Specific astro dynamic: What Jupiter in Cancer might mean for your chart will depend a lot on… your chart! But here are some things that the recent movement of Jupiter into Cancer means to me:
I think about blue whales, the largest animal and one that is so gentle. Watermelons. Fat, full clouds. “(Sittin’ on) The Dock of the Bay” by Otis Redding. It feels like tears welling up in your eyes when you were hoping to cry, either at a sad movie or because you’re seeing something you just love that much. A visitor you don’t have to perform for. Carnations. Charcuterie for dinner. A hug. Sitting on the porch and holding your hand over the top of your wine glass to keep the no-see-ums from a decadent death.
If you missed my announcement last week, I’m getting back on track here! Starting on Sunday, I’ll be sending a second weekly email to Paid Subscribers (you’re all Paid Subscribers for the moment, while I figure this new format out). This week’s Sunday topic is… Pride! Lol. Can’t wait to hear what you think.

Knowing is not enough.
When you were very young, it might have seemed like learning as much as possible about the world could protect you—from embarrassment, from loneliness, from doing something “wrong.” It might have seemed that way to you or I’m just massively projecting. In any case, I thought that if I just learned how to handle things (if I “did the reading”) then handling those things would become extremely manageable. This hasn’t always been exactly the case.
My friend Kelsey and I talk sometimes about this funny thing happening with the younger members of Gen Z (or is it Gen Alpha already?). They know all these psychotherapeutic terms, especially the popular ones like gaslighting and dysphoria and anxiety, but this knowledge won’t keep them from getting gaslit, feeling dysphoria, or needing to learn the difference between a clear message from your gut and run of the mill fear. Humans aren’t equipped with the kind of social brain that allows us to download lessons purely conceptually, we usually have to mess up and live with it ourselves if we want to really understand something.
I’ve seen this play out over and over in my life, but one of the most potent examples relates to a falling out I had with a friend about a year ago. Without getting into all the lurid details, I hadn’t ever really lost a friendship and I don’t think this friend had either. I think of myself as being pretty good at having friends. I try to strike a balance between being invested in people without fully making their problems my own, i.e. I try not to be codependent. This hasn’t always worked perfectly, and it’s something that I was especially inept at when I was younger, but even the friendships where things got rocky have mostly gotten back on track. If they couldn’t, they at least evolved into something new that better suited what we needed. But this falling out last year was bigger and seems less likely that we’ll come back from it.1 Why?
When you start thinking you know all the answers, it’s a good sign that you might be about to make a mistake. The challenges my friend and I were dealing with didn’t newly emerge a year ago, of course, they had been bubbling under the surface for a long time. Whenever one of us would do something that caused those bubbling resentments to burst, I, knowing both of our Enneagram numbers, knowing both of our charts, knowing “us” for almost a decade, thought I understood pretty deeply how and why it happened. When others in my life questioned our dynamic, I didn’t have a hard time explaining why it was actually going great. It all made sense! I could easily connect the dots. I could explain why something felt smaller to me and bigger to her or vice versa. And so I repeatedly affirmed, to her and to me, that this was an okay pattern for us to be in.
I can only speak for myself, but, looking back now with some distance, the space between us was exacerbated by some of these systems we were both using to understand ourselves and other people. I’ve written about the potential for things like the Enneagram or astrology or even just history of intimacy to make us sloppy in relationships before, but, even so, it’s something that is easy to slip into because it’s so enticing. It’s so much easier and more appealing to use the shorthand that these tools offer than it is to puzzle through the right here and now. Much easier to say, “Well, they’re a Six, what else could I expect?” or “With their Cancer placements, you just have to let the emotions pass, ignore it for now.” If you’re ever finding yourself thinking things like that, it should set off alarm bells. When a tool reduces someone’s complexity rather than expands your capacity to appreciate their complexity, you’re in a dangerous place.
The human impulse to systematize and categorize things in the ways that these tools do is itself revealing. We are a kind of animal with a vested interest in trying to make sense of things, to defang the monsters hidden in the dark parts of the map (whether that map is of uncharted oceans or the contours of the psyche). It’s a canon experience when getting into astrology or the Enneagram to run into the acolyte who insists on knowing what category you fit into before they will engage with you. We all know about the house of anarchist poly queers who don’t invite anyone with strong Capricorn placements to their potluck. Obviously, this is bad.
Still, having some kind of context for someone’s behavior, whether from knowing them over the years or by knowing their Enneagram or chart details or whatever has strengthened and prolonged the relationships in my life. It extended my relationship with this friend—there were many wonderful times in our eight-ish years before things really broke down. Ideally these tools are context creators. They can depersonalize things that really ought to not be taken personally. They can help you understand when and why something that is not a disaster to you feels like an existential threat to someone you care about. These kinds of things are valuable when you’re trying to sustain a relationship for the long haul. But it is absolutely not a sufficient quality for being in relationships well. Necessary, but not sufficient.
For someone like me, a person who gets wrapped up in hypotheticals and theoreticals as though it’s my job, striking the balance between trying to “figure out” life and living it is not intuitive. Humility lets you leave room to be surprised and to learn, to see what is really happening. Confidence let’s you take action. On the one hand, you try to clock when you know enough, when you’d benefit from taking decisive action. On the other, you do your best to sit inside of what is happening without trying to cast your preconceived beliefs over it. You learn to wrestle with your own experience. You try to answer the question, “When should I suspend my judgment?” It’s a deceptively challenging reflex to develop.
This tension has implications for more than just our relationships. The balance you reach between humility and confidence influences how you do or do not live your beliefs and values. I think there’s something sticky here, something about God and putting your money where your mouth is, and it connects to my post about saints and politicians. Politicians (we could also call them Evangelists) are the ones who are sure they know God and can articulate all sorts of interesting and powerful things about their knowledge. Saints, on the other hand, would be the ones who focus on having a real experience of God whether they can advertise it well or not. Politicians are writing in the dark about the experiences that saints are keeping to themselves.
I don’t mean to make a false dichotomy, associating the politicians with the overly confident and saints with the overly humble, a kind of “we’re all equally wrong” perspective. As I said in that earlier blog, I think we need more “saints” than politicians if we want to make any serious progressive impact. More action and less talking feels like a great principle for us all to embody. Still, there’s a tension between the two kinds of figures, value in what each approach can offer, and it’s worth learning what we can from that.
Here we can talk about Greta Thunberg. I don’t want to pedestalize her and turn her into some kind of exceptional entity, a person who is better than the rest of us. She is just a person, though a person who has repeatedly demonstrated commitment to experiencing her own progressive values, not just talking about them. I’m sure Greta’s values have evolved and changed as she’s taken action. And while I can’t know how or what has gone on in her head as she makes bold choices and publicly commits to causes that are not always popular, I’d imagine that she is not waiting for a complete and unshakeable understanding of a situation to take action. She seems to understand the concept of “good enough” very well.
Her willingness to commit to a cause makes me think about my own journey with Palestine. It wasn’t that long ago that I would have said, “God, it’s such a complicated issue, I don’t really know enough to speak on it.” From a certain perspective, this might look like humility. What it feels like to me now, looking back, is a resistance to seeing the evidence that’s in front of me and applying my schema of values to it. What it feels like to me now is a desire to avoid engaging with what is really happening and a dependency on pre-written scripts.
This blog is weighed down by my own baggage. This is the part where I admit that I may be sensing something “in the culture” that is really just “in me.” I hope that’s the case! In fact, I’m positive there would be many people who read this and are like, “lol sounds hard, can’t relate.” At the same time, when I think about my tendency to totalize and oversimplify, it feels like this is bigger than a personal quirk. We are all subject to the knowledge that there is an infinite amount of information we could integrate into our understanding of things. We are all subject to a culture that increasingly expects (and polices for) perfection in our actions all the while demanding less and less accountability of those in power. Our ability to even tell the difference between an action and an ephemeral thing (a post, a like, a follow) seems to have eroded.
With today’s media landscape, with the endless scroll, with how we’re being force fed AI, and with an ongoing proliferation of identity-based politics, it can feel like the whole point of life is to understand everything and to act on that understanding without error. One of the big lessons of my Saturn Return, driven in large part by the loss of that friendship, has been that it is not, in fact, the point. Far more often, the point is to live well enough to know you are living well, whatever that means to you. It’s almost always easier not to act on the things we believe in. It’s easier if we can cover all our bases in the being told and the telling. But we have to remember: telling and being told does not make up a life, not really.
Sometimes we ought to act on not quite enough knowledge. I don’t really like it, but it’s true. Waiting until you know enough, until you can articulate exactly what is happening or what you believe or what you fear, will often take too long. Sometimes the consequences of taking too long are minor, but sometimes they are catastrophic. Sometimes taking too long is the difference between being able to correct course and having to simply plan for picking up the pieces after the disaster. And, unfortunately, waiting too long is one of those things that is hard to blame on anyone but yourself.
Did I manage to stick the landing? Did I connect the dots between: a generalized attitude toward knowledge and experience I see in Gen Z/the culture, my own personal experience with losing a relationship partially due to categorical thinking, and the implications of favoring “knowledge” over action when it comes to progressive movements? I’m not positive, but this is getting too long and I’m a couple days late sending!
If you’re still here, thank you. As I’ve repeated ad nauseam, this blog knocked me off track somewhat. Now that I’m wrapping it up, I realize that it doesn’t take an expert in the Enneagram, astrology, or psychology to see why. It’s not easy to reflect on times you feel you messed up, but I appreciate you being here to witness it with me. I’m excited to be moving back into my routine and back into your inboxes.
Until Sunday 🫡
Some things:
This poem, set at a cross street that’s about a mile from my house. God bless.
Brian Wilson passed away. I enjoyed this obituary. Listen to “God Only Knows” and think about how lovely it is to be alive at the same time as great artists.
For levity: an unhinged thread documenting the erratic days leading up to someone’s wedding. This couple has either found their perfect, insane match, or they’re a disaster happening in slow motion.
Always a lot of credit goes to the people who have been my teachers, both directly and through their freely shared knowledge, and so many books.
Of course, maybe I’m wrong! I wouldn’t have predicted a year before it happened that we’d be in this place now, so what do I know, really?
And I see now that I forgot to link the Brian Wilson obit! Here it is: https://pitchfork.com/news/the-beach-boys-brian-wilson-dies-at-82/