You Will Not Make It Out Alive

TL;DR: Love harder and make your own way by embracing risk.

Lately, I’ve been noticing a disturbing trend amongst so many in business and politics. People are playing it safe — for what, I have no idea. But fear and anxiety are palpable in American life and I think it’s because so many of us have forgotten a simple truth:

You will not make it out alive

Let that sit in. [Keep going] You’re not going to live forever. You will die.

If there is one constant enemy of all of us, it isn’t each other — it’s time. Should you not have come to the understanding that it is time that haunts us all, welcome to your new reality.

Now, you get to move past the small things that have been in your way and choose what kind of life you’ll have and what kind of legacy you’ll leave.

We used to be explorers, committed to discovery, and a people who would stand tall against all odds. In my lifetime, I’ve seen us lose that willingness to embrace risk and push through the status quo to make change.

So many organizations are focused on the wrong metric. Ask any number of leaders, and they’ll tell you that they’re concerned with minimizing risk. But this thinking is incomplete.

Leaders need to embrace risk-informed thinking as a means to take on opportunity-based action. If all we think about is the “down-side,” we will find ourselves in a position where all we are doing is losing more slowly. We’re stopping the bleeding but we’re not growing and we certainly are not making the most of what we have.

The best leaders understand that focusing on opportunities creates risk — but that it also inherently creates reward. Most importantly, leaders who embrace risk-informed thinking see that to lose an opportunity is a risk in itself. This quality differentiates Elon Musk, Jack Welch, and Jeff Bezos from so many executives you’ve never heard of who have failed because they were paralyzed by risk.

Remembering that you will not make it out alive can change your perspective on what it means to live. It places your thinking in the present and the future — not in the past.

It is important to remember that life is not a multi-round game. While we play many turns and hands in the various chapters of our lives, in all, we only get one shot. Waiting and holding out — playing it safe — does not improve your position over the long-term so much so that this strategy will bring you the rewards in life that you desire.

Do not fall into the false thinking that life is somehow judging your actions, moving new opportunities to and from you based on your last move, and then doing it again. You and only you are responsible for your moves. They are not governed by anyone else even though we all live in the constraints of society. It is your job to succeed and no one else’s.

Leaders that aim small will miss small — but will also win small. Those that see opportunity and take it will move our human experience forward across generations.

Upon understanding the finite nature of life, you will come to realize that it is also not all about you. It’s about changing everything around you or nothing at all.

The biggest opportunities are in those areas that vault our society forward.

I see so many people dedicating their time on this earth to small pursuits. They get up, go to work, slave away for other people, hate their jobs, return home to a loveless and passionless life, and do it all over again.

Stop. Doing. That.

If you focus on enjoying your life and building things that are meaningful, you can change your future and that of those around you. There is no prize for staying an unhappy person. There is no reward for laboring without love.

The reward that so many of us look for is that of a sense of accomplishment. If that’s you too, then focus on accomplishing things and not on amassing meaningless accolades, fighting with yourself throughout your career, and pushing a boulder up a hill only to have it roll over you time and time again.

I strongly believe that life is about the experience. If you’re so constrained by risk, by what people think, or by admiring the problem — you won’t be able to make the kind of life you really want for yourself or the contribution that others need from you.

Remember that:

“Every man’s life ends the same way. It is only the details of how he lived and how he died that distinguish one man from another.” — Ernest Hemingway

This writing is not to say that you must, under all terms, focus on building greatness. In fact, this writing is meant to inspire action towards happiness as you define it. To aide in that pursuit, I’ll call on a beautiful quite from Jerry Garcia that has come to truly change my thinking.

More than 22 years later, millions of people still listen to the Grateful Dead. In a hundred years from now, I suppose many will as well. But in five hundred, a thousand, a million years — no one will know who they are. While that’s sad, it’s also beautiful. Jerry understood that he’d never make it out alive — and he lived that way.

Joining him is another musical icon in Frank Sinatra. If you’ve never read the lyrics to My Way, you’re missing out on the words of a warrior poet.

“Yes, there were times, I’m sure you knew
When I bit off more than I could chew
But through it all, when there was doubt
I ate it up and spit it out
I faced it all and I stood tall
And did it my way” — Frank Sinatra

There are some people who live life like a tour de force. And while not everyone needs to take on life that way, there are some things that all people should recognize.

Perhaps the most iconic celebrity to embrace the notion that you will never make it out alive was Steve McQueen. His quote is not to say that you should be selfish. Rather, he believes that you should stop living for other people, for what they want, and put their need above yours. The greatest risk in life is not that you will fail. It is to not try at all.

This is not a “live life like there is no tomorrow” proposition. There is tomorrow. And tomorrow after that. But it doesn’t go on forever. Embracing that reality can inspire you to action and catalyze you to give life your all, however you wish to live.

There are so many who seem to be waiting for greatness, for opportunity, and for innovation — and so few who are actively dedicated every day to bringing those virtues into reality. The first step in addressing a problem is realizing that one exists in the first place.

We have a problem. It’s a problem for collective inaction. I think that this is partially due to a lack of understanding that life and everything is finite. Without the constraint of time, you will never be emboldened to act.

You have the opportunity to fight for what you think is right. To take a chance on yourself and your ideas. You can sacrifice and succeed; care about your neighbors and yourself. And you can do it all while making the kind of contribution that you want.

It is possible to vault our society forward if we all gear up together. We can explore the stars, create beauty, generate a bountiful economy, and have peace in our time. But we have to realize that none of it can come with us after we die. We have to come to the understanding that we are doing the work for ourselves and for each other. We have to put down fear and wedge issues and take on risk for the purpose of making a dent in the universe.

Don’t scare so easily. Since you know that you will not make it out alive, everything else falls into perspective.

Cybersecurity executive, recovering startup founder, tech philosopher, hacker, traveler, early-stage investor. Independent. Faithful optimist.

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