In 30 Days, I’ll Be Homeless


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

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

This will be interesting =)

– C

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