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.