some quick thoughts on tripping, five years later
Length: • 7 mins
Annotated by Zeyad Mahran
some quick thoughts on tripping, five years later
I am not an expert and this is not medical advice

Elsa Beskow, Queen Water Lily
- Psilocybin has changed my life and I think it’s directly responsible for many of the positive changes I’ve seen in my work life, friendships and general happiness over the past few years.
- That being said, I think I’m an outlier responder. I think *most people* would benefit from psychedelics, it’s just very possible they’d get like, a 2% or 5% boost in wellbeing instead of a 50% boost. Context and where you’re starting from and who you’re doing it with really matters
- Hilariously, what I thought was my first ever psilocybin trip was actually a 4-AcO-DMT trip. Would highly recommend it—it’s very similar to psilocybin but I find it slightly more euphoric.
- I’ve experimented with LSD, ketamine and 2-CB, but the only psychedelics I’ve done repeatedly and would personally recommend are psilocybin and MDMA.
- If you would describe yourself as currently quite unhappy and searching for more joy and self-love, I would start with MDMA. If you’re generally pretty stable but in some kind of rut or contemplating a big life change, I would start with shrooms.
- To illustrate, my friend said last weekend: Yeah, this guy was asking me how he should decide on the job he does next, and I said, you should take some time off, talk to a lot of people, and do shrooms.
- I would tripsit any friend of mine and I would likely even tripsit friends of friends, but I’m only interested in tripping with people I’m extremely close to. Tripping puts both you and the other person in a very vulnerable state and exposes your psyches to each other in a very intense way. Do not do that with anyone you don’t trust.
- Tripping has made my close friends closer friends. One friend of mine literally does yearly rolls with his group house as a form of conflict resolution. Not for everyone, but it works.
- In the same way, if you’re considering doing psychedelic therapy, I think your bond with the therapist is critical. It’s like actual therapy—probably not going to do anything for you unless the therapist is really good and you like them. I’ve had lots of friends have meh/bad experiences with psychedelic therapy (ketamine/MDMA/ayahuasca etc) and would not universally recommend it at all. The container really matters.
- In fact, if you want to try psychedelics for the first time, I’d probably recommend you do it with a close friend or partner who’s really comfortable with psychedelics.
- To maximize the odds of a great experience, do psychedelics in a location you’re really comfortable with (I like hotel rooms, and cabins, and being outside in a nice park), with a person you love a lot, and don’t do them at a time where you’re extremely stressed, distressed, or feeling particularly unstable. That being said: you cannot control the trip you’re going to have, and you can’t control the other person’s trip.
- If you’re having a bad trip, just relax into it and accept that it’s happening for a reason. Do not fight it. Bad trips get way worse when you start struggling against them.
- You will survive a bad trip. The anecdote I like to share is that on my first ever acid trip many years ago the friend I was tripping with (who was much more experienced than I was) had a seizure and I had to call an ambulance and go with him to a hospital. As you might imagine, we both took some time off psychedelics after that. But it was ultimately totally okay. (And he’s okay now, too).
- Many people have said things to me like, “I’m afraid that if I take psychedelics, I’ll become less motivated.” My reply to that is: 1) I feel like doing psychedelics has helped me immensely with my relationship to work, in terms of both finding work that I was passionate about and working through important blockers. I’m a way more focused, productive (I hate that word, but I don’t know if there’s a good replacement for it) and confident person because I have much better understand of myself and where my attention lies. 2) If you stop wanting to work after doing psychedelics you probably don’t really like what you do. I think that work is a very important component of fulfillment and it’s worth trying to find work you love. 3) Almost everyone I know has done a lot of psychedelics a lot of times, and most of them have very successful careers, so it seems anecdotally untrue to me that people become less motivated after psychedelics. TLDR; if you hate what you do, psychedelics might help you realize that. But in my opinion that’s good and important. If you love what you do, psychedelics will help you deepen your relationship with it.
- A friend took MDMA and one of his primary realizations was, “I really like money.” Not the typical experience, but it really depends on the individual.
- I couldn’t meditate at all before psychedelics; I still don’t meditate that much, but when I do I really enjoy my experience. I can enter the jhanas with some regularly when I attempt to and they’re really great.
- One of the best things you can do in conjunction with psychedelic experimentation is finding a good therapist. A meditation teacher once described it to me as, “Imagine your psyche is a pond full of dirty water. Mindfulness makes you okay with living beside the pond and it not bothering you; therapy helps you slowly replace the pond water bucket by bucket.” I think getting really deep into mindfulness and not doing therapy leads to the type of behavior Sasha describes here (gurus misbehaving and abusing students), essentially. If you become an experienced meditator or develop high equanimity through psychedelics/yoga/etc it becomes easy to feel great nearly all the time, but that doesn’t mean you’ve actually fixed all (or any) of your psychological problems.
- Compared to five years ago, I have way higher equanimity, I’m more fulfilled in my work and personal life, I’m much more in touch with my body and intuition, I feel more connected to my childhood self, and I feel more creative. I would say that many of my close friends have had similar experiences that started with psychedelics. Most of us don’t do psychedelics regularly anymore, which is pretty funny.
- On side effect of psilocybin is that making eye contact with a tree now sometimes spontaneously makes me burst into tears
- Psychedelics have really taught me that I am not a Great Judge of Myself. Like, I really feel that in the past few years I’ve made some meaningful discoveries about joy, love, sex, agency, and spirituality, and I feel bad for my former self who did not know these things. But my past self thought I was perfectly fine (and knowledgeable about all of these things, lol). Sometimes I’ll try to get people I observe to be repressed to do psychedelics in hopes that they’ll be less repressed and they’ll usually be like “What are you talking about I’m perfectly fine. More than fine. GREAT.” Then they’ll try psychedelics and be like “Omg I used to be so anxious and repressed.” Then they might try to evangelize psychedelics to another repressed person in their life, only to be told, “Leave me alone, I’m great.” I’ve made peace with this and find it very funny: this is just the way of things.
- As a result of this realization I take my friends’ observations way more seriously. Like, I consult my closest friends about decisions all the time, Do you think this is a good work idea? Should I move in with this person? and I really pay attention where they’re like, This is a bad idea. Turns out other people can see your shadow way better than you can and can warn you about it.
- I really recommend A Little Book on the Human Shadow by Robert Bly. I also like Already Free by Bruce Tift and Radical Acceptance by Tara Brach. I really like Sasha’s Substack generally and his writing about mindfulness really resonates.
- It can feel a little cringey (for me personally) to write about Buddhism and mindfulness and psychedelics because there’s so much out there already about it. But I’ve resolved to be less embarrassed by something that’s changed my life along every conceivable axis.
- The way I would describe it is that psychedelics can crack open the door to a lot of positive change but you really have to walk through the door yourself and want the change and want to do the work. Lots of people don’t want that and it’s perfectly okay.
- If you’re tripsitting someone else (or tripping with them but you’re the more experienced one), the best thing you can do is be relaxed and present.
- It can be really stressful when you’re tripping with someone and they’re having a bad trip, but try to create space for them and remember that their trip is separate from yours. Just be with them without rejecting their experience or taking it on as yours.
- If you’re doing MDMA, definitely take these supplements.
- I won’t encourage people I don’t personally know to do psychedelics because, well, I don’t know you and I can’t tell you how it’ll turn out for you, but luckily there’s a wealth of knowledge on the Internet.
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