Tip 99: Regret being so cool

How does it feel to be cool? You can't sit around and talk about it.
It's not something you get asked to reflect on in interviews, like being formula one champion.  Noone asks about the gruelling training regime or whether your parents supported you all the way.
You even have to deny it.
"Fucking hipsters," you might say.
Take off your Ray Bans, run your hands through your quiff and lock eyes with your interlocutor to make a searingly honest confession: "I'm a nerd, really."

BONUS TIP: Give up trying to be cool and strike out on your own.  Sell your fixie and burn your desert boots. You could take up long-boarding, for example. I hear that's popular right now.

Tip 92: Spot a celebrity on a bike

Is that Rove Mc-freaking-Manus? Cool! Wait. What is he riding? A Huffy? I can't believe I thought he was cool.

BONUS TIP: Tell the story like this: "Guess what. I saw a poorly maintained huffy out on the street this morning.... And who was riding it? None other than Rove Mc-freaking-Manus! I know! What a dork!"

Tip 72 : Stand for speed bumps

The genetics of the human race are imperilled.
iPhones, powerlines and those glow in the dark stars nine-year-old you stuck all over your bedroom have filled our living environment with enough radiation to have us all riding recumbents within a generation.
You're not going to wear lead undies, but there is one thing you can do to preserve the integrity of your gametes: protect them from impact by standing for speed bumps. 
This is especially true if you prefer boxer shorts or go commando.

BONUS TIP: Grab some mad air as you go over the speed bump, and if there are any suitable parties observing, you may just increase your chances of passing on those genes.

Tip 66: Feel abnormal

You've just emerged from a big meeting and stand by the road shaking hands with important men in very fine suits. They stand on the side of the road looking for taxis. 
Your bike is right there, but you suddenly feel an absence of pride in it, the presence of a sort of weirdness.  Is this shame? 
Do you take the four steps to where your bike is locked and mount it, or wait til they have gone? What will people think?

BONUS TIP: Revel in bike-shame while it lasts. Way things are going, it's something the fixie-buyers of today will never experience.

Tip 63: Sweat

Park your bike and ride the lift up without changing your clothes.
You feel warm but tell yourself you are socially acceptable.  That sprint over the last two kilometres is forgotten.
Inside your climate-controlled office, you swifly turn red and sex-like.  Your shirt sticks to your spine, your face feels hot and your lips are salty.

BONUS TIP: When you go to the morning meeting, put on your jacket to hide the dramatic armpit stains from the women in marketing.  
Soon your entire body is clammy like a diptheria patient.  Before its your turn to speak, your eyebrows will fill with drips that fall on and ruin the notes for your presentation.

Tip 62: Carry something awkward

Sometimes you need to do cargo.
Unless your commute is to work as a double bassist in the symphony orchestra you're gonna struggle. Practice in advance of the unexpected.
Perhaps go by bike to fetch a new bath, buy a dozen cases of beer at the store, or ride your record-breaking squash to the county fair.

BONUS TIP: If you can carry more than 1000 bananas by bike, make sure you record the event and upload it to YouTube, because you are "hangin' with a cool bunch," as they say.

Tip 54: Sample marginalisation

White, educated, politically enfranchised, able-bodied, heterosexual male seeks:
Opportunity to be hated without reason, heckled and assaulted by those more powerful, treated with contempt by law-makers and picked on by law enforcement.

BONUS TIP: Shed your downtrodden status along with your bib shorts each morning when you arrive at the beautifully appointed cycling facilities at your law firm / IT company.