Going Undercover As a Man
An unintentional social experiment
For a time, I lived a double life—working undercover, where I experienced firsthand the stark contrast in how men treat those they perceive as male bosses versus female bosses. It was an unintentional social experiment, one that revealed more than I ever wanted to know about workplace misogyny, power dynamics, and the casual ways men turn professional spaces into hostile environments for women.
I don’t say that lightly. By age 24 I was embroiled in my first sexual harassment civil rights lawsuit, against the government. Several years later, I found myself straddling the line between genders. We all took great pains to conceal our identity, new staffers were required to create new personas, take on new pseudonyms, back in the very early days of remote work.
The Two Versions of Me
I was the no-nonsense, take-no-bullshit boss—respected, obeyed, even admired. Men spoke to me with deference, sought my approval, and aligned themselves with my authority. They accepted my strictness as leadership, my decisiveness as strength, my lack of small talk as focus. My approval was currency. Ironically, I served as the go-between between my two selves for some volunteers. People afraid to approach one version of me sought help from the other.
On the other side, I was myself—a female boss in the exact same sphere, yet suddenly my approach was met with criticism. The same men who respected my authority when they thought I was a man suddenly saw me as an outlet for their endearments, were patronizing, flirtatious. My decisiveness became ‘bossy,’ my strictness ‘bitchy.’ I was no longer a leader; I was a problem. One they complained to me about.
I want to be very clear that my boss was *not* included in this. He was widely regarded as too gruff, downright rude, hostile even. That young man had my back with a ferociousness that endeared him to me, I would give him a kidney even 20 years later. I take great pride in having had a hand in helping him & his now wife realize they were madly in love with each other. Emotions aren’t taboo. Workplace relationships happen. But I’m not talking about connection, I’m talking about the pervasive sexualization of women & all we do.
The Casual Sexism of the Workplace
The shift in treatment wasn’t just about authority—it was about how men perceive women in general. As a man, I was one of them. As a woman, I was a target.
Work Wife Syndrome – I cannot count the number of times I was called someone’s ‘work wife’ as though it were a compliment. Spoiler alert: it’s not. It’s a way to diminish women’s professional presence, to reduce them to a personal accessory rather than an equal.
Inappropriate Comments Disguised as Jokes – Men love to pretend that sexual innuendos, sugar daddy comments, and ‘harmless’ flirtation are just jokes. The reality? They create an unsafe environment where women are forced to smile through discomfort or risk being labeled ‘too sensitive.’ The mental calculus of how to respond is exhausting. Being pregnant & working is a job itself.
The Unwanted Advances – Drunken phone calls, ‘joking’ marriage proposals, outright admissions of infidelity framed as flirtation—men bring sex into professional and casual friendships in a way that women never can without consequence. And when we don’t respond the way they want? We’re suddenly cold, stuck up, or ‘leading them on.’ (one day we’ll do a whole piece on The Friends Zone & how it negates a woman’s value in your life as nothing more than a sex object, but today is not that day)
The Lies – Men told me to my face that they had never said the things they actually said to my (virtual) face. They lied, even knowing that our entire job was to preserve evidence, take screenshots, and document everything. They truly believed their word, as men, would override mine, as a woman. (Again, shout out to my boss for shutting those complaints down, with decisive aggression, he made it clear there was no higher authority than mine when it came to my department & deferred to me without hesitation)
The Enablers - The women who’d tell me to apologize, to smile more, to put up with the inappropriate behavior, the crossing of lines. These women weren’t limited to my work life. I ran up against the same enabling locally, told to humor a man whose behavior had crossed the line, repeatedly. Encouraged to ‘think big’ by another group he joined to stay in my life & expected to tolerate his behavior ‘for the greater good’. Told I was selfish to have boundaries. Progressive groups are not exempt from these behaviors & issues.
The Danger of Navigating Male Egos
Women never know which man will take rejection in stride and which one will turn dangerous. We never know if ignoring an inappropriate comment will be seen as silent consent. We walk a fine line between standing our ground and protecting ourselves from retaliation.
We are forced to tap dance around egos, to soften our edges, to laugh off what makes us uncomfortable. Meanwhile, toxic men at home blame us for the attention we never wanted, and society blames us for not preventing it. It’s the corporate version of ‘but what were you wearing?’
What Needs to Change
Men need to hold other men accountable. Women are exhausted from calling out sexism. If you see a coworker making someone uncomfortable, say something. Shut it down. Don’t laugh along.
Read that 1st one again.
Read. It. Again. Pretend they’re talking about your loved one, if you’re incapable of simply respecting all women. But work on that.
Stop forcing women to manage male emotions. We should not have to cushion, sugarcoat, or downplay our authority to be respected. Treat women in power the way you treat men in power—without entitlement to their time, patience, or personal space.
Believe women. If a woman says a male coworker is behaving inappropriately, believe her. The odds that she is lying are microscopic compared to the number of women who stay silent out of fear.
Final Thoughts
Being perceived as a man in the workplace wasn’t just an eye-opening experience—it was a damning indictment of how little has changed. The respect, camaraderie, and deference I received as a man should be the baseline for all professionals, regardless of gender.
Women shouldn’t have to navigate a minefield of sexualization, dismissal, and danger just to do their jobs. And until men start seeing us as equals—not as work wives, potential conquests, or emotional caretakers—nothing will change.
We deserve better. We always have.
Today’s Assignment: It’s a doozy. From the Oregon Bureau of Labor & Industries Final Orders: pages 4 through 47. Bookmark it, skim it, read it in full & you tell me if they made the right call in 1983. Was Ms Eunice Penny sexually discriminated against at the Salem, Oregon police dept? (spoiler: in this house, we call her Grandma Penny, my children’s Great Grandmother & absolute ICON - she fought the law & the law didn’t win)
~AK