“Unkie Herb, what advice would you give to a boy who will most likely become a bum like yourself?” — Bart Simpson
 “Discarded pizza boxes are an inexpensive source of cheese.” — Herb Powell

I freely admit that the following introduction is overly wordy. Therefore, I have broken it up into three chunks, each of which should give the emotive reader ample opportunity to feel thankful, superior, or that kind of self-gratifying pity that made Upworthy somehow popular. Enjoy.

1. Middle Class Homelessness: Yup, This Is Happening

2. Going Broke: It Sucks

3. Let’s Talk About Politics: Cycling with Trump on the Fury Road

Part 1 — Middle Class Homelessness: Yup, This Is Happening

“You’re going to live in your car?” — Homer Simpson
 “Oh, no, it’s just a little camp out tonight. Then off to my sister’s apartment in Capital City. Hey, what do you think, kids? The big city!” — Ned Flanders

The concept of at least temporary homelessness is something that even well situated people have contemplated. It may just be some variation of “I have to stay with friends or at a hotel for a few weeks”, but not having a kitchen, bathroom, and bed of your own for a little while has crossed most people’s minds. Back before my professional life went completely to shit, I once lived for a month between leases at a friend’s apartment while he and his future wife were out of the country.

Becoming homeless with no scheduled replacement is different, and considerably more disconcerting. The first thing that happens is a daily awareness of the date you have to leave. For me it started months ahead of time. Knowing when the lease expired and that I couldn’t afford something new became one of those facts that crossed my mind several times a day whether I wanted it to or not. Moving in general can cause that to happen, but it’s far more intrusive when you do not have a new place or the income to rent one. At first the count is in months, then it’s a hundred days, then it’s just a few weeks, and before you know it you’re thinking things like, “I’ll go to the store next Tuesday to get food that doesn’t need to be cooked in an oven”.

Thanks to the social capital that comes with a middle class background and a college degree, I had the luxury of not being thrown out on the curb with my meager possessions. I’ve split the five weeks since between my office couch and my sister’s apartment. But my failing company is unlikely to have that office much longer, and my sister’s place is a semi-legally rented basement with no thermostat in which I sleep in the kitchen/living room.*

(*I should point out that it’s a very nicely furnished semi-illegal basement and that my sister is a wonderful and generous person, but it’s not workable as long term housing.)

And so, with my recently returned security deposit check in hand, I decided that living in the wind would be a lot easier and more comfortable with decent equipment. Eleven hundred dollars(!*) later, my bicycle is rigged for long distances and I’ve got a (used) laptop and a (new) cell phone that will let my on-line life continue (work included) even as my meatspace life changes radically. As another demonstration of the money saving power of having non-poor friends, I got a sleeping bag, water bottle, handlebars, and some camping gear for free from people who weren’t using them. That alone probably saved me two hundred bucks.

(*Middle class homelessness is just like every other middle class thing — relatively comfortable and shockingly expensive.)

Home sweet home.

Decent gear or not, however, I now reside at no fixed address. The most pressing and intimidating aspect is the constant insecurity. Even if you live someplace where there’s no need to lock your door, you still have the lock. Your bathroom has a lock. Your bedroom probably has one too. You may live with a bunch of screaming children, but you have at least somewhere to change your clothes, take a shower, or just sit for a minute without worrying about some stranger walking up. A tent near the side of a highway just isn’t the same thing.

None of this concerns me from a physical safety standpoint. I’m a six-three white guy with a shaved head. Nobody’s going to fuck with me unless I give them a reason, and in rural, white America, where I’ll be doing most my of my pedaling, me and my rockin’ farmer’s tan don’t even stick out. But waking up in a place you’ve never been before, where you are tolerably welcome at best, is a lot different than waking up in a familiar bedroom. The feral part of your brain that worries about getting attacked by something with large teeth simply won’t relax without the accustomed reassurance of a roof and walls.

Still, being on a bike and in a tent is a lot safer and less unpleasant than, say, being a refugee caught at the Macedonian border, or burning e-waste for a living in Nigeria, or working in a North Korean salt mine. I may have fallen most of the way out of the comfortable class in America, but I’m still in America, and still a lot better off than people even poorer than me in this great land of ours.

Part 2 — Going Broke: It Sucks

“You deserve all the finest things in the world. And although I can give them to you, they will be repossessed and I will be hunted down like a dog.” — Homer Simpson

My tiny, family software company took one on the chin in the Crash of ’08. And while it survived, and has had many ups and downs since, it’s never recovered. We had an okay 2012, but saw things stall out in 2013. By 2014 a new and general deterioration was apparent, which became critical in 2015. Repeated acts of desperation have maintained a pulse, but they’re getting more frequent and less effective. Even on teevee they only shout “Clear!” so many times before someone says, “Let’s call it”, and that’s about where we are.

Since this is a family company, it’s a more drawn out process than if I’d simply lost my job. Instead of the paychecks just stopping, at first there’s one you have to hold for a few days before depositing. Then there’s ones you can’t cash at all. After that, you get a smaller check just so you have something, and then those, too, become smaller and intermittent. Even living like a monk and surviving on pasta and rice, years of savings can’t withstand that kind of disruption for long, and pretty soon you’re having a very awkward conversation with your landlord. There is still a trickle of revenue, and even the occasional spurt, but we’ve had the “what *is* the furniture worth?” conversation more than once now.

If this were a steady downward process, it’d be easy know when to head for the exit. But then there are good months and encouraging developments, and the dreadful thought of walking away from all that work with nothing to show for it makes you hang on to each one. Basically, a family company is like a tontine with people who share your DNA: it gets *really* grim before it ends.

Which is not to say it’s all bad. Office politics are basically nil, you don’t have to attend pointless meetings, even the occasional overripe fart is cause for laughter rather than any seething, workplace resentment. Crucially, there’s none of the Mickey Mouse bullshit that prevails at so many offices: dress codes, mandatory training sessions, bland holiday acknowledgements, and all the other stuff that made Office Space a cult classic. Case in point: the last time my nominal boss yelled at me was when I was about eleven.

The hands down best part of it is that your efforts are benefiting people you care about, not faceless stockholders or wasteful rich people. There is no way to overstate how much easier that makes putting head to pillow every night.

Nice as all that is when there’s money coming in and growth year-on-year, these days it isn’t paying the bills. The good news is that I’m still *just* this side of the federal definition of homeless. (I don’t have stable housing of my own, but I can still find short term shelter with friends or family.) The bad news is that I have a very mixed score when it comes to risk factors for long term homelessness.

On the good side of the ledger: I’m only recently unemployed (or underemployed, as the case may be), I’m relatively young (36), and I have no arrest history. On the bad side of the ledger, my housing disruption was anticipated but unavoidable, I have significant unsecured debt (usury laws really need to make a comeback), and I’ve recently skipped medical care that affects my ability to work for reasons of cost. And, if we’re being honest, there’s also substance use that crossed from funny into worrying well over a year ago. (Just pot and booze, but still.)

Because this is America and it’s 2016, the unsecured debt and the lack of medical care are intricately intertwined. Like many a foolish small businessman before me, I forwent pay by stacking up a decent credit card balance — twice. (The first time we got back to zero, this time I’m less hopeful.) That lack of pay also led me into the world of Obamacare, which is both a vast improvement over the previous system and a kafkaesque nightmare that borders on a human rights violation. I’m on track to make about $15,000 this year, which means that the federal government will send $223 dollars per month to Blue Cross to “insure” me with a plan that has a $6,350 deductible. In other words, for me to see any benefit from my insurance, I would first need to spend over a third of my annual (pre-tax) income out of pocket. This is somehow legal. #ThanksObama

So last December when I fell off my bike (I sold my car a long time ago) and smashed my shoulder, I didn’t go to the emergency room, or even to the urgent care place around the block. A four figure bill means that I’m bankrupt, which will torch my credit rating, which is just about the last vestige of the steady paycheck life I have left. Beyond the moralizing symbolism of it, a healthy credit number will make it a lot easier for me to rent a place again should I ever have the means, so the shoulder will have to wait. And, hey, my clavicle is still attached at one end out of two, and that ain’t bad. If you count the other side, I’m at three of four, and that’s enough to pass most college and high school classes.

Shoulder selfie!

For the first three months it was getting better; then it stopped getting better. Recently, however, it’s started to get worse. To arrest this deterioration, it will need an X-ray, and then it will likely need surgery. The soonest I’ll be able to afford even the first visit is January, and that’s *if* it holds together until the sign up period in November and *if* I can afford a more expensive plan by then. Life at 138% of federal poverty level sucks unwashed donkey balls. I don’t know how people below that line even manage.

That said, and however much it hurts, my shoulder is still mostly functional. And since it’s lasted eight months with only informal treatment, it can last four more [crosses fingers]. In the meantime, I have much for it to do.

Part 3 — Let’s Talk About Politics: Cycling with Trump on the Fury Road

“You’ll never go broke appealing to the lowest common denominator.” — Lisa Simpson

The hardest realization for political junkies to accept is that most of the happenings they/we obsess over don’t matter a damn. Whether we’re talking about legislative machinations or election results, the story-du-jour rarely affects an outcome. For example, Willard “Mitt” Romney’s remarks castigating “47%” of Americans as hopeless moochers was a nuclear level event for the politics set, but actually mattered very little for his eventual defeat. Similarly, when Ted Cruz and his cadre of fanatics shut the government down in 2013, the widely publicized expectation, left and right, was that it was Bad for Republicans, but the 2014 electorate didn’t care a bit.

That humdrum reality has to be borne in mind at all times as CNN, FOX News, and their counterparts at otherwise respectable publications spend time hopping about over the latest mouth sounds from Donald John Trump, Republican nominee. Did he just insult Latinos? Wink at Illinois nazis? “Soften” his approach to rounding up immigrants? Feh. In all likelihood, none of it will matter.

What will matter is that he has no meaningful ground organization, has barely been advertising, and is generally incompetent as a political candidate. He is going to lose, probably by a huge electoral margin. But saying so won’t generate any clicks, and that matters more than anything else in a time when a lot of news outfits are unscrewing lightbulbs to save on the power bill.

Nevertheless, he is still going to get well over 40% of the vote, probably something just shy of 60 million (60,000,000!) ballots. (For the record: my prediction is that he’ll take every Romney state minus North Carolina and Arizona, that’s 358 for Clinton and 180 for Trump, though I wouldn’t be surprised to see the Buckeye State go Red because Ohio gonna Ohio.) Beyond just casting votes for him, Trump’s unique brand of substance free bitterness has given many of his supporters free license to indulge their worst impulses. Whether this is brown kids getting picked on, wait staff getting stiffed, or this putz, our freak flags are flying.

Dude. You’re giving roided out meatheads a bad rep. Chillax, brah.

Donald Trump’s America is a very peculiar place that is going to come crashing down in just under nine weeks. Like a vanishing natural habitat, I want to see it before it’s gone. The people who vote for him will still be with us, of course, but their plumage won’t be this festive ever again. (Well, I guess one of the Duck Dynasty guys could win the 2020 nomination, but even that probably wouldn’t wind them up as tight as they are now.)

The only viable alternative is a pro-war ex-First Lady with deep ties to some of the crookedest sectors of American business . . . whom I badly want to win. This is some serious banana republic shit, and since I can no longer afford to put a roof over my head, I might as well be there as it happens.

But Trump-Clinton is overdetermined. He’s outmatched in every category from organizing and fundraising to the simple ability to give a coherent speech. The real action this year is on the Senate and House levels, which will go a long way toward determining how functional (or not) our federal government is next year. With that in mind, my planned route will take me through competitive Senate and House races in Michigan, Wisconsin, Illinois, Indiana, Ohio, Pennsylvania, New York and New Hampshire.

In particular, Democratic control over the Senate is looking very dicey indeed. Failure to take the Senate wouldn’t be a Trump level catastrophe, but it would still be very bad. To understand why, just imagine what a freshly returned Red Senate majority will do to the thousand or so nominees Hillary Clinton sends them. If the prospective ambassador to Fiji once filled out a dental insurance form incompletely, Mitch McConnell and Bob Corker will make sure it’s national news for weeks on end. It will be ugly in ways that will make us pine for the days of Trump, and that’s before you start thinking about the possibility of the Supreme Court only having eight or fewer members until sometime next decade.

So, with all that on my mind and a bike seat up my butt, I’m planning to spend the weeks between now and the election doing a bunch of campaign volunteering, and hopefully having enough time left over to mingle with some Trump fans in between. Mindful of the way my luck has been going of late, I wouldn’t be the least bit surprised if I get splattered across a highway ten miles out of town because some guy in a semi was taking a picture of his dick.

But assuming I survive and have the time and energy to type anything up, you can follow along here at this site or on my worthless Twitter feed. Hopefully this fake work will be more fun and interesting than the real work that no longer pays enough for me to have a front door.

Originally published at charliesweatpants.com.