Sneaking Into a New York Rooftop Party

It’s not a secret: doing stupid stuff is a big part of childhood. It helps with self-discovery, the learning process.

But why then, do we stop doing those things as adults? Is it because we know have nothing left to learn?

Obviously not, but many–most–of us act like it. We pretend like we know exactly where we’re headed, and like we know exactly how to get there. We deceive ourselves to such an extent that we grow into people who are afraid to try stuff out. When this happens, we stop connecting with our ever-evolving selves.

Maybe you’re reading this because you don’t know how you ended up where you are. Or maybe you have no idea where you’re heading even though you put on a facade like it’s all cool. Or, maybe you’re just on my mailing list.

Whatever the case, we could all use a gentle reminder to work on ourselves.

Step outside your comfort zone.

Vague, right?

I know.

If you’ve ever seen the movie, Yes Man, you know exactly where saying “yes” to everything can lead you. Jim Carrey, in the movie, went from this loser who sat at home all day to the guy with a million stories to tell, the adventurous traveler, the guy with the perfect relationship.

Why?

Because stepping outside your comfort zone is character building. There’s something to be said for the new experiences he had, but we’ll get to that in the next section.

The reason he attracted his version of a perfect relationship, the reason people wanted to hang out with him, the reason his ex-wife wanted him back, and the reason he was able to transform himself into the person he wanted to be, is because he actually changed his personality.

At the beginning of the movie, Jim Carrey thought he knew what he wanted and where he was headed, even if that was pretty much nowhere. He didn’t realize that there was this whole world out there that he was missing.

“You don’t know what you don’t like until you try it” is not universally true, but most of us take the inverse way too far.

Stepping outside your comfort zone can help you attract the right people and experiences in life, but it can also help you learn more about the world around you.

***

Deborah, my favorite person in the world, once snuck into a New York rooftop party. Just for fun, she was headed out to a meetup event in a skyscraper in Central New York. She went up to the front desk and asked what floor the event was on. Then, she got into the elevator. But the people there weren’t going to that event.

They were way too well-dressed.

“Are you guys headed all headed to ______’s party?” Someone in the elevator asked.

A few nods and yeses. And Deborah, in the fashion of the woman I fell in love with, also said “yes.”

Up at the top of the building came the first road block: there’s a registration desk.

“Hi, what’s your name?”

“Deborah Herry”

“I don’t see you on the list. Are you a journalist?”

“Yes, that’s right..I’m a journalist.”

“Oh great, let me just get you a press badge!”

So Deborah grabs her press badge and walks straight in. The best part? There’s free food and an open cocktail bar. Deborah trotted directly to it.

She felt an exhilaration, like she was working undercover for a competing banking firm..or maybe a foreign country. Would the UK spy on the US?

The point of this story is two-fold: 1) Deborah was exactly herself, and it made everyone else want to be around her, and 2) she learned a lot about the people who attend these kinds of events.

The first part:

Deborah really took advantage of the open bar, and she was the only one who threw down her moves on the dance floor. The question of why they’d splurge for a dance floor if no one was going to use it is beyond me.

But that attitude made everyone want to be around her. Most of us want to be this person, the kind of person Deborah became in that moment. All it takes is a little courage to do something you wouldn’t normally do. Your average person will point to my wife and claim, “well that’s just how she is. It’s a lot harder for me!”

But that’s not true. Deborah became this person, by taking actions like this one. She’s historically been more reserved. At a certain point, you have to decide that you want to act a certain way, you want to feel a certain way, and then act toward achieving it. You’re an important person who can add value to people’s lives. As far as we can tell, Deborah performed with grace in getting into this event, but she was actually terrified to do it.

Why?

Because everyone has fundamental beliefs about how the world works. I consistently think I’m not good enough to accomplish my goals. And Deborah? She used to think she didn’t belong in certain environments. It would stop her from taking advantage of opportunities like this one. She told herself, over and over again, after getting off the elevator, “you belong here. You belong here.”

Deborah learned from this one single experience that you can always make the most of any opportunity if you just set that expectation of yourself.

The second part:

Deborah had never seen a single soul at that party, but that didn’t stop several of them, including the CEO of the company throwing the party, from saying they knew her.

Why did they say they knew her? I have no idea.

But I have a theory.

People in New York are always name-dropping, right? I know, I know it’s a stereotype, but a lot of stereotypes come from somewhere. Deborah met a lot of men, and this is one of several experiences that helped her realize the kind of man she wanted to be with. She knew this New Yorker type of guy wasn’t meant for her. *big smile comes across my face*

She saw signs of insecurity and insincerity, some sort of fakeness around them.

That’s not to say this kind of man will never find love, but Deborah discovered early on that this wasn’t the type of person she wanted to be with. A man at the party would have to go through some serious life evaluation before he was ready to start a life with a woman like Deborah.

Go out and try new things

I promised this section to you, so here you go.

Stepping outside your comfort zone will often lead to “trying new things”, but I want to differentiate them by saying this: while a “stepping outside your comfort zone” mentality can free your mind, trying new things will help you discover what you like and what you don’t like, how you want to interact with the world.

In her teens and early twenties, my beautiful wife worked as a model, acted in several tv shows, and sang in several girl bands. Those experiences taught her everything she needed to know about the entertainment industry. Namely, that after a certain point, she didn’t want to be part of it. But more importantly, she learned that those skills and services apply in every other future business we’d be a part of.

Deborah learned about graphic design and advertisement. Deborah knows how to get photoshoots for free, and she knows how to get press for our business. She became the type of person who’s not afraid to ask for what she wants, not afraid to go out and meet the people she needs to meet (one of my biggest fears).

She met people she never would have met otherwise, and even once got an all expenses paid trip to Singapore from a businesswoman who just “loved her aura”.

Trying new things, especially at a young age, is vital to our mental and emotional development. Before I was 21, I avoided it like the plague, because I thought I knew what I wanted, and I thought I was headed there. Little did I know, I would be stuck in the same cycle for years, and *gasp* it’s not even what I really wanted.

It’s not that it was never what I wanted. At one point I did, but we change over time, and we have to give ourselves the time to figure what we want, how to get there, what’s working, and what’s not.

Time to reflect

I didn’t start getting better at this until I started running. At 21 years old, I started letting my anger out on the trail (it deserved my wrath after all). That gave me 1-2 hours every single day with my thoughts.

And that’s what’s transformed me.

It wasn’t the bad or the good experiences, it was connecting with myself after the fact.

The experience itself would have been null and void if I didn’t stop and take the time to think about where I was, why I thought the things I thought, and where I was headed next.

So many of us live in this never ending cycle of life without reflection (I did, so did the Jim Carrey). The result is we’re stuck in the same place, possibly for eternity. Sure, we may have some idea of where we want to be, but without taking the time to think about how to get there, people seldom “get there”.