First things first. Planning a trip like this does not come lightly to me. A cross country trip, by longboard, is a major event. A life changing experience. And a learning experience. After my mishaps of last year, I have discovered what it’s going to take to make this happen.
My name is Calleigh. I’m 25 years old, living in Boston, Massachusetts. After living as a man for 22 years, I came to terms with my deep instincts and revealed myself to the world as a transgender woman. It has never been easy, and will likely never get any easier. The only thing that ever seemed to take the pain from being an anomaly in society away was skateboarding. I would skate as fast and as far as I could. I have pushed many, many distances, and I’m the only person to ever cross every state line bordering Massachusetts by skateboard. My greatest dream is to skate across the USA, from Boston, MA to Oregon, and I’ve done everything in my power to attempt to make it happen.
The original beginnings of the trip had me renting an apartment in Southborough, MA, where I had just moved in in December of 2014. I completed my first distance skate of Milford, MA to Boston, MA totaling 64 miles in 8 hours on November 11, 2014. At that time, I was on hormones for 6 months, and moved into the apartment in an attempt to escape my family after living with them after a botched attempt at suicide. Moving into the apartment was a poor financial decision, but it gave me the opportunity to finally come out and live as a woman for the first time. My first day living as a woman was December 2, 2014.
I made a Facebook account to “reveal” myself to acquaintances and old friends, and to better network myself. A few people had already heard of my transition, and slowly but surely I was tasked with choosing who I wanted to allow into my new life. Also, Facebook gave me something to do when work at Whole Foods Market and my crazy roommates weren’t enough. I was pretty active on Instagram, which had gained exponentially more followers after I posted a picture of myself in a supergirl costume on Halloween.
So, after actually thinking I was some sort of supergirl from my first distance skate I said to myself, “If I can skate 64 miles, why can’t I skate across the country?” Wanting to move away from everyone and never have to actually deal with the people who knew me from my old life, and especially my parents was a major theme to me at the time. And I had this thought that skateboarding was free transportation, so there would be no need to continue living the way I was.
Of course, the logistics of everything became clear. I made a post on a forum community for longboarders that told of my dreams to complete the skate. I was pretty naive. I predicted that with a little more training by the anticipated leave date of the upcoming September (9 months away), I could theoretically push 100 miles a day. I held onto that thought for a long time.
As the financial side of everything came to light, I realized I needed a source of income that was greater than what I brought in at work. Besides, I was acclimating to paying rent, buying food, paying a phone bill. I just started to get off of my parents bills, paying insurance on my car, and many other financial burdens. I could hardly afford to live the way I was. So, I created a crowd funding account for the trip.
I initially had many sympathy donations. A lot of people were proud of me “coming out” and a few others saw my posts about financially struggling and wanted to help. I racked up about $300 in a week.
My money situation wasn’t getting any better. I had just began classes for my final semester at Salem State University, so now I had a huge gas bill to add to everything already. I couldn’t stop drinking. I would go out to the bar every weekend night with this group of girls from my hometown, and spend a chunk of money I didn’t have on getting drunk. And when I wasn’t going out, I was going through a handle of gin every other night. I would buy marijuana every Friday to pass the time when I wasn’t hanging out with friends.
A big portion of the gender transition that I didn’t expect was a major loss of friends. My friends didn’t want to invite me to their parents houses to hang out anymore, and the guys all wanted to hang out together. The only people I ever saw was the group of girls. I started delving into a more sexual side of me; I started dating men. I had really flown off the handle. I wasn’t being myself, even though I continually expressed that my transition was me “being myself.”
It had to happen eventually with how much I was drinking, but I found myself in jail with a DUI on February 1st. At this point, the donations stopped coming in because my marketing was failing. I was too busy getting drunk and worrying about how feminine I appeared to the world. I went out to my hometown to go to a bar, and drank myself stupid. We switched to a second bar, where we drank under the table, and at some point, we left. I freaked out because I forgot where I parked my car. My friend expressed a hundred times that I could just stay at his place and find it in the morning, but for whatever reason, I was adamant about driving all the way home.
When I did find my car, I went to a fast food place and ordered $50 in food and didn’t eat a single bite of it. I drove around, forgetting where I was, and went straight into a snowbank. It wasn’t an awful crash. I tried to pull my car out of the snow, and if I had a passenger I probably could have done it, but by myself I was useless. A cop cruiser rolled up on me, and from there I was belligerent and trying to get them to leave me alone. I was complacent at first, but they knew who I was and started picking on me for “being in drag,” so I became hostile. I refused to answer their questions, denied a breathalyzer and a field test, and they put me in cuffs. Honestly they didn’t have much proof I was actually drunk, and if I wasn’t such a jerk back to them I probably could have gotten a hand pulling my car out and moved on.
When I got bailed out, my two best friends at the time saved me, but that was the last time I saw them after I slept over. It was that night that I hit rock bottom. My car was impounded, I lost my license, and I had nothing to show for myself. Without a license I had to drop out of school, which came with a hefty price tag, and the instatement of my student loans.
I tried to pay to get my car out of the impound lot, but we had a blizzard the day after and I couldn’t get a ride to the lot. My parents couldn’t afford to loan me money to retrieve the car, and they didn’t want to help me because I ran out on them. There was a huge fight between us, and things were awful. They didn’t accept my transition, and I couldn’t stand being 23 and being told who I could be in the world.
So, the impound bill racked up. I had to pay rent with the little money I had since it was the first of the month, and my phone bill was due. Without a way to get to work, I hopped on my longboard and got to pushing. At this point I had taken out all the money from my fundraiser to help pay my bills. I felt guilty. I felt like I was scamming people to help me pay my bills. In a sense, I was. I did buy a new board with some of the money, but none of it was going to the trip. I was in a bad place.
More fees piled up and piled up. The reality that with all the court dates, the student loan bills, and having no money to compensate was impeding on the cross country skate really sunk in. I kept the fundraiser up just in case anyone happened to donate, so I could keep paying my bills. I was desperate.
My aunt happened to find my fundraiser and donated $600 to me. That was it. I only had my original $300 and her $600, and none of it went to the skate. I admitted to myself that I was never going to make the trip happen by September, and took to longboarding full-time to try and pull myself out of the hole. I was lucky not to lose my job, but because I did feel a serious motivation to get myself off the ground, I pushed every day to get there, 7 miles from my apartment, and 7 miles back home.
I picked up a second job, which the income was exclusively used for skateboards. I started earning my money back, and the $600 from my aunt knocked out a big burden I held. So, feeling on top of the world, I spent $500 on a 2 week trip to Spain. Come to find out I wasn’t eligible for a passport because of court mandated probation, and the trip was non-refundable. I was back down to where I began.
After that little stunt, and working two jobs, and skating all those miles, I decided longboarding was the only chance I got on a day to day basis to feel free. It was the only time I could think, or not think. It didn’t matter what gender I was, who was still my friend, or who I owed money to. It only mattered that I kept my eyes on the road. And I fell in love with that feeling of being free.
So, to rebuild my reputation and plan ahead for a cross country skate trip next year, I began pushing further. I pushed all the way to Hartford, CT (73 miles) in a blizzard one day. I pushed to Providence, RI and back (84 miles). And I pushed to Hampton, NH (71 miles). I just kept kicking and pushing. I had nothing else to do. It was not only a passion, but an escape. If I was going to get people to really believe I was going to complete a trans-american skateboard ride, I had to prove it.
Time went on. Life had me at my worst financially. Things were awful with my family. My roommates went nuts on each other and got evicted, so I had to take over the apartment and paid double what I was already paying. I quit my second job. I had a bunch of bills for things I took out on credit and never paid. My life was in the dumps once again. And to top it all off, I didn’t have a single friend in the world.
I always tried to host parties in my empty apartment. I didn’t like being alone. There was one day I spent $300 on a DJ, booze for everyone, a slip and slide, and other things to throw a huge summer party, and not one single person showed up. Even though I was already at rock bottom, I was six feet under at that point. I did eventually find a roommate, but the toll of skating 14 miles to work every day and back, and feeling trapped in an area I had no friends really got to me.
I jumped at the first opportunity to move out. A coworker was moving to Boston, so I asked if I could have a room and he said yes. I didn’t have any money or a job out there. I knew I didn’t. But I figured I could move in, get hired, and pay up relatively quickly. What I didn’t expect was how hard it would be to get a job as a trans girl. As a guy I was never without a job. I always got hired everywhere I applied. This time around, not so much. I didn’t find a job until October, and I still hadn’t paid a bit of rent for two months or paid any bills. I was royally screwed.
I got evicted at the end of October. I just couldn’t gather the money. I tried to sell the skateboard collection I amassed, but it wasn’t nearly enough to keep a roof over my head. So, my parents came and grabbed all my belongings, and I told them I had a place to stay. I didn’t. I found this really neat overpass in Charlestown, and I slept under there for a few weeks. My money from working wasn’t saving quick enough, and was only enough to feed me every day because I had so few hours.
I couldn’t even think about skating distances. Life just kept beating me down further and further. One night, in the overpass while I was sleeping after finding a party in Boston, I got bit by a Brown Recluse spider. At first I thought it was a zit, then a mosquito bite, but it started getting necrotic to a point where I couldn’t even wear pants. I couldn’t go to a doctor, so I had to use various home remedies and keep it covered for the longest time. I eventually did go to an ER when I started feeling sick. I lied about my name, and ran out of the hospital before they could bill me.
Another aunt of mine found me on the internet and reached out to me. She invited me to live with her while I got back on my feet. I lived with her and her family for nearly a year. She paid for me to go to school again, fed me every night, and was fully supportive of everything I do. Living with her gave me the opportunity to get back into distance skating, this time competitively.
Since living with her I went to Miami, Florida to compete in the Ultraskate, which I placed 2nd for women with 172 miles. I went to Bend, Oregon and placed 2nd in the 10k race and 3rd in the 5k. And after that I went to Atlanta, GA to compete in a 188 mile 3-day race. I placed 1st for women. I felt more than ready to take on the entire country.
It’s been a wild ride with little to no good parts for almost 2 years. I’ve only just begun to get back on my feet financially. I paid off some significant bills and got transportation that isn’t just my skateboard, and I worked hard to keep myself afloat.
But in the last two years I’ve learned so much. I learned what it means to be transgender. It’s not about “becoming a female” it’s about feeling comfortable as myself. It’s about living an honest and open life. I graduated college and made the Dean’s list in my final semester. And I drink very rarely, if at all. I’ve become someone I would respect. And that was what this entire journey was all about.
So now, here I am, after everything, ready to try again. This time for real. I can’t do it alone, just like I couldn’t get to this point alone. I need the kindness of strangers and friends to get me to finally going cross country. And this time it’s not about wanting to get away, or wanting to escape. It’s about doing something amazing, to prove that being transgender isn’t the only thing about me worth anything. It’s about beginning a new chapter of my life where my mind is clear, my goals are set, and a strong support system is in place to push me along.
I want to go to Oregon, and live in Oregon. When I went there, I fell in love with the nature, the air, the people. I never wanted to leave. So I want to go there and finally find peace with myself that doesn’t exist in the city of Boston, where I have to sit idly by as my old friends go on with their lives without me. It’s my turn to do something positive for myself and the world. And I believe that skating cross country is my golden opportunity to make a difference; to really put transgender people like myself on the map, in strength, vigor and resilience.
