We were in the last days of calling ourselves girlbosses and I was pretty sure I was starting to develop a porn addiction out of sheer boredom. With the company, with others, and with myself. We were entrepreneurs called to mission who preached the words of Traction and Rebecca Minkoff as though they were the stone-carved commandments of an ancient civilization whose exact coordinates—like our office decor—were someplace between Giza, Delhi, and Chiang Mai.

On my first day, I was sent our holy text, The Founder, Jen’s debut book that was due to launch the following week, whose contents I would later be quizzed on. The book-buy bestseller was written in the same winning roux of memoir, business, and self-help as the company itself and served, I was told, as a sales funnel designed to introduce people not only to Jen herself, but to the core frameworks of the business that promised to help you gain—sorry “crystallize”—personal brand clarity. In truth, it was a workbook gussied up with the prestige that comes with writing a book to garner credibility—that elusive status that defies the bounds of material reality in that it can, in fact, be created or destroyed.

Working there has since been described to me by a former coworker as, “a bunch of people who had never had a real job managing people who had also never had a real job.” This is true in most respects, but prior to this I had a real job managing communications for Planned Parenthood. I wasn’t the best at it. It was too much work for one person, I was too green to do a lot of it well, and if I’m being honest, it was just not something totally aligned with my aptitudes and a job like that didn’t need someone who only “mostly worked”. As Roe v. Wade was under threat, they needed an all-star while I was probably better equipped to hang the letters on the marquee. All the same, it was real and mattered. So by the time I got Jen’s book, I wielded my cynicism like a scalpel. This was a workplace no matter the fact that the conference rooms were named after crystals.

I didn’t make besties. I didn’t share socials. On more than one occasion, I even told myself, “I’m only paid to know them for 40 hours a week” which sounds mean put to word as, to be clear, no one was outright mean to me. In sentiment, though, I think this Daria-like mantra helped cocoon me from the aspects of working there that would go on to traumatize many of my coworkers.

See, there is a compact you make working for companies built on the tantric devotion to actualization and entrepreneurship. They promise that if you invest your whole self—mind, body, and soul—to the work, you will be fulfilled. In my case, it didn’t matter that the entire company revolved around one woman’s image. We were the future of women in business, a matriarchy, a tribe of women and select gay men battered by the patriarchal corporate world who had found one another and were building a new way forward towards a brighter day.

Early on, there weren’t many of us so the work itself—personal branding and social media management—was large and taxing. The grind of not only writing content, but being on client calls and discovery sessions and devising strategies led a lot of people—including myself—to various degrees of burnout. But for as many vapid, aspiring influencers or corporate heads we got, our branding—women-owned workhorses who got sh*t done—also attracted genuinely great people who I felt privileged to help. National journalists, non-profits, community leaders, and people who needed a reset. These were all people who just didn’t “get” branding, needed help, and somehow wound up in our orbit. Our discovery calls were less intake and more feature interviews or therapy calls where clients would eventually feel comfortable enough expressing some of their most intimate fears, dreams, and insecurities. When we presented brand identities, they’d cry. For the first time in their lives, they’d been truly heard. And we’d tell them all we did was hold up the mirror and thank them for showing up for themselves.

But the thing I realized after about six months of tears was that while I steeled myself against the idea of being our own sort of Swiss Family Robinson in a West Side loft, what I hadn’t hardened myself against was finding genuine satisfaction in what I was doing. We did business differently which I guess meant the hardship came with it. If not quite family, our clients could be quite close to it at times with some of my coworkers attending retirement parties, weddings, or other private affairs. I never personally went quite that far, but the work did demand I care. I had to in order to get the best content out of them. But I also couldn’t just care about it for content’s sake or it would rend my soul from my body. A classic Catch 22. Don’t care too much about work or you’ll lose yourself in it. However, if you don’t care too much, you’ll lose your sense of humanity. So despite my best efforts, I suppose in the battle for myself or my soul, I made the deal to spare my soul and wound up caring for many of my clients.

And then, as happens, they’d leave. Ongoing work wasn’t as magical as the brand identity, internal restructuring, or they could no longer justify spending $8,000 a month on 12 LinkedIn posts. I understood it. I mean, I’m still shocked that anyone could be convinced to care enough to justify that purchase (and not everyone we worked with was exceptionally wealthy, either).

It started wearing on me, though. The time spent getting to know someone, seeing them come to trust you, care about you. There’s an intimacy that comes with inhabiting someone’s voice. And then they’d leave. I don’t want to be overly maudlin and pretend like I was going through some kind of deranged breakup because it wasn’t that at all. It was more like I’d thawed and re-froze my cynicism; its shape stranger and a little uglier each time. I’d go into discovery calls less prepared because what did it matter? Social posts were written with less inspiration. I had realized that with enough practice, I could do my job well enough without needing to try very hard. I found myself less inclined to speak up about toxic aspects of the company because caring too much offered little in return. I could disconnect and protect my peace. Where you’d think that would have felt some kind of liberated, though, I was actually just starting to feel jaded and withdrawn because the nature of the work demanded that you could never truly disconnect if you were to do it well. At best, you could dissociate; at worst you could give in to the tidal wave of plasticized positivity.

I was so bored. Leadership was as well. The difference, though, was they could spin it into their next scalable narrative about how burnt out they had become from growing their six figure business, while I and others simply had to find other ways to keep on keeping on. Suddenly, the bundles of sage on every desk began to look more like funeral bouquets.

In that empty space of attention on calls I didn’t care about, I’d have tabs open to Instagram and X, refreshing almost every other minute in some cases. I’d begun looking expectantly for sexts from guys I’d started messaging online, and finding erotica writers in between. Basically, anything to fill my time and feel something. In all cases, the through line was dopamine. Lots and lots of dopamine, the pursuit of which was splitting my attention span to the point that at times waking life would feel more foreign to me than the feeds and DMs. I knew it was real, but it didn’t feel quite right anymore.

A lot of days, I would tell myself that I needed to do better and wouldn’t check Instagram that day. Sometimes I’d actually honor that. A few times it held for at least five days, but nothing else was as fast as these apps anymore. I still loved reading, but it was getting harder to find books that could capture my attention the same way. At one point, I—bafflingly—told myself I wanted to be a famous comedian because it seemed like a dopamine high that never ended. There’d always be a new notification if I was famous. Truly pathetic lows were reached in this clownish depression.

I told no one about any of this. I felt too ashamed of the fact that I’d become simpler, flatter. My passions, a little dimmer next to the glow of the screen. Maybe others noticed, maybe it was all in my head. I felt guilty that I couldn’t connect more with my empathy enough to care. I was awake to do my daily tasks: breakfast, work, gym, walk outside, read, and—branching all of these tasks—virtually prostrate myself into humiliating positions and admissions. It was almost monastic and the regimen of shame was right. My life was over. I wasn’t an artist. I was a marketer. Even killing myself wouldn’t be enough punishment for this transgression against myself. I had to build a prison befitting my personal lack, and owing to my exemplary executive function, I succeeded. Stupidly, I wished that I could have had substance issues which are extremely complex to treat in their own right, but also have clearer avenues to do so by. Resources are there. AA has pamphlets. My issue, my long recurring problem, was that I loved the rush of destroying my ego and unlike livers, egos are regenerative. I could always fuck it up again. They don’t make pamphlets for treating masochism, just really terrible anthem pop.

I considered attending sex addicts anonymous or improv classes, reasoning with myself that—aside from the overwhelming crowd overlap I’d heard about—these were probably the closest fits to address the problem of a broken ego addicted to the shatter of its grandeur. But it went nowhere. I had been in psychotherapy for a few years at this point, but I was beginning to think my therapist didn’t believe my problems were real when I saw his eyes glaze at the mention of the toll this job was taking on me and the desperation I had to make something of myself. Session after session for months on end, I’d go to his office above the gayest gym on the northside of Chicago and vent, deflect, and air my frustrations—even ones I made up to justify the cost of the session. If I was depressed at the time, it was so buried in the monotony of delusion that I don’t know if anyone, regardless of their degree, could sense it. I’ve always been very good at putting up subtle walls to avoid uncomfortable truths like an alcoholic who hides their liquor bottles from their spouse just so they don’t have to deal with the accusations again.

It only occurred to me later that in many ways, I had become subsumed by the business, unable or unwilling to look inward at the detachment I felt from my actual life so I staked poisoning every relationship I had to avoid doing so. In her 1996 lecture titled “God’s Language” Toni Morrison argued that in most spiritual and religious texts, Hell was more easily imagined and more vibrantly articulated than Heaven. Sitting in the “Zen Den”—a dim, circular room in the middle of the office with bean bag chairs and various books on Eastern and New Age philosophies—and staring at a statue of the goddess Isis obtained on a trip to the Egyptian pyramids to “tap the alien code at its source”, I wasn’t sure I would be fulfilled again, only high. Dread is the sort of maudlin emotion that is too theatrical for the vernacular of the social media age, yet it is both its wellspring and Lazarus pit. You suffer, you anguish, and because the solutions are transactional highs, you inevitably dip and seek it out again. You can meme it until it becomes numb, but then it finds you again.

Our business model operated in much the same way. The minted platitude around the office was, “Own Your Sh*t”, a variation on the phrase that light cannot exist without darkness. Yet even there, light is not the subject, darkness is. It’s the prevailing presence that draws your focus. Much like Morrison argued when she said that, “A non-exclusionary, un-bordered, come-one-come-all paradise, without dread, minus a nemesis, is no paradise at all”, we never defined what the light was, what it constituted, or what the ramifications of living in it were.

It wasn’t just toxically positive; we were living in a salvation, refugee narrative where we’d each washed ashore and found a sort of paradise in the walls of this leaky-roofed loft. It didn’t matter if everyone believed that narrative when they came in. Leadership believing was enough to enforce this cultural dictum which is the problem with most modern religious messaging—reinforcement rather than liberation.” And as in many faiths, Jen sold us the latter for the price of the former believing wholly and truly—I believe from demons of her own—that liberation of the self could never come without such a high cost.

Tim O’Reilly is a writer and sometimes comic living in Chicago. You can find more of their writing on their Substack, God's Lolita. IG: @t1m_0reilly Twitter/X: @TinyTimOReilly

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