The Most Insane People of All Time: #3 Elizabeth Holmes (aka You’re Outta Control!)

Epigraph: 

“This is the dawning of the age of Aquarius…”

— Aquarius/Let the Sunshine In, The 5th Dimension

Elizabeth Holmes emerges in Silicon Valley with the full prodigy package: Stanford dropout, world-changing ambition, and a carefully constructed persona. She leans hard into the comparison with Steve Jobs — black turtlenecks, minimalist language, intense seriousness — and presents herself as the young visionary who will revolutionize medicine. The pitch behind Theranos is irresistible: hundreds of diagnostic tests from a single finger prick. Investors, politicians, and media figures line up. The board fills with heavyweight names including George Shultz, and the company’s valuation soars to roughly $9 billion. Holmes becomes, on paper, the youngest self-made female billionaire. It’s classic Silicon Valley moonshot energy — bold claims, secrecy, and belief outrunning reality.

The problem, as insiders begin to realize, is that the technology doesn’t work at all. Engineers and lab staff struggle to produce reliable results, while Holmes and her partner Ramesh Balwani continue presenting the system as revolutionary. The company begins quietly using conventional lab equipment while maintaining the illusion. Whistleblowers emerge, including Shultz’s own grandson, who raises concerns at significant personal cost. The leadership circles the wagons. Meanwhile, John Carreyrou of The Wall Street Journal begins investigating, encountering secrecy, evasive answers, and mounting contradictions. His reporting — later expanded into the book Bad Blood — becomes the turning point. The narrative collapses, regulators move in, partnerships evaporate, and the once-mythic startup implodes.

Legal consequences follow. Holmes and Balwani are charged with fraud, and after a long, high-profile trial she is convicted on multiple counts. She delays reporting to prison after becoming pregnant, later giving birth with partner Billy Evans. Eventually she begins serving her sentence in a minimum-security federal facility. Even there, the mythology lingers — supporters, critics, and observers debating whether she was a calculating fraud, a true believer, or some combination of both. The arc is striking: Stanford prodigy, Jobs imitation, $9 billion valuation, total collapse, and prison. Less chaotic than John McAfee, less creepy than Keith Raniere, but still unmistakably outta control — a billion-dollar story built on belief, performance, and a technology that never worked.

Steve Jobs represents the template Elizabeth Holmes tried to emulate. Jobs cultivated a minimalist aesthetic, black turtlenecks, product mystique, and a “reality distortion field” that persuaded investors, employees, and customers to believe in things before they fully existed. But the crucial difference is that Jobs ultimately delivered. From the original Macintosh launch in 1984 to the iPod in 2001 and the iPhone in 2007, Apple shipped real, transformative products. Jobs bent reality rhetorically, not technically; Holmes attempted to bend reality where physics and chemistry refused. The comparison highlights both the ambition and the failure — she borrowed the style, but not the substance.

Bernie Madoff represents the classic institutional fraud parallel. A former NASDAQ chairman, Madoff operated a decades-long Ponzi scheme through Bernard L. Madoff Investment Securities, promising steady returns that attracted elite clients, charities, and feeder funds. By the mid-2000s, billions were under management, including investments tied to major institutions and wealthy families. In December 2008, amid the financial crisis, Madoff confessed to his sons, was arrested, and the scheme collapsed, revealing losses estimated at roughly $65 billion in paper value. The deception persisted largely through reputation and trust — investors assumed competence because of his stature. Holmes operated similarly: prestigious board members, high-profile endorsements, and a narrative of inevitability masked a system that didn’t work. Like Madoff, she benefited from credibility cascading downward — once enough influential people believed, the illusion sustained itself.

Sam Bankman-Fried provides the modern startup-era comparison. Bankman-Fried founded the cryptocurrency exchange FTX in 2019, and within a few years it was valued at around $32 billion. He cultivated a quirky, disheveled persona and promoted “effective altruism,” pledging to donate vast sums to global causes. FTX attracted major investors including venture firms and high-profile endorsements, while its sister trading firm Alameda Research operated closely behind the scenes. In November 2022, liquidity concerns triggered a rapid collapse, revealing commingled funds and massive shortfalls. Bankman-Fried was arrested in December 2022 and later convicted in 2023 on fraud and conspiracy charges. The arc mirrors Holmes: meteoric rise, media fascination, complexity masking weakness, and sudden implosion once scrutiny arrived. Where Jobs built something real and Madoff ran a traditional financial fraud, Bankman-Fried and Holmes sit in the same modern category — startup mythology outrunning reality.

In the end, the most astonishing thing about Elizabeth Holmes is not just the scale of the deception but the audacity of it. How, exactly, did she think she was going to get away with it? Blood testing is not social media. It’s not software. It’s chemistry, biology, physics — things that eventually either work or don’t. Yet she and Ramesh Balwani kept pushing forward, covering, deflecting, and doubling down as the gap between claim and reality widened. That’s the outta-control element: the belief that charisma, secrecy, and prestige could override science indefinitely. At some point, the story had to collapse. But like many figures in this series, Holmes seems to have inhabited a gray zone between calculation and belief — part fraud, part self-hypnosis — which made the whole thing both more dangerous and more surreal.

Then there’s the broader cultural context, including the willingness of powerful people to buy in. Even Barack Obama publicly embraced the Theranos narrative early on, holding Holmes up as a symbol of innovation and entrepreneurial promise. Chump. In retrospect, it’s striking how easily the image worked: the black turtleneck, the calm intensity, the world-changing pitch. Smart people — very smart people — saw what they wanted to see. It’s a reminder that charisma plus narrative can override skepticism, especially when wrapped in Silicon Valley optimism. The episode becomes a cautionary tale: will future founders learn from this, or will the same hubris reappear in new forms? The myth of the visionary is powerful, and the temptation to believe in it hasn’t gone away.

The quiet hero of the story, meanwhile, remains the Theranos whistleblower — George Shultz’s grandson — who raised concerns when doing so meant alienating family, risking his career, and standing against a multibillion-dollar narrative. He saw that the technology didn’t work, said so, and held his ground. In a story dominated by hype, status, and belief, that kind of stubborn insistence on reality stands out. Holmes’s rise is outta control, her fall inevitable, but the ending belongs to the people who refused to play along.

Note: If you liked this piece, you may also like the other ones in out “You’re Outta Control” series.

The Most Insane People of All Time (aka You’re Outta Control!): #2 John McAfee

Note: This second installment in The Most Insane People of All Time (aka You’re Outta Control) looks at John McAfee, tracing his evolution from software pioneer to global fugitive, crypto evangelist, and online cult figure. The piece emphasizes the improvisational chaos of his later life and contrasts it with more conventional tech figures like Elon Musk and Bill Gates, arguing that McAfee’s volatility places him in a category of his own. The tone is impressionistic, comparative, and intentionally informal.

Epigraph: 

“I fought the law and the law won…”

— I Fought the Law, The Clash

John McAfee starts in relatively conventional fashion: brilliant programmer, eccentric personality, builds the first widely adopted consumer antivirus software in the late 1980s, and becomes extremely wealthy when McAfee Associates takes off. But even in the early years there’s instability, and a foreshadowing of things to come — drug use, paranoia, erratic business decisions, and a growing anti-authority streak. He sells his stake, drifts through various ventures, and by the late 2000s relocates to Central America, eventually settling in Belize. There he buys beachfront property, hires armed guards, collects dogs, experiments with quasi-scientific projects, and begins acting like a semi-autonomous local strongman. It’s the first fully “outta control” phase: money, isolation, guns, and a man already well inclined toward paranoia.

Then comes the neighbor incident. In 2012, McAfee’s American neighbor, Gregory Faull, is found murdered. McAfee is named a person of interest — never charged — and instead of lying low, he goes fully theatrical. He claims the authorities are targeting him, allegedly evades police by hiding, disguising himself, and moving between safe houses, all while giving interviews and live-tweeting the saga. With girlfriend (later wife) Janice McAfee and various associates in tow, he flees Belize, surfaces in Guatemala, is detained, then ultimately allowed back to the United States. The whole episode is surreal: a tech millionaire allegedly on the run for murder, narrating the chase in real time on social media. It’s not just outta control — it’s performance art.

Back in the U.S., McAfee briefly lands in Florida but quickly re-enters chaos. He promotes cryptocurrencies, launches bizarre tokens, courts publicity, and cultivates a global cult following. He posts paranoid threads about surveillance, claims he lives inside Faraday cages, talks about government plots, and offers wild schemes — including promises to evade arrest by sea, air, or even paragliding into New Mexico to meet with fans! He pops up in unexpected places, from Caribbean boats to European cities, always accompanied by Janice and a rotating cast of loyalists. At one point he tattoos crypto branding onto himself, predicts conspiracies, and positions himself as both fugitive and prophet. The line between performance and belief dissolves completely.

Eventually, legal trouble catches up. U.S. authorities charge him with tax evasion and crypto-related fraud, and he’s arrested in Spain in 2020. From prison he continues tweeting through intermediaries, hinting at conspiracies and insisting he’ll never kill himself. In June 2021, shortly after a Spanish court approves extradition to the United States, McAfee is found dead in his cell — ruled a suicide. His supporters, including Janice, immediately dispute the finding, pointing to earlier posts and tattoos as supposed foreshadowing. The ending is as chaotic as the life: software pioneer turned fugitive, Twitter antihero, crypto evangelist, paranoid showman, and finally a death that only deepened the mythology. Outta control doesn’t even begin to cover it.

Compared to John McAfee, figures like Elon Musk and Bill Gates still look almost conventional — even when they drift into odd territory. Musk’s public persona is chaotic in a very modern way: late-night posting, impulsive announcements, awkward humor, and personal-life theatrics. The relationship with Grimes, the bizarre naming of children, and the infamous weekend when Azealia Banks claimed she was stranded at Musk’s house amid talk of LSD and general weirdness all add to the sense of volatility. Then there are the dad-joke moments — hauling a sink into Twitter headquarters and posting “let that sink in,” which is either performance art or just terrible humor. It’s eccentric, sometimes cringe, occasionally outta control — but the companies still run, rockets still launch, and the chaos never fully escapes the bounds of reality.

Gates, by contrast, is a more old-school eccentric. Bill Gates has the reputation of a hyper-competitive young executive who mellowed into a philanthropic technocrat, but the quirks linger. The awkward dancing, the slightly rumpled appearance, the perennial jokes about dandruff — he has always projected a kind of brilliant-but-uncool energy. The later-life turbulence — divorce from Melinda after decades, scrutiny over his contacts with Jeffrey Epstein, and the general aura of a private billionaire navigating public controversy — adds complexity but not chaos. Gates remains structured, Musk volatile, but both operate within functioning systems. McAfee, meanwhile, is something else entirely: not just eccentric but improvisationally unstable, a man who turned paranoia, fugitivity, and spectacle into a lifestyle. Musk may be chaotic, Gates may be awkward, but McAfee is outta control in a different register altogether.

In the end, John McAfee feels more outta control than Keith Raniere, Elon Musk, or Bill Gates — and that’s saying something. Raniere was creepy and manipulative but small; Musk is chaotic but still tethered to real-world outcomes; Gates is eccentric but fundamentally structured. McAfee, by contrast, seemed to live entirely outside normal constraints. Guns, boats, dogs, girlfriends, crypto tokens, Faraday cages, live-tweeting alleged manhunts, promising wild escapes, drifting between countries — the whole thing reads less like a biography and more like a fever dream. He wasn’t just eccentric; he appeared to improvise his life day by day, escalating the spectacle each time. That kind of volatility is rare. It’s also why he became a cult hero: he embodied a fantasy of total freedom, however reckless, however unsustainable.

Years after his death, the mythology hasn’t faded. Supporters still debate the circumstances, quote his tweets, and treat him as a kind of outlaw technologist who refused to play by the rules. Whether you see him as mad genius, performance artist, or cautionary tale, the scale of the chaos is undeniable. There may have been more dangerous figures, more powerful figures, even more tragic figures — but few as consistently, flamboyantly outta control. That’s what makes McAfee a legend. Not admirable, not necessarily likable, but unforgettable. And like all true originals, there probably won’t be another. So RIP, prayers up, and pour one out for a real one, John Motherfucking McAfee.

Note: If you liked this piece, you may also like the other ones in out “You’re Outta Control” series.

On the Most Outta Control People in History (aka You’re Outta Control!): #1 Keith Rainere

Note: This piece begins a new series, The Most Insane People of All Time (aka You’re Outta Control), which looks at extreme historical and contemporary figures whose behavior, movements, or belief systems veered dramatically beyond the bounds of ordinary reality. The tone is intentionally informal and impressionistic rather than academic, blending biography, cultural memory, and personal reaction. The goal is not exhaustive analysis but a clear read on just how outta control these figures became. This piece takes up the case of Keith Rainere.

Epigraph: 

“Out of control / You’re out of control…”

— Out of Control, The Rolling Stones

Keith Raniere began life in New York in 1960 and built his early identity around claims of extraordinary intelligence and unusual gifts. He cultivated a reputation as a prodigy, a polymath, and a moral philosopher, though many of these claims were exaggerated or unverifiable. In the 1990s he co-founded a multi-level marketing-style company that ran into legal trouble, then pivoted into what became NXIVM, a self-improvement organization marketed as executive success training. Participants attended workshops, advanced through ranks, and absorbed Raniere’s pseudo-philosophical teachings. He adopted the title “Vanguard,” cultivated an inner circle, and emphasized ethics, discipline, and personal growth. Wealthy backers, including Seagram heiress Clare Bronfman, funded the operation for years, allowing NXIVM to expand in upstate New York and attract professionals, actors, and seekers.

Behind the self-help veneer, however, the structure tightened. Raniere exercised increasing control over followers’ lives, and a secret subgroup known as DOS emerged, involving master–slave hierarchies, collateral-based coercion, and branding rituals incorporating his initials. Superman actress Allison Mack played a key role in recruiting members. Investigative reporting in 2017 exposed the group, leading to arrests. Raniere fled to Mexico, where he was found living in a villa with loyal followers, still holding late-night volleyball sessions and maintaining his guru persona. He was arrested in 2018, returned to the United States, convicted on multiple charges, and sentenced to 120 years in prison. The NXIVM empire collapsed, its mythology dissolving into court transcripts and testimony.

And yet what stands out most about Raniere is not grandeur but pettiness. The volleyball — endless, late-night volleyball as the center of spiritual life — already tells you everything you need to know. Important conversations at midnight on the court, guru hanging out in athletic shorts, disciples orbiting. It has strong George Santos energy: self-invented genius, weird rituals, faux casualness masking control. Then the egomania. The IQ mythology, the titles, the little cushion on stage so he’s physically higher than everyone else. It’s not even theatrical; it’s dreary. The branding scandal — initials burned into skin, coercion, sexual manipulation — pushed it fully into outta control territory. And all of it funded for years by the Bronfman money, which makes the whole thing feel even more surreal. Rich people with nothing better to do underwriting a volleyball cult.

What really kills it, though, is the atmosphere. It’s all so fucking boring. Endless seminars. Faux-ethical language. Guru perched slightly above the group. No charisma, no sweep, just control. I basically hate gurus, and Raniere is the worst kind: small, humorless, self-mythologizing. Even when he fled to Mexico, he didn’t become mythic — he just kept playing volleyball in a villa while the walls closed in. Outta control, yes, but also petty. Not a visionary gone wrong, just an egomaniac running a dreary self-help cult.

By contrast, Jim Jones has a sweeping, almost Shakespearean arc. He began as a Midwestern preacher in Indiana in the 1950s, preaching racial integration and social justice at a time when both were rare in American churches. His Peoples Temple grew steadily, and by the mid-1960s he relocated to Northern California, first to Ukiah and then to San Francisco, where he gained real political influence. The early movement was diverse, activist, and in some respects ahead of its time. But alongside the growth came drugs, paranoia, authoritarian theatrics, and increasing control. Facing scrutiny and defectors, Jones moved followers to an agricultural commune in Guyana — Jonestown — deep in the jungle. Life there deteriorated into long work hours, loudspeaker propaganda, and rehearsals for mass suicide. In November 1978, U.S. Congressman Leo Ryan arrived to investigate, accompanied, improbably, by Mark Lane, the JFK conspiracy lawyer hired by the Temple as a defender. After several members attempted to leave, Ryan and others were shot at a nearby airstrip, and Jones ordered the mass murder-suicide — cyanide-laced drink administered to more than 900 people. The trajectory is horrifying, but it has scale: idealism, power, paranoia, catastrophe. You can at least see how it built.

Marshall Applewhite is stranger still. A former music teacher who fell into an intense partnership with Bonnie Nettles, he constructed a theology blending Christianity, UFO lore, and apocalyptic expectation. After Nettles died, Applewhite grew more isolated and doctrinaire, leading the group known as Heaven’s Gate. Members lived communally, detached from ordinary life, waiting for a spacecraft they believed was trailing the Comet Hale–Bopp. In 1997, Applewhite convinced followers that they needed to leave their bodies to board it. Thirty-nine members died in a coordinated mass suicide in Rancho Santa Fe, California, wearing matching clothing and following a carefully staged sequence. The whole thing is eerie rather than theatrical — calm, methodical, and deeply surreal. Of the three, Applewhite may be the most bonkers, but also the most otherworldly, a teacher who wandered into cosmic delusion.

So the comparison is stark. Jones is tragic and terrifying, a charismatic reformer turned paranoid autocrat. Applewhite is cosmic and surreal, a gentle-seeming teacher convinced salvation lay behind a comet. Raniere, by contrast, is just small — petty control dressed up as philosophy, volleyball instead of vision, branding instead of belief. All three are outta control, but in different registers: tragic, cosmic, and contemptible.

On Larry King, the Radio GOAT

Epigraph:

“I listened to the radio / I waited all night long…”
— Radio Radio, Elvis Costello

Note: This piece reflects my personal memories of listening to Larry King’s overnight radio show in the late 1980s and early 1990s, along with later impressions from television appearances, interviews, and conversations with people who knew him. It is written in the spirit of appreciation and nostalgia rather than media criticism, and emphasizes the uniquely loose, humane, and unpredictable quality of King’s radio work, which for me remains the defining core of his legacy.

I grew up listening to Larry King’s overnight radio show between roughly 1988 and 1992, and in my opinion — which in this case happens to be correct — the radio show was much better than the television version that later made him famous. The TV show was good, even great at times, but radio was longer, looser, freer, and far more unpredictable. It had weird guests, weirder callers, and the feeling that anything might happen at two in the morning. That’s where Larry really lived.

I would listen in my bedroom at my parents’ house in Spokane, Washington, the volume turned low, the house quiet, insomnia hovering. The Spokane AM station — KGA 1510 — carried the show from around 9 PM Pacific time, and then, wonderfully, they would just run it again. So I’d listen from nine to midnight, fade, wake up at two or three, and hear the same segment again in a half-dream. The effect was surreal. Didn’t I just hear that caller? Didn’t Larry just say that? It created a strange loop of late-night déjà vu that only made the whole thing more atmospheric. The show felt less like programming and more like a continuous nocturnal conversation.

My friend Kelly Rudd loved Larry too. When we were in high school we were both big fans of the radio show, and we talked about it constantly. There were a couple of things we especially liked. The first was that Larry famously did no preparation. He knew a huge amount about the world, of course, but he didn’t read guests’ books ahead of time. He wanted to come in cold. If his guest was a firefighter, he’d ask, “So what’s it like to be a firefighter?” It sounds lazy, but it was brilliant. By staying open and getting out of the way, he let the conversation go anywhere. The show became eventful.

Another thing we loved was what happened after the guest left. Larry would open the lines and take questions on absolutely anything. Most of the time he was generous and patient, but when callers went off the rails he had a signature phrase. He’d cut them off gently: “Cold compress, ma’am,” or “Cold compress, sir.” Basically: lie down, ice your head, regroup. It was hysterical, especially because he used it sparingly. When “cold compress” dropped, you knew things had gotten weird.

Anyway, Kelly and I loved Larry so much that when the station suddenly dropped the show, Kelly proposed we drive to the radio station and protest. So we skipped school, drove across town, and rang the intercom demanding to speak to someone about the cancellation. The station manager eventually came down and heard us out. We knew we weren’t changing anything, but it felt right to try. Larry never came back to Spokane radio, and the show faded not long after, but the whole episode captured what the show meant to us. It wasn’t just background noise. It felt alive.

Larry’s on-air style was the key. He was unbelievably relaxed. By the late ’80s you could tell he had done thousands of hours. Nothing fazed him. Weird guests, drunk callers, eccentrics — all the same to Larry. He absorbed everything. He had pet phrases — “cold compress” chief among them — and he deployed them like a veteran reliever, only when needed. He famously did no prep, and he leaned into naïve questions. He’d ask something simple and let the guest do the work. The effect was disarming. People opened up. He also had real humanity. He listened. He didn’t mock callers. He didn’t rush them. There was compassion there, and I think that’s what I loved most.

And the show could get wonderfully out of control. In one story Larry told from his Miami days, an adult actress he was interviewing suggested they just have sex during the commercial break. Larry, amused, asked the producers to clear out — but there wasn’t enough time. That kind of anecdote captures the looseness of late-night radio. It wasn’t polished. It was alive.

Larry left the overnight Mutual Radio show in 1994 to focus on television. By then I had already drifted away, but I still caught Larry King Live on CNN over the years. I remember watching during the O. J. Simpson trial while at Otago University in New Zealand, when the show became part of the nightly noise. Later there were the Vladimir Putin interviews — classic Larry, conversational and oddly disarming. And of course there were the great comic moments, like the interview with Jerry Seinfeld where Larry suggested the show had been canceled and Seinfeld snapped back in disbelief, and the Norm Macdonald appearance where Norm kept repeating, “I’m a deeply closeted homosexual,” and Larry tried earnestly to parse it. “So that means you’re gay?” “No, Larry,” Norm replied, “it means I’m deeply closeted.” Pure Larry: sincere confusion meeting absurdist comedy.

Larry’s personal life was famously complicated. He married eight times, had several children — including sons Chance and Cannon later in life — and lived in a kind of perpetual romantic improvisation. The marriages came and went. The last ended painfully and publicly. He once joked he’d never leave his wife unless Angie Dickinson came along — and when she did, he married her. That was Larry: impulsive, affectionate, slightly chaotic. Despite decades of success, he didn’t leave the kind of massive fortune people assumed. The money came and went, as did the marriages. It was a life lived in motion.

My friend Sergio Mandiola actually knew Larry in his later years in Los Angeles. Sergio was running an independent studies program at Beverly Hills High School, and Larry’s sons Cannon and Chance, and he taught his sons for three years. Larry would come by for open nights or just to chat.

Sergio Mandiola: “Larry would come in from time to time and we would talk. He was lovely and open. He talked about his family and his career. One time he told me, ‘Sergio, you should totally have a radio show!’ I was flattered. One thing about Larry is his politics were more to the left than he let on on air. He had strong views and wasn’t afraid to share them in person. Larry was a true mench and I’m glad I got to spend time with him. I miss him.”

In the end, I’ll say it plainly: for me, Larry King is the radio GOAT. There was no one like him, and there probably never will be. It wasn’t just longevity. It was the curiosity, the looseness, the humanity, the love of people, politics, baseball, and life. He trusted the conversation. He let the night unfold.

And then there was that absurd, wonderful USA Today column, which read like a diary gone completely outta control. Mets lose 6–4…Rain in Baltimore…Clinton flies to Ireland…You’d read it and think, Larry, baby, WTF is this? And also, USA Today, WTAF are you doing paying for this? But somehow it worked. It was pure Larry — fragmentary, observational, intimate.

And that’s how I remember him most clearly: late nights in high school, the radio turned low, insomnia hanging in the room, Spokane quiet outside, and the sweet sounds of his voice in my ear. Sometimes I’d listen from nine to midnight, fade, then wake again to the rerun, half-dreaming, half-aware, caught in that strange déjà vu — didn’t I just hear this? — while Larry kept talking, calm as ever, taking calls from truckers and insomniacs and eccentrics. My listening years were brief, but they stuck. And when I think of Larry now, that’s where I go back to: the low hum of AM radio, the half-fade, and the sweet sounds of his voice in my ear.

Dedication:

For the one and only GOAT, Larry Motherfucking King. RIP baby.

On My Curious Relationship with the Enneagram

Note: This piece reflects a personal journey with the Enneagram between 2013 and 2018, including conferences, workshops, and informal conversations. The impressions here are subjective and based on lived experience rather than formal study. I remain intrigued by the Enneagram as a reflective tool, even as I view aspects of the professional community with some skepticism. As always, this is written in a spirit of curiosity, appreciation, and lightness rather than critique for its own sake.

Epigraph
“We’ll take the Skyway / high above that busy little one way”
— Skyway, The Replacements


I first heard of the Enneagram in 2013 at a six-day beginner NLP training in Singapore run by a company called Mind Transformations. The training was led by Barney Wee, a tightly wound but candid guy who shared a lot about his life — past struggles with party drugs, his mentally challenged son, his strict vegetarianism — all delivered with a kind of intense openness that set the tone for the week. His right-hand woman, Angus Lau, was the mother and the emotional center of the operation. Warm, encouraging, and deeply comfortable in what she herself called “woo-woo,” she talked about Sedona hot springs, New Age energies, and personal transformation with complete sincerity. I hit it off with her immediately. She praised my small contributions, which felt good, and we bonded quickly.

There was also Bae, Barney’s younger assistant, mid-twenties, cheerful, cute as a button, and she did props and logistics. The first night in the hotel lobby she broke out a strange psychology-themed board game and we played for a while, and somewhere in the middle of that conversation she mentioned the Enneagram. It was the first time I’d ever heard of it. I was intrigued. On the way back to Japan I stopped for one night in Singapore, wandered into Kinokuniya at Takashimaya on Orchard Road, bought a few introductory books, and started reading them on the plane home. That was the beginning of what I later came to think of as my curious apprenticeship.

For a few years, it was just reading. I typed myself as a 5w4 with a strong 8 lean, which felt roughly right, and I found the system evocative — not scientific exactly, but suggestive, like personality poetry. It seemed to capture tones and tendencies rather than fixed truths, and I liked that. I read more, thought more, and gradually became curious about the actual community.

My first conference came in August 2016 in Minneapolis. I stayed at the hotel hosting the event, down in a quiet basement space, and we were the only people in the area. It was close to the arena where the Minnesota Timberwolves play, and you could walk there through the Skyway, which made me think of the Replacements song which provides the epigraph, and gave the whole weekend a slightly Midwestern, slightly melancholy frame.

I arrived early the first morning — nervous, excited, and very aware that I had done a fair amount of reading but had almost no real-world experience. I grabbed coffee and sat with a pleasant older couple from the Midwest, and before long I was talking about peak experiences and epiphanies and probably talking too much. I was jittery, caffeinated, and eager. They were kind and listened. Later, when I checked the program, I realized the woman was one of the main presenters and a big deal in the community. Run roh. But it was fine. That, in retrospect, was my first brush with the gentle hierarchy of the field.

I also met Jessica Dibb from her Shift Network podcast, which I had been listening to a fair bit and paying far too much for. She was warm, generous, and exactly as open in person as she sounded online. I liked her immediately, and I still think she was providing a real service to the community. But she also seemed, in a way I would come to recognize more clearly later, very much inside the tent. On the podcast, she rarely pushed back, even when guests — including Russ Hudson — leaned on origin stories involving the so-called Desert Fathers that were total bullshit. I knew they were bullshit, and what was worse, he knew it too. And yet there he was, repeating them ad nauseam. The more I heard those claims, the less convincing they sounded. There’s no clear historical transmission, no diagram, no nine-type personality system — just thematic similarities retroactively elevated into lineage. At a certain point, it stops sounding like history and starts sounding like branding. Sorry, but it’s just a bunch of bull. And yet no one inside the community seemed eager to challenge it. The culture, I began to suspect, rewarded agreement.

The rest of Minneapolis was a mix of seriousness and absurdity. I skipped a packed session by Jean Houston — a decision I later half regretted — and instead attended a tiny aromatherapy session run by two Southern women in matching green shirts who were clearly there to sell oils. They were GENKI as hell and the whole thing was unintentionally hilarious. Each day ended with a drum circle led by a ponytailed New Age facilitator, and I found myself unexpectedly moved, tired and open after long days of conversation.

I met a towering gay guy named Ron selling singing bowl CDs, and eventually I met Jean herself. She was drinking white wine, I was drinking red, and she was as warm as could be. We talked about Japan, about why I’d come, and then we danced together for twenty minutes. She killed it. That moment — generous, playful, human — felt like the community at its best.

Two years later I went to the European conference in Amsterdam. By then I felt like I knew a fair amount about the Enneagram. I had been reading deeply in Beatrice Chestnut and related subtype material, and I arrived in what I can only describe as a somewhat provocative mood. I stayed at the Apollo Hotel on the canal and walked to the conference each morning. The first person I met was Lynn, a total riot — from San Francisco originally, recently divorced, now running a Kundalini Yoga studio in Athens. She knew everyone and all the back-channel dynamics, who was sleeping with whom, and we bonded instantly. She quickly became my co-conspirator.

The opening talk by Hudson repeated familiar material, including the Desert Fathers, and I came close to challenging him publicly but somehow held back. I do have a big mouth at times. Big dick energy. Then I heard Tom Condon, tall, white-haired, grounded, integrating NLP and Ericksonian ideas into a practical approach. He is the quiet hero of the piece.

The rest of Amsterdam was lively and strange. A movement-based types exercise nearly ended in an accidental kiss. Lunch ran long, as conference lunches always do, and I met people from all over the world. The closing session paired Chestnut’s academic framing with experiential work, including a moment where a participant broke down emotionally on the floor. The atmosphere oscillated between meaningful and chaotic.

At the end, Lynn urged me to ask a provocative question. I did, politely: which aspect of the Enneagram might not be around in thirty years? Chestnut answered cautiously but clearly: tritype — too complicated, not especially helpful. It was a small ripple, but it felt like testing the edges.

That fall, I brought Condon to Tokyo. I was a member of the International Mental Health Professionals Japan (IMPJ), and when I saw he would be in town I arranged a small talk at TELL the night before the conference. About thirty people came. He gave a clear, practical overview. People loved it. Afterward some of us went to the pub; he declined, needing rest for the next day. He was ripping heaters with me outside, though. Legend.

In the end, my curious apprenticeship with the Enneagram left me with more affection than skepticism, even if the skepticism is real. I learned a lot from the system. I still find the types evocative, even poetic, and I still catch myself using them as a loose lens on people and situations. And I genuinely liked the people. The Enneagram world attracts seekers, therapists, wanderers, and enthusiastic amateurs, and I have a real soft spot for that whole vibe — the openness, the fast intimacy, the willingness to experiment. At its best, the community is warm, generous, and human.

But the professional side of the field also felt small, and because it is small, sometimes insular. Limited conferences, limited airtime, gentle pressure toward agreement. Origin stories harden. Pushback is rare. None of this invalidates the system, but it shapes the culture.

By contrast, the astrology world — much larger, more diffuse — feels more pluralistic. Multiple branches coexist. Disagreement is normal. No single group controls the conversation. The atmosphere, in my experience, is looser, less competitive, more comfortable with divergence.

So where does that leave me? Somewhere in the middle, which is probably where I started. The Enneagram, for me, remains personality poetry — suggestive, useful, occasionally illuminating, but not doctrine. My apprenticeship may have been unusual — Singapore hotel lobbies, Minneapolis skyways, Amsterdam provocations, Tokyo workshops, and smoke breaks with Tom — but I wouldn’t trade it. I learned, I laughed, I met memorable people, and I came away with a tool I still sometimes use, lightly. That’s enough.

Dedication:

For Lynn and Tom.

On Being Early to Shows

Note: Getting to shows early, I realized, isn’t really about beating the crowd but about entering the space before it hardens into an event—when the room is still provisional, the bartender relaxed, the band half-mythical figures moving casually through soundcheck, and the whole night feels less like a performance and more like something forming in real time; you notice the lighting before it matters, the empty floor that will later surge, the stray conversations, the merch table still untouched, and sometimes—if you’re lucky—the musicians themselves, unguarded and human, which subtly rewires the experience so that when the set finally begins you’re not just watching a show but inhabiting a continuum that started hours earlier, a private prelude that rewards patience, sharpens memory, and turns what could have been just another concert into a small, self-contained narrative of anticipation, proximity, and the quiet pleasure of being there before everything becomes official.

Epigraph
“There’s a thin line between a guy with a backstage pass /
and a guy walking around with his gut hanging out like a jackass.”

— Sun Kil Moon, “Ben’s My Friend”

I’ve always been fascinated by the green room. First of all, why green? They can’t all be green. Second, there’s the whole rider situation. The rider is where things get really interesting. I think it was Van Halen who had in their rider that all the brown M&Ms had to be removed from a bowl. This sounds totally bizarre, but the point was attention to detail. If the venue screws up the M&Ms, they might screw up something much more important, like stage rigging or pyrotechnics. The M&Ms were just a test.

Other riders go in different directions. Iggy Pop reportedly asked for things like a Bob Hope impersonator and other surreal odds and ends, more like performance art than hospitality. Meanwhile Beyoncé is famous for highly controlled riders: temperature, lighting, water, environment, everything calibrated. One approach is chaos, the other total control. Both happen in the green room, which most of us never see.

My first concert was Dire Straits in Pullman, Washington, in a big arena. I was nowhere near the green room, of course. Most of us aren’t. So the real question becomes: what happens before the show, if you’re not backstage?

One answer came when I saw They Might Be Giants in Spokane with my friend Kelly Rudd. Kelly told me his cousin was in the opening band. They got paid twenty bucks for the show. The whole band. Twenty dollars. Totally unbelievable. Outta fucking control. TMBG were already a pretty big indie band, “Birdhouse in Your Soul” had been a hit, and I liked “Istanbul (Not Constantinople)” quite a bit. But after hearing that story I never quite looked at them the same way. The green room fantasy took a hit. Backstage wasn’t glamorous. It was twenty bucks and a handshake.

Another time I went to see Cat Power at the old Club Quattro in Osaka. I got there early, of course, and there was an opener dressed like a fairy with fuzzy, messed-up hair who sat down at the piano and proceeded to play dirge after dirge for what felt like an hour. Solo piano can be great, but this was brutal. I honestly thought I might have to cap myself. At some point I checked my ticket just to make sure this wasn’t actually Chan Marshall. It wasn’t. Thank god.

Then Chan came on and instead of playing from the stage like other artists do, she wandered through the crowd with a wireless mic, half-rapping, half-singing, talking, improvising. It wasn’t really a concert. It was more like some kind of performance art happening. Totally outta control. If I’d come late I would have missed the whole bizarre prelude. Being early meant enduring the dirges but also getting the full weirdness of the night.

Another early-arriver adventure came when I saw Deerhunter at the Hostess Club Weekender. These shows started early and stacked openers all day long. I once saw Mogwai at one of these and had to leave after fifteen minutes because I was hungry, tired, faded, and they were boring the living shit out of me. It happens.

The Deerhunter show in Osaka was even more outta control. The headliner was scheduled for 7 PM, but there were something like six openers. One of them was Ivo Watts-Russell of 4AD, a legendary figure, but he droned on so long that by the time Deerhunter came on they only had about forty minutes. Bradford Cox introduced him with dripping sarcasm, emphasizing “LABEL BOSS,” clearly taking the piss because the band’s time had been cut. I ended up having to see them again months later in Nagoya to get the full set. That’s the risk of being early: sometimes the openers eat the show.

The flip side came when I saw The Hold Steady at the Brooklyn Bowl in December 2018. I arrived two hours early, ate a hamburger, and smoked up outside. That’s where I met Austin, a total Steadyhead. He knew everything: lineups, labels, deep cuts, all of it. We talked music, smoked, and waited. When doors opened we grabbed territory near the stage with the other early-arrivers, a semi-cliquey group of diehards.

Later, when Austin wanted to get back to the front for the encore, he told me to follow him. He moved through the crowd at a half jog and the people parted in front of him like he was Barry Sanders hitting holes. Seconds later we were hugging the stage. I knew then I was in the presence of greatness. I also knew he was my friend. I didn’t get the VIP meet and greet, but getting there early gave me something better.

My one true VIP experience came when I saw The Afghan Whigs in Amsterdam in 2017 at the Paradiso Amsterdam, a beautiful converted church. I arrived three hours early, met Greg Dulli and the band, took photos, bought merch, and watched soundcheck with maybe fifteen people. They played “Going to Town” acoustically, which was a revelation. Later they crushed the full electric set, ending with “Faded.” I paid fifty bucks for that meet and greet and it was completely worth it. Being early paid off directly.

Getting to shows early, then, is not really about the green room at all. The green room is a kind of fantasy—green walls, bowls of M&Ms, riders with impossible demands. Most of us never see it, and even when we do, it turns out to be smaller and more ordinary than imagined. And probably not even green. The real action happens in that strange in-between space before the show: the smoking area, the empty floor, the long wait while the openers drift on and off.

If you arrive early, you get all of it. You get the terrible fairy-piano dirges and the label boss who drones on too long. You get the moment of doubt when you check your ticket and wonder if this could possibly be the headliner. You get the rail territory battles and the cliquey early crew. You get the conversations with strangers who turn into temporary friends, like Austin, who parts the crowd like a halfback and gets you back to the stage in seconds. You get the soundcheck if you’re lucky, the acoustic revelation, the quiet before the storm.

Most of all, you get time. And time at a show is a funny thing. Once the lights go down, everything compresses. The band plays, the songs blur together, and before you know it the encore hits and everyone spills out into the night. But if you were there early, the show feels bigger. It has a beginning, a middle, and an end. You saw the room empty and then full. You watched the night assemble itself.

So while some people drift in late, grab a drink, and wait for the headliner, I’ve always preferred the long route. Get there early. Kill time. Smoke a cigarette. Talk to whoever’s around. Endure the openers, good or bad. Maybe you meet someone. Maybe you don’t. Maybe the band walks through the room. Maybe nothing happens at all. But every once in a while, if you’re lucky, something does. And that, in the end, is why I like to be early to shows.

Dedication:

For music lovers everywhere. You are my tribe baby.

On My Dad’s Ridiculous Climbing Strategies

Note: This is a new piece about my dad, Ross Thomas (RO), and his truly unbelievable climbing strategies. The central episode took place in Stehekin, Washington, many years ago, when RO led my brothers and me on an attempt to reach Castle Rock that quickly devolved into heat, dense forest, no water, and general mayhem. There is also a later coda involving a climbing gym in Portland that is, in its own way, even more outta control. This piece is comic in nature, but also affectionate. My dad is a great man, a brave man, and a very game climber. He is just not, in this one specific domain, a planner.

Send lawyers, guns and money — the shit has hit the fan
— Warren Zevon, refracted

RO, is a great man and a terrible climbing strategist. He is brave, energetic, physically game, and in most areas of life basically well organized. He was a good high school English teacher, a very good administrator, and for many years an excellent and meticulous girls’ basketball coach. He is not, in other words, some kind of general life-space incompetent. Quite the opposite. Which is what makes his climbing strategies so difficult to understand.

They are ridiculous. They are unbelievable. They are officially, historically, and totally outta control.

I say this with love.

The central case study here took place in the mid-2000s, let’s say 2005, when our family was staying in Stehekin, Washington, out on Lake Chelan. If you have never been to Stehekin, it is a beautiful and slightly improbable place, the kind of place that already feels like the beginning of a story. Lake Chelan is huge, and you get out there by ferry, which means from the jump there is a sense that you are committing to something. People camp there or stay in cabins. We were in a cabin. My mom Claudia (CL), stayed behind. RO, meanwhile, had a plan.

The plan was that RO and his sons — Mike (MI), Pat (PA), and me — would hike up toward Castle Rock.

Now, one thing about family expeditions is that “the plan” is often not really a collective possession. It belongs to one person. The rest of the group is more or less there to follow along. In this case, the plan belonged entirely to RO. MI and PA and I were, broadly speaking, along for the ride.

As I remember it, we started from Stehekin and walked about three miles just to get to the trailhead, then hiked a few more hours uptrail to where we stopped and camped the first night. It was already a decent undertaking just to get there, but this was, in a sense, merely the prelude. The true RO strategy had not yet fully revealed itself.

At around dusk, after we got to camp and set up the tent and got ourselves sorted for dinner, RO decided he was going to scout the route for the next day. This seemed reasonable enough. It is in fact the sort of thing a prudent leader might do. Only instead of scouting further up the trail, or perhaps generally uphill toward the place we were trying to go, RO for some reason headed downriver.

Why did he do this? We did not know. It was back downhill. It seemed unrelated to the objective. Even at the time it had the feel of one of those decisions that makes perfect sense only to the person making it.

Ross Thomas: The trail kind of petered out eventually and didn’t really lead to Castle Rock anyway.

Fair enough. I want RO’s side of the record included here. But even granting this, and I do grant it, going downriver in the late evening did not strike the rest of us as a strong opening move.

Sure enough, RO fell in the river and got completely soaked.

This was the first of many mistakes he would make on the trip.

He came back to camp late and dripping wet, having apparently developed an immediate a bizarre attachment to that river. The water was cold. The evening was cool. He changed clothes, we had dinner, and we went to bed. At this point, there was still some chance that the next day might somehow become normal.

It did not.

The next morning we got up early, had breakfast, and prepared to head out. My assumption — based on reason, precedent, and the literal existence of trails — was that we would continue on the trail. Instead, RO decided that we were going to bushwhack straight uphill through an extremely dense forest in the blazing heat.

This struck me as a bad plan.

It was a bad plan.

The forest was thick enough that you could not really move with any rhythm. We were not hiking so much as negotiating, arguing, and physically contesting with the landscape. Every movement took extra energy. Progress was incredibly slow. The heat was serious. And the main problem, which quickly became the only problem, was that there was no water. Not a stream. Not a trickle. Not a suspicious puddle. Nothing.

Now, RO for reasons that remain mysterious to me is not a big water drinker. He prefers beer and tea. Under ordinary conditions this is merely a personality trait. On a hot uphill bushwhack through dense forest it becomes a strategic liability.

Naturally, we asked where the water was.

Ross Thomas: I had read in a Fred Beckey book that there was a way to get up to Castle Rock, although I think Beckey had only heard about it and never actually done it himself.

This is, in its way, a perfect Ross Thomas detail. Fred Beckey, the legendary climber, had perhaps heard there was some route, though he had not personally taken it. This was enough for RO. A rumor in a book by a famous climber became an operating plan.

As for the water situation, RO told us — and I remember this vividly — that there might be some in about five miles.

Five miles!!!

We were already fighting for our lives up there, and this crazy man was calmly informing us that in only another five miles there might, possibly, perhaps, be water.

He’s totally outta control.

At some point, after what I recall as roughly three miles of this lunacy, we basically mutinied. Or perhaps mutiny is too strong; let’s call it collective realism. We told RO the obvious, which was that this was not going to work. The route was no good. The heat was too much. There was no water. We had to turn back.

And so we did.

Now the descent was interesting because it brought out our distinct styles. RO, MI, and PA were making their way down carefully, gingerly, responsibly. I, on the other hand, was absolutely flying. Swinging from tree to tree like some kind of deranged monkey, just ripping downhill through the forest. This part RO loves to tell to this day, and I admit it was one of my better athletic showings. I was not going to die of thirst in that forest and I was not going to descend politely either.

Eventually we made it back to camp. Or rather, most of us made it back to camp together. RO, in one of those small but meaningful complications that tend to gather around him in climbing situations, got separated from us and somehow ended up down by the river again.

And yes, he fell in again.

He really must have loved that river.

So now here he comes back to camp once more, drenched, and by this point we are all in total agreement that the trip is over. We are done. It is time to 86 the hell out of there.

So we break camp and head down toward the lake shore. But this presents a new problem. We still have a significant walk to get home — something like another two miles down to the shore and then, as I remember it, another three miles around the lake. And by now it is dusk. So this is not really viable either. We are hot, tired, and in no mood for an elegant final act.

At this point RO does what he often does in these situations, which is simply assume that reality will provide.

He found a guy with a motorboat and asked if he would take us back to Stehekin.

The guy said sure. Fifty bucks.

RO then informed him that he did not actually have fifty dollars on him, but could get it from his wife once we got back to the cabin.

Somehow, by what can only be described as grace, audacity, or a temporary breakdown in the boatman’s judgment, this worked. We got in the boat, got home safely, and made it back in time for dinner.

That was Stehekin.

CODA

You might think the lesson here would have been: bring water, stick to trails, do not base wilderness plans on rumor, avoid rivers if possible, and maybe do not lead your sons into dense forests in the hot sun in search of a semi-mythical route described secondhand by Fred Beckey.

You would be mistaken.

Many years later, when RO was Principal of Valley Catholic High School, he got really into climbing at a gym in Portland. It is a cool place, run by a father and son, and it has beginner, intermediate, and advanced climbs. He took me and MI and PA there, and later my son Hugh as well. Hugh loved it. He scampered up the walls like he had been waiting for exactly this sort of thing his whole life. I like climbing too, though my arms get tired pretty quickly and I tend to fade. MI and PA are both good climbers. RO, to his credit, also has strong stamina.

So one day my wife and Hugh and I were there with him. We’d been climbing for a few hours. I was on the mats, faded, taking a break. Hugh was still going. RO was showing him some moves. Then RO started up one of the big walls — one of the long climbs, the kind where you need the harness.

Only he had forgotten to put the harness on.

Hugh saw this before anyone else did and yelled out:

RO, get down now!

And RO did.

For the next year, RO loved telling the story of how Hugh had saved his life. Quite right too. It is a great story. My son saved my dad from one of my dad’s own ridiculous climbing strategies. The circle was complete.

But then, about a year later, shortly before RO retired from the principal job in 2018, he was back at the gym by himself. This time the only other people there were the owner and his son. And somehow — incredibly, impossibly, yet also in a way entirely consistently with the established Ross Thomas climbing tradition — he forgot the harness again, started up the big wall, and fell.

He crashed all the way down onto the mat.

The mat saved his life, no question. But his feet and knees and legs got absolutely busted up. He was in a wheelchair for months. It was so bad that he had to move temporarily out of the country house in the woods where he lives with CL and into a little bungalow on the Valley Catholic campus owned by the nuns that founded and still run the school. He could barely work. To this day his feet remain a total mess. He has trouble driving and has to drive with his shoes off and wearing some sort of thick sock or something.

At one point we wondered whether he might sue the gym owner for negligence. But RO wanted no part of that. He said it was his own fault, not the owner’s.

Fair enough.

And then, after many months, he mostly recovered. Which means this story has, if not exactly a happy ending, at least a decent one. Better still, as soon as he was recovered he went right back to the gym and started climbing again!

This is what I mean.

His climbing strategies are ridiculous. They are unbelievable. They are officially, historically, and totally outta control. He does not plan for basic things such as the route, the water, or how exactly one might avoid miles of dense forest. He does not always remember the harness. He seems, in climbing situations, to operate according to a distinct internal logic unavailable to the rest of us.

And yet outside of climbing, this makes almost no sense. He is, as I said, a basically well-organized guy. He planned lessons. He coached meticulously. He ran a school. In most areas of life he is not slapdash at all. Which makes the climbing thing not just reckless but anomalous. It is a localized mystery. A glitch in an otherwise coherent system. I do not understand it and at this point I do not expect to.

What I do know is this: to this day I avoid climbing with him because in this one particular area I do not trust his judgment at all.

I love the man. But when it comes to climbing, he is not to be trusted.

Dedication:

For my dad. I love you baby but you are totally outta control.

Things I’m Gonna Pass On

Note: This piece is a companion to “Things That Suck” and “A Little List of Things I Find Interesting.” The three together form a loose trilogy—what I reject, what I notice, and what I choose not to take up. If Things That Suck was reactive and Things I Find Interesting was observational, this one sits somewhere quieter. It’s not about condemnation so much as calibration. These are not necessarily bad things. Many are perfectly fine. Some are, perhaps, even admirable. They’re just… not for me. There’s a difference between disliking something and passing on it. The former makes a claim about the world. The latter makes a claim about yourself. This list is an attempt at the second.

  1. Polar Plunges
  2. Siberia
  3. Prostate Exams
  4. Space Travel
  5. Parallel parking on a busy street
  6. Mt. Everest
  7. Post-COVID facemasks
  8. Voice notes
  9. Hunting
  10. Diving for treasure
  11. Splitting the bill down to the cent
  12. Mall walking
  13. Lines for food over 10 minutes
  14. AI avatars
  15. Smart homes
  16. Phone calls from an unknown number
  17. Endless group photos. Take two, baby.
  18. VIP rooms
  19. White wines over $20
  20. Watersports
  21. Getting tied up in bed
  22. Sleeping outside
  23. Aspartame
  24. Self-checkout machines that talk. I heard you the first time baby.
  25. Trying knots
  26. Expensive art
  27. HOAs
  28. Astringent cleaning products
  29. Porta potties
  30. Claude

The Adventures of the Thin Man and Andrea Available Now!

Well everyone, today is the day. My first novel, The Adventures of the Thin Man and Andrea is now available on Amazon and wherever books are sold.

This one took a while—written in fits and starts, in bars and hotel lobbies here in Kyoto—but it finally found its shape. More than anything, today I just want to thank all the readers of The Kyoto Kibbitzer, wherever you hail from; I’ve always thought of this as an ongoing conversation, and a lot of this book grew out of that exchange.

If you do pick it up, I hope you enjoy the ride—and if it lands for you, a quick review on Amazon would mean a great deal. Thank you, as always, for reading.

Matt

On it, Pete

Note: Some stories get better in the telling. This one doesn’t need to. It arrives fully formed—one line, perfectly placed—and has stayed that way ever since. I’ve told it for years and it still lands exactly the same. No embellishment required.

It’s September, 1989.

Two new teachers had just arrived at St. George’s School in Spokane, WA. These are Paul Hogan and Pete Aiken. Paul would go on to have a long and distinguished career, eventually becoming Principal of Jesuit High School in Portland—a major job, the kind that makes a life. I have no idea where Pete is today.

That night, my dad Ross invited them over to the house for dinner. It was one of those late-summer evenings that still carried a little warmth but hinted at the coming turn. Ross was out back at the grill, working over the barbecue with a beer in hand. The adults clustered nearby, talking, drinking, getting to know the new arrivals. There was that particular tone of adult conversation—half-professional, half-social, everyone just slightly aware of roles and impressions.

Out in the yard, it was just the three of us: Pat, Mike, and me. We were playing catch with a tennis ball. Nothing serious. Just throwing it around, loose, casual, the way kids do when the game isn’t really the point. At some point, either Mike or I made a bad throw. It sailed wide of Pat—too far, too high—and rolled past him.

A completely ordinary moment. The kind of thing that happens a hundred times in a backyard, in a summer, in a childhood.

Pat was six. He didn’t chase the ball. He didn’t complain. He didn’t turn to us. Instead, he turned—calmly, deliberately—and looked over at Pete Aiken, one of the brand-new teachers, a guest in our home, a man he had just met. And in a tone of quiet assurance, as if assigning responsibility in a meeting, he just said:

“On it, Pete.”

That was it. No smile. No wink. No awareness of what had just happened. The ball was recovered. The game went on. The adults kept talking. The evening continued. But something had shifted, just slightly, just enough.

Because in that moment, a six-year-old child had somehow crossed the boundary between worlds—between kids and adults, between play and work—and issued a line that did not belong to him, but fit him perfectly.

I don’t remember what happened next. I only remember that line. And I remember that we have been laughing about it ever since.


The On It Pete Blues (Pete’s POV)

I was new to the city, new shirt, new street,

Standing in a backyard trying hard to be discreet,

Ross on the grill and the talk running deep,

Just another first night—then I heard, “On it, Pete.”

I hadn’t been briefed, hadn’t learned the terrain,

Didn’t know the house or the shape of the game,

Just a beer in my hand, trying not to overreach,

Then a six-year-old turned and delegated to Pete.

Now I’ve worked in schools, I’ve handled my share,

Rooms full of noise, moments needing repair,

But nothing quite like that clean little feat—

Being calmly assigned by a kid in bare feet.

No panic, no pause, no doubt in his beat,

Just a glance and a nod—“On it, Pete.”

And the ball got found, and the night rolled on,

But I knew right then something strange had gone on—

In a yard full of voices, one line cut through the heat:

I wasn’t just visiting.

I was on it.

Pete.

Dedication:

For my brother Pat. And for Pete. Just get on it already baby.

Note: If you liked this story you may also like the stories below, which also cover my time at St. George’s High School.