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The Power of Trip Sitting

I held space for a friend on a psilocybin flight … and it was amazing

Damon Orion

“I wonder what the ocean is up to,” my friend Gene pondered aloud. “Tide in, tide out … what’s the game here?” 

He sounded simultaneously suspicious and intrigued. Shifting his gaze back and forth between me and the waves of the Pacific, he observed that the ocean had a slight sideways current, so that the water was slowly pulling up or down the beach rather than straight in and out. 

All this was proof positive that the psilocybin had kicked in. I was feeling the magic, too, but for me, this manifested in a far less pensive form—namely, a big, toothy smile that would have looked right at home between two thumbs-up emojis. Like an oscillating fan with a happy face sticker on it, I rotated my guileless “Party on, dude!” grin in Gene’s direction. 

“I feel the way a dog must feel when he’s sticking his face out the window of a moving car,” I announced.  

Mind you, I’d taken a lower dose than Gene, and for good reason. Don’t let a little absurdist banter fool you—this was no mere chemical joyride. We were here to do some delicate soul surgery.  

Holiday on the Moon

A week or so earlier, Gene—a close friend of mine since age 12—had notified me by email that he was suffering from severe depression. He mentioned that he was impressed by some recent studies on the antidepressive properties of psychedelic mushrooms and was thinking of giving that a shot. 

I sent a reply confirming that I thought he might benefit from this. I also mentioned that I’d been thinking about taking a little field trip of my own. I wasn’t particularly depressed—and at a time when humanity appears to have forgotten its safe word, and the planet is starting to resemble a rubber ball on a hot barbeque grill, I have no cogent explanation for that—but I was feeling stagnant, and a good mind-lube can be the best rut-buster I know of. 

A couple of emails later, Gene let me know that he wanted to rent an Airbnb and take the medicine with your humble narrator. 

I urged him to consider this carefully. I won’t lie—in my unprofessional opinion, some psychedelic therapy is little more than high-priced trip-sitting. I also have my doubts that tripping in a clinician’s office with an eye mask on is necessarily more therapeutic than going on a DIY cosmic caper with a responsible friend. However, a competent and caring professional might be able to prep Gene for the experience and do follow-up therapy in ways that I couldn’t. 

Depression, I reminded him, was serious business, and I didn’t want to be the guy who persuaded him to go rogue rather than seeking the guidance of a trained specialist. (It goes without saying that the same warning goes out to our readers, and that we don’t encourage anyone to “try this at home.”)

Gene assured me that he was taking his mental health seriously and was taking several steps beyond our little adventure. “I hope that our trip does end up being something of a catalyst for change and perspective-shifting for me, but I'm not simply counting on this and throwing all my eggs in that basket,” he wrote. 

Preparing for Takeoff 

Less than a week later, we met at an Airbnb just a short walk from the ocean. It so happens that at age 16, Gene and I took our first-ever mushroom flight together, so this event had a full-circle feel to it. In honor of a song by Love and Rockets, a psychedelically fueled alternative rock band we both revered in our teens, we were calling this our Holiday on the Moon. 

Now, it’s generally advisable to abstain from taking the medicine when you’re in the role of trip sitter. However, in this situation, I wanted Gene to feel like he was hanging out with an old friend, not being watched over like some kind of patient. So, I joined him in partaking, but I took what they call a “handshake dose.” I’d brushed up on the basics of trip sitting beforehand, and as an experienced psychonaut, I felt I could responsibly hold down the ground control role whilst feeling a little jollier than average. 

In the earliest part of the trip, Gene went into his room, put on a sleep mask and lay down for a while. He left his door slightly ajar, and I sat close by, ready to step in if anything went sideways. 

He emerged a surprisingly short time later, suggesting that we pay a visit to the ocean. 

As we walked, I asked, “What was it like with the sleep mask on?” 

“It was … darker,” he joked. His tone didn’t suggest that he’d confronted any sort of inner darkness, but simply that blocking the light from his eyes hadn’t made much of a change to his state of consciousness.

Digging in the Sand 

Which brings us to the quiet, mostly vacant beach where our narrative began. 

A rich purple hue saturated our surroundings: the waves, the sand, the mollusk shells on the shore, the mountains and even the clouds. It was the same shade of bluish purple I’d once seen spilling onto a napkin from a wet, freshly picked magic mushroom someone gave me. This was the color of psilocybin. 

As we stood on the sand, just a few feet from the ocean, Gene asked, “Do you see a spot where you want to settle in?”

“Umm … right here where we’re standing seems as good as any,” I suggested.    

“I was thinking that, too,” he replied. 

As a lone man flew a high-soaring, multicolored kite nearby, our conversation naturally turned toward the sources of Gene’s hurt: the recent deaths of his mother, stepfather and dog, pressures from work, his wife’s lack of acknowledgment for his exhausting efforts. His calm, fearless commentary prompted questions from me that kept the introspection going. Though the discussion was meaningful, there was never a point when it felt overly dark or heavy. Laughter frequently punctuated the contemplations. 

A repeating theme in Gene’s observations was that he was responsible for his own state of consciousness. As the ever-insightful Love and Rockets once sang, “You can make it dark or fair depending on your point of view.” Each time he voiced that idea, I felt a “Fuck yeah!” in my core, as if he’d just hit the jackpot.  

Eventually, my bladder spoke up, and we quietly headed back to the Airbnb. Still rocking a naïve, stoked-puppy grin, I told Gene, “I don’t think I smile enough. I guess I could think about why, but … why?

“Just smile,” he agreed. 

Leveling Up 

Back at the beach house, we decided to up the dose a little. Still wanting to stay ready for any unexpected events, I was sparing in my self-allotment. “I’m the one holding the kite string here,” I explained. 

An hour or so later, the trip was still completely manageable. I was getting some shimmery visions with closed eyes, and there was a most welcome sense of mild euphoria, but I wasn’t deeply immersed in the enchanted world of alien elves and pulsating tunnels of light. Instead, I felt as though I were watching a positive psychedelic experience through a hole in a fence. 

Considering that he’d taken a stronger dose, Gene seemed surprisingly level-headed as well. As the evening progressed, he talked more about the losses he’d endured and the depression he’d been feeling. Despite the heaviness of the subjects, the mood stayed pleasant. Again, there was never a point where it felt like we might stray into the badlands. 

The Afterglow  

The following day, as we said our goodbyes, Gene remarked, “This has been … therapeutic!”  

For the next two weeks, he consistently reported feeling “pretty damned good” by email. Each of these communiques brought a smile to my face—which, again, doesn’t happen as often as it should. 

Two weeks after our flight, Gene had the first legitimately bad day since our Holiday on the Moon. “It was sort of a surprise, as I have really been surfing on the positive momentum from our trip,” he wrote. “But it also was useful—perhaps even inspiring—to recognize/remember that this is how I was feeling every single day just weeks and months ago, and now it seems so much less ‘my current state’ and more of a feeling that I have sometimes.” 

Three weeks after the journey, he wrote, “I am unambiguously feeling better than I was a month or two ago.” 

Sadly, on the day of this writing—just a little over a month after our little lunar holiday——Gene wrote that the funk had returned for him. So, while our psilocybin session seems to have given him some needed respite from depression, it wasn’t a one-stop cure-all. It should be noted, though, that he’d taken a relatively mild dose without guidance from a licensed therapist before, during and after the session, so perhaps the story doesn’t end here. 

To Gene, and to the countless beings all over the planet who are shouldering overpowering pain: May you know the ridiculous, unreasonable joy that dogs feel when they’re sticking their faces out the windows of moving cars. May you know the agenda-less tranquility of the ocean’s tides as they quietly sway to the rhythms of the eternal What Is. 

And may we all make an effort to smile a little more. I will if you will.  

Damon Orion is a writer, musician, artist, and teacher based in Santa Cruz, CA. He has written for Revolver, Guitar World, Spirituality & Health, Classic Rock, High Times and other publications. Read more of his work at


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