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.