
The following has nothing to do with tech at all: but it has a great deal to do with life, losing and remembering those we have loved. I promise not to wander off the central topic of disruptive technologies more than once or twice a year. Feel free to skip this one and ISTM #19 will be on-topic: I promise.
Charlie O’Brien was my mentor and best friend. He would have turned 80 a couple of days ago, except that he died twenty years back.
This is a eulogy I delivered at his memorial service in July 2002, outside of Boston, where he was from with the ocean as a backdrop—where he was happiest:
“Finally, I have the last word. After 37 years, I’m free of O’Brien’s editing. He can’t hammer me with a: ‘Jesus Christ, Israel, just cut to the bloody chase.’ No more will Charlie tell me to move a graph up here, make a chop there. When I’m done, he doesn’t turn to you and say: ‘What really happened was … .’
Charlie would have enjoyed today. To him, family and friends were as good as it got. Can’t you just picture him sitting here, listening—shaking his head side-to-side, tugging a beer, toking his cigar waiting his turn which would be both wise and
I wish this were a roast. Painfully it is not.”
Essential Jousting
For nearly 40 years, O’Brien and I laughed together, often at the expense of one of us or the other. Jousting was essential to our relationship almost to the end.

So was humor: Hiking three years ago at Tahoe, we sat drying on a rock after he guided us into a snowdrift. Earlier, he had asked me to accept he was going to die which was tough. As we sat there, I asked him if he had any wisdom to impart. “Is there something you now see that you hadn’t seen before? Something that can help those of us you’ll leave behind?”
He thought for a moment. “I might have been wrong about the vitamins,” he said then drifted into silence.
Charlie over the years had consumed entire alphabets of v
Three years later, I would be sitting on a barstool next to Charlie, knowing it was probably for the last time. Cancer and antibiotics had reduced him to sipping a soft drink through a straw. By contrast, I was downing draughts at a steady pace. There was a chance, he said, he’d be taking medical marijuana pills. The juxtaposition of preferred recreational substances would become our last good laugh together.
I cannot believe he’s really gone. I expect to see him at any minute. I picture him packing for yet another trip. Charlie loved to travel.
Our travels together began in 1968 with a hike up a New Hampshire mountain. Over the years we probably took more than 40 trips together, many on extended Thanksgiving weekends.
There were three rules for
(1) An adventure had to be involved.
(2) It had to be cheap.
(3) Neither of us had done it before.
Cheap fell away first. We repeated a few destinations, but the experiences were always different. We did some amazing things.
We once hiked the Grand Canyon in a single day. Charlie packed a beer which he drank when crossing
Fine Day to Die

Sailing to Catalina Island on Manana the boat we owned together–actually, the stern still said “Kewtie Pie with a K” because we never got around to painting the new name after we bought it –we hit a storm and I snarled the jib. We would have motored in, but Charlie had bought another cheap non-marine battery that died. Waves were breaking across our aft and we were losing our heading.
Charlie said it was a fine day to die, but it turned out to be a better day to live.
We were drinking in an Ensenada dance hall where locals paid ten pesetas to foxtrot with extremely short Indian women. Federales with machine guns suddenly appeared, lining up everyone up against the wall to search them, except for the two gringos at the bar.

The last moments of the last night of most jaunts were usually savored on some hotel or motel balcony overlooking outrageous beauty. We’d share cigars, cognac, philosophy
Charlie’s versions of these stories and mine were almost always at odds. It doesn’t matter whose were more accurate. Often, we were both too loaded to know anyway. We shared huge chunks of life together. They were among the best of my life.
Best Friend Ever
I met O’Brien in 1967 at the Quincy Patriot Ledger’s Norwood Office. He was an editor and I a reporter. I applied to be his #2. Everyone thought I was the worst possible choice. But Charlie swung the bat for me, and I got the job. We sat facing each other from midnight to dawn, five nights a week for nearly four years. We got to know each other in eight-hour doses. He was my boss but became my friend and eventually the best friend I would ever have.
We were adventure companions and sailing buddies. As roommates for two
He was always calm—even facing death. Most perils, he described as “a bit hairy.” He called cancer bad luck.
He gave me the two things I need most – encouragement and shit. He gave a lot of people encouragement. He saved the shit for a very few of us. His encouragement pointed me toward the top and his shit stopped me from going over it.
Charlie taught me about life and living; about death and acceptance. He taught me ethics without preaching, about tolerance without suffering assholes and about patience even if I wouldn’t get to the bloody point.

Charlie usually put his focus on others. He was always non-assuming. I never knew him to break a confidence. He contrived little custom rituals with people he liked. He became my wife Paula’s cooking assistant, where he gave her sage advice on children and her husband. He very rarely lost his temper except once when Paula hid his liquor on a camping trip.
Charlie was actually a very simple person. He didn’t change that much in the years I knew him. In the end, he just wanted to have more good days than bad, and the good days were often defined by who he spent them with. He enjoyed reading or hearing “a good yarn.” He cultivated a hard-ass image but everyone knew he was a softie.
Disdain for Republicans
He had disdain for self-important people, Republicans
Above everything, he valued his family and friends, even more so at the end.
Charlie considered himself a better editor than writer. Yet, he authored a truly unforgettable work: “Health Updates,” which we received by email. It broke newspaper rules by burying hard news inside little good news sandwiches. In the middle
I last visited Charlie two weeks before he died. I stayed for only a few minutes because he was clearly suffering. There just weren’t enough good days left.
I miss him terribly. I’d give anything if he could tell me
I’d even give him the last word.
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