In a photograph circa 1967 my cousin Jim and I endure an interminable family portrait session—I still remember itching in my Sunday clothes. While my sister and I sit passively smiling, my cousin Jim can’t hide his contempt for the amateur photographer’s incompetence. It looks like he’s about to lunge from his seat and knock the camera off its tripod.

In another photograph of the same era, Jim and I stand together, each with 22-caliber rifles in hand. We’re ready to go hunting magpies in the river bottoms near our grandparent’s dairy farm in Amalga, Utah, even now a town of perhaps 400 souls, in the far north of the state. In the photo, Jim’s stance and steady glare reveal confidence bordering on defiance. He holds the rifle firmly and bristles at pausing for yet another photo—after all there are magpies to shoot. Then there’s me. I look like I’m afraid I’ll lose my grip on the gun and drop it in the mud. These photographs foretell somehow our future lives. I’ll be accused of reading more into the pictures than others would, but what I see is a fundamental difference in temperament and outlook between my cousin and me that will play out in our future lives.

Jump ahead twenty-five years to 1992. My cousin Jim is at the height of a Wall Street career that has taken him to London. He has worked at three or four top Wall Street firms and his career is now reaching abroad. A few more years down the road he’ll be living near Milan, Italy, a multi-millionaire, retired from investment banking and working as a consultant. Though he and his wife, Laura, endured a decade-long ordeal with in vitro procedures, no small matter, they would soon have two beautiful, healthy daughters. By 1992 Jim was hitting full stride as a skilled economist and investor, a graduate of the London School of Economics. I learn second-hand from friends in a multi-national law firm that he is well known and respected in London’s financial circles. He has the nickname “Lord Jim,” though I’m not sure he was ever aware of it or would have cared. The point is, he could command a conference room, negotiate complex contracts and confidently take on responsibility for billions of dollars without fear. He was a man who could see the big picture. “It’s really just more zeros,” he told me once. “Not as scary as you would think.”

The way I describe his confidence could make it sound like his work was easy for him. Nothing could be further from the truth. During his New York years, Jim’s typical work schedule made what I considered my own “busy” work life look like ongoing vacation in a tropical locale. Every time I visited him, which I did several times by diverting return trips from Washington, DC, or Boston to LaGuardia Airport, I witnessed his work life firsthand. Jim and Laura lived in Morristown, New Jersey. He was up at 5 a.m. to commute into Manhattan. He was lucky when his workday ended at 7 or 8 p.m. He often worked well into the evening. Sometimes, when it was too late and perhaps a little too dangerous to ride the night train, a company limo would drive him back to New Jersey in the early morning hours. When I visited, I would join his grueling routine and knockaround in Manhattan bookstores and museums while he worked. On the trains and subways, he worked. In the evenings after dinner, he worked. Even when he watched the news or a sit-com with Laura and I, he had financial spreadsheets on his lap, and he studied them far more than he watched the screen. He wore a business suit to work every day and a clean starched white shirt. I assumed he must be under intense pressure due to billions of dollars being at stake and the meticulous contracts and reports and mountains of data to decipher, but I was surprised by how personal the scrutiny could be. He told me that in one performance review with his manager, he was told in all seriousness to use more hair gel to keep the hair out of his face. I could never have endured such a scrutinized or high-pressure life, year after year.

My life in 1992 was much different, though not a tropical vacation either. I was into my seventh year working for the same dot.com start-up company that had hired me after graduate school. I traveled several times every year to the same hotels and convention centers in Silicon Valley, Chicago and Washington, D.C., to attend the same trade shows and meet with same media contacts and clients. However, I wasn’t the one directing the strategy or closing deals. Rather I was deep in the weeds, writing software documentation, press releases, case studies, writing articles for niche trade pubs that looked like they were printed in somebody’s basement. I was immersed in the ad hoc guerilla marketing and public relations typical of the dot.com era. Also, in contrast to Jim’s life, I was still single. Traveling to trade shows and teaching literature classes at night often interrupted or strained the long series of half-committed relationships that made up my social life during those years. Business travel was more of an ordeal than I had expected it to be. The small start-up I worked for traveled on the cheap, often booking the less expensive hotels. I usually shared hotel accommodations with colleagues, often four to a room. I couldn’t get enough sleep, none of us could, and we often got sick after week of travel. We spent 12-hour days in exhibit halls, without breaks for lunch or even for the bathroom if conference attendees were clamoring for software demos in the booth. We carried show computers and large display monitors as airline luggage rather than shipping to trade shows in advance. Still, I had the chance to visit the offices of all the big computer magazines of the time in San Francisco, Boston and New York. But, again, I was not the one making the presentations to editors. Rather, I was the guy who taxied the experts around, set up the appointments and travel arrangements, prepared PowerPoint slides, press announcements, feature lists and bullet points for the software experts. Now, it’s true, there were moments that hinted at being at the center of things—the dot.com world did boom after all—though soon to crash. There were dinners at swanky restaurants and futuristic parties with life-sized holographic dancers. But these moments were rare. For the most part, I was firmly, deeply and without any doubt, down in the weeds as I always had been since college and still am to this very day.

Now I want to go back to the summer of 1977, right after my high school graduation, to a time when my cousin and I were still living a similar life—at least the same extended family, neighborhood, school and church. Even then our professional destinies were beginning to show. We set up a modest enterprise together—Cantwell Brothers Landscaping, which lasted for the three months of that 1977 summer and served the need of a half dozen clients at most. We mowed lawns. We weeded and trimmed and raked overgrown suburban yards in Portland, Oregon. We had a rented trailer that we hooked to Jim’s small car to haul yard rubbish to the landfill. As co-owners of this most modest of enterprises we didn’t always agree. For example, we disagreed about how meticulous we should be weeding flowerbeds, because in the plush green world of western Oregon a weed grows back the day after you pull it. Or so it seemed. I was the anal one, down on my knees digging out individual weeds by the roots. Jim used shovels and hoes to clear the flowerbeds quickly, then piled on the bark dust to stifle remaining weeds and present a clean, finished look. And it did look good and people were happy. Even as I stubbornly searched for every weed, I could see Jim’s point. He always won me over in the end. He was and continues to be a mystically persuasive guy, not unlike the Star Wars character Obi Wan Kenobi. No doubt this helped him more than once to navigate a disputed investment decision while toiling away on Wall Street. During that 1977 summer, more times than I can count, we knocked off early in the afternoon, deposited the weeds and grass clippings at the landfill and took an unplanned trip to Cannon Beach or Seaside. We worked hard and fast, then made time for play. On the highway to the beach, we rolled down the windows and cranked up Boston or The Doobie Brothers on the cassette player installed precariously in Jim’s glove compartment.

I mention this 1977 summer because there was one afternoon when our unique personalities came together perfectly. This is how it happened.

We were hired to landscape an apartment complex that was hopelessly overgrown with weeds up to our shoulders and lawns uncut for months. The weeds darkened the windows of the basement level apartments, so it was like those tenants were living under a green-tinted sea. The plan was to spend a week cleaning up the weeds and then plant new flowers and shrubs.

I picked a corner and started pulling up weeds one at a time. Jim did the same, at first, but soon made an amazing discovery: The apartments had already been landscaped. Under the jungle canopy of weeds were tidy rows of decorative rocks, thatches of bracken fern, azaleas, rhododendrons and rose bushes.

Without a word, we both caught hold of the same vision and threw ourselves into the work. We would, as quickly as possible, uncover and reveal this hidden landscaping. We would do it in hours, not days. Jim mowed the neglected lawns while I pulled large thistles away to uncover hidden rhododendrons. We filled the trailer up to overflowing with rubbish in what felt like minutes. When our boss, the uneasy new landlord and property owner, returned at the end of the day, he was astonished by our progress, as if we had performed an act of sorcery. I remember him staring speechless, looking back and forth between us and the unveiled landscaping. He had his hands on his hips as if bracing himself to be the brunt of a practical joke, then finally he let out a chest-heaving sigh and broke into laughter. There were his newly purchased, run-down apartments suddenly transformed, as if by magic. He had expected to pay dearly for new landscaping. Now everything was already there. “How did you do this? Where did the plants come from?”

Our boss had his four young sons with him to take a swim in the outdoor apartment pool. While their Dad gawked at the landscaping miracle, the boys stood impatiently around to him in their swimsuits. One of them yanked at his shirtsleeve. Our boss also wore his swim trunks, revealing pale legs that may never have seen the sun before this day. He also wore a denim shirt and had several towels hanging around his neck. After he recovered himself, he turned back to his small sons and started tossing them into the pool. He laughed and the boys squealed as they flew and plunged in the cool water. This all felt like a ritual celebration of our victory. Then our boss jumped into the pool himself, forgetting to take off his shirt or set aside the towels.

Our boss wasn’t the only one amazed by the transformation. The apartment dwellers returned from work, pausing in front of the building, perhaps wondering if they had come to the wrong place. One renter—a beautiful young twenty-something woman with blond Joni Mitchell hair—opened the window of her basement apartment, squinting up into the sun, and thanked us lavishly. Then she came out and gave Jim a hug. She had tears in her eyes. I have never forgotten how fun it was to watch the work unfold so quickly, not due to our skill exactly, but we got the credit, nonetheless. Jim saw the big picture and we both bent over the weeds to bring our shared vision to fruition. We knew people would be amazed. And indeed, they were.