A Funny Thing Happened on the Way to the Homeless Shelter

A minimalist world traveler living out of carry-on luggage while running a business is not how I’ve always done life. A few years back was the worst collective set of experiences of my life so far, and I thought everything was over other than being actually dead. But I have to back up a little further still… (***SPOILER ALERT***: I didn’t die.)

We’re all familiar with the default life model laid out for us as we’re told to live by parents, teachers, employers, and anyone else involved with making our decisions on life plans growing up in the consumer culture of the United States:

Go to school, get good grades, get a job, buy a house, buy some other stuff, have a family, and someday retire so you can enjoy your own time.

I did most of that, accumulating more toys than I had time to play with. They were stored in my big garage of my big house filled with big piles of things the ads alluded would make me happy and solve all my problems. There was so much shit in the garage that only one of the multiple cars I had at any given time would fit in the 2-car garage, and only if I wasn’t working on a project in there (usually fixing or maintaining one of my other toys).

I worked a lot for someone else, helping build their company while I tried to keep up with maintaining all the cars and toys and other shit I never had time to enjoy because I was too busy working to keep it at all.

Giving it Away

If you weren’t aware of this already, divorces can get expensive. Especially divorces that aren’t happy divorces. Is there a happy divorce? I don’t know, but mine didn’t go the way I hoped.

Among several other obvious problems during this period of my life, I clung to the idea of keeping all my stuff. All these things that meant so much. These cures for any form of discomfort that made my life so much better. I fought pointlessly as I watched all my precious stuff disappear in a variety of new ways I hadn’t even considered prior to this new period of divorcery.

When the debris finally finished falling, I had about 2 bags of clothes, an old desktop computer, and a mountain of debt for things I didn’t even have anymore.

All seemed lost and all that dramatic sounding stuff as far as I was concerned. Here I am in my 30′s with not a thing to my name. This is not the way it’s supposed to be. All that money and stuff I lost. “Wah, wah, wah!” all day long I could whine about it then, and did so.

But a funny thing happened in this new reality I’d never considered once I got a lot of the whining out of my system. I felt relieved.

Not just because the divorce ugliness was over, but because I had a fresh start. I knew somewhere deep down that all this stuff was actually a burden. The ads had lied all along. The feelings you’re supposed to get from having the outside things never actually give you that. Not if you aren’t well on the inside. I suspected it even while I had everything, but it was lost among the thoughts that the next new thing would be the thing that made it all better.

The things are never the answer. Sure, things can help if you have them for the right reason. Nothing wrong with having stuff. So long as it doesn’t really own you.

Now that I had no more things, instead of the dread I felt at losing all my important nonsense from this probably worst situation I’d ever encountered to this point, I felt that situation was really a blessing in disguise. Certainly wasn’t the way I’d have written it, but I was determined to make the best of it.

The Funny Thing About Stereotypes

I can’t tell you how many people tell me now how they envy my lifestyle now. How they “wish” they could do what I do, like it’s some impossible task to slow travel and run a location independent business from anywhere on the planet in the 21st century.

I’m not talking about the stereotypical cube farmer who hates their entry-level office job that tell me this either. I’m talking doctors, lawyers, business owners of all levels. All who feel trapped by their own lifestyle. Feeling like they were sold a bill of goods to do this “right thing” and it would solve all their problems just like buying that ski boat would do for me back then.

It doesn’t matter how much stuff you have or what section of the white collar or blue collar workforce you’re in. If you aren’t doing what brings your life joy every day, you might just be doing it wrong.

Not joy as in “there are never any problems at all in life” and you’re always comfortable and you’re partying “Jordan Belfort before that little FBI thing” -style kind of joy. This isn’t about always being comfortable and partying constantly.

It’s doing the things that you’d be doing even if you won the lottery.

It’s doing the things that you’d do if money was already taken care of for you.

It’s doing the things that don’t make your Sunday evenings a period of dread for the following day.

The things that get you juiced to go spend the day doing because you want to.

Even when the things are hard. Even when it isn’t a party. Even when it isn’t glamorous or fun.

Just the things that must be done for the larger picture. For what you’re building. For the life you’re living. For the childlike joy you used to have before you were taught all these fucking rules about what you’re supposed to be doing instead.

How far will you go?

I didn’t invent any new lifestyle. I am not the first person to do this or anything like this. I am not special or unusual (depending on your definition of unusual). Anyone can do the life they want. It may be tough to get started. You don’t have to do anything dramatic to change your life Fight Club style.

Don’t just dump your husband, moon your boss, and burn your house down with all your stuff in it. You can do it over time. Make changes as you learn.

All you have to do is start. Learn. Look around. Open your eyes. Ask questions.

Always ask questions!

Don’t accept the status quo if it doesn’t suit you. Your friends may think you’re crazy and your family may disown you. But if the way you’re living isn’t leaving you feeling alive most days, it may be time to change something.

It won’t be easy. It won’t be painless. But it will be worth it.

I don’t specifically recommend the tried-and-true method of “Go through unpleasant divorce, lose everything, and flail around figuring it out on your own for several years.” But even it it seems that bad, it may turn out to be a pretty good thing.

What is your experience with things you thought were the worst thing that could happen, and how did you heal the wounds? Let me know in the comments below. Use a fake name or hit the contact page to send me a message if you want it private.

About the author: I write fun Sales Copy for your lagging small biz website & bring you your right people. Also writing about location irrelevant work, life, & play.

2 comments… add one

  • Marianne

    WELL SAID, James!!!

    I am sure I would never have heard this had you still been here, sitting across from me.

  • “I knew somewhere deep down that all this stuff was actually a burden. The ads had lied all along. The feelings you’re supposed to get from having the outside things never actually give you that. Not if you aren’t well on the inside. I suspected it even while I had everything, but it was lost among the thoughts that the next new thing would be the thing that made it all better.

    The things are never the answer.”

    This. The last few years combined with my recent health issues/brush with death are bringing things into extreme clarity. So long I’ve held on to stuff… So much more I’m realizing I need so little of it. I just hope I figure out what I need to flip in my lizard brain to break completely free. Still working on that part.

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