My father was a professional smuggler — it took a midlife crisis for me to try drugs.

I live in the mountains of Idaho and commute by bush plane to Palo Alto. There are 800 backcountry airstrips here but landing at Palo Alto is actually one of the most challenging in GA (general aviation): it’s the busiest, shortest runway in the US, perhaps anywhere. Made of landfill and jutting out into the south bay, it’s like landing on an aircraft carrier.

I commute to one of the leading VCs in tech and this might seem like an adventurous life. But it’s nothing compared to the life my father lived. He was the last of a great kind and it sickens me to see him struggle with joining the modern age, barking at Siri and slamming shut his enormous laptop. I don’t think my father actually ever did any drugs but he was a professional smuggler and moved all kinds of exotic things. At only half his weight (a former boxer) and picking up only two of his four languages, I was content to live a modern if not curtailed version of his life as a headhunter for one of the most successful investors of all time, going on 15 years now.

We had a good run (staffing a lot of the so-called PayPal mafia companies) and last year I relocated my family to a small town in central Idaho, population 2740. Our house is a run down but architecturally significant wooden structure that sits at the confluence of two rivers. Giant beams milled from dead fall ponderosa, dry stacked stone on the exterior and a standing-seam metal roof that blasts with percussion during our summer afternoon monsoons. The perfect place to try psychedelics for the first time.

The problem is that I’m 47.

I’m married, with two young daughters, and I’ve never done drugs before.

My wife found herself at a dinner, and later breakfast, with Dr. Andrew Weil (of Timothy Leary fame) and Michael Pollan. By now everybody has read Pollan’s book and his position on mid-life drug use for therapeutic aims is no secret. Ever since that breakfast, Wendy has been on me about trying psilocybin, a word I could hardly pronounce, but for reasons I could well understand: each year since turning the high-water mark of 40, I had slipped deeper and deeper into depression.

This took a long time to accept. After all, all the outside markers that I had “made it” were there: I flew a plane to work, lived on a farm on the Big Sur coast, was married to a beautiful woman and had two darling little girls. I was surrounded by a small but close-knit group of guys that did annual trips like riding the Baja 1000 or remote fly-in airstrips in the northern Mojave. How in the world could I be lonely?

Loneliness I would later realize is exactly where a lot of us sit: disconnected in an over-connected world.

Skipping lightly over the seven years since my milestone birthday (when I attempted even to retire), I found myself on the verge of losing my marriage and most of my friends. “You’re being a bonehead” my neighbor and good friend said to me eventually. I’ll spare this post the ugly details.

Eventually the day arrived when Wendy came home and threw down a bag of mushrooms. “The kids are with Brian and Amy; I’ve cleared your schedule. Your own mother sent these. We’re going to trip”.

I tried every excuse. “But what about intention? Set and setting!” I texted my therapist. I tried anything to get out of it. If ever there was evidence of being a control freak, it was the four hours leading up to sucking on those wet-wood tasting mushrooms.

I managed to listen to Tim Ferris’ podcast in the morning. (For another time I have a story about swimming out to an island with Tim and getting there, me naked, him clothed, and having the most awkward of conversations with Mr. Four Hour Body.) I learned that John Hopkins University was taking a clinical approach, treating people indoors, blindfolded with nothing but music. Being a kind of a dark guy, I skipped the usual Pink Floyd stuff and went right for Verdi’s Requiem. I had Rachmaninoff’s vespers ready. I wondered: would the genus gymnopilus require Dance Macabre in G Minor, while simple psilocin need only Beethoven’s 5th or Carmina Burana? What I was hoping for, though, was something more like an afternoon with Holst and The Planets.

Instead, I ended up dancing until midnight, in locked embrace with Wendy, to Steve Winwood. What? The early 80s?

A quick diversion: I’ve been very surprised at the variety of reactions to SIP during Covid. Colleagues that couldn’t go 15 minutes without a trip to Starbucks found their car batteries dead and frequently lost their phones. Self described isolationists like myself, who bragged about doing 10 day silent retreats, fell apart.

So it is with mushrooms I believe.

I am by nature a spiritual-oriented person and expected to plunge backward through my third eye, “dying before I died”. I expected the kind of experience described by an old traveler friend of my father’s, and noted ethnobiologist, Wade Davis, who described doing the Brazilian hallucinogenic ayahuasca as “being shot of a barrel lined with baroque paintings and landing on a sea of electricity”.

After taking what amounted to almost a double dose over 4 hours (nothing was happening), I eventually settled into doing the dishes. No past life avatars speaking several languages on multi-dimensional frequencies here! Just me, the barking dog, and a slightly elevated sense of shimmering leaves. I thought the river was louder but realized the gardener had turned up my Japanese fountain.

Around about 4 hours I gave up and went to the tried and true drug, of the kind grown in southern France. An Australe, a young 2016, was a perfect match for the fried chicken Wendy picked up for our post-trip repast.

Here all the credit goes to Catalans because this grape does wonders for psilocybin: the show was on!

Wendy and I walked down to where the two rivers meet and briefly worried that we’d never make it back. A giant wind storm picked up. The mountains became obscured in woolen coats that made like a front of World War I soldiers coming down the valley. Let me be clear: I was not hallucinating. No trees bending into the forms of rainbow taffy; just the wind. Gold epaulets appeared on the river, as if they had fallen off the marching soldiers, and beautiful as it was, it was clear that it was only the rippling water shimmering. I hoped to talk to a fish, and a few rose, but only to go after the same hatch the cliff swallows were diving for. Our dog got harassed by a plover whose nest must have been in the river bank grass somewhere. We found two chairs and sat down in silence. The last time we were in those chairs we discussed divorce.

Eventually we walked back to the house. The trip never truly took flight. But it was beautiful. Time slowed down. I wondered why I worry about money so much. I didn’t see a lot of relation to material things at all. Time seemed to matter very significantly and I wondered what we do with it all. Wendy appeared brilliantly, walking in front of me in jean cut-offs, dark and tan. I remember thinking “this isn’t the trip I expected, but it’s exactly what I needed”.

We danced until midnight. We made love. We cried at what terrible parents we are and made plans to leave early in my plane for some of the backcountry airstrips I had been wanting to show Wendy. It was nice to leave the night open to more adventure the next day.

Instead, I awoke at 5:30 with a desperate high desert thirst. Strangely I went to a group exercise class full of all women. When my heart rate hit 180bpm, and I heard “COMMON GIRLS, FAT IS YOUR ENEMY!” I thought, “why didn’t I try cocaine?”.