Amy Writes Words
Amy Writes Words
How to Talk To Me About Amy Wears Boots: A Primer, for Men

How to Talk To Me About Amy Wears Boots: A Primer, for Men

Amy Writes Words #23

Hi again it’s me, Amy, with a weekly newsletter slash podcast about tech, management, gender, mental illness, and sometimes fashion. This week, what do you do about a problem like Amy Wears Boots, a primer just for men.

But first, if you’re reading this on the internet why not subscribe, and if you’re subscribed already why not upgrade to a paying subscription because that’s how you show you love and appreciate all the work I put into this?

Okay, let’s move on to our topic for the day.

Sometimes men are confused about how to interact with me around my Amy Wears Boots project. I just hit 5,000 followers on Instagram and am building a mailing list with plans to start a membership site that will generate income for the project, so this problem is not going to go away.

Actually, when I say that men are confused I mean that most men are not confused, but that they sometimes express confusion about why I get angry about men who theoretically could be confused.

I bring this up now because I recently received an email from a recruiter about, ostensibly, career opportunities for me as an engineering leader. 

It started like so: “Hey Amy - I've just thoroughly enjoyed the last 20 mins taking in some of your internet presence. I confess @amywearsboots took up the largest slice of that time.”

I complained about this email to a friend of mine and he was confused.1 Maybe that guy is just confused, he said. Because, well, you are putting it out there. My friend didn’t mean “you were asking for it.” He really meant “might it not be genuinely confusing?”

No, it really shouldn’t be.

So okay, let’s get this part straight. Yeah, I post my body on the internet. I’m damn proud of my body and I’m damn proud of the work I put into that project. I’ve explained elsewhere how much I’ve learned from it and how hard I have had to work, and you might think it’s all just thirst trap but if you look into it even the tiniest bit you can see it’s actually a long-running art project through which I explore some really difficult themes: about aging, about gender, about sexuality, about power, about mental illness, about love, and about trauma. Not that this should matter, because people are entitled to share their bodies with the world. Aside from the artistic goals of the project, I like to bring joy to the world, and guess what, humans like to look at pictures of people being beautiful.

The fact that I am beautiful on the internet has nothing to do with whether it’s appropriate to hit on me in a recruiting email.


My friend who thought maybe other men are confused is a good person. I love him. But the men who are problems for me are hardly ever confused. They actually know perfectly well what they’re doing and they hide behind confusion to dodge responsibility. Because other men haven’t experienced the differences between genuine mutual interest (complexity), a one-sided interest that nevertheless respects boundaries, and harassment, they are easily convinced to buy into this confusion defense.

The other thing going on is that most men cannot read creep signals the way that women can. 

To give a very basic example, Max and I were watching an episode of The Wire recently and at one point I said “ugh, that guy’s about to creep on her” and Max was like “really?” and then the guy creeped on her and I was like “didn’t you see how he was standing?” 

But he didn’t see how the guy was standing because he hasn’t spent his whole life being creeped on and observing other women be creeped on and getting extremely good at reading that data.

And hey, I get it. Max is as feminist as they come but the mind does not get good at detecting patterns that are not very important to it, like when a man is standing too close to a woman in a way that is ever so slightly menacing. 

I understand that it’s hard for well-meaning men to see. If it had been necessary to their survival and bodily integrity to see things they would see them. And they could learn to see them if they chose to devote their attention to it, but if that’s too much work they could also just, I dunno, believe that women see stuff they don’t and it’s not because we’re imagining things. 

Like, would you tell a mushroom forager that there aren’t any hen-of-the-woods in that forest because you went for a stroll there and you didn’t see them? What the fuck are they selling you then?

Either learn to find mushrooms or believe the people who tell you they are there, and for god’s sake don’t tell them there aren’t any mushrooms when they are holding a mushroom in their hand and explaining to you exactly why it is a mushroom. 


Because men don’t generally see what women see they are easily bamboozled by other men into believing those other men are simply confused.

Meanwhile we’re not living in a Jane Austen novel, where people are constantly almost just realizing they are in love with each other but then accidentally getting engaged to the wrong person instead. Misunderstandings and confusion do happen but they’re rare and obvious cases, and the rest of the time what you have is a combination of deliberate ignorance, knowing a thing is bad but doing it anyway because you have poor impulse control, and actual malice. All of it hiding behind “that’s not what I meant,” “I didn’t mean to,” and “wow, paranoid much?”


Let’s go back to this recruiter. Every woman I’ve shown that email to agrees with me that it’s grossly inappropriate. 

“But, Amy, you do put that content out there.” 

Yes, that is true. But context matters. If you are emailing me about career opportunities as an engineering leader and you’ve spent any time at all checking out my internet presence then you have about 5 million things that you could lead with that are germane to engineering leadership. If you instead tell me how you just spent 20 minutes “thoroughly” enjoying my Instagram, well, that is a choice. It’s a choice to focus on an aspect of my life that is not relevant to the topic of the email. 

Even so, there are ways he could have pulled it off. “I love your sense of style,” he might have said. “You take incredible photographs”. “I have some job opportunities in fashion tech that could be up your alley.” 

He didn’t do any of those things. It’s not an accident.


Anyways just to eliminate the confusion defense (haha, this won’t really eliminate it, because the harassers weren’t confused in the first place, but let’s pretend), here are some guidelines about things you can say to me about Amy Wears Boots and under what conditions you can say them. Don’t @ me.


Nothing at all. Nothing is always a great thing to say about Amy Wears Boots, especially if you do not know me. If you do not know me and you are also approaching me about a job opportunity that is related to my work as an engineering leader and not related to anything to do with Instagram, fashion, photography, social marketing, or the Creator economy, nothing at all is the very safest thing for you to say.


If you don’t know me, but you’re approaching me about an engineering opportunity where Amy Wears Boots is relevant, such as a fashion, marketing, photography, or a Creator economy business, you can say something like “among many reasons I thought you might be a good fit for this job is that it’s clear from your Amy Wears Boots project that x is of interest to you”.


If you don’t know me and are approaching me about work as an engineer and there is no connection to the job opportunity itself it is still probably fine for you to say any of the following about Amy Wears Boots:

  • “You have a great sense of style!”

  • “You take amazing photographs!”

  • “I love your boot collection! I collect (sneakers|beanie babies|pokémon|bowties)”

  • “You have so much creative energy!”

  • “You’re so strong.”

  • “You’ve really mastered that crow pose.”

  • “I saw you’re learning to roller skate?”

  • “I can see you have a lot of commitment to this project, it’s been 2 years now!”

  • “I find it really inspirational.”


In the course of a conversation in which we are generally discussing business, it is appropriate to ask me to talk about the business side of Amy Wears Boots. “I’m curious to learn more about your business model, technical choices, and sales and marketing strategies for your Amy Wears Boots project. Would you be willing to share more?” 

There’s plenty to talk about here. 10 years ago I didn’t really understand why the marketing folks were always asking for landing pages (which the engineering team often had to build from scratch for them, like cavepeople!) and now I’m looking at my landing page stats in ConvertKit like, every day. I have a spreadsheet comparing SaaS products as I gear up toward monetizing the project, and I’m A/B testing email subject lines. I’ve done a ton of user research to find the intersection of what my followers will pay for and what makes sense for me to offer. And I’m busy trying to figure out what my MVP is and what other experiments I want to run to find out what my best strategies are to generate real income. 

If you ask about the business side, however, you should be prepared to hear some about how payment processors, social media platforms, and other SaaS products make online businesses difficult for sex workers in ways that peripherally impact me even though I am not myself a sex worker.2 I am spending a lot of time reading the Terms of Service for every platform and product I am thinking of using and I will have to carefully read every single ToS update for any product I use for Amy Wears Boots, even though all of the content I offer is solidly PG-13. 3

If the fact that my art is adjacent to sex work and hence sex work may come up when I talk about it makes you uncomfortable, don’t ask.4


If you are not writing to me explicitly and primarily about Amy Wears Boots, that project should not be the first or only part of my online presence you mention. 

I have an entire list of talks, articles, and podcasts that are directly relevant to engineering leadership, and I write two separate newsletters every single week on a wide range of topics. You really shouldn’t have any trouble whatsoever finding something else to make that human connection with me.

If you only mention the @amywearsboots Instagram account, which you “thoroughly enjoyed”, don’t mention any actual job opportunities, and then ask to get on a call with me to talk about these vague not-mentioned opportunities “or just have an intro call for the fun of it,” well, that doesn’t sound much like a recruiting email, that sounds like you are hitting on me.5

Just so we’re super clear, if you’re an engineering recruiter you should not email engineers you do not know and hit on them under the thin pretense of having some vague opportunities that might be of interest to them.

(In fact, hitting on a stranger over email is generally a bad practice, but I’m not getting into that right now.)


If in fact your primary interest in me is Amy Wears Boots, or if you’re contacting me for work directly having to do with that project (photography, commissions, collabs, modeling), then state that explicitly, use my Amy Wears Boots contact email, and it remains poor form to hit on me.


If you follow me on Instagram I have a story highlight over there explaining the boundaries of how you may interact with me there, some of which you would think would be obvious, like maybe don’t say you would like to kidnap me.6


If you really are interested in working or talking with me about two separate projects, an Amy Wears Boots project and some other engineering-related project, you can go ahead and try to walk that line but I’d recommend at least two women -- both of whom care about you and neither of whom approve of Ann Coulter --  read the email before you send it.


Why is this directed to men only? 

Because I’ve never once been sexually harassed or hit on at an inappropriate time by another woman or a nonbinary person.7 

I will not be taking questions.

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As always, if I’m quoting or paraphrasing a friend or acquaintance I send a draft to them and request feedback and sometimes make changes based on the feedback. I did not, however, ask for feedback from the recruiter, as those are verbatim quotes from an email he definitely sent me.


For the record I believe sex work by adults should be fully legalized and I support sex workers in their fight for safer working conditions.


While Terms of Service are generally boring, a few years ago I was up late reading IFTTT’s ToS (yes, I was manic) and they explicitly prohibited the use of IFTTT in the operation of nuclear submarines, which makes sense, because if you’re automating your nuclear sub with a SaaS product we are all sincerely fucked. Sadly today that explicit callout has been reduced to the general but less evocative injunction not to use it "in connection with life support systems, or other mission critical applications where human life or property may be at stake.”


People who want to stay in touch with me via IG but are uncomfortable following an account whose bio includes the word “fetish” have a completely different account they can follow, @amymakespix, which is mostly cat pics, food pics, and interesting bark.


You may wonder if I offered this feedback directly to the recruiter in question. I did not. I judge that doing so would not result in a positive outcome for me personally or in his having any kind of feminist epiphany.


If you say to me “that’s the price you pay for putting it out there, Amy” I will refer you to every woman on Twitter with over 10,000 followers, not showing her body at all even and still getting harassed and threatened every day. The reason Twitter remains a reasonably non-harassing place for me isn’t because I don’t show my body over there but because I’m not popular enough.


yes of course this happens sometimes. I’m not invalidating anyone’s experience of being harassed or pursued inappropriately by a woman or nonbinary person. It’s not the main harassment problem women face, however, and that’s the problem I’m talking about here.

Amy Writes Words
Amy Writes Words
Amy Writes Words, the newsletter, only in podcast form so you can listen to it instead of read it. I have not figured out the footnotes situation yet.