When it’s a nice weekend afternoon in Chicago, I stroll over to this little park in the middle of town. I’ll usually put on a blazer and button down, pack a little lunch, put some whiskey in a flask, and just people watch for the day.
It’s barely even a park, really. It’s just a little 25 foot-by-50 foot triangular brick area in a ritzy part of town with a beautiful, old water fountain, a little gelato & coffee stand, and park benches everywhere. It’s very old school and European-looking. You go there and you feel like you’re transported to 1920’s Paris.
On those sunny afternoons, the place is teeming with well-dressed, older guys drinking a cup of coffee, playing chess, smoking cigars, and watching the remains of the day go by. Sometimes they bring a gal with them but, regardless, it’s a Man’s World over there.
The park is hilariously known as “The Viagra Triangle”, for its shape and prevalence of rich, older guys on the hunt for young tail.
One of my favorite things to do is to chat up perfect strangers and this is, by far, my favorite place to do it. The more I started to get to know these older guys, the more I realized that they had a secret that a lot of us are looking for the answer to…
These older fellas know what it means to be truly happy, confident, and cool.
These guys have vastly different personalities and backgrounds.
Some are working class, retired firemen, while others are wealthy lawyers, doctors, and bankers. Hell, there’s even an old rock musician who was pretty famous in the 80’s.
Regardless of their differences, though, these fellas all know the secret to living the good life.
In my five or six years of chatting with these guys, I’ve learned volumes of wisdom about living a fulfilling life – a life that is teeming with adventure, joy, and epitomizes charisma.
In this post, I’m going to share with you a few of the big lessons from Ernie, Richard, Gino, and their ballsy, cigar chomping, big hearted buddies.
Appreciating the Small Moments
I think this is the foundation of living the good life, regardless of your age.
Our society has us constantly distracted by our iPhones and images in the media having us think that the only way to be happy is to have more shit that is shiny, expensive, and bright.
We often put our attention on these grandiose things while forgetting about the simple things, the small moments.
These small moments are everything in life. They are all we have. It’s the deep love of the inconsequential, seemingly mundane experiences of our everyday life.
It may sound trite, but life is made of moments – one after another.
Too often, we only focus on and work towards the big moments, the major experiences – the next vacation, the new job, finding a partner – and trivialize the way that cute girl on the train smiled as us.
These cool, old guys understand that life does not have to be lived in the frenetic, fast-paced way so many of us have chosen to live our lives (to our own detriment). They know that slowing down to count their blessings, being grateful for the moments they have, and the seemingly inconsequential acts of kindness a stranger showed are the keys to real, lasting happiness.
There is no regret or sense of loss in these guys. There is only gratitude that fills them up and the sureness that “everything is gonna be OK”. And, if that statement isn’t the epitome of “cool”, I don’t know what is.
Create this mindset in yourself and you won’t be one of those unfortunate people whose final thoughts are filled with regret and fear. You will be a person at peace with yourself. You will look at every experience as the embodiment of good fate and joy.
Developing a practice of mindfulness will really help you set your course for learning this type of appreciation.
The trance DJ’s Above & Beyond have a great song – “Small Moments Like These” – that pretty much sums this up. There’s not a lyric in the song but the music and the video epitomizes everything about this principle:
And, don’t forget…as the last shot of the Above & Beyond video says, “Life is made of small moments like these…thank you for being there”. That’s the message, guys.
Mastering the Fine Art of “Not Giving A Shit”
This is easily my favorite part about cool old guys.
Old fellas have this air of not giving two shits about anything.
They’re usually hilariously bold in their behavior and speech, saying and doing whatever is on their mind. For as much as these older cats might ruffle some feathers, we all secretly love them for taking their rightful seat at the throne as King.
This is also the easiest to describe and, perhaps, the hardest to actually do.
These older fellas have many years of life experience on you. You can’t get that from a blog or a book.
They might have fought in the military, been married, divorced, raised a few kids, started a few successful business, and gone through more hell than you can ever imagine. These are experiences that will forever alter your view of the world – and yourself.
When I say “not giving a shit”, it doesn’t mean being reckless or callous.
It means you are fully aware of your desires and what you want to say, unafraid to take action and express yourself. You’re also cognizant of the fact that actions have consequences and risks involved. And, these risks rarely outweigh the excitement of saying what’s on your mind and doing what you want.
I think this boldness comes from a long life lived, taking bold, decisive action and doing what makes you happy.
It’s also fueled by the regret that comes from having not taken a few risks in their life that they probably should. With their days dwindling in front of them, they know you only have so much time to stake your claim in this world and they do so fervently.
These guys know what the playwright George Bernard Shaw knew, that “youth is wasted on the young”.
They know there is no better time than right now to start that business, to stick up for something and say “No! Fuck that!”, to boldly flirt with that girl, to take any and all calculated risks in life, and generally do whatever makes your clock tick.
You’ve Got a Gang of Friends
This one was a lesson that took me a while to learn.
As someone whose natural attitude is “I can do this myself” and leaned towards being a loner, I downplayed the importance of having a solid group of guys around me.
Sure, I had a few buddies who I enjoyed being around but it took me years to see our friendship for what it really, truly is.
We’re a tribe, a gang, a posse. A textbook motley crew.
A longstanding group of fellas that have you back, listen to you when you need to air things out, will loan you a few bucks when you’re down on your luck. They’re your sounding board for your crazy ass ideas, your grand plans, your dreams, and your stupid jokes.
These are cats who’ve seen you at your worst, picked your ass up and helped you put the pieces back together, and tell you when you’re being an idiot.
To put it bluntly, as one of the fellas in my gang says, “We know each other’s secrets. We all know where the bodies are buried”.
Between talking to the old guys in the park and having my buddies stand strident next to me, I began to understand the importance of having a tight group of friends into your golden years.
I mean, hell, I’m only 32 and it’s very plain to see that without your gang next to you (never behind), you’re missing out on a lot of love, hilarious moments, ridiculous stories, and awesome feedback.
Yes, to actually succeed in anything in life, YOU have to put your head down and get to work. No one else can do it for you. But, you need your crew right alongside you while you do it.
When I chat with these old fellas in the park, they all have the wildest, most hilarious stories that are meant to be told over glasses of whiskey and beer.
It takes them 10 minutes to tell the goddamn story because it’s being told by four different guys from four different angles, punctuated by uproarious laughter and tangential stories. It’s pure fucking joy.
It’s rare you create these memories alone. Your buddies all bring something to the table, adding another dimension of crazy to the equation.
Knowing A Thing or Two About Romance
Much like having a solid group of friends, having a way about you that embodies love and romance will serve you well into your golden years.
Man or woman, gay or straight, this still stands.
It’s what makes those cute, old couples so goddamn sweet.
It’s what gives those spry, older guys the twinkle in their eyes that belies the youthful, mischievous spirit that is undeniably awesome to be around.
It’s part of what makes old married couples still in love after 40, 50 years.
Romance is the sweet disposition that stems from both an acknowledgment of inevitable loss – that is to say, life is short and nothing lasts forever – and an unbreakable optimism, a grand belief that all is well in the world and everything is generally getting better. Delusion or not, that’s not my concern.
The fact is, romance puts a jolt of hope, excitement, allure, and inspiration into the lives of even the otherwise cynical and dull.
You see, romance is not picking flowers and overly saccharine displays of affection. That’s for the greeting card companies, chick flicks, and the generally uncreative.
Romance provides a respite from the banality of the business of life, injecting adventure, desire, and creativity into the everyday and mundane. It’s the bold gestures that make the profane suddenly sacred.
It is equal parts compassion, curiosity, and desire, all done with a certain insouciance and devil-may-care boldness.
Romance is for the dreamers and optimists. They may have been wronged or hurt in the past, but you can never call them jaded or broken hearted. They still believe in love and that good things can happen.
These concepts might sound youthful and naive as one gets older. That’s just a lack of will and creativity, if nothing else. Spontaneity and curiosity know nothing of your grey hairs or crow’s feet.
These are all tremendous definitions of romance but if you need the real definition, try this on for size:
Romance is listening to the passion, openness, hope, and curiosity that resides in your soul and giving that to the World and your work.
Live this credo to the letter – on your own goddamn terms – and start creating stories worth telling. Doctor’s Orders: Do this until your last breath, every day, for the rest of your life.
Which brings me to my last point…
Be at Peace with Dying
I saved the heaviest for last.
Death is not a fun thing to ponder. We never want the party to stop and end the love, joy, and prosperity we have.
But, it happens.
I have no idea what it’s like to die and no one else does either.
I write about this for two reasons:
First, as you get older, you naturally start losing friends and loved ones to unfortunate causes. This makes you much more cognizant of how short your life really can be.
Second, even at 32, I’ve had a number of people close to me die at a pretty early age.
I lost my father when I was 21, as well as four friends in 2014 alone. 2014 was a tough year. I’ve gotten a glimpse of the real brevity of life and how appreciating your very limited time on This Big Blue Rock can bring much joy to the rest of your days.
After much contemplation, I began to see my father as just a guy. He was no saint. He was certainly not the ideal dad, to be sure, but he did the best he could and he loved me. This lifted the weight of judgment and regret off my shoulders. I could forgive him and move on.
Thinking about the sudden loss of another friend (who started off as a musical idol of mine when I was 14) had me make sure that I never left a word unsaid, a need unspoken until it was too late.
Don’t hesitate to tell someone you love them, that you are there for them, that you will be their rock. Don’t wait because tomorrow may never come.
Reflecting upon the loss you’ve experienced in your life – along with your inevitable demise – is a tremendous way to both heal the hurt and bring appreciation to the life you have left.
Understanding this will lift the weight of expectation and actually start to usher in a new, lively form of spontaneity into your life.
You have a deep understanding that your days are numbered and, while that’s too bad, you have no choice but to make the best of them. Those old fellas get this and that’s part of what makes them appreciate the small moments in life, be ruthless motherfuckers, and spontaneous romantics all at the same time.
When you learn to accept your limited days…
You learn to love deeply, firmly, and unconditionally.
You create a solid, steadfastness that comes with accepting death as inevitable. It’s not necessarily a lack of fear; instead, it’s a conquering of fear. You’ve made your peace with the inevitable and you can move on.
You learn that the best time to express yourself is right now and the best way to do it is fervently & honestly.
You create a great humbleness to your life that will have you tread a little lighter in the world.
You will discover a newfound compassion for all types of people. This will have you begin to understand that everyone has fears, insecurities, and is terrified of dying. Even the biggest jerks and cocksuckers out there feel these things.
Do not fear death, guys. It’s inevitable.
I make no promises of a rebirth, 72 virgins, or a blissful afterlife, but this much I know to be true:
Know that you have an unknowable amount of time on Earth to fill with art you made, songs you wrote, love you gave, and adventures you had. Let death be a fire under your ass that tells you to go forth and give of yourself fully to the World. If you do this, you’ll never run on empty and struggle, you’ll just simply cease to be one day and a tree or flowers will grow in your place. All that will be left of you will be your ashes and – should you do it right – a powerful legacy of love, creativity, and steadfast determination.
Peace & Charisma,