A Winning Hand

You gotta know when to hold ‘em and know when to fold ‘em.

Kenny Rogers’ The Gambler is famously hokey. It amounts to three and a half minutes of non-advice about how to find a winning hand — both in card games and in life.

The song was well past its peak when I was a teenager. You’d hear it now and then out in public, but not frequently enough.

Truth be told, we could have used a bit more Kenny Rogers back then. For plenty of us were in big trouble.

You see, poker was gaining popularity nationally. And online poker was becoming prevalent. Many of my teenage peers were caught up in the craze, mesmerized by the allure of massive payouts.

Yet, most of these teens had little experience managing money. And when the winning hands dwindled — when the bluffing and bravado went up in smoke — some ended up deep in the hole to entities determined to collect.

It was a real problem. One that threatened to haunt my generation for years to come.


I didn’t get swept up by the online poker craze as a teenager. And I didn’t end up with a mountain of debt.

There were two factors guarding me from such a fate. I was extremely risk averse. And I was bad at poker.

I played the game now and then — mostly at family game nights or gatherings with friends. I knew what a Royal Flush and a Full House were. And I could usually identify a winning hand.

But when I didn’t have that hand, I was toast.

Yes, I was proficient at playing the cards I was dealt. But when it came to reading the table, I was a novice.

I never bluffed. And wouldn’t dare call out others for doing so.

I didn’t win much this way. But I didn’t lose big either.

All this was extremely on brand for my life at the time.

I tried to shy away from false pretense as a teenager. Sure, my fashion sense and musical taste were less than authentic. But when it came to items of substance, I focused on the tasks directly in front of me. This ethos made me a solid student and a reliable friend.

Yet, as I grew older, I began to stray from this path. I started dreaming big, making grand plans, and racking up assumptions.

And just like those amateur teenage poker players, I got burned.


2.0 in 2020.

That was the name of my now-infamous plan to take my life to the next level.

It had already been quite the ride for me in early adulthood. I’d moved to faraway West Texas to work in TV news, only to ultimately leave that industry and move east to Dallas.

I’d landed on my feet and built a stable career in digital marketing. But I feared that I’d plateaued, and I saw few advancement opportunities out there.

Rather than play the cards I was dealt, I yearned to build myself a winning hand.

So, I bet big. I enrolled in business school, while still working full time. And as I neared the finish line of my Masters of Business Administration studies, I set objectives for myself.

Getting a new job was paramount. But not just any job. I needed an “MBA job” in marketing at a major company in the area. And it had to happen not long after graduation, while my degree was still “fresh.”

By my estimations, this metamorphosis needed to be in full swing by the time 2020 rolled around. Hence, the 2.0 in 2020 moniker.

At first, things looked promising. I made it all the way to a final round of interviews with a prominent global brand. I had some other promising prospects as well.

But then, things dried up. The interview requests dwindled, and I got snubbed for an internal promotion.

As my self-imposed deadline of 2020 approached, I felt as if I was holding anything but a winning hand.

Then, a global pandemic arrived.

With the world shutting down, I felt compelled to hang on to what I had. My home, my friends, and my job.

This feeling only intensified when my employer was acquired. The future of my position was shaky, and I prayed that my income would continue to come in.

2.0 in 2020 had gone up in flames spectacularly. I had retreated into my shell in response, waiting in vain for the firestorm to abate.v

But I grew bored after a time. And I got bold.

I landed a role on my new employer’s marketing team — finally getting that MBA job I’d yearned for. I joined some local running groups and started medaling in races. I trekked around the country more than I had in years.

Like a phoenix, I’d risen from the ashes. I was making my own luck, and I was thriving.

But a big part of me wondered how much of all this was real. And I feared that I’d become Icarus, flying too close to the sun.

My fears were soon realized.

I got sick on a work trip and then hit a few bumpy patches at work. I got injured, putting an abrupt pause to my running exploits. I faded away from friends and family, losing confidence in myself throughout the ordeal.

I was frustrated. I was dispirited. I was lost.

The ghost of 2.0 in 2020 had burned me once again.


What is a winning hand?

I asked this rhetorically one night, as I stared aimlessly at the living room wall.

Through all the ups and downs, my North Star had remained constant. But it was evident that I had no idea what that star was.

It seemed best to get back to basics. To stop waffling between honest play and the bluff. To stop looking at the cards altogether.

The planning hadn’t led to the payoff. The house got the last laugh every time.

It would be far better for me to take things one day at a time. To look at what’s in right front of me and to react accordingly.

I’ve started taking this approach a bit more. And thus far, I’m happy with the results.

There’s a poignant lesson in here for all of us.

While we might desire to upgrade our hand through bluster and bravado to find success, we might have all we need already. It’s likely been there the whole time. We just hadn’t bothered to look for it before.

Success can be found in stillness. In simplicity. In the six inches in front of our face.

It’s our job — our obligation — to open our eyes to it. Let’s do so.

Playing the Cards

The bus came to a stop two blocks south of New York’s LaGuardia Airport and opened its doors. The chilly fall air rushed in, accompanied by the dueling sounds of highway traffic and an airplane taking off.

As I treasured this peaceful moment, I gazed out the window at the house across the street. It was a decent sized home, complete with a garage and a balcony that was now bathed in afternoon sunlight. It seemed like a decent enough place to live — aside from the constant roar of jet engines and whoosh of highway traffic.

“Who would ever want to live here?” I asked myself. “Maybe this is where people in New York get houses on the cheap.”

My mind drifted east, to a home about two miles past the end of the airport’s other runway. That’s where my mother grew up, and where my grandparents lived for 60 years. That modest rowhouse was no stranger to the roar of jet engines either. In fact, as the story goes, the first time my father set foot in the house, he ducked each time he heard a plane overhead.

As I write this, my grandparents’ longtime home is in the process of being placed on the market. My grandfather has passed on, and my grandmother moved into an apartment in Manhattan with my parents a few months ago. The neighborhood has changed too — what was once a majority white is now predominantly Chinese — and this shift has sent housing prices skyrocketing. So, despite my musings, I know that proximity to the roar from Runway 13 doesn’t bring down housing prices.

Still, I posit that living under a flight path is a nuisance. Which leads to a key question: If we make our own destinies, why would we settle for a scenario with unwanted variables?

Much of our decision has to do with playing the cards we’re dealt.

Consider this. From the day we’re brought home from the hospital, the house we live in is just home. As children, we don’t know what all went into our parents’ decision on where to purchase their home, or the hoops they might jump through to maintain it financially.

But as we grow older and move out on our own, we think about things from a more practical perspective. What do we want our living space to look like? What do we want easy access to? Who must we be near to? And — perhaps most importantly — how much can we pay for all of this?

The answers to these questions help determine our actions, even if it means moving to a tiny, overpriced studio apartment with no counter space, or getting a roommate or three.

These situations might be perplexing to me, as I rent a decent sized apartment in North Texas. But if living in New York City — or San Francisco, or Austin or Uptown Dallas — is important to others, they’ll be willing to sacrifice space, privacy, amenities and even peace and quiet. Heck they might not even notice what they gave up in the process after a spell of time has passed.

It all comes down to perspective.

For example, when my grandparents moved into their home in 1957, it was almost considered a move to the suburbs. The home had everything a suburbanite might need — a garage, a nice enough kitchen and access to a highway built under the brand-new Interstate Highway System. The airport was there, but air travel wasn’t nearly as pervasive as it is now, and many of the loudest jumbo jets had yet to be created.

In 2017, it’s expensive to live anywhere in New York City. Yet the demand is there, particularly on the neighborhood level. Even with the small size of my grandparents’ longtime home, and the adjacent noise and traffic issues, someone will pay a premium for it, as it provides access to living in a coveted neighborhood.

Perhaps the people who live in that home two blocks from LaGuardia — the one I saw from the bus — perhaps they have a similar story to my grandparents, where they bought the home generations ago. Or perhaps they’re like the eventual owners of my grandparents’ home, where they found what might seem to the layperson as an untenable location to be anything but. Perhaps members of that family work at the airport, or for the airlines, and location trumps peace and quiet. Who knows.

What I do know is this: When it comes to where we live, and how, not all is how it appears on the surface. It’s a reflection of the hand we’re dealt, and the cards we play.