Menstruating in Silicon Valley

Even with my perfect, made-to-order, massive-stroke-of-luck off-ramp, the tech world made extra sure that I knew exactly where I stood on the way out

Illustration by Stephanie Davidson, @asiwillit

I can’t say exactly when my leaving Silicon Valley began. There was no grand reckoning but a series of so many hairline fractures, barely perceptible, which were lengthened and widened incident by tiny incident. Early on, sometime around 2015, I was in the audience of a fireside chat about venture capital investment (oh god, not another one of those). This event took place on an upper floor of a downtown San Francisco high rise, dutifully appointed with the current tech aesthetic: an open floor plan, one brightly colored wall, a ping pong table, and a refrigerator stocked with the seltzer brand of the moment. The place smelled mildly of beer from the ever-full keg, and one could catch a whiff of mediterranean food from the catered employee lunch. The featured investor was from a venture fund called Homebrew, which consisted of two men who had left bigger funds, come up with a unique, value-add investment thesis, raised some tens of millions of dollars, and named themselves Managing Partners. This was a boom time, a golden age of early startup investment, when an influx of institutional investors wanted to get money into barely-existing-yet companies. Two-man funds like Homebrew were popping up like crocuses in spring, and the newly minted Managing Partners regularly sat on panels where us peon-trepreneurs could come to bask in their ideas and perspectives. 

The investor from Homebrew sat calf-over-thigh in an armchair at the front of the room. His head was clean shaven and shining in the fluorescent light, his posture calm and assured, his smile knowing, his crisp button-down fashionably paired with colorful sneakers. At this time, I hadn’t raised any venture capital successfully and was unsure if I ever would, despite the conventional wisdom that all one needed these days was an idea and five powerpoint slides and seed investors would be stuffing money into your account. My infant business, conversely, was balanced delicately on the threadbare faith of a couple underpaid employees and the alleged gumption of me and my cofounder, an asset I was also unsure we actually possessed. Therefore, I was really at this event to wait for the networking session after the talk, to try and meet the Managing Partner, to grasp at a little wedge in the sheer face of Silicon Valley and attempt to get a hold. 

There is one clip from that fireside chat that sticks with me, other than the investor’s rejection of my company at the end when I finally squeezed through the crowd to introduce myself, (“that’s not really within our focus area.”) At one point the moderator, faceless and gender-less in my recollection, asked the Managing Partner what his worst job was. The investor related that when he was in high school, he had a job that included cleaning bathrooms. Specifically, in the woman’s bathroom, he was responsible for emptying That Box. 

“You know the box that I’m talking about,” he scanned the room with that knowing smile and a disbelieving head nod, overhead light gleaming off his smooth skull.  

I felt a flicker of unease in my stomach. It was around that year, my twenty-seventh, that I started viscerally wanting a child. This was too early by the standards of my city. The average age of a first time mother in San Francisco is thirty-two, but by twenty-seven, I couldn’t look away from a baby on the street. At the time, both my partner and I were still playing out our parts on the stage of great career ambition, so I would brush off my deep biological urge with dismissive statements like, “my body is ready, but my mind is not.” 

Because I actively thought about childbearing, a lot, my period was a force to which I was gratefully subject. Each month it brought minor pains and sour moods and zits on my chin, but every time it came regularly, it was a tiny prayer answered, an egg ready to be fertilized. I had one friend who, coming off ten years of taking the pill, could not get a period (we realized only in our late twenties and early thirties, when the price had already been paid, the potential toll of ingesting synthetic hormones for ten or fifteen years, or the cost of hosting in your cervix for a decade a copper wire whose express purpose is to cause constant low-grade internal inflammation.) But I was lucky, despite my own years of hormones and copper implants, that my period was regular and appeared ready for me when I was ready. 

Sitting in the Homebrew panel at age twenty-seven considering the man on stage cleaning out That Box when he was a teenager, I felt that unease, but why exactly? A dose of shame about my role in filling those boxes, perhaps. How disgusting that I left a trail of bloody cotton behind me each month that someone else had to clean up. I would not choose to do that job either (though of course, I do it in my own home.)  Even more problematic, I now can see, was that this comment gave me a specific feeling that would become a hallmark of my time in the Valley: a feeling that I existed in an entirely different reality from the people around me, particularly people who were successful and rich and therefore, we assume, correct. My own reality is that every month, I reach into my vagina to insert tampons that collect blood, a byproduct of the process that enables human reproduction in women. I often, accidentally, get that blood on my hands during this process. Sometimes it leaks through my underwear and onto my sheets, or worse, onto a chair. Public bathrooms provide a convenient and discrete place for me to discard the sanitary products that enable to me stay out in public during the menstruation phase of my cycle each month. If That Box weren’t there, and some bathrooms do lack it, I would be stuck wrapping my tampons and pads in thick wads of toilet paper and stowing them in my jacket pocket or purse, hoping that the blood doesn’t soak through before I can find a trashcan to stealthily deposit the humiliating bundle (which, like many women, I have done). My impression, looking back, is that the man on stage would have liked to see this experience eliminated, or at least shunted back to the women or to the help, where it could be done secretly and out-of-sight so that no one like him would have to experience the discomfort of seeing it.

At the time though, sitting at the feet of the Managing Partner, I simply felt a nebulous ickiness. I wondered if the other women in the audience, dotted throughout the Homebrew fireside chat like diversity sprinkles, felt a similar current of something-not-quite-right. I might have said to myself then that the comment seemed a little inappropriate? Or maybe I’m just being oversensitive? Probably. Forget it Rachel, just let it go.

And I did dutifully let it go, very quickly indeed. I had a company to start, people to meet, money to raise. But it was a tiny wedge jammed into a tiny fracture between my world and the Valley. Here and there these wedges were lodged, levering back and forth, slowly, imperceptibly lengthening and widening the cracks. In this case, I had a bodily experience of monthly periods and felt that there could be nothing more sublime than holding a baby, those were my facts. The world around me, at the very least, ignored those experiences which were foundational to my internal life, and perhaps even disdained them a little.

***

Because I was in California and a city dweller, and a talker about ideas at dinner parties, and a sometimes-explorer of alternative medicine, I knew of an alternative lifestyle philosophy encouraging women to orient life activities and work around the menstrual cycle. Throughout the four phases of the menstrual cycle, hormonal changes cause varying levels of energy and shifting moods, and the idea is that rather than forcing ourselves to maintain a constant approach to life and work, women would do better to respect the early parts of the cycle as times of energy and optimism and respect the later phases of the cycle as times of introversion and rest. I both admired this idea as possessing a unique wisdom and dismissed as completely unrealistic in my own life. What was I going to do as a fledgeling entrepreneur, cancel meetings that fell during my luteal phase? Decline conference invitations because I was respecting my private biological cycle? No, as an entrepreneur one must hustle, as they say, all the time, not two weeks a month. ABC, man (Always Be Closing). I did not need to introspect about my period, I needed money and customers. 

My hustle peaked in the second and third years of my business when we were barely surviving, still dragging ourselves across the floor trying to achieve any kind of real liftoff. I would go to conferences alone, where I had the wonderful opportunity to meet forty or sixty thousand strangers. The people I needed to meet were mostly men, mostly in their forties, fifties and sixties, because this was the healthcare industry and, like most industries, that’s who runs it. I forced myself to strike up conversation in lines, to sit at tables with strangers and to generally do that awful “so what do you do” dance with as many people as possible in a day. I could not, obviously, share anything remotely like my real thoughts: So what do you do? I am passionate about growing my family, and I want a baby so badly that I regularly listen to parenting podcasts. I also run a healthcare technology company. 

In these circumstances, I was playing a role, pretending to be someone else, the difficulty of this heightened by my introversion and teenage-looking face, which made me feel like a tiny little insignificant dweeby nothing faker loser in any professional environment. (Yes, many have told me that looking young is a good problem to have. Yes, it is a good problem to have if your goal is to attract the attention of men who like young-looking women, or if your goal is to make other, older-looking women who are also steeped in our youth-obsessed culture envious of you. It is not a good problem to have as a female CEO in Silicon Valley trying to be taken seriously). Each interaction was weighed down with a deep feeling that I wasn’t the type of person who could be taken seriously, and this made me exhausted. A day at a conference left me drained of all energy, crawling into my stiff hotel sheets at eight in the evening, wracked with guilt about skipping the nighttime networking opportunities but unable to remain upright. 

Through one of these mammoth efforts I succeeded in meeting an executive whose company did something related to ours, I can’t remember what. He invited me out to dinner and I hoped to use the time to progress towards a business deal. The prospect of such a dinner struck in me a persistent nausea for many hours leading up to the event, but I would do what I had to do for the business. 

On this night, this man decided to give me some spontaneous sales coaching.

“You see,” he said, “if you are going to sell me something, you really have to convince me that I want it.” He had a little smirk going at the edges of his mouth, his salt and pepper beard twitching upward and his eyes fixed on mine. 

“Like, for example, if you were going to try and get me to leave my wife, you would really, really have to convince me.” 

That was the sales advice. I smiled lightly and nodded, because that was the best I could do at the time. Then, in short order, he told me that he and his wife had separated, and that he was fascinated by me. I believe I produced a soft retort that I had a boyfriend, and he chuckled that this fact was unimportant, and we both, somehow, lightly laughed it off—hah! Hah! I don’t remember the rest of the meal, just my relief as I declined a ride home and scurried down to a train platform, finally alone again.

There were many similar incidents, of course. There was the rich man who invited me to visit him for business purposes and then began rubbing my feet. The rich man who told me his wife had cancer as he stroked my lower back over my pencil skirt. The less unbelievable but more common run-of-the-mill after-work drinks that were laced with innuendo. Each of these inspired in me again that feeling of living in a different reality than the people who surrounded me, and who I relied on, like I was suddenly out of my body observing a phenomenon that must have been impossible. People don’t actually say these things, this often, in the real world, right? I would leave and review the facts: he had definitely been there, he had definitely been a rich man, definitely said those things. But there were no other witnesses, I couldn’t be sure. Maybe I misremembered? Misunderstood? Maybe I was being oversensitive? Maybe I was just PMSing? Each time I went home and recounted the events to my boyfriend and later husband, who invariably said some version of, “what the heck? I’m so sorry. I can’t believe these things actually happen.” Yes, for all we heard about and believed in the problem of sexism and sexual harassment in the workplace, these incidents were still shocking to both of us. 

Since many of the powerful and rich people I needed to know were men over forty, and since an alarming number of rich men over forty showed an interest in my business only to reveal later that the interest was in me, I began to feel a sick dread upon meeting any new one of these. Networking became not only difficult due to my introversion, but a minefield of potential creeps that I both wanted to avoid and had to engage with, because they were the people who mattered. There was no option to avoid them, let alone confront them, not if I wanted my business to succeed, and look, I wasn’t a failing type of person, I could endure, I was strong, I would prove it. I forged ahead. 

But something was shifting nonetheless, against my will, against my vigorous attempts to shut my eyes and ears tightly against it: the fractures between my reality and the reality of the Valley had widened and become visible to the naked eye. My dim awareness of something-terribly-wrong was slowly building, an inconvenient awareness, because it could not be resolved without herculean stand-taking, and potentially a complete disavowal of everything I had worked on for many years.

Now, out of that world, some years later, I find myself looking out the window dreaming up what might have made these men feel as uncomfortable and confused as I felt in those many moments. Suppose I invited Mister Sales Coach out to dinner and began with an overview of the menstrual cycle and my current position within it. I have some advice for you, I would say, I am in my low-energy luteal phase right now, so that means it is best for you to speak softly around me and not talk too much. I would prefer to reflect on the past versus looking forward, and the topics that most interest me are children and families. Got it? I am certain he would never meet with me again. On the contrary, I kept going back and back and back, like a masochist, or an addict, or like someone with something enormous to prove.

***

I had to get out. I would quit. I decided to quit. I decided to quit so many times in years four and five as my mental and physical health gave out and my body threw up flag after flag, followed by desperate pleas, followed by code red alarms. I had diarrhea for two years straight, and bursts of wild dread-fueled anger on Sundays, and four months when almost every evening I would come home and break out in itchy hives up and down my legs. The stress caused panic attacks and worsening of my lifelong OCD, each of these phrases a whole world of suffering. Finally, I set an end date with my co-founder—I was too miserable, I couldn’t do this anymore. 

But the date came and went and I didn’t leave. I am still sorting through why I stayed, how I could possibly have stayed, even when it was that bad, and you will see me consider it many ways here in this newsletter over time. I am fascinated by the question of how one can be both so privileged and so miserable. I was so damn lucky to have the opportunity to start a company in Silicon Valley at all—because my parents were upper middle class, because I am able-bodied and white, because I was trained at private schools in how to engage with rich people—and yet I was so miserable I was killing myself, quite literally, I believe now, moving myself closer to death. What? How? That makes no sense. 

To put it simply, (and this is the subject of a lifelong inquiry, which I will treat here with one paragraph), the way I understand that seemingly insane decision to keep going despite everything is this: I had a subconscious sense that the scenario where I failed at my startup would somehow be even more painful than the current scenario of running the startup in a state of total misery. Because, stupidly, accidentally, predictably, I had come to equate myself with my work, so leaving meant inviting in an awful, empty, dark void where there was once self-worth. Leave and I would be faced with the overwhelming project of actually considering what makes a person’s life worthwhile. And the terrifying prospect that perhaps my own life was not.

***

Five years in, an acquirer magically came along, miraculously looking to buy a company doing exactly what we did. By god, I was going to take the deal. Look, I’ve only ever whispered this to my closest confidents because it is not cool or well-respected to be desperate to sell your company in the Valley, it is a bad negotiating position, to say the least. But come hell or high water, I was going to take that damn deal. As I negotiated the sale of my company, I met dutifully with my investors to build support for the acquisition and gather advice. In one of these meetings, I sat in a bright office across a table from yet another rich man, and he told me earnestly that if the sale of a company nets a person three to six million dollars (in other words, if you suddenly have between three and six million dollars in cash, after taxes, in your bank account, let’s say tomorrow), in his words, “nothing really happens.” 

“Three to six?” He said casually, “you get a million dollar downpayment on a house, your kids college is paid for, you get a start on retirement savings, and that’s it, nothing really happens.” He told me of the evidence: founders that he has known have sold their companies and gotten this amount of money in their bank accounts, and they think, “wow, this is amazing!” Then they wake up a year later and they realize, as he put it, that nothing in their life has really changed.  

The framework continued. Six to twelve million dollars in cash in the bank, the investor said, and you start to gain some work flexibility. You never have to work a job you don’t like again, you can always quit and take a year off. But you’ll still have to work. 

Twelve to twenty-five million dollars in the bank, he continued, and you never have to work again. You’re still living on a budget, but you don’t have to work. 

With twenty-five to fifty million dollars, you can start doing extravagant things: yachts, villas, jets. “Just to rent, not to buy.” 

There were more tiers, fifty to a hundred, a hundred to a hundred fifty, (million dollars that is,) but I was lost in the previous claims, trying to swim once again out of an experience that was drifting quickly away from what I thought to be—what I knew to be?—reality.

“See,” he concluded, “you have got to decide what you want all that work to buy you. Once you know what you want to buy with all the hard work you have put in, then you can decide what you are willing to sell for.”

I said he told me this earnestly, which may seem overly charitable because it implies a pure intention and maybe a measure of naiveté. But actually, I think in the end it was indeed earnestness. He was genuinely trying to help me, I believe that. And I think, and one almost can’t believe it in our America, even really rich men can be naive.

It’s difficult to know the best place to enter the terrain of his comments, but I’ll try and stay within the bounds of this topic we’re exploring here: how my womanhood opened a chasm between me and Silicon Valley in so many subtle ways. I won’t dwell on the fact, for example, that the average American has less than five thousand dollars in savings, and that during the COVID pandemic one third of Americans say they or someone in their family used up all or most of their savings. Ok, never mind, I will dwell on it, it’s worth dwelling on. Just speaking for myself, I would say that the “nothing” listed by this man—kids’ college paid for, retirement savings started, a million dollar downpayment on a house—sounds pretty goddamn life-altering, and to sit across the table from someone who thinks otherwise is yet another kind of cracking of reality. I also would take issue with, among so many other things, the notion that with twenty-five million dollars in the bank, one would still be “living on a budget.” My reality, an extremely privileged reality, was that thirty thousand dollars would cover the cost of conceiving my first child, which had to be done through three rounds of IVF, and which was the thing I wanted most in the world, something I would have traded everything else for. Thirty thousand dollars for my baby is both an outrageous sum of money and a small fraction of this man’s nothing amount. I may have even paid some amount of money to never again have to attend a networking event with the goal of impressing prowling sixty-year-olds (but impressing them only with my mind, not my body; being smart and attention-grabbing and interesting, but not sexually appealing or “fascinating” in that other way—you know, that old task). And my goodness sir, in your world is there such a thing as enough?

I am proud to say here, reader, that when the investor’s framework had been fully presented, I said to the him, bravely, “the first tier sounds pretty good to me.” That this is a brave thing to say to a rich man, that this was one of the first times I ever disagreed with that other world verbally and to a man’s face, (can you even call this “disagreement?”), that the confidence to say such a thing took so long to build in me, is stunning. I didn’t say, “and it seems to me your framework is misguided,” or more to the point, “what the fuck man, your framework is delusional, this meeting is over,” and I hope that someday I have the courage to do so.

***

Not all women would feel this way, of course, and the only woman I’m talking about here is me. I feel like I had the luck of lottery winner to have landed on a neat off-ramp from the Valley, the acquisition of my startup, and I therefore I was never required to make the much more difficult decision to close up shop and pack my bags out of there, head hung low and labeling myself a Failure. (Interestingly, even having sold my company, I still feel deeply like a failure, and prefer not to think or talk about my startup. Sometimes when I accidentally conjure a scene from the time when I was running my company, the nerves in my gut all flutter at once giving me a little bump of nausea. This suggests that feeling like a failure has very little to do with the outcome of the startup and much more to do with the workings of my own mind.) I never had the courage to leave, and I persisted in that world despite the obvious signs of delusion and foolishness and the shades of evil, and it so happened that the place didn’t fully break me before I found my exit. 

But trust you me, even with my perfect, made-to-order, massive-stroke-of-luck off-ramp, the tech world made extra sure that I knew exactly where I stood on the way out. My only female investor, feeling that I didn’t negotiate the acquisition aggressively enough and should have gotten twice the money I did, in the final weeks of my business, told me that I was the reason there is a gender pay gap, because women like me don’t push harder for what we deserve. 

Women like me? Who start a company in Silicon Valley? The reason for the gender pay gap? Yet another alleged truth, coming from a rich (and therefore, we assume, correct?) person, put forth with such unwavering conviction, yet again in a room with no other witness to validate my disbelief, yet again a truth that seemed to me so cosmically misguided that either they or I truly must be going insane.

And so we come to our point, these “women like me,” highly educated, privileged and ambitious women who trained our whole lives for this very type of success, and how we (not all of us, not even most; an unquantifiable number, but I am certain many,) silently exit the Valley and places like it. We leave as the fractures between our world and that world become cracks, and the cracks become canyons. My exit was not, in fact, a matter of choosing casually to be done after a moderately successful run, but at some point sooner or later needing to get out for the sake of remaining a sane person living on solid ground. Let me pause here to say that I am not asking to be congratulated for leaving the Valley when I did, after I had reaped its rewards, it was not at all heroic. I have a yet unresolved relationship with the money that I got from that world. As culture critic Jia Tolentino put it, scathingly, beautifully: “It is not brave, strictly speaking, for a woman to do the things that will make her rich and famous.” I was telling a comedian friend of mine how ashamed I am of that money, and he said, Rachel, you pulled off a heist. You got out with the loot. I liked that. It is notable that I prefer to think of myself as a thief over thinking of myself as what I was, a willing collaborator in and benefactor of a world I find mostly despicable. 

Though I lacked the conviction and courage to leave earlier, I know this to be true: existing across two such different realities can only be managed for so long before one must choose which reality resides deep in her wise gut, where she will be able to live out a fulfilled life, and which reality is in fact a major, ongoing, endless exercise in low-level real-world gaslighting. So, I agree with my one female investor in one way. There may be an aspect of my actions that contributes to the gender pay gap in the particular type of elite job that I occupied, where we even have a choice at all. In so many cases “women like me” end up needing to choose in which reality to reside, and some number of us do not choose the one where business meetings always might end with a sexual proposition, and people believe six million dollars to be a small sum. But I would insist, obviously, that the root cause of the problem is not the woman’s decision to trust her get the fuck out instinct, but the nature of the alternate reality she is escaping.

Let me put this here on the page while I have the courage, so that I don’t forget it: I am more certain than ever that I was the one with the clearer eyes in all those surreal moments. It wasn’t some superior genius that kept me with one foot on the real earth, but a part of me I would generally call my womanhood: the baby-wanting, soft-spoken, objectified, menstruating, sensitive, cyclical part of me that forced certain priorities and intuited a concept of enough. This womanhood overrode some other, also very strong, impulse to continue believing in and seeking the Silicon Valley version of success. And well, I daresay, that was a great gift. 

I’m curious…

Have you existed across two different realities? How did you manage it, are you still managing it?

Have you ever “won” at something but still felt like a failure?

Tell me in the comments.

**Quick head’s up: I am now officially on maternity leave! During this time, my wonderful consultant/collaborator

Erin Shetron

will be doing some light moderation, so look for her name and please keep supporting each other in the comment sections. After nearly a year of working with Erin to define and shape this newsletter, I am confident that she will bring only the best Inner Workings vibes to the conversation.

While I’m offline, I’ll be sharing updated favorites from my archives as well as some new work that I’ve been saving up, covering topics from feeling meek at the doctor, being a CEO in Silicon Valley, gardening, forest bathing, trying to control our bodies and so much more! These include some of my favorite long-form essays, which were developed over many months, as well as shorter essays like the ones I typically send weekly. I would love to hear what you think, I am hopeful they’ll be a salve in the slow winter months.

And special gratitude (again) to all you subscribers who are choosing to stick with me through this leave. You make this whole thing work and lay the foundation for what’s to come at Inner Workings and beyond. I am sending you so much love.

XO, Rachel.