Source: I Was The Office Sub Publisher: Cartoons Hate Her | Author: Cartoons Hate Her Published: January 26, 2026 | Archived: March 21, 2026

sorry for another secretary reference i apologize im so sorry

When I was twenty-three, I was working my second-ever full time job as an account manager at a failing mobile app advertisement startup in San Francisco. My boss, Vince, was a notoriously difficult fifty-five-year-old CRO. Multiple employees had quit specifically because of him and his peculiarities. I stayed around—not because I liked him, but because I was afraid nobody else would hire me. Remember, it was 2012. I know the zoomers believe the 2010s were a golden age for the economy, but college grads were literally fighting over jobs that didn’t have salaries.

Vince did not look like your typical tech C-level executive. He was a hustler of the ‘90s, with no college degree, who built his career selling floppy disks out of his van. He was desperate to get in this big “technology thing.” He didn’t know how to use Gmail or Powerpoint. But beyond all the external quirks, he was the biggest control freak I might ever meet in my life. I noticed it early on in my tenure at that company, when a client requested an insertion order contract. I sent it over, thinking nothing of it, because I had done it before. In fact, I felt pretty good about myself, this big Boss Lady with the IO—look at me! I was just like Angelica’s mom in Rugrats. But when Vince found out, he was irate. Apparently I needed his approval for all IOs. He didn’t scream at me, but he came close. I remember standing by his desk while he sat and shook his head, staring at my disgrace of an unauthorized IO. I was terrified I was about to be fired, just a few weeks into my job.

“You will never send another one like this until I tell you to,” he finally said, softly but furiously, on the brink of losing it.

“Fair enough,” I said.

“No.”

“What?”

“You don’t say ‘fair enough.’ Fair enough implies that you have control over the situation. It implies that you’re agreeing to what I’m telling you. I didn’t ask for your opinion. It’s not your choice to agree. You don’t say ‘fair enough.’ You say ‘yes.’”

Now, I should point out that Vince was much older than I am, not good looking, and I was not single. I realize now that had these conditions been met, I probably would have just…I don’t know, gotten horny? But I wasn’t thinking about sex anyway. I was thinking about work—more specifically “not getting fired.” And I realized that if I wanted to stay calm in the workplace, I needed something very specific: a person with authority telling me exactly what to do.

Over my time with Vince, I had more and more control taken away from me—not in a way that was abusive or illegal (I was free to leave at any time, and I didn’t want to) but in a way that made it very difficult to ever manifest confidence or independence.

For example, we “weren’t allowed” to email clients who came from countries that Vince didn’t like. He had a firm anti-Israel rule, not because of any moral or activist beliefs about Israel, but from a history of Israeli companies being difficult to work with (this was actually extremely well-founded, as far as the mobile app industry went.) There were other clients who were blacklisted due to old personal beefs, such as an extremely annoying Australian guy named Ollie who was later blacklisted again at a completely different company for threatening to fly to San Francisco and show up at our office unannounced after a billing dispute. When I had a hard time remembering all of Vince’s rules and nemeses, he declared he had to approve every single prospect I emailed. He upped the ante and decided that any external email at all, even one in an existing thread, had to be approved before it could be sent out.

By the time I had been working there for a year, everything I did had to be run by Vince. It almost felt that there was no point in me even working there because he controlled every email I sent, every contract I finished, every prospect I called. Even after giving his approval, he demanded to be CCed on every single email I sent. Sometimes he would stand behind me and just dictate an email that he could have sent himself. He even controlled the punctuation I use (he banned periods at the ends of paragraphs.) He would complain about how busy he was, but he could have saved a lot of time by just letting me do my work. To make matters more frustrating, while Vince was the bottleneck for all of my work that needed his approval, he would mosey around the office and peek behind my shoulder to admonish me for doing “non-work related things”…while I waited for him to approve the stuff I needed to be doing.

By the time I left, I was thrilled to part ways with Vince. Nothing he did was lawsuit-worthy, but he was, as you can imagine, very fucking annoying. But he left an impression on me that lasted basically my entire career: I could not do anything on my own. The idea of “autonomy” was terrifying. I needed someone to tell me what to do and take the terrifying risk of being responsible for a mistake out of my hands.

At future companies, I worked for bosses who were nothing like Vince. Some were good, some were bad, but none were hell-bent on monitoring my every move or insisting permission be obtained before I did anything. In fact, every single company that interviewed me prided itself on giving employees a great deal of autonomy. They mentioned “autonomy” along with perks like unlimited PTO, like it was supposed to be something exciting and rare. In hindsight, these bosses wanted employees who never needed direction, but also miraculously did everything right. I was not their person.

I’m sure a lot of people took the autonomy thing and ran with it. But as I became more senior in my career, it became more and more terrifying. Other employees would run wild and come up with product ideas, and every single time I would say, “Wait, we’re allowed to do that? Who let them do that? They didn’t even ask permission!”

It didn’t help that the few times I went rogue and did things without approval, even at companies that repeatedly valorized statements like “Better to beg for forgiveness than ask for permission,” I got in trouble. For example, at one company that explicitly venerated risk-taking in its company mission, I took the initiative to create a meme-based pitch deck that used pop culture references. Not wanting to be a complete maverick, I checked with our legal team, who approved it. The client absolutely loved it, and so did my peers, but my manager pulled me into a room and yelled at me in a frenzied panic because he was convinced the entire company would be sued for IP violation and we would “wind up on the front page of The New York Times.” HR got involved. It was bad.

I would schedule meetings without having someone else double-check, and something would go wrong—the room wouldn’t be properly booked, the calendar invite wouldn’t show up for everyone, I wouldn’t put in the right time zone. Once I was admonished for scheduling a client meeting in a room without enough chairs, necessitating one (1) chair be moved from a different conference room, which is apparently the corporate equivalent of a grease fire on a highway, and came up in my performance review. I felt chronically incompetent and childish. I even got nervous sending out basic calendar invites with links to conference calls, afraid I had sent the wrong link, hadn’t sent a link at all, or blacked out and wrote a racial slur in place of a link. I worked at one very small startup where the office manager doubled as everything remotely administrative, and after being disciplined for a typo in a contract, I got into the habit of sending her all of my contracts ahead of time so she could double-check them. I also got in trouble for that, because it wasn’t her job. But what was I supposed to do—just do my own work? We had already established I was terrible at that!

Frequently, if a client asked me a question about our products, I would tell them I needed to double check with my manager, just to be 100% sure that I wasn’t wrong. When these calls were shadowed, my manager pushed me to just answer these questions on my own, because I likely knew the answer and didn’t need to be 100% sure every single time. He told me that I was projecting a lack of confidence, which would make the client unconfident in our products. I took his advice, and during a very limited and brand new beta launch, confidently answered a very niche question based on what little information I had. I turned out to be wrong. I was disciplined and dinged on my performance review for this mistake. Never again.

These managers wanted autonomy only as it existed without the risk of mistakes. To my knowledge, this doesn’t exist. Although other employees managed to pull it off, so it was probably my fault. Either way, this was not a good framework for me at all. It was somehow more anxiety-provoking and frustrating than just being micromanaged.

I got good feedback sometimes, but it always echoed the same basic sentiment: when she is told what to do, she does it extremely well. I never missed deadlines. I never dropped the ball on projects. When I was given a clear assignment, I often did it perfectly. Whenever we had a clear, quantitative goal, I always hit it. Frequently, I exceeded expectations if I was given explicit instructions (explicit in this sense meaning “complete 100 client calls a quarter” not “get on your knees” although really, what’s the difference?) I simply couldn’t direct myself.

Unbeknownst to me, I was becoming the office sub, and nobody liked it. I wanted someone to take away this anxiety, to take away control, to take away accountability. To tell me what to do. But last I checked, asking your boss to be your dom was an HR violation.

With the exception of Vince, none of my bosses had much interest in actually bossing me around. Almost all of them told me they wanted me to be a self-starter. But I couldn’t help but feel that every time I attempted to self-start, everything went wrong. I was told repeatedly that there were “no stupid questions,” and yet, I was admonished after meetings for asking things I shouldn’t have asked. I was told that “we love to hear ideas,” but every idea I had was rejected.

As I’ve mentioned many times before, I was fired. A lot. And while it was never for gross misconduct or breeches of ethics, my inability to work autonomously came up time and time again. The manager firing me would also concede that my performance was excellent when I was being micromanaged. I kept thinking to myself, don’t you want a subordinate? Don’t you want obedience? But I had taken it too far. I needed so much direction, so much permission, so much approval, that I was unable to do anything at all.

When I eventually stumbled into a director-level role (which I wrote about here) I felt completely over my head. My boss, again, had told me how strongly he valued autonomy. He didn’t even work in the same location as I did, and barely spoke to me. I often just had no work to do at all. Perhaps he was hoping I would just create work for myself, but with zero direction I didn’t know what that would even be. One time, I randomly designed a bunch of new icons for our press kit, even though nobody asked me to, just to justify my existence. Sometimes, in the most professional way I could, I would ask him to please…tell me what to do. He declined, saying that his goal was to empower me to write my own path. Cool, bro, now really, tell me what to do.

I managed to stick around at that company for an insanely long amount of time, not by becoming autonomous in my actual work, but by putting my “autonomy” into things I knew I couldn’t screw up, like organizing people’s birthday parties and charitable donations. When it came to dealing with clients or vendors, I froze. I deferred to more experienced people on the calls. I filled the silent spaces by verbosely agreeing with other people who seemed smart. Sometimes, some well-meaning man would comment that nobody had given me a chance to speak and defer to me in order to be a “good ally,” and all I wanted to say was, fuck you! I was hiding on purpose! Be a feminist ally and talk over me!

When I think about my long track record of getting fired, some of it probably has to do with my inability (or refusal) to travel because of my anxiety, or the fact that I made so many small mistakes. But I think those issues may have been survivable if I had felt comfortable making my own decisions, or if I projected an air of confidence literally ever. I still can’t wrap my head around how badly my own decisions went on the occasion that I chose to ignore the nagging voice in my head about needing approval and permission. Maybe I was just never destined for corporate. Maybe I’m literally really stupid. But none of this was because I was rogue and insubordinate. I was too compliant, too obedient, to the point that I was unable to function without someone making all my decisions for me and ordering me around.

In case you’re wondering, none of this turned me on at all. I don’t know if that would have been different if I had been single and attracted to any of my bosses, although obviously everyone except Vince was far too hands-off for my proclivities. Perhaps in a different timeline in a different dimension, I was a bombshell of a scandalous workplace lawsuit. There is a reason it eventually turned me on when my husband got promoted to the exact role that would theoretically manage me, albeit at a different company. But at the time, I didn’t see any of this as part of my sexuality. Generally, I wasn’t aroused, I wasn’t thinking about sex, I was thinking about losing my health insurance.

And while we are on the topic of sex, I’m sure someone reading this will be like “Akshually I’m part of the kink community and this is called being a maladapted child, NOT a sub, you DON’T know what you’re talking about, a REAL sub doesn’t feel this way, we actually feel EMPOWERED” and to you I say, you cannot just invalidate my lived experience and kinkshame me!!!

But now that I’m out of the corporate workplace, I’ve had a chance to reflect on the first decade of my career and all the reasons that it was such a dumpster fire compared even to your average under-performer. And the only thing that I can conclude is that whatever personality defect I have which makes me incapable of expressing sexual desire without permission—the same thing that makes me allergic to making any sexual requests of my husband, let alone “taking charge” during sex—must be the same thing that prevented me from making any sort of workplace decision.

I also don’t think this tendency began with Vince. My mother has told me that when I was little—three, maybe four—she took me to an Easter egg hunt where a big sack of candy-filled eggs was emptied onto a yard. The other children immediately ran for the eggs, but I kept looking back, as if waiting for my mom to tell me it was okay. Even after she encouraged me, I avoided the hotspots where the other kids were rushing for eggs, and went after eggs on the perimeter of the hunt where the other kids weren’t searching. Ultimately, I left the hunt with the fewest eggs. She joked that she had the “irrational” thought that I would grow up incapable of asserting myself in the workplace. But as it turns out, she wasn’t wrong. I was probably just born like this.

Sometimes, I assume everyone is like me, and then I’m confronted with the reality that I’m actually just kind of weird. I was with a mom friend the other day when I received a text from my husband, requesting duck for dinner and then instructing me the exact time to put the duck in the oven, and when to turn the heat down and up. “Why is he texting you this?” she asked. “My husband would never text me that.”

“I kind of…want him to?”

“That’s not annoying? I would kill my husband if he texted me that.”

“How else would I be sure that I’m roasting the duck correctly?”

Sometimes, I wonder if this is all just a symptom of my OCD. While some people with OCD might become control freaks, what if others need to be controlled? Would I have needed so much direction at work if I wasn’t pathologically afraid of making mistakes? Would I have still liked the duck-roasting texts if I was confident I could roast a duck without any direction?

But this tendency persists even in arenas where I’m fairly confident, and in situations where I have no reason to fear failure. When I examined my sexuality and uncovered that I really don’t like initiating sex, it was in a relationship (my marriage) where I had absolutely zero reason to believe that expressions of sexuality would be rebuffed or rejected. In fact, I was 100% confident that if I initiated sex with my husband, he’d say yes. And yet, the entire concept made me uncomfortable and embarrassed. Perhaps it’s all about my OCD in another way—with so much anxiety constantly buzzing around my brain, the more decisions that can be made for me will keep me calmer, and therefore more likely to enjoy myself. Yes, even if those decisions weren’t the exact ones I’d have made myself.

Obviously, this tendency royally screwed me in the corporate workplace. But now I’m on Substack, where hundreds if not thousands of people give me unsolicited feedback and tell me exactly what to do every single day—often while clearly agitated. My friends have joked that thousands of people are paying to verbally abuse me. Maybe, in a weird way, being the office sub became a superpower that enabled me to deal with thousands of imperious subscriber demands and complaints every single day. I’m just hoping none of you expect me to book a conference call—I can’t make any promises about the amount of chairs.