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It is the winter of 2014 and I am lost, both in an industrial corridor of Chicago and generally, in life.
It has been almost three years since I got a graduate degree in journalism and I only have a handful of bylines. I wasted the Canadian work visa I got from going to grad school in Montréal. A year ago, I moved back home to Milwaukee to take care of my grandma, who is now dead.
As I wander through a desolate area between Bucktown and Lincoln Park, trying to find The Hideout, I think about my grandma—a hard-working immigrant who came to Wisconsin from Ecuador in the 1950s—and how disappointed she was with the aimless globetrotting and underpaid freelancing that has characterized my young adulthood thus far.
The cold-ass, end of February, Chicago wind pummeling my face feels like mi abuelita trying to slap some sense into me from the great beyond.
The summer before, journalistic curiosity brought me to Detroit. At the time, the city was filing for bankruptcy and Michael Bay was shooting Transformers: Age of Extinction in downtown, transforming it to look like a Chinese city, which is ironic as hell. The trip yielded an 8,000-word piece that I was not able to sell and that ended up on my blog, like most things from my early writing “career.”
The trip to Detroit also turned me onto a band called The Hounds Below, which was led by Jason Stollsteimer, who is best known for fronting The Von Bondies—they had that 2004 hit “C’Mon C’Mon”—and for getting punched in the face by Jack White.
The Hounds Below are playing The Hideout this winter night in 2014. I have never heard of the place, but apparently it is a Chicago institution that dates back to 1934.
As Throop Street turns into Wabansia Avenue, The Hideout appears like a mirage in the desert. But, you know, a frozen-ass desert.
The Hideout is a two-story, 18th century house smack dab in the middle of factory buildings. It kind of reminds me of Detroit, except in “the D” there would be a single house and literally nothing else around it, save some overgrown grass and cracked sidewalks.
The Hideout is more than a cozy bar-slash-storied venue. It is a spiritual center. It is a monument to a time when America still cared about poetry and protest songs. It is an oasis.
Unfortunately, in the not-so-distant future, The Hideout will sit in the shadow of a multi-billion dollar residential and commercial development known as Lincoln Yards.
This does not surprise me. Late capitalism is an unrelenting wave, crashing down all around us. Blighted industrial areas become playgrounds for the rich. Lincoln Yards will become Dumbo on the North Branch. Gentrification is the new normal.
This winter night in 2014, as I drunkenly sway and sing along to the overly earnest ballads of another indie rock band that will be lost to the annals of time, what I cannot foresee is that in four years I will return to The Hideout as the guardian of a teenage boy, to see the comedian Brandon Wardell.
It is Christmas morning 2015 and we are all together as a family under one roof—myself, my future fiancée, her 10-year-old son and her 4-year-old daughter. We have been living together for a couple of months and dating for about a year, minus the month we split up because I freaked out over the prospect of life as a stepdad.
It is now the boy who is freaking out. He has just unwrapped his big present, a brand new iPad. He is jumping and screaming and thanking us. His mom and I look at each other with naive satisfaction, unaware of how much drama the device will cause, how many new passwords we will have to create, and how many times he will have it taken away.
The boy, like most of his generation—and ours—is helplessly addicted to technology. But it is not all selfies and games for him. More than anything, he craves information. Before the iPad he devoured books, magazines, anything he could get his hands on. The problem is that if a physical copy of the New Yorker is mid-grade weed, the iPad is pure heroin.
Regulating a kid’s iPad time is a challenge I did not expect to face in my late twenties. On our first date, I told the boy’s mom that women had pretty much dictated my path up until that point and I was planning on breaking the trend. I said that my time in Milwaukee was limited and within a year I would probably be living in Ecuador. But then we fell in love. And now I am trying to make sure these kids eat their damn vegetables.
Whenever we get into an argument with the boy about his abuse of technology, or about his lack of effort in school, I try to convey one simple idea: each day you wake up, you have a choice to either create or consume.
I am not saying that I expect him to produce a dope beat or write a hilarious sketch every day, but those are things he can do.
Creation can be as simple as a conversation or a home-cooked meal. Putting down your phone or your iPad and letting your mind wander, letting thoughts form, that is creation.
People who make an effort to create on a daily basis tend to be happier than those who do not, regardless of the outcome, because the process of creation is rewarding in and of itself.
For middle school boys, few concerns are more pressing than being cool. To this end, I try to communicate to the boy that being cool by virtue of consumption—like the clothes you wear—is tenuous, while being a creator is a far sturdier source of cool.
Likewise, consumption is a costly and sketchy source of happiness. Not to mention, when consumption is your primary concern you are more likely to end up working a job you hate to maintain your paper chase.
When it comes to being a creative professional, the boy’s mom and I are not as evangelical, because we are both struggling creatives—if you consider my freelance writing a creative endeavor.
Nevertheless, we surround the boy and his sister with art and culture. We encourage and support their interests. We take them to see and do cool shit.
Naturally, when the boy asks me to take him to see his favorite comedian, Brandon Wardell, at The Hideout in June 2018, of course I say yes. I even take it a step further.
It is the spring of 2012 and I am holding a bag of bagels, standing at the base of One World Trade. The building has just become the tallest in New York City, though the spire will not be installed for another year. Across the street is the offices of the magazine Fast Company.
Like a dumbass, I sent a bunch of unsolicited pitch emails to magazine editors in an attempt to get the first thing I wrote out of grad school published. Not one of them garners a response, and I am positive not one of them is ever opened.
And so, I have resorted to impersonating a bagel delivery guy to grab the ear of an editor.
As you can imagine, security at the New York headquarters of Fast Company—across the street from the new World Trade Center—is very tight, so I opt for plan B and head to Midtown Manhattan.
A year earlier, I am sitting in my Magazine Writing class in Montréal. Graduation is right around the corner. We are worried about getting a job, because it is 2011 and journalism is—to put it lightly—in flux.
Our professor does not attempt to assuage our concerns. Instead, he recommends that we start by writing about something that we love, because at least it will be a topic we should be familiar with.
In the spring of 2011, that is comedy.
Growing up in the 1990s, I inherited a love of sketch and stand-up from my dad. Then, coming of age during the George W. Bush years, comedy became essential. By 2011, I am regularly listening to comedy podcasts.
Internet exclusive audio had been around since the mid 2000s, but the popularity of WTF with Marc Maron created a podcast boom in the early 2010s that has resulted in virtually every single comedian having their own podcast today.
That might sound kind of insane, but it has been great for comedians and their fans. Podcasting gives comics unprecedented control over their careers and it offers fans a treasure trove of content. This is a cultural development I felt was worthy of a feature story.
And so, after finishing grad school, I set out to write about the genesis of comedy podcasting. I end up with a 4,000-word piece that includes the voices of Marc Maron, Stephen Merchant, Scott Aukerman, Matt Belknap, Paul F. Tompkins, and other innovators of the burgeoning medium.
As mentioned, I tried to get the story published in a major magazine. I thought it deserved to be in Rolling Stone. But I do not know anyone in that office.
After chickening out on the Fast Company bagel delivery, I find myself trailing a bearded hippie onto an elevator and into the offices of High Times.
“Who ordered the bagels?” the secretary impatiently shouts, for the second time, into the adjacent room, where the employees of America’s best known cannabis culture magazine toil in cubicles more tidy than you might expect.
You see, back in the day High Times covered a spectrum of counter-culture topics and I deluded myself into thinking they might again.
After about a minute of awkward silence, I confess my real intentions to the secretary. Amazingly, she does not kick me out, but escorts me into the office of an assistant publisher.
This man is another bearded hippie, with long flowing white hair, cargo pants and a warm smile. He humors me for a few minutes before explaining why the story will not work for their magazine, namely because it has nothing to do with weed or Snoop Dogg or Willie Nelson.
I end up giving away this story—that I worked on for like six months—to a comedy website based in San Francisco that has since been acquired by Vulture.com, a subsidiary of New York Magazine. It is shared on Twitter by Marc Maron and others, it does numbers, but I never see a dime. Sadly, this becomes a trend.
Most of the things I write over the next couple of years are profiles of comedians like Hannibal Buress, Maria Bamford and James Adomian, that are published on websites based in Montréal, Toronto and New York City, which I am never paid for, though I do receive a press pass to the Montréal Just for Laughs Comedy Festival two years in a row.
It is the summer of 2018 and my future stepson and I are about to be escorted onto the back patio of Chance the Rapper’s manager’s Wicker Park apartment by the comedian Brandon Wardell.
When the 25-year-old walks through the front gate and introduces himself, the 13-year-old silently shakes his hand and eagerly nods his head. He is completely starstruck.
In 2014, after moving back to Milwaukee, my writing begins to veer away from comedy and focuses more on music. In 2016, I am hired by Wisconsin Gazette to write a local music column and I start freelancing for the website of 88Nine Radio Milwaukee.
However, I never stop listening to comedy podcasts. My (re)introduction to Brandon Wardell happens while listening to Howard Kremer and Kulap Vilaysack’s show Who Charted? On the episode Brandon loses his shit over a fire-ass Carly Rae Jepsen song. I am immediately on board.
Turns out, that was not my introduction to Brandon. I actually saw him open for alt comedy icon and dramatic TV star Bob Odenkirk in November 2014. I even wrote some nice things about his set. I attribute this lapse in memory to the fact that I was falling in love at the time.
Whatever the case, Brandon’s show at The Hideout in 2018 presents an opportunity to earn some cool points and respect from the boy whose mother I love.
The night the boy tells me that Brandon is playing The Hideout, I check their website to see if the show is all-ages. It says it is 21+. I call to see if they will make an exception. The person on the other end of the phone replies, “As long as you’re with him, it’s cool.”
I reach out to Brandon’s people to see if he will be available for an in-person interview while in Chicago, with the angle being that the boy would join me and prepare some of his own questions. They oblige.
As is my process, I do a deep internet dive and binge Brandon and Jack Wagner’s podcast Yeah, But Still. I learn the basic biographical information that most fans should be familiar with—Brandon was born in 1992, his dad was a troop, so the family moved around a lot, but he went to high school in the suburbs of D.C. His mom is from the Philippines and teaches Zumba. He has a little sister. Despite the relocations—he had the unfortunate luck of living in Alabama for seventh grade—Brandon, unlike most comics, comes from what appears to be a stable, happy home.
Brandon seems to have got his edge online. As a kid, he spends a lot of time posting on internet forums. He becomes obsessed with baseball during the period when he lives in Washington state and Japanese superstar Ichiro Suzuki leads the Seattle Mariners.
In middle school, Brandon takes pride in exclusively listening to novelty music by “Weird Al” Yankovic and Flight of the Conchords. In high school, he becomes a comedy nerd. He volunteers at a local festival where he meets headlining comics and is inspired to start performing. He does his first open mic at 17. He fumbles around so badly that the crowd thinks he is doing an Andy Kaufman-esque bit and it kills.
As a rising star in the D.C. comedy scene, Brandon visits Los Angeles to test the waters. Shortly thereafter, he drops out of college and moves across the country, arriving in L.A. during the same month of 2014 that I discovered The Hideout. His ascent in the L.A. comedy scene is swift.
Bob Odenkirk taps Brandon for a tour and a live album recording. Brandon even appears on the cover of the record, which is like the alt comedy equivalent of being made by the mob.
In 2015, Brandon’s online activity goes wild. Over the next two years or so, he averages 20 to 30 Tweets per day. He becomes known as a “millennial whisperer,” does some freelance writing, some on-camera work, becomes a Drake fanboy, tours with Bo Burnham, and continues to hone his stand-up.
This period reaches its zenith in 2016 when Brandon popularizes the “Dicks out for Harambe” meme by making a Vine with the actor Danny Trejo. The six-second video catapults him to internet stardom and garners him a “Hot Comedian” write-up in Rolling Stone. It is at this time that my future stepson discovers Brandon.
“Dicks out for Harambe,” like some of the best absurd internet phenomena, is eventually co-opted by the alt-right. Once this happens, Brandon and the University of Wisconsin-Milwaukee student who introduced it to the internet distance themselves from it.
Listening to Brandon on his podcast, it becomes clear that he regrets much of his online activity during this time. He claims it was “fueled by manic depression,” and calls Twitter “a website that rewards mental illness,” a notion verified by the election of Donald Trump.
Brandon’s most memorable physical feature is his baby face, which serves him well when he is a hot young comic. By 2018, with his podcast taking off and his deleting of old Tweets, Brandon appears to be in the midst of an “adult rebrand”—a throwaway joke that seems to ring true.
This is the angle I am thinking about working as we head into our interview with Brandon. I see myself writing a piece that might inspire my future stepson to do better at regulating his internet use.
Sitting in Pat the Manager’s patio, the boy is clearly nervous. Brandon compliments his fit, which puts the boy at ease, though he refuses to ask his questions first.
I start out by talking about the Montréal Just for Laughs Festival, which is the biggest comedy event in the world and the best attended by the entertainment industry. I ask Brandon about his audition for New Faces in 2012 and whether he thinks the festival remains relevant. He says it is “no longer a be-all, end-all situation,” but he thinks it still matters. According to Brandon, comedians should focus on self-generating work. For starters, he suggests hosting a podcast and running a monthly stand-up show.
When it’s the boy’s turn, he begins with a “Dicks out for Harambe” question. Brandon does a decent job of hiding his exasperation with the topic. He expresses regret, calling it “by far the dumbest part of my life.”
The mood loosens considerably when the boy poses his second question.
“What’s your favorite Soulja Boy Tweet?”
Now this is journalism. As Brandon begins to answer, he and the boy recite the Tweet verbatim in unison. My day has been made.
The conversation shifts to the roots of internet rap and the immortality of Lil B, which reminds me of one of my favorite Brandon quotes.
“Lil B’s influenced my comedy 100 times more than old SNL.”
After about a half-hour, we wrap up the interview and say our goodbyes.
The next time we see Brandon he is onstage at The Hideout, working the sold out crowd with a mix of cheeky one-liners, wild characters, silly stories and funny observations culled from his eight years in the game.
Despite claiming to be a retired aux cord DJ, Brandon re-emerges after a standing ovation for an impromptu aux cord set—complete with the Carly Rae Jepsen banger and the track “Chicago” by Sufjan Stevens, who happens to be Brandon’s favorite musician—plus a meet and greet with fans. The boy gets a picture and a quick chat with him.
Later, the boy points out how Brandon made time for everybody in the room. Onstage, Brandon may be doing a send-up of toxic masculinity and awful Reddit subcultures, but offstage he is an absolute sweetheart.
Since I began freelance writing almost ten years ago, one of my best friends has worked at The New York Times. Not once have I sent him a pitch, but that day in Chicago with Brandon inspires me to reach out. Brandon agrees to some follow-up phone interviews. After these conversations I put together a pitch and my friend at the Times passes it along to the appropriate editor.
It is the fall of 2014 and I am in an Uber on my way to the opening night party of the Milwaukee Film Festival. I am on assignment for a local online publication. To be clear, the MFF might not have the prestige and star power of Sundance or Cannes, but it is, in fact, pretty badass. This is mainly due to the Oriental Theatre, a 1927 movie palace with East Indian decor that is hands down the best place to see a film in the Midwest—yes, better than anywhere in Chicago.
Anyways, I am late to the party because I was just at the Pabst Theater, another Milwaukee gem, arguably one of the top ten venues in the nation, and where I will see Brandon open for Bob Odenkirk two months later.
On this night at the Pabst I not only see Tim Heidecker and Eric Wareheim of the cult TV show Tim and Eric Awesome Show, Great Job!, but also the amazing John C. Reilly in character as Dr. Steve Brule. I am riding high.
Once inside the party, I grab a drink and sample what is left of the hors d’oeuvres. I do not see anyone I know except my boss at the online publication. He invites me to an afterparty at a nearby bar. I have missed the live bands. There is not much happening on the dance floor.
I should mention that I am wearing a pastel colored floral baseball cap—backwards—and a burgundy velvet jacket. It is a wild fit.
Within forty minutes of my arrival the party is over. We make our way down the stairs and out the door, where a red carpet awaits. It is on this red carpet that a beautiful brunette with red lipstick and a teal top turns to me and changes my life.
“Are you my new BFF?”
What an opening line.
She invites me to a nearby bar. It is a different bar than the one my boss is at, but I could care less. The bar that she and her friend take me to is very hip and very packed. I offer to get drinks. It takes forever. Eventually, she joins me in line. Lightning strikes. At the end of the night, instead of writing her number on my hand, she draws stars.
At this point, it is only a matter of time.
It is two months later and I am walking up to the same building where we met outside on the red carpet. The local university is hosting an interactive art exhibit at the building on this night. She is already there and she has company—her two little ones.
I see the boy first. He is nine-years-old with shaggy hair and a black leather jacket. When his mom introduces me to him he is polite, as he is with all strangers, but he is guarded. I can sense his fear, anger, and apprehension. It will take us a couple of years to build trust.
The girl is three-years-old. The severity of her parents split has not yet sunk in. She does not understand who I am or what I represent. I find her waddling down a hallway. With no hesitation, she gives me her hand.
From that moment on we become best buddies. The transition from friend to father figure is bumpy and continues to require new approaches and adjustments, but damn, those first few months are bliss.
It is the fall of 2018 and I am standing outside of a public high school in the most incarcerated zip code in America. In the past, driving through this Milwaukee neighborhood has prompted a drug dealer in a car to aggressively honk at me and ask “You tryna party?” Because why else would a young white guy be there other than to buy drugs?
Today, I am in a line that stretches farther than I can see. It includes many white and black people. We are here because Barack Obama will be here. It is a week before the 2018 midterm elections.
The first time I share the same air as Barack Obama is Election Night 2008. I am in Chicago, champagne drunk off my ass, a hapless recent college grad with a one-way ticket to London, a six-month U.K. work visa, and no real plans for my return to the States.
I miss half of Obama’s victory speech outrunning a cop who spots me pissing in an underground parking structure. I make it back for the second half. When the speech ends the crowd explodes with joy and we parade down Michigan Avenue with the fullest of hearts.
This time I have my shit together. I will not miss any of Obama’s speech. Waiting in line, I am reading Chasing the Scream by Johann Hari. It is a phenomenal book about the global drug war. It is the kind of multi-year, multi-nation investigative journalism I can only dream about, because as a parent it would be tough to commit that much time and travel to a project.
I sometimes feel like a phony when I call myself a parent. Sure, I live with the kids, I spend time with them, I care for them, I listen to them, their mom and I split rent and other expenses, but she does so much more. She is an incredible mom and I simply follow her lead when it comes to parenting.
When I was a kid I wanted to be famous, like, I suspect, most Americans. My plan was to go to New York University, study with Spike Lee and become a celebrated writer/director. I was going to make thought-provoking films that inspire social and political change, keep my integrity and make a lot of money, so I could give back, live comfortably, and help my parents retire early.
I worked hard in school and was on track to get into NYU, but when it came time to go to college, I opted for the debt-free route of a nearby public university, courtesy of scholarships and my hard-working, blue-collar parents.
That debtless freedom allowed me to get a work visa, which I used to live in Scotland and travel around Europe the year after undergrad. One country led to another, one career path led to another, and the dream was deferred.
Don't get it twisted though, I have always wanted kids. For whatever reason, when I was young and a girl would break my heart, I would daydream about traveling the world with my kid as a single dad, but I would have preferred a nuclear family. Later, after learning about overpopulation, systemic injustice, and the foster care system, I became open to adoption.
However, being a stepdad—especially when the kids biological dad is around and problematic—can be pretty frightening.
Early on in our relationship, I read a Facebook post that scares me. It is one of the those sharebait-y, who-knows-if-it’s-true posts about a stepdad who does everything for his stepdaughter, who pays for her wedding, but who is replaced at the last minute by her deadbeat bio-dad and does not get to walk her down the aisle.
The message was clear—no matter how much you love them and care for them, you will never replace their biological dad.
For someone with an admittedly outsized ego, that is a hard pill to swallow.
Over the last five years, my fiancée has chipped away at that ego, and I am a better man for it. Slowly but surely, I have made sacrifices and prioritized my family. I have started to look more realistically at my freelance writing career, which has been subsidized by a substitute teaching job since I moved back to Milwaukee.
While my writing career may be trending upwards in one sense—I have won multiple local awards, I have my first book coming out, I have interviewed some fascinating people like Kamasi Washington, Giannis Antetokounmpo, and Lauren Mayberry—there has been no financial windfall to match.
The freelance pay rates I receive cannot support a family, or would require me to work so much that I would barely see my family. The full-time job I was offered by a publication that has since folded, the same paper whose ghost of a website you might be reading this on, paid less than substitute teaching. To top it off, the book project has left me in considerable debt.
The fact is that journalism has been slowly bleeding out since the introduction of the home computer and is now directly under attack from the President of the United States. Today, my local daily newspaper is barely enough kindling to start a fire. In January of this year alone, more than two-thousand people who write for the internet lost their jobs.
Two days before the Obama event I get an email from my friend at The New York Times. The editor thinks the focus of my pitch is not there yet and is not convinced the timing is right, but offers feedback and says they are open to a re-pitch.
During our first phone conversation, I ask Brandon what he thinks caused the “manic depression” that fueled his Tweet storm of 2015/2016. He gives a non-answer. He mentions the “quick high” he got from Twitter, which he no longer gets. I ask if reading books, which he is trying to do more of, is a conscious effort to counter his internet addiction. Another vague non-answer.
I start to doubt the recovering internet addict/maturing comedian angle. I remember being the boy’s age and how much unregulated time I spent in AOL chat rooms and on Instant Messenger. I wonder if it is even fair to use Brandon’s story to teach the boy a lesson?
Back at the high school, we make it through security and enter the gymnasium. The atmosphere is absolutely electric. Local singer Lex Allen does a gorgeous rendition of the national anthem. The anticipation builds as each of the Wisconsin Democrats deliver their stump speech. When Obama finally takes the stage the crowd showers him with love. He is just as charismatic and inspiring as ever.
It is the winter of 2019 and my fiancée and I are driving from Milwaukee to Columbia, Missouri. We are heading to the True/False Film Festival where she has been hired to work.
My fiancée is a visual artist specializing in stage design and installation. This will be her fifth festival in the last year. They have taken us all over North America. At these events we are warmly welcomed by the local arts community, her “lofi magic” transforms a space and comes alive with music, lights, and energy, and we discover new art and new friends.
These trips have fast become my favorite activity of all-time.
It is the day of Michael Cohen’s congressional testimony. The hearing coincides perfectly with our drive to Columbia, so we listen to most of it. The best is saved for last. That is, questions from the freshmen members of Congress, chief among them being a 29-year-old Democrat from New York’s 14th district named Alexandria Ocasio-Cortez, better known as AOC.
Her time is short. Her questions are smart. She is a star in the making.
The next day, while my fiancée and I are in the middle of a marathon installation at the Blue Note Theater in downtown Columbia, AOC appears in front of us, 50-feet tall. It is the opening scene of the documentary Knock Down the House, which follows four women who run for office in 2018.
AOC is in a bathroom applying makeup and making a lighthearted point about gender inequality as it relates to fashion choices for politicians. We see this scene a few more times as the projectionist tests the equipment.
The day after, we watch the entire film with a sold-out crowd. The moment AOC appears on screen the room erupts with cheers. By the time the credits roll, the theater is brimming with emotion. Director Rachel Lears receives a standing ovation before her Q & A.
At this point, AOC may be known more for how much she is hated by the right than how much she is loved by the left. This, I think, is a sign of her power. She is so sharp, so charming, and so adept at social media that the right is deathly afraid of what she could become.
It’s funny, older people think AOC is some kind of unicorn because she is good-looking, good at Twitter, and not afraid to challenge American exceptionalism, but she is similar to my peers. What sets her apart is that instead of being cynical and self-serving—like most of us—she had the guts to put skin in the game and join the circus.
A popular criticism of AOC is her opposition to the deal that would have put a secondary Amazon headquarters in Queens. Her amplification of a grassroots movement against the deal helped put it to bed, which is used to paint her as a “job killer.” But AOC’s position on the Amazon deal was a principled stance rooted in her millennial brand of democratic socialism, which rejects massive government subsidies to companies that already get tax breaks, especially one that does not even pay federal income tax.
The increasing appeal of socialism in America is a direct result of Reagan-era deregulation, which has allowed corporations to post record profits, pay out their CEOs at ever-increasing rates, receive government handouts and bailouts, all while undercutting the working class. Essentially, we have created a system that offers safety nets and socialism for corporations, while working people endure cut-throat capitalism.
In 2020, Donald Trump will run on the supposed strength of the economy, but AOC reminds us that not all jobs are good jobs.
Earlier in the winter of 2019, my fiancée and I are on a belated birthday getaway in Chicago. We are heading to The Hideout to see the comedians Patti Harrison, Mitra Jouhari, and Catherine Cohen.
It is my fiancée’s first trip to The Hideout. Wabansia Avenue is wearing a thick coat of snow on this January night. It feels like we are walking in a snow globe as we trek to the venue. We enter the front door, shake off our boots and cozy up to the bar.
“Oh my God, I love this place!” my fiancée exclaims.
There is no opening act on the bill, but Tim Tuten, co-owner of The Hideout, takes the stage. He is feeling himself and popping off about the Lincoln Yards plan. He urges the crowd to join the fight against the development and to show up at the next city council meeting to express their opposition.
The original plan for Lincoln Yards included entertainment venues to be run by Live Nation, which would have been devastating to The Hideout and other independent venues in town. These have since been eliminated, but the developers are still on track to receive significant tax breaks to build a mini-downtown that most locals do not want, which will primarily benefit the wealthy.
Meanwhile, Chicago Public Schools is starved for funding.
This is Gentrification 101.
It is time we call gentrification what it is—the pendulum of white flight swinging back from the suburbs to the cities. There may be some people of color moving into gentrified areas, but generations of institutionalized racism has kept communities of color from building wealth, so it is mostly young white people moving into neighborhoods their elders abandoned.
Since I bought tickets to see Brandon Wardell at The Hideout in 2018, I have been receiving the venue’s email newsletter. The week before the birthday getaway I learn that the musician/comedian/video editor DJ Douggpound, best known for his editing work on Tim and Eric Awesome Show, Great Job!, will be playing The Hideout in March. However, the show is at 10 p.m. on a school night.
This is a bummer, because the boy and I would have to drive down and back from Milwaukee, which is a bit more than an hour north of Chicago. His mother is not down for this plan. Yet, I desperately want the boy to see Douggpound live, because Doug is a singular talent who combines many of the boy’s interests.
The boy is a budding musician, producer and DJ, with great taste in comedy. No surprise, whenever we take the iPad, internet and video games away, his first instinct is to make music or silly graphics, which kind of makes us want to take those things away permanently.
I reach out to Douggpound via email to see if he can swing a show in Milwaukee the same week as his Hideout gig. He replies that while he would like to, he agreed to a radius clause prohibiting such a show.
While slightly drunk at the True/False Film Festival, a day after seeing the comedian Nathan Fielder’s film Finding Frances, hours after seeing a talk with Tim Heidecker, and moments after walking into the VIP entrance of a club behind these two comic geniuses, I convince my fiancée to let me take the boy to see DJ Douggpound at The Hideout.
It is the spring of 2019 and I am in front of a fourth grade classroom, reading a book about a hamster named Humphrey. Summer vacation is fast approaching. The students are antsy. Visions of swimming pools, bike rides, and staying up late dance in their heads. Most could care less about Humphrey. My mind is also distracted, because a high-profile interview that I conducted the week before is set to publish within minutes, and I am trying to formulate what I will say about it on Twitter.
Much of my time as a substitute teacher has been spent this way—with my attention split between the students and my latest writing assignment. This does not make me the best substitute teacher, but I am not the worst either. I listen to the students, I help them out whenever I can, and I make it a point to connect with at least one student each day. But as a general rule, I seek out high school positions where the students will be able to keep themselves busy or at least not throw chairs at each other, so I can simultaneously get some of my own work done.
In the last two years I have managed to land two long-term positions, which are much preferred to day-to-day subbing. Long-term gigs give you time to build relationships with students and actually teach them, instead of being treated like a subhuman babysitter.
The fourth grade position comes a week after finishing one of these long-term gigs. It is jarring to be back at a day-to-day job. After getting the students started on their science research and posting my article on Twitter, I walk around the room, answering questions and offering guidance. Being on my feet and engaging with students feels much better than sitting at a computer and agonizing over my words. Getting out of my head and giving myself over to the students makes me feel whole.
A couple years back, my fiancée quit her day job to become a full-time artist. It has not been easy for us. She too has had to subsidize her income. Walking to that fourth grade classroom I admire a series of farm animal paintings she did with K4 students as part of a residency.
The reality is that running a household with the income of two struggling creatives is not sustainable. Sure, it is meaningful and our kids are continually inspired by her artwork and my writing, but that will not get us our own house with a driveway, a basketball hoop, a garden and a dog. It will not pay off her private art school debt. It will not allow us to visit my brother and his wife in England. It will not take away the anxiety she experiences every day—wondering when the next festival job or school residency will come along so she can help out with groceries and pay rent.
I walk out of the Obama event in the fall of 2018 with a full heart, much like Election Night 2008, but this time I also have a clear mind. I open my phone and respond to the email from my friend at The New York Times. I tell him that I will not be sending the editor a new pitch. I am aware of what a Times byline would mean to my career. I am not prepared to head down that path—to accelerate the freelance struggle. Instead, I enroll in a program to become a licensed English teacher.
I always saw myself becoming a teacher, but I thought it would be after a successful career as a writer/director. I have been haunted by saying “Those who cannot do, teach.” I considered becoming a full-time teacher as equivalent to failure.
Today I see it differently. I look at my family—at my incredibly talented fiancée, our strong-willed little girl and our brilliant teenage boy—and I realize that whatever I can do to help them succeed is the opposite of failure. I realize that I am happier when I live and work for others.
When I get home from work the day the boy and I are going to Chicago to see DJ Douggpound he is on the iPad. This is how I find him most days when I come home. With high school on the horizon, girls in the mix, and his image being his greatest concern, Instagram is now his primary obsession. The struggle continues.
“Hey, grab your glasses, a snack and a water bottle, we’re going to The Hideout to see Douggpound,” I tell him.
Usually when he is on the iPad and we talk to him, he acknowledges us without looking up. Not this time.
The boy is ecstatic. We jump in my car and head south. I let him DJ the drive. We talk about music, sports, and a little bit about the future. He has so much life ahead of him.
We make good time by Chicago traffic standards and arrive at The Hideout almost three hours before the show is scheduled to start. I suggest we pop in and check out the situation before going to grab something to eat. When we walk in the woman at the door asks for his ID and I tell her that he is fourteen and my stepson.
“Ummm…” she stutters.
“We’ve got tickets to the show later. I brought him to see Brandon Wardell last summer and it was all good,” I say.
“Wait, you were at the show yesterday?” she asks. (Brandon played The Hideout the day before.)
“No. Last summer. I called ahead and the person I talked to said it was cool,” I reply, starting to get nervous.
“That was an early show,” says another woman from behind the bar.
“I don’t think he can be at the show tonight. It says 21 plus right there on the website. Let me get the manager,” she adds.
The boy and I look at each other. He is uncomfortable. I am embarrassed and angry. I can feel the rug being pulled out from under us. The manager walks in from the venue. He has already been briefed on the situation.
“I’m really sorry. I understand you brought him last summer, but things have changed,” he says.
“Man, but we drove down from Milwaukee just for this show,” I plead.
At this moment, Brandon appears from behind the door that leads to the green room. Once again, the boy is starstruck. I am desperate.
“Yo Brandon! Good to see you again man! Dude, we came to your show last summer and now they’re not letting the boy in tonight. What’s the deal?”
What a sad, shitty move on my part. I regret it immediately. Part of me wonders if I had actually followed through on The New York Times profile would Brandon have stuck his neck out for us? I also wonder if The Hideout’s strict enforcement of the age limit has something to do with their public opposition to the Lincoln Yards development.
Brandon does not engage with my plea. The boy steps in and makes friendly small-talk with him. The manager offers to refund the tickets in cash and throws in extra for gas. It is not a bad deal, but I still feel terrible.
On the drive back to Milwaukee the boy keeps our spirits up. He is excited to have seen and talked to Brandon again. On our way out of the city we take a picture outside the Illinois Bone & Joint Institute, which we joked about being our reason for coming to Chicago on our drive in. We have dinner at a travel plaza. The boy is grateful for the meal and the impromptu trip, despite how it turned out.
As we pass the Klement’s Sausage Co. factory and the Milwaukee skyline appears, I think about how this night is kind of emblematic of my life. Things have definitely not turned out the way I planned when I was the boy’s age, but I have had a lot of unexpected fun along the way.
When I was 18, my goal was to be famous by 26, because that is when Kanye West broke big, and he was one of my heroes. Not to take anything away from his artistic accomplishments, but considering where Kanye’s ego-driven attitude has taken him these days, I am not sure he is the best role model. I now look to a different Chicago guy for guidance.
It was during Barack Obama’s speech at the high school on Milwaukee’s near north side that I decided to become a full-time teacher.
From the outside, it might look like I am giving up on my dream of being a writer/director. But the dream was always rooted in making a difference and inspiring positive change in the world. Now I realize that I can do that more directly by teaching and mentoring youth. I also realize it is a decision based on what is best for my family, what I am good at, and what satisfies my soul. Plus, I lost the desire to be famous.
To be sure, I will never stop writing. I did not stop when I was living in Scotland and working temp jobs. I did not stop when I was working on a farm in Oregon. And I did not stop when I was in between Montréal and Milwaukee, scraping together a life.
It is a few days after working in the fourth grade classroom. My family and I are on a road trip to Canada where my fiancée will work at another festival. Our first stop is Detroit. We head straight to a DIY skate spot the boy knows about.
The skate spot is located northeast of downtown. The neighborhood seems a bit sketchy, but so is almost everywhere in Detroit. My fiancée does not think it is a good idea to be there. The boy does not protest. I, however, insist that him and I check it out while the ladies stay in the car.
There are a handful of adult skaters and a pair of preteen boys on bicycles at the spot. The boy does not hesitate to jump in. I sit on a log with a nice view of the action. There is graffiti on everything. The vibe is chill. It is a sunny day. There is even a place for the little girl to run around.
After about five minutes I head back to the car. As I am walking, a black car pulls up and a skinny, grey-haired white guy gets out and grabs a skateboard from the trunk.
“Look at this lame-ass suburban dad,” I think to myself.
I jog down the hill. When I reach the sidewalk the man turns around. He is a few feet in front of me. We nod at each other and he smiles. I do a double take.
I try to calculate in my head how many skate spots there are in the world. Indoor, outdoor, recreational, professional, municipal, DIY, all the backyard ramps and converted pools. I would guess there are well over a million, but I do not know much about skateboarding.
However, I do know what Tony Hawk looks like.
Of all the skate spots in the world, the most famous skateboarder on the planet just happened to swing by this one spot in Detroit on this one day, five minutes after we arrived en route from Milwaukee.
Very rarely do I cuss in front of the little girl, but when I get to the car I lean into the window and say, “It’s cool. There’s a log we can sit on and a place for her to play. Also, TONY FUCKING HAWK IS HERE.”
I see the boy’s face light up the moment he realizes who the old guy is. Sitting on the log, Tony does a grind right in front of me and smiles just as he did when we first nodded at each other. Later, he watches the boy skate and gives him advice.
Tony spends ten minutes or so trying to land this one trick. It seems pretty difficult, but then again, he is Tony Hawk. He gets frustrated with himself, but he is persistent. After one fall he does not get up for almost a minute. We all look at each other like, “Did we just see the end of Tony Hawk’s career? Are we going to have to take Tony Hawk to the hospital?”
Tony gets up, eventually lands the trick, and we give him a round of applause. Before we leave the boy gets up the nerve to ask for a selfie. Then I see TONY FUCKING HAWK fix his hair as the boy readies the phone camera. What a way to start the road trip. It feels like a sign that we are on the right path.
Then, a few days later, the boy and I take an Uber to a beach in Toronto, we dig our feet in the sand and we enjoy Vampire Weekend’s first show on the Father Of The Bride Tour—the boy’s surprise eighth grade graduation gift.
It is foggy, overcast, and there will be patches of rain, but as I have found, the best concerts are in the rain.
Look outside at the raincoats coming, say oh.
Hey, hey, hey, hey.