One Month Homeless: The Good, the Bad, and the Ugly

The Good, the Bad, the Ugly

The truth is more surprising than fiction…

That’s what my friend Joe Johnson said after introducing me to a friend of his who had just heard me say that I’m homeless. The onslaught of questions that followed reminded me that I’ve been meaning to sit down and consider what my life is like right now. Things are moving so fast that it’s hard for me to really consider what’s going on, instead, I often find myself simply jumping from one thing to the next.

I’ve made it a full month without a regular place to sleep. Actually, almost a month and a half now. I was planning on writing this post on October 1st, but as has been the case with many things in my life recently, it’s been hard to make time for it. A lot has changed since going homeless over a month ago. And that’s the topic of this post. The good, the bad, and the “ugly” of my transition into this new lifestyle. The change has been overwhelmingly good. But it’s not all rainbows and unicorns.


  1. $$$. I’m saving bundles of money. No rent, no electric bill, no internet bill. Additionally, not drinking has saved my wallet as well.
  2. Healthy eating. I eat spinach for breakfast. Along with chard, kale, brussels sprouts, olive oil,
    Healthy food

    Guac-broc with egg, banana, and salmon.

    cinnamon, and flax seeds. The rest of the day is similarly themed. This diet started as a way to strengthen my immune system, but the energy and “clean feeling” benefits have bolstered my resolve to keep this going strong.

  3. Healthy moving. I workout every morning before work. This started with the intention of getting my brain functional in the morning as I was ditching my morning coffee routine, but I also see the value to my health and physical fitness.
  4. Time. I don’t vacuum carpet, mop floors, change bed sheets, wipe down dusty surfaces, or take out trash/recycling. That’s a lot of extra time I can re-purpose.
  5. Learning. Not having a place to recline and be lazy means I’m almost constantly in a state of action. From taking an online course on the history of our species to studying the fundamentals of entrepreneurship to lunch dates with local innovators to stay abreast of progress… I’m soaking in the knowledge.
  6. Comfort zone. What I’m doing is still outside of my comfort zone (though I’m growing more comfortable with it every day.) Having made this big leap, other things outside my realm of comfort have become more attainable. Hand stands in public places, dancing with strangers outside the subway station… I’ve even started going to church on Sundays to challenge my non-belief.


  1. Lack of sleep. I average 5 hours of sleep a night. For someone used to a solid 7.5 hours a night, it’s a significant change.
  2. Bug bites. I know they’re necessary for our existence, but damn… bugs are all over the place. #notinmybackyard (or rather… #notinmywoods)
  3. Stupid mistakes. I’m finding myself making mistakes due to not being able to always anticipate the consequences in my new environment. For example… diving into my hygiene container to “discover” my razor had slipped out of it’s holder. Or… the fact that I haven’t done laundry in 3 weeks due to timing issues. Thank you Ministry of Supply for creating awesome non-iron and super wrinkle resistant clothing.


  1. Relationships. Out of everything, my personal relationships have likely taken the biggest toll thus far. How do you maintain an intimate relationship without personal space of your own? It’s difficult, that’s for sure. Even friendships aren’t as easy to maintain since I’ve thrown a ton of activities into my life. This is definitely an area I need to work on.


And there you have it folks… the good, the bad, and the ugly of my homeless lifestyle (thus far.) I’m wiped and not going to review this so apologies in advance for any mistakes / errors.

4 Comments on “One Month Homeless: The Good, the Bad, and the Ugly

  1. For a second I got really excited because I thought that photo was actually you. It would’ve been super epic. Anyway, good to hear that you’re doing well and learning lots. Thanks for keeping us updated!

  2. Yeehaw!! Happy Birthday brotha, glad to hear all is well on the Western Front.

  3. Hello. 2 AM, found your website by mistake (I was actually searching for articles on “focus”) and I like it very much.

    I can’t say that I have the balls to do this but I’ve had my own six month period of couch surfing just for the same of it.

    However … Your last update was one year ago. What is new? What happened?

    • Hi Razvan,

      Thank you for your comment – I’m glad you like the site. You’re right, I haven’t updated this in quite awhile.

      After 4 months sleeping outside I paid off $25,000 in debt and moved into a cheap apartment where I could begin my new life as a debt-free man.

      Are you currently couch surfing? How goes your journey?

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