On authentic relationships

Why write now?

Every time I make a post on social media, including here, I feel like a hypocrite. I couldn’t quite find a crisp answer for why, so here’s my attempt to articulate it.

I’ve spent the first chaotic weeks of 2025 trying to stitch together this post about why I find myself trying to write here. I have written privately for decades, scattered essays and journaling and random musings all over Pages and Notes and Evernote and emails and DMs and texts and some handwritten as well, but I’ve always been resistant to writing publicly. I’ve never wanted to create online content and spend more of my time at a screen. In fact, I started out trying to avoid making any digital content at all.

When I had the unexpected inspiration in 2018 to turn astrology into a job after decades of working closely with it, my plan was to be completely offline. My business cards read Jessica Josephine, private astrologer because I wanted to be unreachable if you didn’t know me or someone who did. No advertising, just word of mouth, little black book. I wanted and still want to serve people who didn’t think having a private, dedicated astrological advisor was indispensable… until they tried it. I sometimes talked about being “the Heidi Fleiss of astrology...” but that metaphor doesn’t land right with everyone. Maybe there’s only one of me, and no comparison will do.

Back then, I had a husband with a great job and I live in an area where residents employ personal advisors of all kinds, from Pilates teachers to decorators to therapists and executive coaches. I’m not too far from places where astrologers who started their practice in the 1970s still hang shingles at their brick-and-mortar offices. I thought I could slowly build a business while I didn’t have the pressure to fully support myself and my son.

I had recently left working at Instagram, where the user base was furiously doubling every six months or so, and more and more of our public life was migrating online. I believed that other people would soon grow tired of disappearing into their screens as I had. I thought, this may never work, but I can start little by little to connect with other people in a completely analog and handmade way, and see what comes out of it.

Excited to make a gorgeous art project out of my new idea, I worked with a talented brand designer who created beautiful paper materials for me, thick saturated envelopes and cards that have only seen a few mailings. I imagined my clients would work with me in my office, and I made a few house calls. For my retainer clients, I’d text them all the time, with thoughts and insights and examples right as I pieced them all together. I imagined the elegant gifts and unique artwork I could create for those who believed in committing to our relationship. I developed the idea of group readings like little parties, recognizing that a group of people who know each other well can help each one get more out of an astrology reading, and I got to test it. I also pictured private booths at events, and hosting little entertainment sessions alongside a larger party.

Then, the pandemic happened. Not only did our lives move even further online, my marriage suddenly ended and I had to return to full-time, overtime remote computer work. I swore it wasn’t the end of my dream, but it was a deferral. I conceded I had to have an online presence, so I put up a website as as elegant and handmade-looking as I could and made little starts at writing, social media, and video, little stabs at Canva, Fiverr, iMovie, and Capcut. I’m thrilled that a lot of the art projects I imagined for this business have already been put into practice (see testimonials), while some are still waiting for their début. But I resisted producing online content at a regular pace. When I started writing this, I had to tangle with the resistance again. Am I being authentic? Why am I writing online, if my goal is to create a completely offline, personal relationship with clients?

This is what I came up with. For almost three decades, I used astrology to dissect my own life and my friends’ lives, and I developed shared narratives over time that I still update. It was a way for me to tell a story that the people around me and I were acting in. I introduced ideas to the people who tolerated me being an astrology nerd, and went deep with the ones who were already into it. Others taught me their own language: tarot, plant medicine, or whatever magic spoke to them the most. I realized I had definitely been writing, but for a very specific medium: the long, intense, interruptible, usually asynchronous, emoji- and reaction-mediated text conversations that get built over years and years.

During the same years, I paid for my first readings with professional astrologers. Some of those relationships grew into teaching and mentorship, some into friendships, and some into trusted advisors for specific topics or problems. I noticed this happened with the ones whose public writing I really connected with, writing that led me to carry on a conversation in my head with them. An example is Eric Francis, who I have been reading online for almost twenty years. Another is the late Dawn Bodrogi, who taught me about secondary progressions using Donald Trump’s chart in the spring of 2016, and I’ll certainly never forget what she said to me about it. Another one is Michael Lutin, who left this plane in November last year, and with whom I have continued to have conversations in my head and in my dreams ever since. Another is Jaeden Roberts, whose book carried me through a few fire walks. Another is my friend and personal astrologer, DK Brainard.

So in order for you to have a conversation in your head with me, I have to be writing here. If you find yourself thinking about what I wrote later, integrating it, arguing with it, laughing at it, making mental notes about it, then you’ll know it’s interesting enough to keep having that conversation with me. That’s how we’ll develop a relationship. But it’s going to be a slow burn.

--JJ

Postscript: There is only a tiny handful of writers that I read every word they publish, and it’s usually because it’s medium- to low-volume. Some people I subscribe to generate absurd volumes of content, and even more content about how they strategize, optimize, and automate their production of content. And it’s not low quality-- it’s just literally too much to read every day. I can’t spend any more time staring at the phone screen, I rarely finish any of these long reads, and then I’m filled with FOMO, having bookmarked a bunch of great quality content that I know I desperately need to catch up on later. I just don’t have the aspiration to produce anything at that rate. I’m starting to believe that no reader enjoys this kind of content as much as the writer does. It really would be nice to spend most of my time writing about things I care about, but I tend to think these channels all end up as one-sided conversations even when they’re hosting interview guests. I’m brave enough to just leave this here as an open record of how I may end up a hypocrite in the future, if it turns out I do like shouting into the void.