You remember the last time you passed a homeless person? That’s not a trick question to make you feel bad about the fact that you don’t help the homeless nearly enough and you’re probably going to hell for it. It’s just a clever opening sentence to set up this next sentence. In the greater metropolitan area of Manhattan, your answer is probably going to be “Earlier today.” Even if you don’t know for sure, it’s a safe bet you did. ‘Cause there are a fair amount of homeless people here.

With the concentration of homeless people in the city, at some point in your tenure here you think about what it would be like to be homeless. Which is to say I’ve thought about what it would be like if I were homeless. And I know one thing. I’d be terrible at it.

Now, to be clear, my intent is not to make fun of the hardships homeless people endure. Their struggle is real, and the generalizations I may make are intended to highlight my own personal idiosyncrasies. In other words you’re (hopefully) gonna be laughing at me, which is good, and not homeless people, which is bad. OK, awkward stuff done with, on to awkward funny stuff.

Right off the bat, I know I wouldn’t really have a problem with is going to the bathroom. I could always street-pee. It’s not preferable, but I’m well-versed in it. If you’ve had a night out on the town in this city, you’ve most likely at some point executed the street-pee, as eloquently described in this sketch. But that’s really unnecessary (at least during normal working hours). As most seasoned city-folk know, you can bust up into most any Starbucks and use the bathrooms with no problems. And since Starbucks is ubiquitous, there really shouldn’t be an issue with finding a bathroom. Sure, I’d have to overcome my personal problems with pooping in public places, but I’m confident I could find a special Starbucks that feels “safe.”

Probably my biggest problem with being homeless would have to be cleanliness. Someone somewhere said that “Cleanliness is next to godliness.” That person is my personal hero. Hopefully that person wasn’t terrible in all other aspects of humanity, ‘cause I don’t want to idolize a monster (albeit a clean one). My point is that I am a clean person. I shower daily (sometimes twice, like if I do something strenuous like walk up and down the stairs). I change into crisp, fresh, undergarments with the same regularity, and I am hyper aware of smells on both ends of the spectrum (from BO to Axe Body Spray). This means that I would still be keepin’ it fresh in spite of my homelessness. But keeping it fresh means that my panhandling abilities would be greatly diminished.

There’s a fine line of appearance when panhandling, or begging as people not in the 19th century tend to call it. If you look too well-kempt, as I surely would, people would immediately dismiss you as a scammer trying to make a quick buck. But on the other end, you can’t look like a complete mess. If your clothes are completely in tatters and you’re caked in dirt, people will be too repulsed to give you money (unless they’re one of those rare “good people who can look beyond appearances”). The most successful would have to be slightly run down, a little rough around the edges, but with an appearance of trying to keep it together. What that  conveys is “I just fell on hard times for a little and could use help from my fellow man.”

Ruminating on how appearance affects return on investment in begging actually highlights the overall reason I’d be terrible as a homeless person. Which is that it’s dominated by the unknown. When my roommate got one of those refillable coffee pods for his Keurig, I didn’t know how to use it, so my ass was on my computer looking up the manual AND an accompanying video (the key is to use a medium grind, and keep the coffee below the inner lip). And that’s an admittedly insignificant thing in my life. So I would definitely need to research being homeless before I’d be comfortable doing it. Is there a rule about sleeping on a park bench? How do I keep warm when it’s cold, or cool off when it’s hot? Where are the nearest soup kitchens, and how does that work? You just go in and get handed a bowl of soup? I’d be on my phone constantly Googling things. And that’s an issue, ‘cause I imagine I wouldn’t be able to afford a good service plan.

I don’t know, maybe that means I’d actually be an efficient homeless person. I’d have a log of all the Starbucks and which ones restock their toilet paper with the most regularity. I’d be constantly copy-editing my speech when asking for money, and if it wasn’t effective I’d try to do some market research to figure out how to best revise my strategy. I’d have accurate records of which trains are best for sleeping, and quarterly meetings (with myself) where I’d review revenue charts. At the very least, I know I’ve got the facial hair for it.

All that being said, being homeless is a harsh reality. I feel for the people out there who are struggling. I hope I don’t ever have to experience that reality, and I wish I could help more than I can. If you want to help too, you can donate to the following charity: http://www.coalitionforthehomeless.org/

And please let me know what word resonated most with you when I come by to ask for spare change.