The last time I was in Chicago for more than a day, I didn’t want to waste my time on the bullshit that tourists tend to waste their time on. To be fair, I was in love, so that’s where a lot of my attention was going. I was seventeen. The fact that I was going to Chicago at all didn’t really interest me. I was running away from home for two weeks, and it was the easiest thing in the world to narrow the gaze of my focus solely on the person I was running away from home to be with. Chicago had always been an intriguing city to me. On some level, I’m sure I was looking forward to adding the city to the list of places I had been to since coming to the States in 1998. But love was determined to win every day I planned to be there, and I wasn’t interested in doing a thing to change that.

I can tell you a little bit about the city from that first visit of substance. I remember Chicago Union Station. I remember the movie theater we went to, along with some of the places we stopped at that were in one of the suburban areas just outside the city. Then she kissed me outside the Canal street entrance, and the congested landscape became a blank slate. I don’t recall much else.

That was twelve years ago. I get a little dazed when I think about how much time has gone by. She and I still speak. She’s a very different person now. I’d like to at least pretend that I am, too. The person I was in 2002 detested the idea of doing anything that was big in the tourist trade. In 2014, I’m a little more open-minded. My friend Danny said that he wanted someone to tag along on his trip to Chicago. I had a reading in Denver with a group of some of the most awe-inspiring, brilliant, funny writers and artists I have ever known. Danny’s timeline for his Chicago trip made it possible to tag along, stay behind in Chicago for a day, get my ass to Denver, do the reading, and then make the long trip back to Virginia.

There were a million little things (don’t dispute that number, I counted) that needed to be done. I knew that. I also knew that I do not have as much patience to manipulate those details into cooperating as I used to. I’m probably a different person now. I’m certainly older. By virtue of all that good timing, the trip would be staggering into anticlimactic territory on the day of my birthday. I would be turning 29. That’s a few decades away from being what most people would consider old, but 29 isn’t young either. It’s a point in which a lot of things that still feel fresh to you are suddenly 10, 15, 20 years old. You start to notice things you didn’t notice before—like the way your parents are a lot older than they were in the photographs they took with you when you were a baby.

I love being on the road for long periods of time, which anyone who has been stuck talking to me at a party for more than eight seconds will tell you. I flew from Canada to the U.S. and back again twice when I was twelve. I stopped paying attention to the number of miles I’ve spent on Greyhound since 1999, one that figure reached 30,000 miles. That’s not even taking into account cars and trains. I like travel. I like the cityscape that’s ready to greet me like a brother previously thought dead. I like (most of) the people I meet, (most of) the surprises that compete for my attention, the hotel rooms, the couches of friends, the small towns that dominate my imagination for a few minutes, and everything else you can imagine. It’s the kind of romanticism that’s both healthy and a little pitiful. But I’m a different person now. If I learned anything from going from Virginia, to Chicago, to Boulder, to Denver, to Richmond, VA, and then back home, it’s that the romanticism is a little more ambitious these days.

As I got ready to leave home, as I was stunned over and over again by the generosity of those who helped me pay for the train tickets via GoFundMe (a special thanks to Leila Younes for telling me to just stop being a little bitch about using crowdfunding to appeal to people), I felt like I was ready. The schedule was such that I would be on the road for almost two weeks, nearly three. I had done that before. Granted, it had been a long time since I had bounced around the United States with that kind of frequency, but I felt like I was ready. Even now, I’ll still go somewhere and bother a rich, diverse cast of friends and strangers for stretches of two or three weeks, sometimes longer. It’s just that for the last three or four years, I’ve confined that sort of thing to one or two states. I had not gone further than New York in several years. I hadn’t been to Denver since 2007. This trip to Chicago, Denver, and elsewhere was going to be the sort of road trip I had not undertaken in while. I packed two bags, set aside the money I had saved, and thought about the person I had become since traveling from Virginia to California by Greyhound seven years earlier.

For a trip like that, you have to be patient, enjoy a certain amount of abuse, and have a willingness to construct standup comedy routines out of situations that most people find unpleasant, even horrifying.

I believed I could still do that. Although since that trip, I had become a person who could rise quickly and easily to ferocious impatience on a run from Richmond to Washington, D.C. A change like that has to mean that I’m a different person now. But I still felt like I was ready to move in perfect rhythm to both the certain and uncertain entities that are inherent in lengthy bouts of randomized, hectic road travel.

I didn’t sleep the night before Danny picked me up. These days, even the most severe panic attacks fall short in trying to keep me awake. That’s become the rule, but this was obviously different. There were people to see, places to go, books to promote. The reading in Denver was the centerpiece of everything. I had two (now three) books coming out later in the year, a novel and a collection of poetry. I had two literary magazines/publishing companies that I wanted to champion. The reading in Denver would put me on a stage that guaranteed an opportunity to promote myself and associated with my career that means something to me. It was going to be a chance to meet people I had been looking forward to meeting for months or even longer than that. Reading before the crowd everyone at Kleft Jaw hoped would jam the Mercury Café was a performance I couldn’t afford to fuck up. I kept in mind my past experiences with stage acting, live comedy, and everything else I’ve done while other people my age were finishing college and considering a second or third marriage. The novel (Bondage Night at Darling Cara’s) and the poetry collection (Clouds of Hungry Dogs) would give me the material I needed for an evening with a crowd that important. The things I had done in the past that would technically qualify me as a performer would do the rest. I had to believe that. I had no choice.

You have to believe those things. No one is going to force you to take the kinds of chances that come with writing, submitting manuscripts, and opting to share those things with a room full of people of varying degrees of interest. You don’t have to be an arrogant prick with mountains stuck in the soles of your shoes. All you really need to do is believe that everything is worth enough of a damn to risk making a fool of yourself. Burn the house down with that mentality, wonder what could have been, or wonder what in the hell went wrong. Those are generally the three choices you get to work with. I won’t tell you how to go about getting into a headspace that makes it possible to be both humble and confident enough to think that people want to hear what you have to say. The only thing I will tell you that for me personally, I’ve always preferred being a failure (because there are thousands of possibilities that exist within failing) to being a coward. The books I’m still planning to release this year represent a culmination of seventeen years as a writer. This is not the time to balk at the chance to promote those books, become dazzled to hell and back in the company of extraordinary people, and take in a few of the sights along the way.

All of those thoughts were on my mind as Danny and I sped along towards the friend of his that we were going to stay with overnight in Pittsburgh. Danny has been a friend of mine for almost as long as I have been attending and staffing east coast Anime conventions. We had driven together to Memphis once to help his girlfriend move, so we already knew that we could be in the car with one another for several hours at a time without someone suddenly picking up an accidental case of being brutally murdered. If I ever make up a serious list of the best people I’ve ever traveled with, Danny will be somewhere in the top three.

We left Virginia on the afternoon of the 13th. We made it to Pittsburgh well after midnight the next day. The trip up to that point was sustaining itself just fine on pure adrenaline. We were both relieved to be away from the day-to-day nonsense of our respective lives. Danny was going to Chicago to fulfill a few lifelong dreams for his birthday. I was tagging along because I wanted new memories of the city. We kept each other company with music and the kind of bullshitting amongst old friends that rarely gets old. Exhausted by the time we hit Pittsburgh, we still wound up staying up with his friend until well past dawn, doing shots while discussing nothing in particular. Even if turns out that I’m a different person now, that was still the kind of thing that I can almost always find time for. The neighbors across the street were getting ready for work around 5 A.M. Another neighbor got up around 7 to work on their lawn. I tipped my beer to all of them. They didn’t notice.

No one was wasted, but no one was feeling particularly perky at the breakfast place the three of us went to. Coffee and omelets that can topple skyscrapers with ease improved our spirits by small leaps and cautious bounds. It was then I learned that when it came to fulfilling promises, my new anxiety meds and how they reacted to alcohol was a warning that was not going to fuck around. It gave me flu-like symptoms that dogged me all the way from Pittsburgh to Chicago. I’m not sure what kind of reward Danny is entitled for putting up with that, but I do know it’s something more substantial than what I’m capable of envisioning. Is there a medal for such a thing? Can I get him on a game show that dumps a garbage bag full of twenties on his head just for showing up? If those things are possible, let me know.

As Danny’s Chicago bucket list played its opening number, the reading in Denver became bigger and bigger in my mind. I imagined stealing the show, coming off well enough, bombing in mid-sentence, and everything in-between. My feelings about the show veered wildly between Christmas Eve fervor and New Year’s Day depression. Those wildly opposing moods warred enough to make me consciously grateful to have a fantastic friend and a monstrous city to keep me distracted. I told myself to relax, to remember that there was nothing I could do about the Mercury Café until I was there. Metaphorically speaking, I held my spirits over the edge of a balcony of a hotel taller than the Sears tower, and I ordered myself to have a great goddamn time. That did the trick, although I occasionally had to revisit that concept. Danny’s itinerary was thankfully such that I usually didn’t have a lot of time to think clearly.

Speaking of the Sears Tower: Don’t pay any attention to the fact that it is now called Willis Tower. People you have never met before in your life will correct you with a slight gleam of savage violence in their eyes. I didn’t know beforehand that changing the name of the tower had inspired a lot of anger and hurt feelings from the citizens of Chicago. I know that now. Unless you like apologizing to people whose names you don’t even know, just assume that everyone still calls it Sears Tower.

Whatever you decide to call it (I’m not even fucking kidding, don’t call it Willis Tower), the view is breathtaking. The glass walkway wasn’t the mildly disconcerting experience that some people claim it to be. But it was still fun. It was the kind of touristy thing I had detested in 2002. I even bought a small bear in a sweater featuring the word “Chicago” from the gift shop. Tiny gestures and reactions like those have to mean that I’m a different person. Either way, it was hard to not be impressed by the fact that I was surrounded by people from all over the world. The two young girls who took Danny and I’s picture on the glass walkway barely spoke English. They still understood what we wanted them to do. Anyone would have. I found that charming enough to wish I had been more open to tourist destinations in the past.

Denver and the Mercury Café muttered all kinds of things in the back of my head. The days in Chicago kept me from worrying about much of anything. Even though the Cubs lost, the history and ghosts of Wrigley Field were so active, they could have provided illumination for a night game. We ate enough Chicago-style pizza to understand why the city struggles with obesity a little harder than a lot of other places do. We met Chris Jericho, one of my favorite wrestlers for almost 20 years at this point, after witnessing the kind of exceptional heavy metal show that generally alluded me when I went to such things as a teenager. Jericho was good enough to take a picture with us. Not even the fact that my face looks like I want to wear his skin and dominate the 90s WCW cruiserweight division dampens the thrill I continue to get from that photo.

Every memory I could share with you about Chicago could make for an article unto itself. That doesn’t mean it would be an interesting article. It just means that I could easily go on that long about seeing the new Godzilla in a theater packed with enthusiastic believers in the King of the Monsters. I could write a short novel on everything I saw and heard over the course of the several combined miles of city streets that Danny and I walked. There is at least a couple of poems that could be slapped together to accurately describe the weather, the buildings, the river that followed us along as we walked with the girls we met who were doing a formal dress photo shoot near Navy Pier.

And if I wanted to tell you about the way Danny’s constant joy at crossing so many things off his to-do list made me think of all the things I still want to do in my travels in the U.S./Canada and beyond, we would be here all night.

Meeting my friend Megan for the first time, visiting a sprawling, old-school video arcade in Brookfield called Galloping Ghost, sitting on the L Train as it flew through the city. None of those things brought back memories from my time in Chicago in 2002 that I had previously forgotten. But those memories did come up an awful lot. I wondered what my seventeen-year-old counterpart would have made of everything we crammed into those four days in 2014. I even thought about the girl I had loved back then, wondering the way casual idiots do what it would have been like if we gone to small venue concerts and Sears Tower together. Nothing of any use or meaning came of those thoughts. They were just neon signs that occasionally bullied all other contemplations into the background. As I think about it now, I was probably just trying to keep the anxiety about Denver to a dull roar.

I had a night to myself in the hotel after Danny left to return to Virginia. I spent that evening drinking citrus vodka (look, it was on sale), watching movies on Netflix, and making sure I had everything packed for the train ride to Denver. Getting to Denver would lead to getting on a bus to Boulder. That would keep me occupied for a couple of days. Then I would go back to Denver, hopefully survive the reading at the Mercury Café, hopefully find a place to stay for my last night in that city, and then get back on the train to meet up with friends in Virginia. Keeping the plan in mind kept me calm. It also made me impatient, but it was the kind of impatience that I can keep on a low, almost soothing burn. When I left Chicago Union Station, I was as ready for Denver as I was ever going to be.

Most of the train ride consisted of daydreams about the reading. Some of them were so unrealistically optimistic that I felt embarrassed. Others were grounded in the probable, hopeful reality of contributing to what Kleft Jaw as a whole wanted to accomplish. A few were mired in the kind of negativity that people expect of me. I made a few friends on the train that I will never, ever see again. Here and there, I kicked myself for the thousands and thousands of cramped, stressful, ugly miles I had logged on Greyhound. Amtrak is certainly imperfect, but as far as the ride to Denver was concerned, it was disconcertingly straightforward. It was damn near seductive in how comfortable it was for the most part.

Another thing about me that has driven cohorts, friends, and girlfriends bug-fucking-nuts for most of my life is my ability (some would call it a compulsion) to talk with just about anyone I come across. Partially a means of managing my constant social anxiety and partially the desire to just meet people, it’s a wonderful way to pass the time. My Facebook friends list recently passed the 1000 milestone, and that’s not because I’ll accept bots and lunatics who claim to remember me from a past life. The vast majority of those 1000 friends are people I either keep in touch with on a regular basis or met simply because I can never top talking to strangers. A lot of the friendships that have come out of that mindset are casual, but some of them have led to wonderful surprises and alterations to the DNA of my day-to-day life. I can see why chatting up anyone who will stand still long enough to return the favor is annoying to the people who are already with me. I’m never going to apologize for it.

I mention this only because I probably told sixty, seventy people (including the mayor of Denver, who I met by chance at a coffee shop near the Mercury Café) about the reading. It wasn’t that I was expecting those people to show up. It was an icebreaker that came out the honor involved with even being a part of Kleft Jaw to begin with. My career over the past ten years has always enjoyed the benefit of being involved with one creative community or another. Over the past couple of years, the people I have met through Kleft Jaw and Drunk Monkeys has put me into a class of writers, editors, artists, and others I can’t believe I know and work alongside. I was grateful for that as I met up with my friend Monica (a phenomenal actress I met when New Voices produced my play in Richmond in 2003) in Boulder. I was grateful for that in the weeks and days leading up to leaving for Chicago. I’m grateful for that now. Short of sexual favors to those who give me the many benefits of their professional experience and insight, there are only but so many ways I can express and share that gratitude. One way would be to give the best performance I possibly could at the reading. Another way would be to tell every single person on the planet that something remarkable was going on, and that they really needed to know about it.

It’s a lot like being in a cult. Except that no one is wearing a uniform, the Kool-Aid is only spiked with rum, and the only time anyone gets worked up (in the best way possible) is when they’re arguing about the merits of the beat poets.

I tell people like Frankie Metro, Dustin Holland (Kleft Jaw folks who shocked and awed the crowd at the reading into a mild coma), and Matthew Guerruckey about how much their contributions and support mean to me. Being a cheerleader for their publications and others isn’t done solely with self-interest as the motivator. It’s because there is sincere pleasure to be found in playing a small part in making sure everyone gets to do what they have always wanted to do. That means being a shameless carnival barker for not just myself but for things and ideas I’m part of.

As it turned out, I did get one of those out-of-nowhere friendships out of all those poor people I accosted between Virginia and Boulder. It would give me something to do when the reading was over, but it also reminded me that the capacity for anything to happen is something that hasn’t changed a bit in my heart and mind through the years. I might be a different person now then I was 10 or 15 years ago, but that’s something that remains exactly the same.

Old friends, giant goddamn mountains, stress reduction products that are blissfully, logically legal in the state of Colorado, and the weird things that happen to your brain when the time zone changes kept me occupied in Boulder. I was the fattest man in one of the healthiest cities in America, but that only bothered me occasionally. The rest of the time was spent either annoying Monica’s friends (or so it seemed) or being so tired that I barely noticed that the Mercury Café reading was sitting right on my chest. I was up by seven A.M. the morning of the show. Try as I might, I couldn’t force time to move at a speed more to my liking. All I could do was stare at the endless, gorgeous Colorado sky and wonder how even a hardened local could just walk past the giant goddamn mountains without being amazed.

Getting into Denver for the show several hours early meant killing time. That’s been something I have been reasonably proficient at for most of my life. This involved staring at the bus depot that specialized in running people from El Paso to Los Angles, meeting the mayor (nice guy), getting coffee at two different restaurants, and telling myself that when the show started, I was going to do a good job. There was also a text message from someone who I had apparently met on the short bus ride from Denver to Boulder. It took me a moment to remember who they were, but when I did, we made plans to hang out the day after the show. Meanwhile, the doors for Mercury opened up. People started to appear. I started meeting the people I had worked with at Kleft Jaw for the past several months. Dustin Holland was the infectiously enthusiastic, terminally creative prodigy I had assumed he would be. Frankie Met spoke and moved with the same ferocious energy and talent that makes him one of the best writers and editors (and soon to be series regular on Better Call Saul) in the business today. Lindsey Thomas came armed with Blind Date at the Glass Eye Disco, one of the funniest books I’ve read in years. Kick Holland had me laughing to the point of wondering how he could top his casual comments when he took to the stage later for some standup. Mik Everett had a stage presence strong enough to tear my eyes off when all we were doing was meeting for the first time. The list goes on. Everyone who came to see the show came with open minds and a couple of bucks. Everyone who came to perform came to make sure Kleft Jaw did well enough to magically seep into the consciousness of the whole city and run for governor of the state.

And how did I do? I could have been better.

Is it possible that I stretched myself too thin by opening the show with standup and doing my reading later on? I don’t think that’s the culprit. Nor can I really blame that I had to switch from the prepared material I was going to read to something I was unfamiliar with at the last second. Talk to me about how I did on either of the times when I took to the stage to face the crowd, and I’ll probably tell you then what I can tell you now: I just didn’t meet my expectations.

Realistically, was my first time doing standup in five years pretty good? Probably, for the most part, yeah. Was the fact that I was sweating as though my body was trying to call off an oncoming stroke something that was as painfully obvious to me as it was to everyone who watched me read a short story from the fourth issue of Kleft Jaw? Maybe. Does it even fucking matter? If I’m going to blame anything for not giving the kind of performances I thought I was capable of giving, it’s going to be unrealistic expectations. Spectacular Hollywood fantasies of the most unreasonable kind had been part of the rotation in my thoughts since the moment I had committed to being in Denver. It wasn’t until after the show that I realized that I had been setting myself up to reach a milestone that no one could ever hope to reach.

I was good, but not great. In the end, I was able to play the small part in helping Kleft Jaw succeed that night that I had wanted to play. Everyone at that show was astonishing. Whoever you are, I wish you could have been there for it. Every voice at the Mercury Café that night had singular talents and unique personalities. Connor Magyar gave the crowd an acoustic set that was better than any other acoustic set that could have possibly been going on in the state of Colorado that night. Mj Taylor read the kind of work that I wish I could write. Kick Holland created the kind of comedic performance art that makes the bulk of Comedy Central’s current stars look like hucksters working an old folk’s home telethon. When those of us staying in Denver that night gathered later at the downtown Magnolia Hotel, no one (except for me) was saying anything but positive things. It wasn’t a series of feel-good chants and congratulations that ultimately were just bullshit trying to suffocate reality. That’s because the reality was that Kleft Jaw had exceeded the collective expectations of putting on a great evening of poetry, fiction, music, comedy, and everything else we jammed into the three hour running time the venue gave us.

Frankie, Dustin, and I stalked the streets of Denver later on, trying to find a place that was still open that would serve us food. I mostly just listened to them talk. It was good conversation. It was a good moment. The city was centuries’ worth of distance beneath our feet. I felt ludicrously optimistic about the future. It was almost dawn when the last of us finally nodded off. When I broke off from the group later that day, the abrupt disconnection to that kind of energy left me feeling empty but still aware of that future. It was a depression that came fast and swallowed my heart, but I knew it wouldn’t last forever. After I met up with the new friend I had met on that bus that went from Boulder to Denver a few days earlier (which included seeing X-Men: Days of Future Past with her), I sat against the window in her apartment. I watched the small patches of humanity interact with the staggering beauty of a view that included the sky, those goddamn mountains, and the Colorado Convention Center. It was the kind of view that granted me the perspective I needed. Even then, it was hard to keep up with everything that had happened over the past several days. I still missed everyone from Kleft Jaw, but I also felt.

The concept of feeling like a writer is pure nonsense and a mildly disgusting form of vanity. But over the course of the night I spent smoking and watching drunks carry each other home from the view of my new friend’s apartment, with two books coming out, with an entire community of amazing people counting me amongst their own, I felt more like a writer than I had in years. I felt like a different person than I was 5, 10, 15 years ago.

Unfortunately, that enthusiasm took a series of beatings on the journey back home. It started with my 6 PM departure time stretching to the point of not being able to leave Denver until early the next morning. Meeting a 78-year-old woman who was traveling from Denver to Florida on her own with her more humor and energy than I will ever have made things a little better, but it became very clear very quickly that all the good luck I had been spending in Chicago, Boulder, Denver, and elsewhere was pretty close to the point of being empty. I was out of money, increasingly annoyed by the few cigarette breaks Amtrak allowed, and unable to relax enough to get any sleep. Not even the sorrowful one-horse towns of states like Nebraska and West Virginia could keep me distracted. The friends in Richmond were still waiting for me, and my exasperation to get to that point rose to the level of mild madness.

This was the point in which I realized that I truly wasn’t the sort of traveler I had been years before. I was suck of the travel and sick of the eccentric faces. I was ready to spend a couple of days with my friends in Richmond, get the tattoo for my 29th birthday that had been a topic of discussion with those friends, and move from that point to go back to the painful quiet and loneliness of the routine I have at home. Burnt out far earlier than I would have been ten years ago, the constant delays due to weather and an inability to keep the schedule didn’t help my mood. The delay in Denver turned into being put in a hotel in Chicago overnight. That turned into missing my train in D.C. That turned into arriving in Richmond with two hours left on the clock for my birthday, nearly two days later than I had promised my friends I would be. A decade earlier, going a day without food or coffee would have been a mild discomfort. In 2014 it made me swear repeatedly that I was never going to take the fucking train ever again.

I probably will. The guy from Chicago moving to Newport News, VA to find work after his factory back home had been closed told me I was full of shit. He laughed when he said that to me over cigarettes and getting to know each other in D.C. I had to laugh, too. The act was just enough to get me to my friends in Richmond with a few pieces of my sanity still intact.

By the way, if you’re ever in the mood for an expensive, pretentious hotel where they’re going to treat you badly if they’re only putting up with you because Amtrak made them, I highly recommend the Swissotel Chicago. Tell them Gabriel Ricard sent you, and get 15% off the way they’re going to look at you like you’re stoned on mouthwash.

I turned 29 without the universe crumbling on top of my huge skull. This occurred over the course of the train ride and ended just shy of being picked up in Richmond. Drinks were poured. Gleeful stupidity held sway. I got one of the tattoos I’ve been planning to get for the past 20 years of my life. Pittsburgh, Chicago, Nebraska, Boulder, Denver, and all the other places and people left me feeling two or three seconds behind the pace of the world as it existed in Richmond. Even the version of me that existed in 2002, the one that was supposedly younger, with more energy and better humor about long delays in stations, even that guy would have been exhausted at the end of this.

I’m a different person now. I’ve got three books coming out, a family that shockingly continues to love me, people who endure my genetic defaults and odd features, and enough in the way of potential and time that I really can’t complain. Although I can. And I’m sure I will.

Even so, I’ve got too many places to go, too many things to do, and too many people to see. I’m getting older here and there, but I can’t slow down. I don’t have the time to do anything but move forward and wish I could go a little faster than that.

When the fuck do we leave?