Two years ago, when I first went temporarily homeless willingly, it was a bittersweet pill to swallow. I had quietly left Toronto with little support, and actually, to a bit of criticism. As I tucked my -10 degree sleeping bag over myself in preparation for a cold night in my car, somewhere along the interstate between Wisconsin and South Dakota, I confess I felt a little alone with a tinge of self-pity over my life situation.
I wasn’t used to not knowing where I would be the next day or week. I wasn’t used to not having a familiar place to return to. I wasn’t used to the uncertainty. I wasn’t sure how long I could pull of such a lifestyle or if I had made the right choice. I wasn’t used to being in the full driver seat of my life and having so much control over my time and location.
So there I was, watching the snow fall on my car, lost in a moment of doubt, wondering if the next days, weeks, and months would lead to something fruitful…
…
Fortunately, it was a short-lived moment because I remembered, this is what I wanted.
I wanted to pick up and leave off, not weighed down by a long rent lease or mortgage payments.
I wanted to live somewhere else in the world.
I wanted to know what life was like for other people, outside my familiar surroundings.
I wanted the freedom to go wherever, whenever, I pleased.
That was my first taste of that life. And I loved it. It wasn’t long ago, but thinking of sleeping by myself in that cold car and cooking breakfast at a Walmart picnic table the next morning sounds beautifully nostalgic now. It was the start of discovering some purpose in my life, and that I was moving towards that unknown purpose.
Since then, if you’ve followed me on Twitter or Facebook, you’ve probably seen that I’ve moved around quite a bit, often finding a place to stay, but sometimes not. Every time I cross a border and fill in the entry card, I’m not sure what to write when I reach the “Address of Accommodations” box. I’ve been homeless at times on two continents since that first night in my car and must have slept in over 50 different places in the past year. Let me set something straight though. I’m not glamourizing being homeless because I know it’s not always great for those who haven’t chosen it. Being homeless may sound bad to most, but in my case, it’s not. It’s like a side salad that comes with my choices, and I accept it graciously.
Many posts ago, I turned a few heads when I wrote that if you want something, you have to want it really badly, almost like it’s a life-threatening situation. Really think about that again. If there’s something you want, what are you willing to do for it? What comforts and routines are you willing to give up?
I see this situation all the time now. I see someone who wants something really bad, gets a momentary adrenaline pump, and genuinely seems to want to go for it. And then, reality, other people’s reality, kicks them in the butt. “Reality” people bombard the dreamers with their “expertise”, tell them the flaws with their plan, or raise doubt in the dreamer’s mind: It’s already been done. What are you going to do when you come back? How are you going to survive? No one’s done that before. (To me, the last statement sounds like opportunity!)
Alas, as soon as the dream has come, it just as quickly disappears. The rookie dreamer realizes he/she can’t give up their security, lifestyle, or even creature comforts to pursue a dream. They sink back into their routines. The dream becomes taboo to talk about – regret brushed under the carpet. I don’t blame them. Once you get stuck in a certain familiar lifestyle and routine, it’s hard to enact change.
Perhaps it’s not natural to experience so much upheaval and uncertainty. For many people, even a mild disruption to their daily patterns – a subway delay, bad coffee, daylight savings time (the lose-an-hour spring one) – warrants a mild panic attack or generates enough cause for a rant. Maybe unpredictability shortens your life, but I’d choose a short, well-lived life over a long, mediocre one in a heartbeat.
Look, you don’t have to liquidate your house and assets and leave like I did to pursue a dream or to live on purpose. But what about eliminating some excess in your life? How about trimming some of that fat, like the time wasted accumulating things or trying to please everyone in your life? What about negotiating more free time for yourself? What about giving up a few hours of sleep or TV each night to work on something important? What about seriously breaking your old programming, your old routines, and your definition of reality?
The late Steve Jobs said, “Don’t let the noise of other’s opinions drown out your own inner voice.” Digest what Steve said for a moment. Then turn the switch on.
Now,
…
… define your reality.
…
…
Next,
…
… believe in it!

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