One of my friends died. Three weeks ago today, I got the news.

People - myself included - always ask, after hearing of a death, whether or not it was expected. Though in 50 years on this planet, I’ve yet to be convinced that it’s really better in the end, one way or the other, whether people know ahead of time or not. There’s normally enough sorrow and grief to go around, either way. It’s just that sometimes the pain for those left behind is sharp and terrible, entangled with the shock of a thing the heart is ill-equipped to easily comprehend. And other times that same pain is metered slowly, like the drip of an aging faucet, grinding away mercilessly at the nerves and emotions of the dying and those who love him, for a long time.

But they both hurt.

My friend’s death wasn’t expected. But it wasn’t unexpected, either. He died, in a sense, as he lived: In a manner that’s hard to explain. He would’ve loved hearing me say that.

It’s entirely typical that I don’t remember where I put my keys, or what I was doing a week ago Thursday. But I remember the day Jack barged into my life, unannounced, in 1994. If you had met him even once, you’d remember the day, too.

It was in Chattanooga, not long after my first day on a new job. I was a freshly-minted Assistant Manager. That’s corporate-speak for a kid who hasn’t the slightest understanding of what’s going on. I had started with the company only a year before, as a grain trader.

Having not yet learned how much I did not know about grain trading, or for that matter, why we were trading grain in the first place, I was sent to an interview with an older gentleman. His name was familiar to me from the corporate shareholder reports. I certainly didn’t read those, or even really look them over, because they were the domain of people who actually had shares. But his name was near the top, and therefore noticeable enough, apparently, that I’d seen it during a 30-second cursory glance. He was a Something-Something-Emeritus, it said. A title which earned him, at the very least, I remember thinking, a lot of pictures of him with other guys in suits, which hung on the wall of his cavernous, walnut-paneled corner office.

To this day, I don’t know if it was because the interview went exceptionally well, or because it was a marked failure, but a few days later my wife Amy and I found ourselves on the bench seat of our 4-cylinder Dodge Aries, as the highways of Illinois and Kentucky gave way to those of Tennessee in front of the bug-riddled windshield.

My new job was to learn how to run flour mills. At this stage of my life, I had a general idea - a feeling, really - that flour was made mostly out of wheat. Some vague memories of my mom using it to make a number of things I’d later sneak up to my room before supper, told me that it was white. If questioned directly, I likely couldn’t have come up with any other real qualities of the product that would indicate expertise in milling. Management material, in other words.

And that reality was settling in on me like a cold, heavy fog, as I sat at my desk, marinating in my own ineptitude. As a twenty-something young man, still drying the water from behind his ears, I found myself surrounded by people much older and wiser than me. People who knew enough about how flour was milled to communicate fluently in the practiced-jargon of it all: Falling numbers, gravity tables, conversions, high-ash clear streams.

And against that backdrop, Jack walked in one day, two hours late. And he really didn’t just walk in, either. He blustered in, loudly and smiling. Humming what I would later come to know as one of his go-to nameless songs, into which he would launch whenever he felt the atmosphere was just too quiet. His face had the tan of one who played endless golf, or owned a boat. As I found out later, both were true, although the boat also doubled as his house. Blond hair hung below the collar of his dress shirt, which was unbuttoned one button too many. Shirt sleeves rolled to his elbow, in his arms he carried several boxes of donuts which he slung onto the desks of secretaries and accountants he had not yet met. He wasn’t wearing a tie. Dress code required a tie.

Of course code also required us to not be two hours late. Jack didn’t seem to care about that, either.

Not long after that day, the manager was transferred to the corporate office. And in came a new manager. Young. Lawrence was just a few years older than me. He was buttoned-up, meticulous. The hardworking son of a Kansas dairy farmer. He used his words deliberately, and was unfailingly polite. As far away from Jack, personality-wise, as I was. And the three of us became fast friends immediately.

Lawrence and I watched Jack’s exploits like an Oscar-winning movie. He was unlike anything we’d experienced. He was a salesman, and a good one. A phenomenal one, in fact. He could drink like a fish, but rarely did. Lawrence and I would sit at dinners with customers, sipping our iced teas, while Jack was inhaling mixed drinks like water. The reason for that, we later understood, is that it was water. He was doing it to make the customers around him - customers who were inhaling mixed drinks - more comfortable. And likely, because it made them more pliable, too.

Jack dealt with attorneys like most of us deal with the sales clerk at the store - comfortably, and without really thinking about it. Like it was something that happened during the course of everyday existence. For Jack, it was. He was always doing something that skirted just this side of the law. And, for all we knew, maybe even swerved across to the other side a time or two. That’s how you figure out what you can and can’t do, he’d say. Lawrence and I just figured there was a book of laws somewhere that would tell us the same thing, should we find ourselves wondering.

He knew everyone. By that, I don’t mean he knew their names. I mean that when you went anywhere in public with him, insurance agents, roofers, lawyers, plumbers, policemen, judges - salesmen from competing companies - would stop and talk to him. He’d know their wives names. The age of their kids. Where they vacationed. He’d know their favorite restaurants, information which he’d later use to send them gift certificates on their birthdays. Which he also knew.

His life was an endless series of the strange and wild. Like the time his jaw was shattered by the errant swing of a prison inmate, when Jack was on a team that played prison baseball games as practice. Or the time he broke it off with the Dallas Cowboy cheerleader, because he got tired of the travel. He started an underground nightclub of sorts, catering to college kids and staffed by a group of local characters. He personally took home $60,000 the first year it was in business…when he was 16 years old. He started a large and successful driving range on a piece of land designated as a floodplain. He couldn’t find a developer to help him with the labor for a price he could afford, so he rented a bulldozer and built it himself, while he was working a full time job as a traveling salesman.

Or the time he became a first-year member of one of the oldest, most formidably-conservative and formal invitation-only associations in our industry, by attending one of their gatherings at the swimming pool of a high-end country club. When he undressed poolside to go for a swim, his head-to-toe tattoos were revealed to the shocked stares and near total silence of the blue-blooded onlookers. When he dove in, and emerged with all of the recently-applied fake tattoos having washed away, he was met again with shocked stares and even more silence. Only this time they were followed by deafening cheers and laughter, and an instant invitation to join an organization other salesmen had tried unsuccessfully for years to crack.

But for all his bluster and bravado, Jack was equally interested in my quiet reserve. He would ask serious questions - about my opinions on Christianity, politics, family. In that way, he was an enigma. The stereotypical party guy, with a thoughtful and introspective streak a mile wide, that he only showed to a very few. He had many friends in his younger years, and he worried about them all. Wanted to make sure they were going to be ok. It always concerned him, that there was maybe something he should be doing for them, that he didn’t know about. He volunteered to work for the Special Olympics - a program he talked about until his last day. He loved it.

He told me on more than one occasion that he thought of himself as a lifeguard, more than anything else. Helping those who needed it, even when they didn’t know they needed it.

He said it thoughtfully, as though he were describing something to me about himself that I didn’t already know.

His confidence influenced me in a lasting way. As a scared kid swimming in big water, the young me was living life with constant glances over my shoulder. Waiting for the other shoe to drop. In constant fear of being wrong, of showing my true colors; as the clueless kid I really was, every move I made was defensive. I couldn’t seem to just relax, work hard, and let things happen in due time. There was worrying to be done. The future couldn’t get here quickly enough, for me. I only wanted to reach a level of competency, and fit in. But to Jack, every moment was an opportunity. Another sale. Another crazy idea. Another experience. Another friend. The future was something that would take care of itself. Worry was a waste of time.

Through watching and experiencing Jack, I began, for the first time, to really understand that no breathing person could make you feel or do anything. You could allow them to persuade, influence or guilt you, but in the end, whatever happened as a result, was your decision. A point which, to him, made fretting about things utterly pointless.

The three of us only spent a year in the same office. Looking back, it seems like it was a lifetime. Each of us went our own ways, eventually. Lawrence and Jack kept in touch through work, but in time, I moved on to a job with a different company. We lost track of each other as time began to pass, as it always does, quickly and forgettably, when we aren’t minding it. A year turned into ten, and then into twenty and change. Every time I thought of looking one of them up, of calling them, just to see how things were going, something came up. Life, as they say, always got in the way.

And then one day a few years ago, I got a call at work. There were two guys on a conference call holding for me, they said. One of them claimed he was my boss, that he was sick of waiting for me, and he needed me on the phone right now. And even after all those years, the name crossed my mind immediately: Jack. The only guy I could think of who would’ve introduced himself that way. When I heard Jack and Lawrence on the other end, the decades evaporated. We were instantly the three young guys in Tennessee again, at the beginning of their careers. Laughing, joking, reliving stories from back in the day.

When the opportunity to meet them in person arose just a month or two later, I jumped on it.

Jack wasn’t well. I could tell from the moment I saw him that, even though his deep, booming voice was the same, and his memory was impeccable, he was frail and halting. His easy grin was weaker now, creased with the lines of age and a conflicted soul. He spoke in guarded words, when he spoke at all. He still had the same joking demeanor - quick with one-liners that he’d deliver without even a ghost of thought as to whether his words were appropriate to present company. And then, as before, people loved him for it. He was still my friend, but he wasn’t the same old fiery Jack I once knew. He knew it, too, and I could tell it bothered him.

That visit turned into several more, as I traveled to see Jack where he now lived in South Carolina. He was still involved in the commodities business. But rather than the jet-setting, hard-charging everyday golfer I remembered, he rarely left his house now. He conducted his business as chief buyer for a large company entirely by telephone. The same phone he used to call me three or four times a week, nearly every week of the ensuing years. “Me at twenty percent is still better than most of these other clowns at a hundred” he’d say, and laugh. He was probably right. But he said it to convince himself it was true. We both knew that.

And like old times, Jack reveled in stories of his younger days, relating over and again the crazy stunts he pulled. Some of the stories I knew, many I didn’t. And we talked, as we did long ago, about Christianity, politics, family. His daughter would be there that Christmas, he said, and he was nervous. He was proud of her. He wanted to make sure she loved being there.

For the first time in more than a decade, he had pulled his decorations out - and there were a lot. His house looked liked the picture windows at Macy’s during the Thanksgiving parade. He had loved Christmas once. And any other excuse for a festival. He wanted to feel that excitement again, and wanted his daughter to feel it, too.

As always, his friends were important to him. He told me so, over and over. That he loved me. That he was so happy we had reconnected. That Lawrence and I were his two solid pals, and that our friendship gave his life meaning. We even had the opportunity to do some business together, the three of us. Our career paths had swerved in wildly different directions, and yet all maintained a similar thread - such that Jack was even working to sway Lawrence to come work for the company he now worked for. He loved the family who owned the company. They were his friends. They needed Lawrence, he said. And they did. And Lawrence, after weeks of constant needling, as only Jack could dole it out, eventually did take the job.

On a Tuesday evening, Lawrence inked the deal with company officials. He was excited to tell Jack, because he knew he would be elated. He wanted to tell him personally. But he knew Jack would be sleeping, so he would call him Wednesday.

On Wednesday morning, Lawrence and I each got a call. The call that caused this story. That Jack went to sleep Tuesday night, and never woke up.

The last thing he did was to get his old friends connected with his new ones. He wanted to make sure everyone was going to be ok.

Lawrence and I have stayed closely in contact, both through helping with Jack’s affairs in any small way we can, but also through shared memories of old times. It’s a friendship rekindled because of Jack, that will not fall by the wayside a second time.

He starts his new job - the one Jack convinced him to take - in October. He’s looking forward to it. And Jack was right - he is perfect for it. And the family he’ll work for, just like Lawrence, is kind and humble and successful and smart. It’s a perfect match. Jack knew it was.

Whether or not his death was expected is irrelevant; a matter of perspective and speculation. Even now, as I think of him, I’m saddened by the misfortunes that seemed to befall Jack in droves, late in his life. Some of those misfortunes the result, to be sure, of wheels set in motion many years before. As is reasonably expected, the product of a fast life is by definition a short one.

I wish I could’ve been there with him earlier. Maybe I could’ve done something then, so that some of his troubles weren’t so big now. Or at least I could’ve sat with him, so that if he suffered, he didn’t suffer alone.

But even in death, Jack is still offering perspective to me. His smiling, humming likeness will always barge into my thoughts. My age alone precludes me from being the scared kid swimming in big water any longer. Now I’m the old guy who still feels that way sometimes. I still find myself thinking back to that time when Jack, two hours late and wholly unworried, burst into the room to make my life better. To make sure I was ok.

And I think of the later times, too. When Jack, his persona faded compared with the blazing shimmer of his youth, taught me once again, that the things I worry so much about, are all wrong. He was flawed, as we all are flawed. And he knew it. But he also knew that flaws did not define a person. They did not determine how you loved your friends.

And he knew that position in life doesn’t matter. The crowd can do what they want. Being a personality - an influencer - a bright and shining star, is a fine way to be. If you have a light that burns brightly, let it shine. But it only shines for a season. For every day after, it’s not about you. It’s about how you make people feel. How you care for them. How you make sure they’re ok. It’s relationships that matter.

And when he died, I experienced the profound and humbling realization that Jack did more to care for his friends as a recluse - a nearly-invisible man with a failing heart - than I’ve done in five decades in a life of relative ease and comfort.

In that sense, Jack’s heart wasn’t failing at all.

And that is my purpose, now - to remember that, when conditions aren’t easy. To make sure I don’t lose sight of the things that matter.

For the friend you were back then, to the new kid in Tennessee; and the friend you were when I was older and gray, and needed you more than I realized:

Thanks Jack. I miss you, brother.