The Planning Paradox

I love it when a plan comes together.

If you’ve ever seen The A Team, you’ll find this phrase familiar. Colonel Hannibal Smith uttered it dozens of times — in both the 1980s TV series and the 2010 film adaptation.

The phrase resonates with us because we find it serendipitous.

It’s a magical feeling when everything just works. But it feels ever more satisfying when we play a part in making that outcome happen.

We are better positioned to make the most of our good fortune. For the groundwork has already been laid.

This is why many of us obsess with planning. With envisioning the possibilities and putting in the work to make them a reality.

We fill our calendars, set budgets and forecast possibilities. We give ourselves marching orders and then follow them religiously.

It’s dutiful work. Routine work, even.

But it might be a waste of our time.


 

God laughs at your plans.

This phrase makes me wince.

Not because I’m one to question God’s work. Far from it.

No, this phrase makes me wince because of the utter futility it describes. Specifically, that of making plans and seeing them go to waste.

For I am a planner.

I relish the opportunity to prepare for what lies ahead. In fact, one could say I obsess about it.

I chart out my meals for the upcoming week even before I make my way through the supermarket aisles. I get tickets to sports events or concerts weeks ahead of time. I show up to the airport two hours early to ensure my checked luggage makes it on the plane.

I even regiment my days. I set an early alarm on weekdays so that I can work out, freshen up and take care of other household tasks before I even head out the door to work. And I make sure to wake up with the sun on weekends so that errands don’t eat up too much of my day.

My calendar is my compass throughout this process. I want to make sure I’m on time, on budget and on top of things.

Above all else, I want to maintain control. After all, such tendencies are in my nature.

Still, I know I’m fighting an uphill battle.

For all measure of obstacles lie in my wake — from real-time changes in the weather forecast to daily fluctuations in my health. There’s no sure way to see these coming, which means advance preparation for them is, at best, half-baked.

Even on the micro level, unpredictability abounds. Friends and family can put together last-minute events. A sudden traffic jam on the highway can make that trip to the airport take twice as long as it should. A supply-chain issue can leave many of the supermarket shelves barren at the moment I’m pushing my cart down the aisle.

And when it does — when God laughs — it can be utterly frustrating.

I’ll seethe as I think of all the energy I’ve wasted preparing for a future that turned into pure fiction. I’ll lament being blindsided by the current reality. And I’ll second guess every plan that led me into the current predicament.

This is not the best response to unpredictability. But when you obsess over planning, it’s often Live by the sword. Die by the sword.

And all too often, I find the bitter end of that proverb.


Is planning futile?

Not exactly.

Certainly, an overarching reliance on a plan can hurt. My own experience bears that out. So does the failure of the Centralized Economic Planning philosophy under the Soviet bloc.

But going without a concrete plan can be just as devastating. When Napoleon invaded Russia in 1812, for instance, there was no plan for how his army would handle the upcoming winter. The harsh conditions decimated the troops nearly as much as the Russian forces did, leading to a humiliating defeat.

The overarching lesson is that planning is important. But only to a point.

We have to be ready for what should come to pass. But also to expect the unexpected.

I call this The Planning Paradox.


The Planning Paradox is an uncomfortable concept.

For it demands that we do our due diligence, yet still be ready to turn on a dime.

Few of us are naturally that agile. On the contrary, we tend to fall into one of two camps: The Planners and the Reacters.

Planners do what they can to control their environment ahead of time. Reacters analyze the environment in the moment and respond to it ad hoc.

In order to find success in life — in work, in relationships and elsewhere — we need to use each trait. But only one of them is inherently dominant in each of us.

Personality tests help surface that dominant trait by forcing us choose between them on each question. They embolden us to circle the wagons around our position of strength.

But The Planning Paradox challenges us to broaden our approach.

The Planning Paradox first encourages us to embrace the dark side. To learn how to manage the approach we naturally repel.

For Planners, this means accepting the chaos and going with the flow. For Reacters, it means taking the time to prepare for future outcomes.

Then, The Planning Paradox requires us to combine the two approaches into a single protocol. One that sets the rules of engagement, and then determines the conditions for breaking those rules.

This is not an easy ask. And the ambiguity of it can weigh on us. But the strain is for our benefit.

For such an exercise encourages us to think on our feet. To get comfortable with the uncomfortable. To add slack to our rigid approach.

These are the muscles we need to flex. These are the skills we need to master in order to thrive in a world that’s equal parts routine and unpredictable.

So, let’s stop fighting the Planning Paradox. Let’s stop ruing the energy we waste on plans that go bust. Let’s stop wishing that the world did away with schedules altogether.

Let’s get out of our corners. Let’s get used to thinking outside the box.

That is our only way forward in this perfectly imperfect world.

On The Precipice

I’m on the edge of glory, and I’m hanging on a moment of truth.

These iconic Lady GaGa song lyrics speak volumes.

Whether we’re watching our favorite TV show, playing Monday Morning Quarterback after a football game or researching business case studies for work, the narratives we absorb have one thing in common.

They hang on the precipice. On the point of divergence between what got us here and where we’re going from here.

These cliffhanger moments are both overdramatic and overly cliché. But we continue to see them because they work.

That feeling of being on the edge of something new exhilarates us. Much like the moment before that first big drop on our favorite roller coaster, we can feel the butterflies of anticipation.

We’re addicted to this narrative. And the content creators are addicted to our addiction.

So, the literature we read, the hot air we listen to on the radio, the moving pictures we binge on our flatscreen TVs — all are filled with moments of truth.

It’s as if these game changing moments are a dime a dozen, just waiting for us to grab them.

They shouldn’t be.

You see, continually living life on the precipice is as irresponsible as it is exhilarating.

For those turning point moments are more than just high drama. They’re often the result of a lack of prior execution.

If the person or company facing a moment of truth had acted earlier, their future wouldn’t hinge on one make-or-break decision.

Debate the thought process for the fourth down play all you want. If you’d moved the ball enough on the first three downs, it wouldn’t have come down to one play.

Evaluate that big acquisition all you want. If the company had kept its financial health in order, then maybe it wouldn’t have had to bet the farm on such a risky move.

Glorify Jordan Belfort’s life all you want. But The Wolf of Wall Street wouldn’t be writing memoirs and sales coaching books for restitution money if he hadn’t spent years defrauding investors.

Yes, just like our fixation with the Rock Bottom Paradox, we can’t seem to move off of the life-and-death moments. We celebrate the winners and take lessons from the losers — all without realizing that all participants have already lost.

The real winners? They’re the ones who never brought their venture to the edge of a cliff. They planned ahead, executed with consistent precisions and heeded the warning signs of lurking danger.

You don’t hear about these winners, because their stories are wholly unmemorable. The highs and lows of their journey don’t captivate our imagination, call to our fears or stimulate our aspirations.

Make no mistake, though. This is the path we should follow.

It’s far more likely to get us to where we want to go. And it’s far less likely to put us in a spot where we risk losing it all.

So, forget the fancy narratives and the juicy cliffhangers.

The steady path forward is enough.

Read and React

According to plan.

We cling to these words like gospel. We strive to stay on schedule, on point, on task. To proceed down the path we’re intended to follow.

If everything goes according to plan, life is good. But all too often, it doesn’t. After all, the saying goes, “God laughs at your plans.”

When things go awry, we find ourselves in a world of trouble. Suddenly, we have 99 problems and can’t even solve one.

Why do we put ourselves through this dance? In part because we can’t bear the alternative.

We can’t stand to live in the moment.


There’s a stigma to living in the moment. One that states those who choose to live this way must throw all cares and responsibilities away.

This couldn’t be further from the truth.

Sure, there are some people who approach life with a Key West attitude. But most people don’t have that luxury. Most people have families, occupations and other pressing concerns to tend to.

Yet even with these concerns, these people can adopt a Live in the Moment mentality — assuming they approach it the right way.

How so?

By following the Read and React framework.


If you’ve played chess — or football —  you’re likely familiar with the Read and React framework. It requires looking at the situation around you and then reacting accordingly in the moment.

While Read and React doesn’t prepare you for what’s coming ahead of time, it does the next best thing. It helps you control the outcome.

By practicing these principles time and again, we become more proficient at reacting to an increasing number of situations — or Reads, if you will. We become seemingly unflappable and action-driven.

Even in the wake of unpredictable outcomes, we can remain prepared. Prepared to respond. Prepared to capitalize. Prepared to lead.


Many of us practice the Read and React framework in our occupations — particularly if we work in a volatile profession. For example, I used it daily while working as a TV news producer. Practicing the framework helped me better adjust to the unpredictable nature of news — and therefore become better at my job.

So why not carry the same principles over to our lives?

After all, everyday life is chock full of unpredictability. Aside from the sun rising in the east and setting in the west, it’s one of the few things we can count on.

Why waste our energy and effort planning every detail of our lives? All that guarantees us is angst and stress when things inevitably go off track.

Instead, why don’t we live in the moment? Why don’t we change our approach to read what’s going on around us and then react accordingly?

It takes less effort to do this than it does to make plans that might never come to fruition. And we’ll be better prepared to handle life’s frequent surprises with poise and precision.

This process will make us more Zen. More relaxed. More pleasant to be around.

In short, it will lead to more positive outcomes.

What’s not to like?


Now, of course, we can’t live in the moment all the time. Planning remains critical for several aspects of our lives.

But let’s keep it to that.

Let’s plan only in situations where it’s only absolutely necessary, and Read and React to everything else.

We’ll be better for it.