333. The Deadlines That Matters Most

There always seem to be deadlines in my life that are haunting me. It's the reality of my mortality. And then one day everything changed.

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My name is Jeff Matlow. I help leaders solve big problems fast.

NOTE: This article is not the article I started writing. You’ll understand why in a second.

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I’m on a deadline.
There always seems to be deadlines haunting me.

Thirty minutes ago, I was in the zone. I was writing an article about an interesting leadership lesson. It’s insightful. It’s funny. I love it and I think you will too.

The stress of this impending deadline was diminishing with every word I wrote. But then I got a text from one of my close college friends.

Bernadine died from a brain tumor.
She had two kids.
She was in her fifties.

Bernadine is a mutual friend of ours from college.

Notice, I said she “is a mutual friend.” I can’t yet get myself to say she “was a mutual friend.”
It’s still too new. Too raw.

I can’t believe she’s dead.

After a few minutes, I tried to finish writing that leadership article. I’m on a deadline, I need to get it done.

But I can’t. I’ve lost the drive.
There’s no way I’m going to hit that deadline.

The subject of life’s leadership lessons seems so insignificant once you’re forced to think deeper about life and its lessons.

The Illusion Of The Eternal Deadline

It was Jean Paul Sartre who said, “Life has no meaning the moment you lose the illusion of being eternal."

Those words are never as impactful as when you confront your mortality, as when your friends start dying.

Those words were never as impactful to me as they are right now.

Thirty minutes ago, I was fine. But now the deadlines taunt me like a wasp on honey-covered hands. It seems that no matter what I do, I’m going to get stung.

I can’t write when my friends are dying. That’s the irony of the deadlines. It’s the dead that stop the lines.

When your friends are dying, you think about deadlines in a different way. You think about life in a different way.

I’m not saying deadlines don’t matter anymore - they still do. I’m saying that you begin to question the importance of each one.

As if every moment is more fragile than before. As if every second needs to be more meaningful and poetically pertinent than the last.

Suddenly, I’m striving to live a massively meaningful existence. I’m crawling through the barren sun-soaked desert of life, extremely dehydrated and craving for a drop of meaning.

I want to say things I’ve never said. Important things. Life-altering things.

I want to say things that are more meaningful than my obsessions with leadership lessons.

When your friends are dying, you want to scream about the things that your friends no longer have the voice to voice.
You want to make a difference.

This feeling started simmering a few years back.

Pete’s Deadlines

Pete died of stage 4 brain cancer.
He had four kids.
He was in his 40s.

Pete was a friend from college. Not a close friend, but close enough for me to be heartbroken.

I went for long, emotional runs after Pete died. The song “Swim” was playing in my ears, louder and louder with each repetition, as I tried to process the fact that my peers had begun perishing. The song was written by Andrew McMahon of Jack’s Mannequin while he was battling leukemia.

You gotta swim, swim for your life
Swim for the music that saves you
When you're not so sure you'll survive

Something slightly changed in me forever when Pete passed. It’s not like mortality smacked me across the face. It didn’t. But it tapped me on the shoulder and began to regularly remind me it was there.
Watching.
Waiting.

We spend so much time racing toward deadlines that we forget where the road ends. Or when it ends.

A lot of the time, we forget that it even has an ending at all.
We assume it’s a long, endless stretch that fades away over the horizon.

But every road has an ending. Every deadline has a date.

I thought of this again in 2020 when mortality decided to scream in my ear. It scared the shitballs out of me.

Matt’s Deadlines

Matt died of unknown causes.
He had three kids.
He was in his fifties.

Things became real with Matt. He was a friend from college - one I was closer to than Pete.

Contrary to what we expected of him during those drunken dorm room days, Matt became a lawyer and built a wonderful, loving life for himself and his family.

He was on a Zoom meeting when, in an instant, he went silent and dropped from the call.

He dropped.
Literally.

He was dead before his body hit the floor.

Worst Zoom call ever.

Pietta’s Deadlines

Let me be clear, I’m not at an age where my friends should be dying. My parents are at that age. Not me.

This is not what is supposed to happen. I don’t like it. I don’t want it. I’m not prepared.

But that’s the thing about deadlines, you’re not always as prepared as you wish you were.

I felt that way a few months ago.

Pietta died from Stage 4 cancer.
She has a 15-year-old daughter.
She was in her 40s.

Mortality didn’t scream at me when Pietta died. He didn’t punch me or mock me. He just sat quietly on my shoulder as I stared at the horizon, lost in thought about Pietta and Pete and Matt and Bernadine. I was also thinking about my other friends struggling with cancer and tumors and strokes. People like Evelyn and Mark and Darby and Dan.

Mortality sat there on my shoulder, elbows on its knees and head in its hands, silently staring out at the sunset with me. That’s when I realized that mortality wasn’t the enemy I thought it was. He wasn’t the villain trying to get me. In that moment, I realized mortality was my friend.

“I told you,” he said. “I’m here for you. I’m not going anywhere.”

I’m not sure I find comfort in that. But I’m not sure I find fear.

While I was getting these thoughts out of my head and into words, I got a call from Pietta’s husband-now-widower. We’ve been close friends since second grade.

Our friendship is like the mafia. We can never leave it. We know too much.

“Do you feel a greater sense of mortality after going through all that with Pietta?” I asked him.

“Absolutely,” he said after a pause in thought. “But the thing is, I’m no longer scared of dying. I realize… well, I guess I realize that it’s all okay.”

The Finish Lines

I’m a goal-driven person. Always have been. I choose a finish line and a deadline, then I obsess about getting there.

My next article. My next meeting. My courses, books, and client commitments. There’s always something pending for me. Always a new goal to attain.

I used to think these deadlines were all finish lines. I used to think that my journey forward was what mattered most.

But now I’ve realized I’m wrong.
The journey is still important, so is the goal, but maybe it’s not the ride to the deadline that matters most; the important thing is the wake I leave behind.

The importance is not about the length of the road left in front of us, but in the impact and inspiration we leave behind for others to build upon.

The Important Deadlines

I’ve started to think of my deadlines differently.

Not just by what’s due, but by what’s truly important.
Who matters.
What matters.
And how so much of it simply doesn’t.

I’ve realized that life’s ultimate deadline isn’t something to fear. Your eventual mortality is also not something to fear. In fact, if you’re lucky, mortality will silently sit on your shoulders and be the reminder you need to always show up with the best version of you that you can be.

Not everything in life will be finished when our time is done. But in the words of Brian Andreas, we are guaranteed to complete everything that is most important to us.

Once you realize that, life becomes a lot easier.

It’s no longer a rush to do it all, but a matter of simply setting priorities.
I’m still going to write that leadership article. I promise you I will.

Just not today.
I’ve got more important deadlines to meet.

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