The Complete Guide to Living & Getting Lucky in a Big City

Re-posted from:

Big cities are my addiction.

As a wide-eyed guy with Midwest determination, a big city makes me feel like damn near anything is within my reach. It energizes me.

But, cities can easily overwhelm you. It’s understandable.

Living in Chicago, San Francisco, and Bangkok over the last 13 years, I’ve discovered the beautiful side of the overwhelming experience of city life. There’s a litany of incredible social connections, business opportunities, and romantic experiences to be had.

Yet, I see so many of my fellow big city residents falling into a routine of convenience — limiting their lives to easy apartment living, their 4 friends from work, and the 2 bars they go to every week.

If you live in a big city, you can readily create interesting social experiences if you know where to look. Here, let me show you.

Why Even Bother Living in a Big City? Because Physicists Say So.

There’s a lot to hate about living in a big city.

Homeless people pee on the train that is already running late. People can be colossal assholes. Stupid political protesters will back up traffic. And, worst of all, liquor is expensive.

These are just a few of my personal complaints lodged against the fine cities of Chicago and San Francisco. But, I’m not moving to the suburbs anytime soon. Why?

Because of a little principle physicists call “collision density”.

In physics, collision density is the rate that different elements in a system will interact with each other.

In non-nerd terms, it means the likelihood that that you’re going to interact with someone interesting, unique, and creative is much higher in cities.

Let’s look at it…

You start with an economically viable city and throw in a growing art & technology scene. You’re going to attract scads of well-educated, creative, ambitious people who want to meet other likeminded folks.

Said smart people form companies, finance an art scene with profits from the company, attracting more people to the city, real estate values go up, people now have disposable income to explore their creative sides and become more interesting.

Thus, the virtuous cycle of capitalism creating interesting experiences…if you’re there for it, that is.

You’re Not A Kid Anymore. Start Talking To Strangers.

Showing up to a big city with a suitcase and a dream isn’t going to cut it. You have to reach out and make connections before anything else happens.

And, the best way to do that? Start talking to strangers.

Jane Jacobs, author of The Death and Life of Great American Cities (who you will see quoted liberally here), understood this well:

[Big cities] are not like suburbs, only denser. They differ from towns and suburbs in basic ways, and one of these is that cities are, by definition, full of strangers.”

And, lots of strangers means lots of fun.

I’m a huge advocate of consistently talking to strangers as the quickest way to beat your social anxiety and becoming a more socially fluid person.

To this day, I still go out at least one day a week just to talk to strangers. I plan my errands around the best places to meet a lot of people in one spot — shopping centers, the grocery store, trains, the gym, bars, coffee shops…you name it.

Talking to strangers is a lot of fucking fun.

The rush you get by meeting someone new and interesting is addicting. The experience of learning their story and seeing all of their personal nuances unfold in front of you — there’s nothing else I’d rather do.

The ability to have a great conversation with anyone is the life skill that — when practiced passionately and frequently — will pay dividends on a daily basis in the form of new friends, lovers, business connections, and ridiculous stories worth re-telling.

I’m not joking when I tell you to talk to people everywhere you go.

Don’t limit yourself to only chatting up cute girls or people you want to do business with — it’s lame to be a situational success. Be an always-on, 24/7 student of other people who wants to hear more of their story.

Introduce yourself to everyone and be the ‘Welcome Wagon’ who ushers in a good time everywhere you go. Sincere compliments, positive social energy, and general good vibes are free — give them away liberally to everyone:

The barista, your Uber driver, the old lady at the grocery store, the guy in the elevator, the cute girl waiting for the crosswalk, the guy who owns the corner store, and the group of bros at the bar.

Everyone deserves good social vibes.

And, while you’re at the bar…

Always Eat At The Bar.

As with most imporant lessons in life, the most qualified advice on the subject of hanging out in bars comes from Ernest Hemingway:

Don’t bother with churches, government buildings, or city squares. If you want to know about a culture, spend a night in its bars.”

Papa couldn’t be more correct.

Having your daily bread while sidled up to a long pine bar brings some kind of magic to the otherwise pedestrian experience of dinner. It opens you up to I-can’t-tell-you-how-many-more social possibilities.

The bar is ground-zero for interesting social opportunities.

I’ve had loads of people invite me to a party, ask me to interview for a job, become new coaching clients, or try to set me up with their girl friends just by virtue of being there and chatting them up.

It’s collision density in its finest form.

A Brief Guide to the Cool, Interesting People You’ll Meet at the Bar

1) People with a drink are almost always more fun and friendly than their sober selves. They don’t call it ‘social lubricant’ for nothin’.

2) Bartenders are social hubs who know the stories of everyone in the bar, where the afterparty is, and — if you’re a gem to them — will buy you a round of drinks. They’re some of the best people to know.

3) Awkward first dates from the Internet — it’s instant conversational fodder and incredible entertainment to just eavesdrop. Strike up a conversation with the failed Romeo & Juliet for bonus points (and her number).

And, my personal favorite:

4) The out-of-town visitors. In my experience, these are the best people to meet at a bar. They’re the ones ask you where they should go next. They’re open to new experiences and ready to have a great time.

Hanging out with out-of-towners is a great way to be a tourist in your own city — you get the chance to see your home through fresh eyes.

I recently struck up conversation with a very cool group of Canadian tourists while having lunch at a bar. We ended up spending the next 14 hours together. We had dinner, went to a dirty burlesque show, saw two bar fights, met a few girls, told stupid jokes, and had ridiculously great conversation.

That’s the kind of experience you’re gunning for.

A Quick & Dirty Guide to Bar Etiquette

There’s an art to sitting at the bar that only time (and cocktails) will develop. But, there’s a few traits that will make a novice nearly indistinguishable from a seasoned man-about-town:

1) Always Start Conversations: People are more social at bars but you should never wait for someone else to make the good times happen. If you someone who looks interesting, let them know. A person of good social vibes always gives it away freely.

2) Be Great To The Bartender: This is probably the most important rule, especially if you plan on coming back to this bar. First, tip them well — bartending is a hard job and this shows you appreciate it. Second, always be accommodating and never pushy, especially when they get busy. Third, take a genuine interest in them and show them love when they make you a great cocktail or suggest a good beer. Four, become a regular at their bar — remember their name, show up regularly, be their customer, and follow the above rules.

3) Always Have Options: This is especially important if you’re looking for a proper night out. Have a few next steps available at the ready should you meet a cool group of people.

Invite the perfect strangers to a house party, blues bar, a cool cocktail lounge, an afterhours, or a nightclub. You officially become the social hub and rolling with 8 people is always more fun than being out by yourself.

4) Buy A Round of Drinks: It’s an instant party starter if you’ve been chatting with some cool folks for a while. I highly recommend you do it next time. It’s a lost habit of ours, being generous and cool.

Just last week, I sat down at a bar and started chatting with a group of smart, hilarious dudes about 10 years my senior. I decided to buy them a round of drinks and keep the party going.

Turns out these guys were all hot shit investment bankers and they invited me to a lobster and champagne dinner on their dime (Thanks, Goldman-Sachs! You may have imploded the economy but the roasted red snapper was delicious.). We ended up partying until 1AM and they offered me a job interview, should I ever want to break into the business.

A Few Notes On Buying Drinks: Do this after you’ve been talking to them for a while; it’s weird and awkward to just buy total strangers a round of drinks. Remember, you’re not buying their friendship; it’s just a great way to be generous, build a connection, and create a good vibe. Don’t expect anything out of it…but it almost always comes back to you.

A Final Note on Sitting at the Bar

While I advocate that you always make the first move, bars make everyone more friendly. If you’ve got a good positive vibe to you, people will chat you up too.

I do most of my writing at two hotel bars in Chicago. You’d be surprised how many people strike up conversations with me because I’m writing in a notebook. I’ve met some fascinating strangers and sweet women this way.

There’s something unique about a good bar and its ability to create social magic. Even a busy bar has a meditative quality due to the plethora of social options open to you if you seek them out.

Next time you go out for dinner, forget grabbing a window seat with a crisp linen tablecloth. Sit at the bar, order a glass of whiskey, and watch the world unfold itself for you.

Seek Out The Inconvenient.

There’s nothing hard or stressful about living in a big city anymore. Everything you need is basically on-demand, built in, and close by.

You can have your dry cleaning picked up and delivered without ever seeing the inside of laundromat. (Wash Club)

You can have your groceries delivered. (Peapod)

And, if you’re me and my roommate, you can order 4 cookies from your phone at 10PM on a Sunday. (Über Eats)

Chicago is loaded with these ‘all in one’ apartment buildings, complete with a movie theater, a gym (full of unused weights and crowded treadmills), grocery store, wine bar, coffee shop, nail salon, and dry cleaners.

It’s convenient to live here, yes.

But, there’s a hitch…

You’ll rarely make connections and write a story worth remembering in a life focused on convenience. This lifestyle of ease requires you to invest little effort and risk almost nothing.

Now, I’m not telling you to delete your Über app or anything — that would be stupid.

I’m only asking you to consider the words of Jane Jacobs:

“When…convenience sets in; the small, the various and the personal wither away.”

Never all your life to get too easy, comfortable, or convenient. Too much routine dulls your personality.

This is when you stop painting with all the colors and only paint in shades of grey. This is how your muscles atrophy. This is precisely when you ‘get old’.

Instead, seek out those experiences that make you look someone in the eye; experiences that give your equal measures of excitement and anxiety; and experiences that you put you within arm’s reach of countless possible people to connect with.

Want to create a life of interesting options? Start by giving up what’s easy for what’s almost guaranteed to be exciting.

Develop A Thick Skin, But A Soft Touch.

The last 2,000 words have sang the praises of living in a big city.

There’s countless opportunities for career growth, building friendships, experiencing new art and music, having sex, finding love, partying, growing up, and being inspired.

But, there are some distinct downsides to urban living in 2017 that might make you think twice about calling it ‘home’.

Couple a large pool of attractive, successful people with the ‘dates on demand’ from dating apps and you have a perfect storm for dating. People have more options today and are more likely to forget about any one individual. The ease and surplus of dating has cheapened it.

Relatedly, the sheer number of fun events going on in the city at any one time increases the likelihood of someone — even a friend — canceling plans on you at the last minute…or just flat out flaking on you.

Fewer and fewer people will give you a definite “Yes” or “No” answer to an invitation. Instead, replacing it with a “that might be kind of fun” or “yeah, we’ll see, maybe”.

This is all compounded by many people having very little time to spare. Many of city dwellers are career-driven and work longer hours, have ‘side hustles’ that eat into our time, the time demands of a long-term relationship, and a generally wide social circle.

These are all harsh realities of city living. To deal with these, I advise you to develop a ‘thick skin’, of sorts.

It’s an acceptance that she may never call back and that your buddy might cancel on you at the last minute. Not everyone does it but it happens enough to be annoying. You just let it roll off you back and move on.

There’s an upside to all of this, though…

The disposable, impersonal nature of social interactions we’re all becoming used to can be used to your advantage. Becoming a genuine, curious person who gives warm social vibes is a refreshing departure from the flakes and social robots staring at their phones. You immediately set yourself above the rest.

This is the mindset that will win you social success in life.

Take this advice to heart, stay curious, be charismatic, and be that person.