Essays on Technology and Culture

How To Be Myself

About a month ago, my mind went back to an experience I had in Oulu, Finland, for the Air Guitar World Championships in August of 2018. We had gathered at an island cabin for an event we called “Airentation,” and were introducing ourselves to each other. A friend of mine who I’d met at my first air guitar competition, Justin Howard, better known as Nordic Thunder, told us his story. To retell it here would take too long, but what stuck with me was something he said about how the air guitar community taught him about himself, and how to “be a man.”

Through out my life, I’ve always felt as though I didn’t fit. As a child, as a teenager, and as an adult, I always felt as though I was at a remove from the world at large. Unwilling to accept that I was the problem, I took the attitude that “If there’s nothing wrong with me, maybe there’s something wrong with the universe.” This changed once I got a proper ADHD diagnosis in 2016. I came to the conclusion—a mistaken conclusion—that medication would solve this, bringing me more in tune with the world around me. To a certain degree, it did, but there was something that didn’t fit right. I would figure it out.

It took until 2018, and my trip to Oulu, for things to click, and realizing that took a while. After I returned to to normal life, I began to make changes to how I presented myself to the world. At first, these were an extension of personal changes I had made starting in 2017, where I’d made it a point to get in better shape and lose weight.

The first thing I did was trim my long, bushy beard to a close-cropped one. For the hair on my head, I had been shaving the back and sides, but I decided to let the long part of my hair grow, giving me a long, floppy, asymmetrical haircut that was androgynous. My mode of dress began to change, with more fitted clothing, more exploration of colors and patterns. I began to wear nail polish on a daily basis, even to work. Inspired by a comic by Mattie Lubchansky, I started wearing a little bit of makeup when I went out on weekends. On New Year’s Eve of 2018, I took what I considered to be the true first step of figuring out who I was and how I fit into the world: I got my ears pierced. I began to wear subtle jewelry: metal bracelets, rings, and a thin silver chain with an octopus charm that was a birthday gift from my partner.

I was coming to the realization that presenting myself to the world in a way that read as stereotypically male no longer felt right. It may never had felt right, in retrospect. The more I moved away from masculine presentation, the better I felt about myself. I had found the missing piece, or at least begun to work out the shape of what was missing. I started to use they/them pronouns for myself. As 2019 continued, I wound up splitting myself in two—the feminine, true-to-myself version of me that I put into the world on nights and weekends, and the somewhat effeminate, but still masculine self I presented to the world during the work week. It became a relief to come home, strip off the more traditionally masculine clothing of the work day, switch to leggings and a t-shirt dress, and be a form of myself that felt more comfortable.

As 2019 progressed, so did my exploration. Living in New York City, I was lucky enough to have access to spaces where it was safe to explore my presentation, my identity, my gender, and I used those spaces to their full potential. The moment where it sunk in about what was missing and where I needed to go, came a few days before Halloween. I was going out to a dance party, and had decided to go out in “costume” as a stereotypical goth girl in a Wednesday Addams dress. In preparation, I bought a black wig, and shaved off my close-cropped beard. When I looked at myself in the mirror, clean-shaven, with the black wig, makeup, dress, and a padded bra, I could only say one word: “Fuck.”

As I looked in the mirror, the ramifications were clear to me, though I was hesitant to follow through. The person in the mirror was who I was supposed to be. The path was clear, but I knew I couldn’t yet walk it. There was fear, there was trepidation, and I needed to address those before I could even consider taking another step down that path. Despite those fears, I consider that night out to be the first time I went out into the world as myself.

One of the common ideas of the traditional transgender narrative is the concept of physical dysphoria—the sense that something is wrong with one’s body, and how it connects to their assigned gender at birth. This is something I never experienced much of. Not to say that there weren’t aspects of my body I was unhappy with, but they were small things—my weight, but also my chest. I have always had a minor case of gynecomastia, and while it never bothered me enough to address it, my feelings about it gave me pause. “If I feel this way about my chest now,” I thought, “what makes me think that hormones and developing real breasts will be any better?”

I chewed on this. My body, though not ideal, was something I’d grown to accept and appreciate, both for what it was, and what I had done to improve it. Despite this, I also knew that there would be other benefits to HRT that I knew I wanted—it would change my brain’s internal wiring in a lot of ways, and put me more in touch with my emotions. What I experienced in my life was a different form of dysphoria: social dysphoria. I knew many of the expectations that come from being assigned male at birth were expectations I could not fulfill, and many of which I never wanted to fulfill in the first place.

My male-presenting and male-identifying life was a series of wearing different, ill-fitting “Man costumes.” Some fit better than others, but even the ones that fit best began to ride up or chafe after a while, so I would put it aside, and find another one that felt like it fit me better. By the end of 2019, it was apparent that I was running out of male-coded costumes to wear that had even the slightest appeal to me. How the world saw me—as a man—no longer mapped to how I saw myself, and I knew I had to change this. Hormones were the last hurdle to jump to make that happen. After speaking with my therapist about it in January of 2020, I decided that by the end of April I would start hormone replacement therapy. I would try it for a month, at least, and see how I felt. If it was beneficial, I’d keep it up.

The April deadline was one born out of practicality. At the time, I was employed as a contractor, and the six-month contract was running out. It was unclear if my contract would be extended, if I would be hired, or if I would need to find another job. As a safety measure, I began to look for new, full-time work, hoping I could land in a place where I could have good health insurance, and would be safe to transition at. To aid in this, I cut my floppy hair to a buzzcut, stripped off my nail polish, and put the feminine version of myself into a closet, so as to present to the world as someone normal, someone it was safe to hire. My contract job ended, and I was let go, but I got lucky. At the end of February, I began working for a well known New York City museum as their Email Marketing Manager.

Two weeks later, the COVID-19 Pandemic forced the museum to close its doors to visitors. Everything was in chaos, though my job was safe. In the chaos of the first few weeks of the pandemic, starting hormones, and medically transitioning took a back seat to navigating the changed world. In time, I managed to secure a telehealth appointment with a doctor at Planned Parenthood, and on April 24th, 2020, I received a prescription for Estradiol. I masked up, walked to a nearby pharmacy to pick it up, and took my first dose.

My original transition plan was to live for the most part in “stealth mode,” presenting as male—as best as I could—while my body changed. I had planned a trip back to Finland the end of August, and hoped that when I returned, I could make a more public coming out at my new job. The pandemic, of course, threw all of that into disarray, though it had a small benefit. As long as I wasn’t on a Zoom call, I could present however I wanted at home, and even when I was on Zoom, as long as I was masculine from the shoulders-up, nobody would notice a thing. I could at least live like myself in isolation without fear.

What I did not expect was for hormones to hit me as quickly as they did. By June, I had developed a more prominent chest, and hiding it from the world in the few times I went out into it was becoming more difficult—not that I wanted to hide it at all. The changes to my body were one thing, but the changes to how I felt were another. While things in my head were far from perfect, I did feel a sense of completeness. I was no longer two people, hiding one side of myself from the work-a-day world, and letting my true self out at night. I was whole. I felt more connected to my changing body, in a way that is difficult to explain in words.

I came out to my parents by phone in June of 2020, and to my work a couple weeks later by email. To my surprise, my social transition was much smoother than I ever expected it to be. Every trans person has heard the horror stories of coming out: losing friends, losing family, losing jobs, constant misgendering and abuse. I have been lucky enough to experience none of these things. The worst that happened was a coworker calling me the wrong name on Zoom on my first day as Rachel—and even that was because she hadn’t seen my email yet. This was easily understood, and more easily forgiven.

The next few months were a blur. A good friend moved back home to Helsinki, as the pandemic had destroyed her livelihood. There was a COVID-safe camping trip in September with a group of queer friends, and in October, I filed a petition to legally change my name to Rachel Anderson. It took time to complete the process, but on December 30th, 2020, nearly two years after I began trying to figure out my identity, I’d completed the first, legal step to being who I truly am.

Just over a month ago as I write this, I travelled to Chicago, for the 2021 US Air Guitar National Championships. The entire US Air Guitar apparatus moved online in 2020 to allow for virtual competitions, but the state of the world had improved to the point where we could come together in person again, from across the nation. I jumped at the chance to go, not just because it would be my first chance to travel in over a year, aside from seeing my parents in Philadelphia for Easter, but because I wanted to reunite with some of my friends in that community.

Yet, I had a fair bit of anxiety going into it. The last time I saw any of these people had been August of 2019, in Nashville, and while I was in my exploratory, genderqueer period then, I was going by my old name, and I looked and presented somewhat masculine. Even though they had all known about my transition, and had expressed support, I worried how I would be received and how I would be perceived.

I worried for nothing. It felt like old times.

On our last full day in Chicago, sitting on a rooftop at a bar and restaurant, I confessed my anxiety to a friend who told me that “I think we’ve seen the most authentic you yet.” I had to agree.

I think this is one of the key things a lot of people don’t understand about being transgender. Transitioning isn’t always about becoming someone else—it’s about becoming the person we are. It’s about being more true to ourselves. I lived for thirty-five years in a cloud of confusion, wondering why I felt strange and out of place in the world. Was there something wrong with me, or something wrong with the universe? It’s not an either/or question with a simple answer. All I can say for certain is that I know I am who I am, and that I no longer feel as out of place in the world around me.

There’s a way to go yet. I may be out, and I may be seen in the world as who I am, but transitioning is a long process, and there’s more to be done about the social, legal, and physical aspects of transition. I’m in the process of updating names on various accounts, getting new personal documentation, and even working towards getting gender-affirming surgery. I am, however, at a place where I can look back on the journey and understand how it began and how I got here. I need to get it into words, and share it, mostly for myself.

I am Rachel. I am transgender. I use either she/her or they/them pronouns. Am I a woman? I don’t know, but woman feels close enough for government work. Am I a man? No, I am not. I am, however, myself. That is the most important thing, and it’s the thing that has been missing from my life for far too long.

Just Do The Thing: A Programming Project

I went to college to study Computer Science. It ended badly. I wanted to learn to write code, maybe make computer games. I ended up taking the same math class seven times in three semesters (they were half-semester courses, and one try was a two-week rush session between semesters). I ended up failing out, and refocusing on earning a degree in English.

Back in November, I decided it was high time to get back in the game. Knowing I teach myself best when I have a project to work on, I picked up a couple of eBooks, scoured Google and StackExchange, and began working on an app idea I’ve had bouncing around in my head for probably close to two years. I decided to build it in Vanilla JavaScript, with a little help from jQuery, since I already have solid fundamentals in HTML and CSS.

It’s a simple app: a tool for tracking goal progress. You check in every day, and mark whether you accomplished your daily goal or not. You only get to track one goal at a time, and you get a one-day grace period if you fail to check in. I call it: Just Do The Thing. Since late November, I built it out from a basic prototype into a largely fully-functional in-browser web app. It stores all its data in the browser using Local Storage, and has only two dependencies: jQuery, and calendar-base, ’cause who the hell wants to write their own calendaring system?

Amazingly, a lot of CS 101 came right back to me. I had to adapt a bit to JavaScript—my programming courses were taught in C++, and I hadn’t touched JavaScript as a hobbyist in about fifteen years. Thank goodness for the wealth of programming knowledge on the web. Whenever I hit a roadblock on how to do something, I was only a search away from help. As for roadblocks on program logic—I was on my own. So far, so good.

I’m now ready to show off the fruits of my labors. You can find the code at, and you’re encouraged to poke and prod it to see where it breaks. Just today, I finally cracked (I hope) a long-standing bug based on my incorrect assumptions around date math, which means it actually works the way I intend.

There’s still more to be done. I don’t want to rely on native alerts, and the app itself is still pretty homely. Once it’s feature-complete, I’ll be making it look pretty, adding some responsive layout functionality, and throwing it up at You can expect an announcement here, when that happens.

For Hire

For the past eighteen months, I’ve been working in medical journalism as a Web Producer. It’s an okay job, but I’m starting to get restless. The problem with most publishing, even in the specialities and trades, is that advertising rules everything. I’m just not satisfied with a job that prioritizes advertisers over a more important mission. So, I’m reaching out to my audience, in the hopes that I can find a decent job that lets me grow and learn while accomplishing great things. If you think that might be a job you know about, please read on.

First, a little about me:

If you want a résumé, you can find a PDF at this link, but a résumé doesn’t tell the whole story, only skills. I’m able to sling HTML emails, manage a CMS, organize events, and drive user growth, sure, but it’s all stuff I learned either by myself, or on the job.

That I have the job I’m in now is a testament to years of self-taught skills. I’ve been doing stuff on the Web since I was thirteen—more than half my life. It’s how I got a job with a Fintech startup, Trusted Insight. They took a chance, because I had a blog, a podcast, a social media presence, and I was willing to learn the trade. And learn I can, especially when I have a project. Heck, at my current job, I taught myself some VBA so I could speed up a recurring task in Excel when setting up new email lists.

If you’re in a specialized field, I can learn that quick. I went from no knowledge of institutional investment to managing a 65,000 member institutional investment community inside of a year. I went into medical journalism with no understanding of medicine, and now I know… stuff. Not as much as I learned at Trusted Insight, but I know a bit about the drug approval process with the FDA, about HIPAA guidelines, and the ACA.

Whatever you’re doing, I’ll learn, and pick it up fast.

Just one note: I’m not able to up and relocate right now, so I’d prefer if you’re either located in New York City, or you let people work remote. Either is fine, but I prefer to have an office to go to, if I can.

Second, a little about you.

You do work with a greater purpose—something that solves problems and makes the world better. Not just for people with money to burn and no patience (looking at you, “sharing economy” startups). I’ve got bigger picture stuff in mind: putting technology and the skill of how to use it in the hands of the disadvantaged—and getting them jobs—working to fix climate change, a broken government, or you just have a really cool app that helps a people in ways more interesting than summoning food, laundry, or a taxicab. You don’t have to be saving the world, just making people’s lives measurably better.

You’re also dedicated to solving problems and to making something truly awesome. You have people who show the passion they have for their work, and inspire each other to do better. I’ve been in too many offices where the work is just drudgery, and while every day can’t be one where you innovate, break through, and accomplish miracles, it would if we’re all in it together when there’s drudgery to be done. I’ve worked for a six-person startup, a multi-thousand employee international publishing company, a 25-person telesales and fundraising team, and in a 100-person government office. As long as I’m on a team that works tightly together, I can handle pretty much any size organization.

Think we can make something awesome together?

I hope so too. If you’ve got a lead, get in touch. There’s contact info in my résumé, but my contact page is right here, and you can even select “I want to hire you” as an option, if you want.

A Few Words of Explanation

It appears I touched a nerve with my previous piece, “Productivity Über Alles.” I was wary of posting it, worried that it would be taken the wrong way by Internet friends who are entrepreneurs, or that it would be a seen as a giant flameout, akin to Merlin Mann’s (in)famous “Merlin Labs!” video. It took some coaxing from said Internet friends, entrepreneur and corporate stooge alike, to convince me otherwise.

The post came in a burst of sheer frustration—a tough day at my corporate stooge job, combined with frustration about the sheer volume of crap that had been flowing into my inboxes about working for oneself, finding focus, doing your best independent work, and so much other stuff. When I read that article on people listening to audiobooks at 2x to better cram more information in, well, I snapped. Nothing against Shawn Blanc, and Mike Vardy, of course. They work hard, and I’m sure someone will get value out of their stuff. I just can’t mentally justify dropping $250 on a course on how to focus—and that’s probably cheap, really. The reason why is personal—I did blow $400 on a goddamn smartwatch, after all—but I’m sure it’s not exclusive to me.

So much of the rhetoric around “do what you love,” “work for yourself,” and anything that puts independence above everything else rings painfully shallow and hollow to my ears. My natural cynicism is to assume that someone has something to sell me, usually because they do. It feels like “make-believe help,” to borrow a phrase from Merlin. Something something “Facebook group about creative productivity,” am I right? There’s no shortage of a market for various panaceas to assuage the frustrated cubicle-dweller that they too can be an entrepreneur and, if not make it rich, at least be more fulfilled in life, by working for themselves. Hell, even those scummy “sharing economy” companies use the “entrepreneur” thing to justify having a giant pool of contract workers with no benefits and shitty pay. That alone should be a clue as to how bullshit the term “entrepreneur” is these days.

At least in the giant swimming pool called “technology” upon which I have been sitting on the edge of the shallow end of, with my toes in the water, the entrepreneur is lionized out of proportion. The only people in technology who get multiple hagiographic biographies and docudramas are the rich, white men who started companies and got successful. Not every startup CEO wants to be the next Steve Jobs or Mark Zuckerberg, but every VC wants to find the next Steve Jobs or Mark Zuckerberg, so hey, if you can’t be Steve or Mark, at least look and act the part, and maybe the VC gods will shine down upon you. From my perspective, it feels like if you’re not working 80 hours a week for equity and the promise of a payday, or pulling down six figures at an established startup for the same amount of hours, you’re nothing.

Few things appeal to me less than the idea of working more than 40 hours a week, by the way. I held down two jobs for 52 hours a week, for a couple years, and it was killing me. But that’s what I had to do to keep my head above water, and pay down my student loans. I’m keeping afloat now, but I also had the luxury of my parents paying off a chunk when they sold their house. Even if I had been doing “something I love” for both of those jobs (and I wasn’t, by any stretch), I would still be exhausted at the end of each work week, ready to find some distraction to make me forget my misery. I certainly wouldn’t be working on the next thing. It takes a certain type of personality to make that work, and that ain’t mine.

That’s one of the things that irked me the most, and lead to my piece, the one-size-fits-all advice of “WORK FOR YOURSELF OR BE A MISERABLE FAILURE” mantra that runs through way too much of the tech-focused media I consume. It’s in my inbox, it’s in my podcast app, it’s in the various websites I check during downtime at work. It manifests itself as “THE ROBOTS ARE COMING FOR YOUR JOBS” on the one end, and “BE FULFILLED AND MAYBE GET RICH” on the other. Neither is compelling. if I cared about making money, I wouldn’t have gotten a degree in English.

And that’s the other problem. The demand for more. Life hacks, and efficiency, and ways to crank out more widgets, book more clients, maximize income, maximize shareholder value, maximize all of it. I don’t care. I wouldn’t say no to more money. I am $36,000 in debt, and have a small problem with buying gizmos with pictures of fruit on them (and concert tickets), after all. But I don’t want more money if it means more agony: chasing down invoices, pushing for the next client, marketing yourself, paying taxes on 1099 income. None of this appeals to me, and I can see it tainting the work I ostensibly want to do and love. Okay, fine, all things in life come with stuff you don’t like. My corporate stooge job isn’t a walk in the park, but the agony is manageable, and it usually ends at 5:00 every day. In the calculus of the life I want for myself, A boring desk job for The Man, with moderate agony looks preferable to a job working for Myself, with increased agony.

This isn’t exactly a new struggle on my part, just one thrown into sharper focus after a bad day and some frustrating timing. I’ve long struggled to figure out just what the hell I want out of my life. All I’ve got so far is just a huge, and growing, list of what I don’t want. Maybe some of those things on that list will fall off and I’ll re-evaluate them, but that’s a ways away. In the meantime, I just want a little less agony, and a lot less people screaming in my ears about how I shouldn’t be chained to someone else’s desk for 40 hours a week, and instead be working for myself… and buying their how-to guide to maximize every hour I spend doing it.

Eight hours for Work, Eight hours for Rest, Eight Hours for What We Will

I’m Afraid

I’ve been thinking a lot about unpleasant things in my past, and unpleasant things in my present, and how they all relate. Not all of it has been the healthiest kind of thinking, either. But, as is the nature of the human mind, we dwell on the unpleasantries of our past, and the things we cannot change. This is the stuff that keeps so many of us up at night. Through all the thinking, I’ve found a common thread to unite the dark moments in my past, and explain the situations of my present—fear.

A while back, there was a small Twitter meme on determining your “burlesque name.” Your first name is your favorite drink, your last name: your greatest fear. I couldn’t decide whether I would be Bourbon Failure or Bourbon Success. The only thing I was sure of was bourbon.

Fear of failure is easy to explain. In the aftermath of failure, things are often measurably worse. You’re our time, money, possibly a home, or friends, or even your entire way of life. “They can’t eat you,” the saying goes. That’s true. I’ve failed many times, and I’ve managed to survive each time, but I always worry that the next one will be the end. I worry, no matter how many times I remind myself that there are nets to catch me when I fall.. I worry that the nets will fail. That I’ll be falling so fast, carrying so much dead weight, that each and every last net will snap as I hit it. And where does that leave me?

Fear of success? That’s a harder one to explain. The thing about success is that it means the expectations get higher with each success you had. The higher the bar is set, the harder you have to work to reach it, the more ends up at stake. There’s more to lose, and then we’re back to fear of failure. I hate the push to compete. The most immediate experience of this came in my first full-time job out of college, working for an abysmal B2B telemarketing firm. The attitude when I walked in every morning was “What have you done for me today?” Even if you managed to hit your expected lead count for the day, or for the week, or for the month, each day the slate was wiped clean, and everyone knew it.

I’m afraid when I’m not in control, because the unknown force of the universe’s apathy could choose to destroy all I’ve built. I’m afraid when I am in control, because I could just as easily destroy it all through my own action. Or inaction.

So I’m afraid. Because of the fear, I’m overly cautious. I often don’t make a change until the way to go is either obvious, or when there’s no other choice. I cling for dear life to whatever handhold I can find. It’s easier than fighting the fear. I’m even afraid as I write this piece. I’m afraid that it’s too honest in a social media age where one is expected to project unwavering confidence at all times, the better to attract whatever metric you want to grow. I’m afraid that it’ll be seen as disingenuous, that I’m faking it to earn sympathy. I’m afraid, as I often am, that it’s the last thing I’ll ever write, and that when I sit down to write again, there will be nothing to say.

There’s solidarity in fear, I suppose. Before I wrote this, I re-watched Merlin Mann’s “Scared Shitless” talk from Webstock 2011. It’s worth a watch for all of us. Even people who have succeeded by some measure are afraid—often of their success, or the potential to fail again. There’s always something to keep us up at night, worrying, wondering, angry, miserable, or some combination thereof. We’re all scared little animals in the dark, and I’m trying to take some solace in that.