted or rejected based on the most superficial things.

Since you’re physically imperfect, you already know that people treat you differently based on your appearance, so the good news is that about 80% of your appearance, the way you present yourself to the world, can be changed and improved significantly.


I’m not an expert on men’s fashion (and certainly not women’s fashion) but I do practice a modicum of fashion common sense which I'll impart to you.


The most commonly committed fashion sin is wearing clothes that don’t fit you. Especially baggy clothes. Unless you are really muscular baggy does not look good.

Baggy look

From the barrios of Mexico City to the slums of New Delhi, there is an almost universal average guy uniform of jeans, a t-shirt, and tennis shoes. It’s hard to make this look good unless a) you are conspicuously muscular b) the jeans are a fancy designer brand or c) +$100 brand new high fashion tennis shoes.

average guy

I’ll encourage you instead to go with a button-down shirt, jeans, and leather shoes. It’s a simple upgrade that costs about the same, is equally comfortable yet makes you look a whole lot smarter.
If I’m going out to socialize I take about two minutes to iron my button-down shirts. Which makes them look about 200% better.


If I’m doing something social I always wear leather shoes. Don’t wear tennis shoes or trainers unless you’re doing something athletic or sitting at home.

I wash my shoes once a week. Which keeps them looking new for about a year, as opposed to looking worn out after just a few months of use.


If you dislike clothing shopping as much as I do, don’t invest in a look that’s going to go out of style in a year or two. I remember about 10 years ago the hood look was really popular; everyone was rocking these silly pseudo-sports Jerseys trying to look like a rapper. Now it’s this lumberjack look with a beard, unkempt hair, and a flannel shirt or dorky sweater. In a few years, perhaps the popular in look may be to look like you just survived a war zone.

I’ve always been loyal to the classic, clean-cut preppy look, which I suspect will never go out of style. I have shirts that I bought 10 years ago which are still quite fashionable.


I don’t do any egregiously bad mismatching. No yellows with greens. No white undershirts with button-down shirts. No white calf-length socks with tennis shoes (or sandals!) No Adidas trainers with a suit jacket. Don’t leave your house looking like this!

You can make your lower body look about 10X better by actually wearing pants that are about the same length as your legs. Whenever I buy pants I spend the extra $10 to get them tailored and it makes them look like pants that cost about $80 more than they actually did.

I always have one ostentatious fashion item. It might be white pants, a beige suit jacket, a vest with a cool pattern, designer jeans, etc that makes me stand out from the crowd. Something conspicuous enough that people will notice this stylish item before they notice my crossed eye. Right now it’s a cool Zara blazer that cost about $35.

Jonathan in looking fly

I spend very little time and money on fashion but I’m easily in the top 10% of most fashionable guys. Most guys are so clueless and willingly ignorant when it comes to fashion that if you pay just a little bit of attention, you’ll look better than most.

My brother (who is not cross eyed) is in really good shape, he lifts weights and consumes protein shakes with almost religious discipline; he’s lean and muscular but you would not know it from looking at him…

He goes for this casual-sporty look; wearing baggy shirts and jeans that almost totally obscure his great body. I’m not going to tell my brother how to live his life unless he asks me for advice but I think it’s pretty silly to spend all that time and money building a body but not spend just a little bit more time and money selecting fashionable clothing that shows it off. Kind of like buying a Ferrari and then just leaving it in the garage all the time.

For comparison check out a few photos of my friend Brian...

As you can see his thoughtful selection of clothing shows off the body that he’s worked so hard on.

A few men’s fashion resources worth taking a gander at before you drop some coin on upgrading your look.

Male Grooming

I’m also not a grooming expert, but again, if you apply a little common sense you will look better than most!

Right now this scruffy look is really in with a lot of superfluous facial hair, unless you’re in a band or have just awesome facial symmetry pass on this look! Unless your facial hair comes in like Blackbeard’s just go with the clean-shaven look.

Male Grooming

Thanks to my mom I’m blessed with this thick, wavy hair but many guys have some thinning and male pattern baldness that starts to become apparent in their third or fourth decade of life. If this is the reality staring you back in the mirror don’t try to fight it with a comb-over! Just shave it all off. The totally bald, chrome dome look, best exhibited by the rapper Pitbull is very sexy and masculine.

I’ll also advise against long hair. Unless you have Fabio’s facial structure and musculature it’s going to make you look feminine. Also (this may be a glaring case of confirmation bias) I have NEVER gotten to know a guy with long, flowing hair who was a cool guy. Every single one seemed to be kind of weird, antisocial, and/or dramatic. I don’t trust guys with long hair now, to be honest.

Like me, you’ve probably scoffed at haircuts that are priced at $50 or $100. Here’s a secret of good-looking people, stylists who charge $50 or $100 are often experts who will really know how to style your hair to compliment your face. The haircut that makes Brad Pitt look like a dangerous secret agent is not going to have the same effect on Sean Connery. If you shell out for a top-shelf haircut once the stylist will craft your hair into something that is uniquely you. Then immediately take photos of it from several different angles with your smartphone. Then in two months or whenever you need a haircut next, go back to the $15 barber and show him the photos of what you want, and often he’ll be able to duplicate it at a fraction of the original cost. So it’s an investment.

New haircut

XX Sexual Marketplace Dynamics

beautyI’m not even going to try to give grooming advice to members of the fairer sex reading this, I suspect that would be tantamount to a bicycle mechanic advising a Ferrari mechanic, but think about this…
The most attractive women in your city (the 9s and 10s, if we are going to use the silly 1–10 scale) are nearly impossible to compete with in terms of raw genetic advantage unless you are going to get thousands of dollars worth of plastic surgery done and just live in the gym. However, many of those most attractive women treat their beauty the same way a 21-year-old guy would if you tossed him the keys to a brand-new Ferrari.

  • They like to show it off to everybody at nearly every opportunity.
  • They do almost nothing to maintain its mechanics beyond the most superficial and skin-deep. Practicing little-to-no discipline with their exercise regimen, diet, or lifestyle.
  • They’ll generally be irresponsible and careless with it. Drinking alcohol, smoking cigarettes, doing recreational drugs, going for late-night drunk food, etc.

In 10 years, it won’t look so hot anymore and it definitely won’t be the high-performance machine that it was.

If you as a woman choose the path less traveled of discipline and maintain your machinery, by early middle age your beauty will be about on parity with the 10/10 cheerleader or go-go dancer that everyone was in love with once. 
Also, pop culture has done this funny thing of encouraging women to dress down. Attractive women so take their good looks for granted that they often lazily dress down to a sporty or rocker-chic look

I’m amazed at how many women I meet at social events and parties look like they just rolled out of bed. Sometimes I think women are getting just as apathetic as guys are about their appearances. This is good news for you if you’re a smart enough lady to stay in shape and dress with a little more feminine style!

Attractiveness is relative, ladies. A “7” in Berlin, Germany is very different than a “7” in Medellin, Colombia. If you live anywhere else other than Medellin, Manhattan, Moscow, or glitzy downtown Kyiv, Ukraine, you can give yourself a serious advantage in life, love, and business by just paying a little extra attention to your appearance.

Hacking Your Face

Those who are concerned about their aesthetics should know that you can biohack your face.

Handsome Man  Beautiful woman

Facial structure reflects your hormonal profile and general health. Consistently when you meet a really healthy guy or gal that spends a lot of time in the gym they have this tight angular facial structure — they look hot! If you’ve read any of Ayn Rand’s novels you’ll remember these vivid descriptions of the protagonists’ faces, the good guys consistently have these sharp, decisive-looking faces.

I certainly notice a difference in the attractiveness of my cheekbones and facial structure if I’ve been eating right, avoiding booze, and going to the gym. If I’m lazy about my diet, not exercising, and drinking socially a few times a week I have more of a round baby face.

In the biohacking chapters, we’ll delve into how exactly you can get your testosterone up with exercise along with cleaning up your diet to decrease inflammation and body fat — your face will look better!

Losing weight

Losing weight

Losing some weight might also help your appearance, although honestly style and swagger make a bigger difference than a few pounds around the middle. I would upgrade your wardrobe first.

In the two chapters addressing diet (Biohacking Diet (with just $1) and Beating Depression) I’ll go more in-depth into the Biohacking stuff but to summarize; the most effective lifestyle tools (in descending order of effectiveness) to change your body shape are…

  1. Diet
  2. Fasting
  3. Exercise

So if you want to lose some weight start by getting your diet optimized and integrating fasting into your lifestyle before signing up for 20 personal training sessions. You’ll see yourself transform physically all the faster.

Still skeptical?

If you are skeptical that people will treat you differently because of something as superficial as clothing and grooming; go to a department store that has a very flexible return policy and splurge a little on a fancy outfit; get it tailored or have one of the retail employees there help you select something that looks good on you.
Then wear it to a party, social gathering, or just put it on and walk around the downtown part of your city and I think you’ll be pleasantly surprised at how differently people treat you.

Fun times!

Appearance hacking is counter-intuitive because a lot of us think logically that what matters is…

  • Who we are
  • What we do
  • What we say

But people really do judge you by how you look. Nobody is ever going to think you’re an idiot because you’ve been meticulous about your appearance but a lot of people will secretly disdain you for being careless about it.

Your job is to be the most stylish person in the room. If you aren’t, by default thanks to your physical imperfection, you’ll be the most physically awkward person in the room.

To summarize

  • Your aesthetics really do matter. People will treat you better if you look better. Luckily, improving your aesthetics is easy.
  • Wear clothing that fits your body.
  • Instead of following trends or alternative styles, go with the smart, timeless preppy look.
  • If you’re a guy, you can easily get into the top 10% by just paying a little bit of attention to your appearance.
  • If you’re a woman, because of sexual marketplace dynamics, you have a significant advantage in life if you maintain your girlish figure into your fourth decade.
  • If you need to lose weight start by changing your diet.

From my book How to Be Cross Eyed: Thriving Despite Your Physical Imperfection — a mémoire and lifehacking manifesto

How to Be Cross Eyed [Second Edition]
Category: Book

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