Every week I set aside 30 minutes to sit back, relax, turn on Netflix, and go through the week’s accumulation of junk mail. One pile for recycling, one pile for shredding, and one pile for further investigation. After wading through 7 new offers for “pre-approved” credit cards and 4 offers for debt-consolidation services, I came across this…

Health bill

Not the most pleasant news to receive on a relaxing Sunday. Turns out I have unpaid health bills from awhile back when I decided to undergo a series of tests to figure out what was wrong with me (turns out I simply had a persistent cold). The worst part? Turns out they didn’t have my insurance on file and thus, I’m footing the full bill… yikes. Even the mis-addressed Victoria’s Secret magazine wasn’t enough to cheer me up after that.

So what now?

Now… I fight it. Armed with health insurance information and the knowledge that bill collection is a huge pain in the ass for health care organizations, I’m going to do my best to cut this down to a fraction of the total. #onwardho!

Homeless in 29 days.

After a tame Friday night (remember – no drinking this month), I woke up early feeling refreshed. After a little work and an episode of How I Met Your Mother (hilarious), I biked into Cambridge for brunch at a colleague’s restaurant. Today was their first day open and I was their 1st customer. Tasty food, nice atmosphere, and friendly staff. But my visit wasn’t just for the free Mexican tapas… the restaurant is close to a bike path that would lead me out of the city and close to some woodsy areas. Back on the bike!

Heading out of the city on the bike path, I had one mission: FIND A NEW HOME. I need to find a spot where I can sleep at night. Preferably away from people and any well-trafficked areas.

At first pickings were pretty slim. Every bit of foliage that might offer some respite from the public was accompanied by beer cans and plastic bags… indicating the likely presence of homeless.

About 5 miles outside of Cambridge I found myself noticing more and more foliage. Quickly the bike path surroundings transitioned from small bushes and shrubbery to big bushes and forest. A couple miles further and I discovered a path leading me into the forest. Win!

Following this path inwards and delighting at the noticeable lack of beer cans, I found a divergent path that led to a small clearing. My new home? I was immediately attacked my swarms of mosquitos (note to self: buy bug repellent) but the location couldn’t have been better. Secluded, quiet, and with some flat-ish space to lay upon. I made note of the location and returned to Boston.

That was all fine and dandy, however, the real challenge for the day hadn’t begun…

I had two social outings after my excursion into the woods:

  1. Attending a small fundraiser for Perfect Miss New England, and
  2. A “white party” with a bunch of rich people

Both involved plenty of alcohol, and both were with complete strangers. Challenge… ACCEPTED!

A few weeks back I’d danced salsa with the “Miss”…

Salsa with stranger

…and she invited me to her fundraiser. Which centered around a drinking game. Soda water and lime for me =)

I leave the Miss and her crew behind and head to the White party, which I assume is titled as such for the group that I hear is behind it, Charles White, the apartment complex in Back Bay.

I arrive to find a celebration of white, as in, the absence of color. My dark blue jeans and blue striped shirt stand out enough to get the host’s attention: “You’re wearing color?! OK you have to get punished. Drink this shot.”

Less than 5 minutes into the party and I’m put on the spot with a drink.

So did I give in and conform for social norms’ sake? Hell no! I took the shot and handed it off to someone else. Now where can I get me some soda water and lime?

The rest of the evening was spent doing the typical “meet & greet” routine while dodging jello shots. I’ll admit it wasn’t the easiest to deal with considering I had my future homelessness on the brain, but it was something worth getting used to.

White party

I’m off to bed. I need to enjoy it while I have it!

It’s the tail end of the 1st of August, and as of today, I have exactly 30 days to prepare for my newest experiment: leaving my apartment behind, ditching the majority of my possessions, and living in the great outdoors.

It’s pretty wild, but I’m not going “Into the Wild” wild here… I’m still working my full-time tech startup job and doing consulting work on the side. It’ll be a huge change in my lifestyle — no kitchen for cooking, no couch for relaxing, no bed for romancing. But freedom’s worth it. And that’s exactly what I’m going after here: FREEDOM. Freedom from debt and the stress associated with it. Freedom from being on edge at work knowing that if I lose my job I’m royally fucked. Freedom to operate in the world knowing that I have the ability to go anywhere and do anything.

I’m chasing financial freedom. But that’s not all…

Ever since the the elementary school playground, the middle school hallways, and the high school parties, I’ve been extremely shy. You wouldn’t know it if you saw me, and my friends would tell you I’m full of shit, but it’s true. I was the kid who was asked out by girls but was so full of self-doubt and insecurity that I assumed they were doing it out of pity and not because they wanted to go out with me. In high school I had a girlfriend (we only dated because my friend pushed me to give her attention and she ended up asking me out) who once, while we were making out in a car, asked me, “do you not want to have sex with me?” !!!!! I wanted nothing more! But not knowing the “rules” of relationship intimacy and being afraid to push the boundaries, I never dared go any further than kissing. To her question, I assured her I most definitely DID want to have sex with her… but as I never initiated, nothing ever came of it and we split up shortly after.

Since then I’ve come a long way. I’ve walked around Boston high-fiving strangers, complimented almost everyone that passed by me on the street, asked strangers to dance salsa with me in public (and then proceeded to actually do it), and pretended to know people and then gave them a big hug while they awkwardly hugged back whilst trying to recall who I was. I’ve come a long way indeed.


One’s comfort zone is a dynamic beast. While you might feel on top of the world as you do cartwheels down a busy street one day, the next day it takes willpower just to greet a stranger as you wait in the elevator. There are a variety of factors that play into this — context, mood, time since last push beyond one’s comfort zone — but the end result is the same: your comfort zone grows or shrinks depending on whether you’re leaning forward or slouching backward. And for me, it’s time to lean forward. HARD. (Sheryl Sandberg knows what’s good.)


In the spirit of leaning into mine, I’m joining Tim Ferris in a NOBNOM month. For the month of August, I will observe the following rules:


Alcohol temporarily and artificially expands one’s comfort zone and lowers testosterone. Masturbation temporarily satisfies the endless need for physical intimacy with others.

This NOBNOM-ness is only a small part in preparing for the great leap I’m making on August 31st (homelessness.) But it’s a start.

As I approach “H-Day” I’ll be planning for my new lifestyle, pushing myself outside of my comfort zone, and chronicling my experiences online. You can observe my steady descent into madness* right here on homelesscharles.com.

*my friends are placing bets on how long I’ll last

This will be interesting =)

– C