In the beginning…

I’ve always been a geek. When I was in the third grade, I wanted to grow up to be an Egyptologist (or maybe a Marine Biologist; I changed my mind often). My dad built custom computers for a living, and early on, he taught me how to build and wire a computer from spare components.

I built my first web page when I was eleven years old; basic HTML, tables for layout, animated GIFs, and all. My first true web site that actually had more than one page was a Star Trek: Voyager fan site. For that site, I learned how to use frames to make a site that looked like a Star Trek computer interface, and I found Javascript snippets that allowed me to change content in one frame when a new page loaded in another frame.

As I learned more and more about the web, I was hooked. I started learning about PHP, and realized I could make header and footer files, so that I didn’t have to edit every web page on my site when I added a new page.

Discovering WordPress

And then, about 12 years ago, I installed WordPress for the first time. Blogging was this brand new thing that lots of other geeks were doing, and so I jumped on the bandwagon. I was 19 years old, living with my mom, working a low-paying job at a book store, and going to school part time. Ya know, basically living the dream.

WordPress was just about a year old at this point. There were no plugins or themes; you hacked core if you wanted to change the look of your blog. It was like the Wild West.

And I loved it.

Really, I enjoyed the process of changing the layout of my blog, editing the “theme” to make it look how I wanted. I got more of a kick out of that, than I did actually writing about myself.

Fast forward a few years; I left the book store I’d been working at behind, and started working as a Pharmacy Technician. I loved that job, but it was stressful. I got yelled at by patients when their doctor didn’t call in their prescription, and somehow it was my fault their copay went up when their insurance changed in the new year.

Blogging became sort of a catharsis; a way to vent when I got home about everything that stressed me out during the day.

It also helped me find community. I followed and commented on a ton of other pharmacy blogs. The pharmacy blogging community was, and still is, a really tight-knit group. I made friends in the WordPress Forums. I made friends from all over the world and all walks of life.

In 2009, I moved here to New York, from where I’d grown up, in the Washington, DC area. I’d only been to New York a couple of times before; once on a school field trip, and once to see a comedy film at the Staten Island film festival.

But I needed a change of scenery from the non-stop politics of the DC beltway, and after that trip to New York, I had decided that I wanted to move here.

My first WordCamp

New York City, my home for a little over five years.

Fairly soon after I got to New York, I learned that there was going to be this event called “WordCamp,” where you could spend two whole days learning about WordPress and meeting other people from the WordPress community. And tickets were only $40, including a t-shirt and lunch on both days!

Now, I’d just moved to New York. I was working in a retail job, and I was renting a room in an apartment in Washington Heights (the upper end of Manhattan).

There were nights I ate popcorn for dinner because I didn’t get paid until Friday. I was lucky if I had ramen.

So, as you might imagine, even $40 for something like this was hard to come by.

And then, I heard that if you volunteered at WordCamp, you could get a free ticket! For anybody  who knows me, it’ll come as no great shock that I spent most of the weekend volunteering. I’d only signed up to help with folding t-shirts the night before, and to help with registration on both mornings.

But I ended up spending most of the event walking from room to room, making sure everything was running on time.

By the end of Saturday, I was exhausted, but I was hooked.

I’m an introvert; socializing doesn’t come easy for me. But volunteering at WordCamp gave me a purpose in talking to people. My common interest with other attendees made it easy to strike up conversation.

After lunch on Sunday, my feet had finally given out, and I’d collapsed in a chair in our registration area.

And finally, Sunday afternoon, as WordCamp was ending, and everybody was coming down from the high generated by all of the weekend’s excitement, I found out that there was going to be another WordCamp in Boston a couple of months later.

For those two months, I scrimped and saved, begged and borrowed, every penny I could, and just barely managed to come up with enough to take the bus up to Boston for the weekend. I made even more friends, from even more places. They didn’t need any more volunteers, so I actually spent the weekend attending sessions!

Over the course of that weekend, I found myself talking with people in the hallways a lot. And I guess I sounded like I knew what I was talking about, because a lot of those conversations involved me giving advice about people’s sites, what plugin to use to solve a problem, stuff like that.

And I realized a couple of things:

A. I knew way more about WordPress than I realized, and

B. I really loved being able to help people.


Over the next couple of years, I went to half a dozen WordCamps, in Philadelphia, Baltimore, Chicago, New York again.

I became hooked on traveling. Every few months, I visited a new city for the first time. I used WordCamp as an excuse to visit my older brothers in Minneapolis. I volunteered or spoke at almost every WordCamp I went to. And I ended up becoming one of the lead organizers for WordCamp NYC in 2012 and 2014.

By that time, I’d also moved on from working in a pharmacy to working at the Apple Store. I eventually moved to the Genius Bar, where, even though it wasn’t WordPress, I got to help people solve tech problems.

It was a job I enjoyed a lot more, one that payed a decent amount better, and made it easier to travel to far off places–which at this point, I already knew I couldn’t get enough of.

I wanted to travel the world.

It became an obsession, really. I spent hours online reading stories about people traveling around, working odd jobs here and there to make their way from country to country. And then, I found out, since I was under 30, I was eligible for something called a “Working Holiday” visa in Australia. Basically, it lets you move there for up to a year and work to pay your way, with the only caveat being you could only work for the same company for up to 6 months.

So again, I scrimped and I saved, and planned for over a year. The visa itself cost almost $500, but that was nothing compared to the total cost of picking up roots and moving halfway around the world. It certainly wasn’t cheap, but I was lucky enough to be in a position in life that allowed me to do it. For that whole year, I didn’t go out to the movies. I rarely ate out, even at fast food. Foolishly or not, I took some money out of my 401k, so that I’d have enough money to get me through until I could get set up down under.

And when I had enough money, I bought a one way ticket from New York to Australia.

My finger hovered over that “purchase” button for what seemed like hours, but was probably just a few minutes. After I clicked, a wave of emotion hit me like a tsunami:

I worked at the iconic glass cube on Fifth Avenue in New York (we often called it the Fruit Stand). This was taken on my last morning of work before setting off for the great unknown.

“Wow, I’m really doing this!”

“Wait, am I really doing this?”

“Oh, crap, I’m really doing this.”

A few months later, I said goodbye to my job at the Apple Store. I’d worked there for nearly 4 years, and some of my coworkers were my closest friends. My last day was the iPhone 6 launch.

Apple has a tradition of “clapping out” employees on their last day, and at the end of my final shift, I was no exception. My coworkers gathered in the hallway outside the backroom, cheered for me, hugged me–I was in tears. It really hadn’t hit me until this moment that I was leaving almost everything and everyone I knew behind.

I did have a few stops on my way out of the country. I wanted to visit my family in Minnesota one more time before leaving. Also, WordCamp San Francisco, which I’d been asked to help run volunteers for, was happening a couple of weeks before I was due to leave. So I decided to spend a few weeks in California.

The first WordCamp that changed my life

Most of the people who ran WordCamp San Francisco worked at Automattic, the company that runs WordPress.com, Jetpack, Akismet, and more. And I’d been wanting to work for Automattic ever since my very first WordCamp, when I first met people who worked there.

I was too busy making sure everything was in place for volunteers at WCSF, but I did manage to take one photo during lunch.

I arrived in San Francisco about a week before WordCamp, and spent the week working out of Automattic’s offices there, making sure everything was in place for the weekend. I got to talk to even more Automatticians, and since I was in charge of volunteers for the weekend, I got to boss a lot of them around.

I had a rare opportunity to spend a lot of time with the people who worked there. An experience made even more rare by the fact that, since pretty much everybody at the company works from home–wherever that may be–it’s not very often that that many employees are in one place.

By the end of the weekend, more than one of them encouraged me to submit an application to work for Automattic.

And I could feel in my bones that it was where I was supposed to be. So that very night, I polished up my resume, and sent it in by email.

But the application process takes time–WordCamp ended, and I had a plane to catch.

Out into the great unknown

Before I left the US altogether, I visited a few friends in San Diego, and even attended one last WordCamp–the smallest one to date, with only about 50 attendees–WordCamp Ventura. It was one last opportunity to see and make friends before leaving a continent behind.

I boarded a plane at LAX at about 9:00 on a Tuesday night. I should have been exhausted, but I was so excited, I had energy to burn. Sitting there on the tarmac, waiting for takeoff, I reflected on how far I’d come, and how far I was about to go, and even though I had a 12-hour overnight flight ahead of me, I didn’t sleep a wink.

As luck would have it, the best flight deal I could find from the US to Australia had a layover in Fiji, for just under 24 hours. When I booked the flight, I checked, and it turned out making the layover 5 days instead of one only added about $100 to the cost of the flight. I found accommodation at a hostel right on the beach for about $8/night, and that included a free ride to and from the airport.

I was like “$150 side trip to Fiji for 5 days? Sign me up!”

I got to the hostel about 6:00 in the morning, long before my bed was ready; check-in was normally at 1pm, I was told.

Being awake for 36 hours finally had caught up to me, so I collapsed in a hammock outside in the shade, and finally went to sleep.

The view from the hammock I slept in while waiting for my bed to be ready.

They managed to get my bed ready a couple hours early, and so at 11:00, I dragged my feet and my suitcase over to the building I’d be sleeping in for the next few days, and slept until just after dusk.

I spent the next few days lounging in hammocks, taking swims in the ocean, and exploring the tiny town of Nandi just outside of the airport. I took day tours, and spent an afternoon relaxing in mud baths, then getting a deep tissue massage that seemed to go on forever. One day, a bunch of people from the hostel took a bus all the way across the island–about a 2 hour journey–to watch a Rugby tournament that some of the hostel’s staff members were playing in. Our team didn’t win, but it was fun to watch, so we didn’t care.

We spent the nights sitting around a fire, singing songs, and drinking Kava–a somewhat intoxicating drink that tasted like dirt, but made you happy and carefree.

Those five days seemed like a lifetime, but they did finally end, and I had another plane to catch.

Back to reality

When I first laid eyes on the Sydney Opera House, I stood in wonder for what felt like hours.

So, after one last flight, this one, mercifully only about 5 hours, I finally landed in Australia, Sydney to be exact. As corny as it sounds, I’d fallen in love with the city after watching Finding Nemo.

I had spent so much time planning the “getting to Australia,” part of my journey, that I didn’t really have any solid plans for what to do after I got there.

The first order of business was finding a long-term place to stay, and the second was finding a job.

I had originally planned to transfer to an Apple Store in Sydney. But, as happens in large companies, I got caught in a quagmire of bureaucracy, and didn’t actually have a job waiting for me when I got to Australia. I met with managers at the store, and they were excited to have me come aboard, but there was a lot of red tape to get through.

And so a couple of months went by, and my savings were rapidly depleting.

For a couple of weeks, just to pay my rent and buy some food, I spent hours every day as a street performer in one of the popular shopping areas in Sydney.

I’d gone to the Aussie equivalent of Best Buy, bought an amp and a microphone, and connected it all to my phone playing some Karaoke tracks.

It was summertime, and just before Christmas, so there were lots of shoppers out and about, and in a giving mood. The Saturday before Christmas, I took in $300 in about 4 hours. It was really fun, and I made a lot of friends in other buskers, and some of our regular fans, but I couldn’t keep it up forever.

Finally, a paycheck…

Just as my savings were about to run out, and it looked like I might have to borrow money to head back to the States, I heard back from Apple. They wanted me to start working at the store in a couple of weeks. On that very same day, I got an email from Automattic. Over the previous few weeks, I’d interviewed with a hiring manager, and done a small project, and that day, they asked me to start a 6 week trial as a Happiness Engineer.

I’d gone from having no jobs, singing on the street just so I wouldn’t be living on the street, to having two full time jobs at the same time, and raking in the dough.

And so, I would wake up early in the morning, and spend a couple hours answering WordPress support tickets, then walk to the Apple Store and work a full 8 hour shift, and still come home and spend a few more hours working on tickets. I didn’t take a day off for over a month.

But, six weeks into my trial, I found out I was going to be passed on to Automattic’s CEO– a guy you might have heard of, named Matt Mullenweg–for the final interview. I had to ping him every day to ask if he was available, and after about a week, we chatted for hours-six long, but engaging hours, about everything from Karaoke, to what books I liked, to my traveling around the world.

And at the end of the chat, Matt offered me the job. I would start full time at Automattic in a couple of weeks.

And so, I gave my notice at Apple, and to celebrate, in the long weekend I had before starting at Automattic, I took a trip to the Great Barrier Reef.

The kangaroos at the sanctuary were quite friendly! As long as you had food to offer them, anyway.

I had to fly up to Brisbane, then take an all day tour bus to a town hear the coast. We stopped at tourist traps along the way, including a sanctuary for kangaroos, koalas, emus, and more. That evening, we finally got to a small coastal town, with a population of maybe a few hundred.

The next day, the winds were too high on the seas for us to safely take a boat out. Instead, our tour guide took us to the top of a cliff overlooking the beach that night.

There were no cities for miles around, and I saw the entirety of the Milky Way in the sky for the first time in my life. That had a profound effect on me; it really hit home just how insignificant we really are in the universe.

The next day, we took a boat out to the reef, and I got to snorkel for a few hours. I did what Finding Nemo had made me want to do; watch see turtles play and look for “annemenenennones.”

And I found Nemo!

On my own for the first time…

Once I got back to Sydney, it was time to buckle down, and get to work. I had to buy, then set up my new computer. I went through some more training, settled into a routine, and attended my team’s weekly chats, which were at midnight, thanks to the time zone difference.

That didn’t stop me from exploring, though.

40,000 feet over the Australian outback, on my way to Bali, it seemed like I was over an alien planet.

Easter weekend, I took a side trip to Bali, Indonesia; flying there was actually cheaper than most destinations within Australia!

I traveled inland to a small town near the center of the island named Ubud. And while I was there, I stayed in a treehouse (albeit, a treehouse with wifi and air conditioning).

Every night, I got a full body oil massage for about $15 USD. I went to a monkey forest reserve, and spent hours playing with the monkeys. One even climbed up on my shoulder to grab a piece of fruit I was offering it.

A month or so later, I went to a WordCamp in Brisbane. Since I could work from anywhere, I rented an AirBNB for the month there, and had an apartment all to myself, for the first time in my life.

A moment in crisis

It’s funny how living in a place by yourself is a completely different mentality from sharing one with family or roommates.

What I didn’t know was just how much it would affect me.

You see, I’d been struggling with something all my life; something I’d kept hidden from everybody around me, sometimes even from myself.

Growing up, I always knew I was different somehow. It wasn’t until my teenage years that I was able to put a name to it, though.

All my life, I was told I was a boy, by family, by friends, by society. I believed it, too. After all, if everyone calls you something for long enough, you tend to end up believing it’s true.

But, in my heart, I knew I was different. I was really a girl.

I’d find out later that this was called being transgender.

Looking back, I can see signs that I wasn’t what everyone thought I was from my earliest memories, but it wasn’t until puberty hit that everything really started feeling wrong. My body wasn’t growing the way it was supposed to.

The teen years are known for being a pressure-filled, anxiety-ridden period in anybody’s life.

Mine was that way for the same reasons as most teenagers, but also because I had to hide who I really was. At the time, all I knew about trans people was what you saw on Maury and Jerry Springer, and the occasional transphobic jokes in TV shows and movies.

I didn’t want to be one of those caricatures, so I buried my feelings deep down into myself, so that eventually, even I believed they weren’t real.

But, every once in a while, they’d resurface. And I’d bury them back down because I was afraid. I was afraid that roommates would see me for the impostor that I felt like. Or that they’d be disgusted. I could never let my guard down.

When I moved into that first apartment of my own, though, a couple of things happened:

First, I was able to let my guard down. There was nobody around to worry about seeing me.

More importantly, though, I came across a Facebook post of a former coworker who had transitioned earlier in the year.

She’d originally made a big post on Facebook announcing that she was transitioning, but it happened during a time when I wasn’t really looking at Facebook, and by the time I was looking again, I had missed the post, and she had changed her name and profile image, so that I didn’t put two and two together.

But in June, for the first time since transitioning (that I saw anyway), she posted a picture of herself. I practically did that double-take that they show in cartoons: “Is that who I think it is?”

And so, I spent that evening reading back through all of her posts from the last six months. She talked about the feelings she’d had since she was a kid, and how she came to terms with them.

I sat there for hours, until the sun came up. At some point–I don’t know when–I started sobbing. Everything she was saying punched me in the gut like a prize-fighter.

These were the same feelings I’d suppressed all of these years–to a tee.

I’ve heard before that when you’re transgender, before you can accept yourself and start to transition, two things need to happen:

First, you need to realize you can do it.

Then, you need to realize that you can do it.

I already knew that it was possible to transition. Back when I worked in the pharmacy, I filled lots of hormone prescriptions for trans women.

But reading my friend’s posts helped me realize that transitioning was something I could do. That I needed to do.

I was in crisis mode. I was half a world away from everyone I knew, my family, my friends.

I was scared. I wanted to go home, but I still had about four months to go until I came back to the US.

Starting a new journey, while already on another one

I wanted to go home early. Several times, I’d gone to booking sites, and held my finger over the purchase button with a different kind of trepidation than I’d had when I originally bought my ticket to Australia.

But I’d already agreed to speak at a WordCamp in Pune, India in September, so if I went home early, it would mean cancelling that (and letting down one of my coworkers who’d worked hard to get me invited and approved to go in the first place).

So, I carried on. I found a therapist that would talk with me online, to help me through all of the anxiety and depression I was going through. By the time we finished a couple of sessions, I was absolutely certain that transitioning was right for me.

I muddled through the rest of my time abroad. I didn’t really go out much and explore the cities I had left to visit, though I did some. I’d started chatting with my friend whose posts had led to my own epiphany. Both she and the therapist I was talking to helped me through the worst of the homesickness.

I kept working, and eventually, the trip to India came. I had a weekend in Pune, a month in Mumbai, then back home to the US. I enjoyed India a lot. I met a lot of people at WordCamp, who treated me like a rockstar for working at Automattic. And oh yeah, Topher (ya know, the guy who runs this site?) was there, too. <img src="https://s.w.org/images/core/emoji/72x72/1f642.png" alt="

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