Reckoning with the Wreckage

It was a great morning for a run.

The air was crisp. The stars in the sky were bright. The humidity was low.

And as I took my first few strides, my worries faded away.

I was in my element. I felt strong. I felt free.

But I knew it wouldn’t last.

I sensed the change around the two-mile mark. I ignored the beeping of my watch, telling me how far I’d come. But I couldn’t avoid the tightness in my calf muscles, telling me I didn’t have much more left to go.

It was the same tightness I’d felt at this point – or earlier – on every run I’d been on for the past eight months. If I didn’t stop and stretch soon, my stride would start to falter. My legs would lock up, leading my feet to feel like anvils. The discomfort would prove excruciating – and potentially damage-inducing.

I managed to make it another mile this time, stopping as my watch beeped its Mile 3 warning. As I stretched, I felt the chilly air hit my body. I was shivering and sweating at the same time.

I’d never contended with this dueling sensation before. Because in autumns past, I would never have broken stride this early. On crisp mornings like this, I’d have gone six or seven miles before I even considered stopping. And by then, even the coolest air would have felt balmy.

But those days were long gone. This was my reality now.

And it wasn’t likely to change.


A friend of mine once spoke of the significance of the age of 26.

There’s nothing given to us at that age. By the time we hit 26, we can already do everything from buying a lottery ticket to renting a car.

But 26, my friend posited, is when life starts to take for the first time.

Young adults might be able to party as voraciously as they did in college without consequence. But 26 hits different. Newly minted 26-year-olds need a minute, an hour, even a whole day to recover.

I can’t speak to this all that well. By the time I’d hit my mid-twenties, my wildest days were behind me. I was hitting the gym more. I was going to bed earlier. And I had given up fast food.

But now, more than a decade later, I feel the weight of my friend’s words.

For despite my best efforts, time has caught up with me. The force of its impact has sent me hurtling to the ground. And it’s taking me longer and longer to get back up.

I’m consistently exhausted now, often irritable, and immensely perplexed. How is everything that was once so easy now so difficult?

There are no easy answers. Only more unsettling questions.


As I stood there stretching my calves, I took a moment to consider what had been.

On those autumn mornings of yesteryear, the miles flew by because I was chasing something greater.

I was a competitive runner back then. I entered in several distance races a year. And I brought back hardware in most of them.

I had the talent and the willpower to deliver excellence. But I had no idea how quickly the sand would run out of the hourglass.

When my first injury hit, I moped about it for a week. But then I thrust myself into the rehab process, determined to come back stronger than before.

My zeal backfired. I picked up two new injuries in short order, one of which required surgery. Two months in a walking boot ensured, followed by four months of physical therapy.

By now, my fiery defiance had been doused. Just getting back to running regularly would be a victory, considering how far I’d fallen.

Amazingly, I achieved that victory, and even began a race training block. But I sustained two more injuries in the ensuing months, forcing me to shelve my plans once again.

I was now in the valley of that prolonged disaster. I was a shell of my former self. And I was growing more and more certain that I’d remain in that state.

But instead of wallowing in self-pity for my present, I was full of indignation for my past.

Sure, my exploits back then had put plenty of silverware on the wall. Medals for podium finishes and age group wins. A plaque for breaking the tape in a backwoods 5K.

But those mementos represented only a fraction of my potential.

I could have done better, I told myself. I could have dreamed bigger, tried harder, achieved more.

If I had gone all-in during those peak years, maybe I wouldn’t feel so hollow. There would be no unfinished business festering as Father Time stripped my speed and stamina away.

But I hadn’t.

And now, I was out in the cold. Literally.

I was left reckoning with the wreckage of it all.


God, grant me the serenity to accept the things I cannot change, the courage to change the things I can, and the wisdom to know the difference.

The words of The Serenity Prayer are omnipresent in my mind. I’ve leaned on their wisdom countless times throughout the years.

Much is made of the middle and the end of the prayer. After all, courage and wisdom are desirable traits in our society.

But it all starts with acceptance. Which – according to the Kubler-Ross Model – is where the grieving process ends.

I don’t think this is a coincidence.

Grief is the one of the most powerful emotions we experience in life. It’s visceral, multifaceted, and inevitable. It washes over us, regardless of whether we’re ready for the force of its mighty wave.

It’s only when the tide has gone back out that we can see what’s left behind. And that we can use those odds and ends to build back up anew.

This is the evident when we lose loved ones. While we miss them dearly, we must find some way to propel ourselves forward.

Yet, it’s just as applicable when the loss is less existential — such as our youth, our ability, or our potential.

I am finding that out firsthand.

I was once a great runner. Just as I was once an emerging marketer. Just as I was once a young man.

I am none of those things anymore. Time and its companions have taken much of the shine off me.

I’ve seen it. I’ve felt it. I’ve grieved it.

But now is the time to get off the mat.

Now is the time for me to accept it all. What I was. What I am. What I can still become.

And now is the time to follow that revised path.

Reckoning with the wreckage might be a solemn obligation. But it’s an obligation, nonetheless.

Mile by mile, I’m honored to take the mantle of its responsibility.

The Extension Trap

The images were horrifying.

In the heart of Chicago, railroad tracks were on fire.

This seemed to be disastrous for America’s third-largest city. Track fires would jam up rail traffic, disrupting commuters and putting a halt to freight deliveries. And the flames could easily threaten nearby structures — a possibility that had literally burned Chicago before.

But appearances can be deceiving.

Indeed, the flames were no accident. Maintenance crews had intentionally set the tracks ablaze to preserve them.

An arctic blast had hit Illinois, sending temperatures well below 0. And in those conditions, exposed metal can shrink.

Narrower tracks cannot properly hold train wheels. They make derailments likely.

Setting the tracks on fire caused the metal to expand, canceling out the damage from the biting cold. The trains kept running, and life kept churning.

Those blazing railroad tracks kept everything in equilibrium.


Several years later, another picture of fiery metal made the rounds.

This time, a metal dumpster was on fire. And the image of it was all over the Internet.

Now, an inferno of a trash receptacle doesn’t mean much on its own. Burning trash is still trash.

But what those bins represented? That certainly struck a chord.

The dumpster fire images were referencing WeWork, a once ballyhooed company that had hit a rough patch.

WeWork had started as an office co-working company — one of the first of its kind. It was a darling of the start-up world and a tempting target for venture funding.

The ingredients for success were there. And the company began to scale.

But once WeWork announced plans to incorporate as a publicly traded company, the wheels fell off.

Investors started diffing into WeWork’s finances, and they didn’t like what they saw.

The company appeared to be spending far more money than it brought in, and there seemed to be no end in sight for this pattern.

WeWork’s CEO and co-founder dismissed these concerns, stating that the company was doing far more than running a business. It was sparking a movement — a physical social network that replaced Me with We.

To this end, WeWork had already created a co-living brand called WeLive and an education concept called WeGrow. There were plans for banks, shipping, and airlines as well.

Venture investors had long looked beyond these red flags of excess. But public investors were less easily mesmerized. They wanted a return on their investment, and they saw right through the house of cards.

The fallout was brutal. WeWork saw its valuation plummet, canceled its Initial Public Offering, and laid off thousands of its workers. WeLive and WeGrow were put on ice. And the CEO was forced to resign.

There are plenty of reasons for WeWork’s collapse. Case studies and TV dramas will likely cover them for years to come. But I’d like to focus on just one.

WeWork’s failed, in part, because the burgeoning company fell into The Extension Trap.

WeWork expanded too fast, without a plan for sustaining such growth. Worse still, it pitched itself as a lifestyle movement before ensuring its core business was viable.

There was only one way out of this trap. WeWork was forced to shrink like those Chicago rail tracks, simply to get to where it should have been at all along.

The company does still exists today, and it’s now publicly traded. But that damage from its foray into The Extension Trap? It’s likely to linger for years.


The WeWork dumpster fire and the Chicago track fire have each been on my mind recently.

For as I write this, winter is setting in. And as the temperatures plummet, the world around us gets visibly smaller.

Indeed, signs of withering are everywhere. The economy is teetering, with high interest rates and higher inflation spooking off investors. And several companies have started to lay off many of their workers.

As the cold, hard reality of these cuts sinks in, the rationale remains consistent. We expanded too fast, and now the winds have changed.

On its face, such an explanation makes sense. This is the way modern markets work; investors and businesses are simply operating within those parameters.

But, come on.

Is this really the way we want to live? Are these really the values we want to espouse?

I would say not.

When it comes to eating, a cycle of binging and purging is labeled a disorder. It’s a problem — one not to be practiced or written off as trivial.

So why do we give a free pass for this behavior more broadly? Why do we keep taking the bait when we clearly know better?

Its maddening. But it doesn’t have to be inevitable.


The start of winter, with its shorter days and location at the tail end of the calendar, can seem like the lean times.

Paradoxically, it’s also the season of excess.

This is the time of the year where we overextend ourselves. Where we fill our calendars with gatherings. Where we indulge ourselves with sweets. Where we empty the coffers while shopping for gifts.

For several weeks, we lure ourselves into The Extension Trap, in the name of holiday spirit.

Of course, we can’t sustain this behavior. So once the holiday lights dim and the ornaments go back into storage, we adjust back to our regular patterns. And we do our best to ignore the pain this readjustment causes us.

It doesn’t have to be this way.

We can resolve to stop this madness. To say No more often. To choose not to overextend ourselves.

It’s a singular action, a drop in the bucket in the grand scheme of things. But as more and more of us head that direction, that ripple can become a wave. And perhaps, these expectations of overextension will go away.

And it doesn’t have to stop there.

Investors are people. So are members of the C-Suite. They too have lives outside of the office. They too have families and social circles.

If our movement crosses the tipping point, it can influence their decisions. And it can shift the contours in which we operate.

That would truly be a paradigm shift. But it can’t happen unless we make the first move.

So, let’s be bold. Let’s be brave. Let’s be smart.

Let’s practice moderation and steer clear of The Extension Trap.

It’s our best path forward.