Leaping Into The Unknown

On October 1st, my partner Rio and I packed my little Chevy Spark with my cat, Cleo, and all the belongings we could cram into its Little Tikes-esque body, setting out on our Farwell Tour of America. The end goal: moving to Portugal. Saying goodbye hasn’t been easy – I fell in love with Wisconsin shortly after moving there over 11 years ago. I was freshly 22 years old, ready for a new beginning. It was in the rolling hills of the Midwest, along the glistening shore of the inland ocean of Lake Michigan that I found myself. Between the nose-hair freezing gusts of cold in the winter and the gentle summer breezes that carry fireflies and humming cicadas, I was able to build my adult self, free from ties of the past. I found community, friends, and chosen family. I found a sky large enough to hold my sometimes too-heavy heart. I found calm in the placid rolling hills. I found space to simply be, and in that space, I unearthed myself.

At the end of 2021, I made the leap from Appleton to Milwaukee. Appleton served me well for a time, while I finished school at Lawrence University and spent time growing into myself. However, I craved more – more people, more diversity, more culture. After landing in Milwaukee, I found a place I felt I could put down roots and settle. I had no intention of leaving – Milwaukee is a beautiful city. Large enough to have the perks of a big city, and small enough to not have some of the hassles of a big city. Milwaukee is a city of communities – its residents understand the need for building community, and actively do the work to build them. Despite its potholes and crazy drivers, I love this city. However, everything changed after the election.

The decision to leave the country was not easy, but the warning signs started adding up quickly. On day two of the current administration, an executive order was released labeling trans people as ideological extremists, as “corrosive […] on the entire American system.” Further orders and official proclamations issued by the administration label trans people as dangerous, harmful, anti-American, dishonest, and evil. This language is not hyperbolic; it is directly pulled from the executive orders and other statements issued from the White House (read more at the White House’s website – Executive Order “Defending Women From Gender Ideology Extremism” issued January 20, 2025; Executive Order “Prioritizing Military Excellence and Readiness” issued January 27, 2025; Executive Order “Protecting Children From Chemical and Surgical Mutilation” issued January 28, 2025; Executive Order “Ending Radical Indoctrination in K-12 Schooling” issued January 29, 2025; Executive Order “Keeping Men Out of Women’s Sports” issued February 5, 2025; Proclamation “National Child Abuse Prevention Month, 2025” issued April 3, 2025; Memorandum “Countering Domestic Terrorism and Organized Political Violence” issued September 25, 2025 – this list is not comprehensive; I stopped checking regularly in April). Most recently, the administration has labeled people “promoting gender extremism” as domestic terrorists. What exactly that entails is still being hashed out as I write this.

Language is more than just rhetoric. It begets policy, it begets violence. So far in 2025, there have been 616 anti-LGBTQ bills proposed across the US according to the ACLU. 71 one of these have been passed into law. This isn’t including national bills – according to translegislation.com, there have been 1,014 anti-trans bills proposed across the US, including 104 on the national level. According to this source, 124 of these bills, including some national bills, have been passed into law. These bills range across a wide array of issues – most importantly include access to bathrooms and medical care. The fight around medical care has been framed as an issue just around children, but states have taken that further to denying medical care for trans people regardless of age. Beyond just bills, the federal government keeps trying to remove health coverage for trans people under Medicaid. Already, certain sectors of the government’s medical plans no longer cover gender affirming care for adults. Gender-affirming care is life-saving care. I would not be here today without it.

I am afraid, to say the least. I no longer can change my gender marker on my green card. For now, I can change my gender marker on my drivers license, but I’m not holding my breath on having that right for much longer. How soon before I can no longer access my medical care on government insurance? How soon before that trickles into private insurance? Employment discrimination against trans people is legal again. Housing discrimination is not far behind, if not already there. Religious exemptions are permitted in many states, meaning a ER doctor can legally deny me care because they do not want to treat a trans body. How likely is that to happen? you may ask. If you were me, would you want to risk it to find out? Language begets violence. The dehumanization and demonization of trans people is promoting vitriol and hate. Trans people already face violence at greater rates than our cis counterparts, and this administration is emboldening people to continue to do so.

Beyond violence – I am an immigrant. I do not have citizenship in the US. My parents moved to the US from Canada when I was a kid, and I’ve had a green card for over two decades. I carry an immense amount of privilege for being white and male-passing; my “belonging” in the US has never been questioned due to this fact. However, I have also now been labeled as anti-American, as destructive. How long before I am deemed too anti-American to stay, just for being trans? Considering the US is now authorized to deport people not to their country of origin, rather to other countries, like prisons in El Salvador, I certainly do not want to stick around to find out.

I refuse to stay in a country where I will lose access to medical care. I refuse to stay in a country where I fear being deported simply for existing. Perhaps everything will blow over. Perhaps the institutions of checks and balances will keep a semblance of sanity. Perhaps. These are the questions I weighed, and ultimately decided I wanted to protect my peace. Why wait to see if the other shoe will fall, if I can instead leave now?

On a lighter note, this move is more than just an escape. Rather, escape is a motivator for a change that was already brewing. Rio had been considering moving to another country for a few years, and I had been itching for a new adventure. Working an office job 9-to-5 was draining me – as much as I loved my job, the structure of “normal” work started to suffocate me. I found myself thinking, “There has to be something else.” Rio and I started talking about options abroad – their father lives in Scotland in a hippie community, and there are places around the world carving spaces for intentional community living. This felt like a good place to start exploring “something else.”

After toying around with the idea of moving out of the country since the end of 2024, a few months into 2025 we made the decision to leave. The question was where, and how? We considered Scotland for a period of time, but it quickly became apparent the UK government seems to be following the US’s lead on anti-trans laws. There was also the question of immigration pathways – unless you are rich, moving to another country is not a simple as packing your bags and booking a flight. You need visas, and visas that allow you to work and reside long-term in a country have a massive number of hoops to jump through. In many countries, unless you are joining family or a spouse already in the country, the pathways in are a) purchasing property; b) having a job offer; or c) being a highly-skilled worker in a field that a country needs workers in (typically, tech, scientific research, and the medical field).

An exception to this was Portugal, which offers a Job Seeker Visa. This visa allowed potential job seekers to enter the country for 4-6 months with the intent to search for a sponsored job, which opens the path to permanent residency and eventually citizenship. We found an option that was the perfect fit – we could spend time fully immersed in the language to pick up functional Portuguese and be able to make network connections to assist in landing a job. Plus, Portugal has a low cost of living, ranks high regarding LGBTQ+ rights, and has amazing weather! Rio’s father has some connections in Portugal with people doing interesting work around community building as well, so the pathway to Portugal felt both achievable and in line with what we were looking for. With this option in mind, we had the “where” and the “how” squared away.

When, then? I wanted to be out of the country by the end of the year, given the political climate growing rapidly hostile towards trans folks. Additionally, our lease was ending October 1, with no option to extend month-to-month since our landlord was selling the house. Conveniently, Rio’s mother was planning on traveling for a few months at the end of the year and needed someone to housesit. We decided to set out on a grand road trip of the US, dubbed our Farewell Tour, ending in California for a few months while we finalized our plans to make the leap across the pond.

Naturally, I prefer to have my ducks in a row prior to major changes. Moving, on its own, is a headache. Add in the bureaucratic nightmare that is international immigration, reducing belongings to fit in a few suitcases, and the time it takes to go through immigration pathways – we were left with a brain-boggling number of moving parts to consider, and a tight timeline to boot. To meet my general timeline of leaving as soon as possible, it has required a leap of faith. We are jumping into the foggy unknown of the future, trusting it will work out one way or another. It has forced me to believe and trust that so long as I am orienting each action, each step, towards the goal set out in front of me, I will eventually reach there. I do see all the steps required to get to my goal, but it’s like I’m lining up dominoes out of order. Some items are set in stone, and others are pending, but I have to keep setting up the dominoes as they come along so that when the final piece falls into place, we can move forward quickly. Honestly, the last 6 months, I’ve felt like Charlie from that It’s Always Sunny In Philadelphia meme trying to get everything to line up.

Despite knowing how we are getting to Portugal, there are so many other uncertainties. Will I get a job? Can I learn Portuguese fast enough? How will the culture shock go? Did I make a mistake quitting my job before I had a visa in hand?

I am leaping into the unknown. Terrifying and exhilarating. Perhaps I am setting myself up for colossal failure, but to subject myself to the risk of greatest failure also opens up the opportunity for the greatest success. I do not know what the future has in store, but isn’t that what makes it such a fantastic adventure? To quote Calvin in Bill Watterson’s final comic strip from Calvin & Hobbes, “It’s a magical world, Hobbes, ol’ buddy… let’s go exploring!”

Up Next…

A Road Trip and Speedbumps

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