Tell the Truth, Tell the Truth, Tell the Truth: What It’s Really Like To Be Self-Employed and Building a Tiny House.


I have too many dreams.

So many dreams.

I live in a cabin in the woods in Idaho. I live in France in a big house in the countryside. I live in London, or Stockholm, or Copenhagen. I don’t own a car. I bike everywhere, I shop at marketplaces, I challenge my brain by speaking another language.

I collect most of these dreams from the Internet. You know why? You do know why. It’s the inherent understanding everyone has when they sign on. It goes like this:

Everyone’s life is better than yours.

Online is a dangerous place.

I had the nicest email from a reader the other day, truly, and I don’t want to make light of how good the note made me feel, and how happy I am to have inspired him. The note said that Casey and I were living his dream in regards to the tiny house and the cabin. In that particular moment, I wanted to write back and say “We’ll sell it all to you right now. How much?”

You see, living differently has a price. It’s painful. It is sacrifice and sweat and blood and tears and I mean all four of those literally. It’s emotional pain. It’s physical pain. And because it’s different, you have no one to guide you or support you but yourself because everyone around you is in a normal house, with a mortgage, at a normal job where you get paid every two weeks as long as you show up and contribute a bit here and there.

The Bucolic Plague is a book I turn to in my moments of utmost desperation. I realize now that I turn to it because its author is telling the truth, and in my moments of desperation, I need to hear someone telling the truth. Telling the truth is something I’ve been scared to do here. I don’t want to be judged. I don’t want advice. I don’t want assistance. I don’t want to feel I have to qualify my words or decisions to anyone. I’m scared to write this, but I can’t contribute an incomplete picture anymore. I see it too often on the digital pages I visit. I go online seeking connection. To people. To their stories. When I read only stories about perfection, I feel inadequate. I can’t play with that game any longer. You’ve heard about the good stuff. This post is showing another side.

My life is not perfect. Money is up and down and up again. Being self-employed and owning two small businesses is work times work times work. Being self-employed doesn’t mean that you don’t have a boss, and that things are free-wheeling and flexible and four-hours-of-work-a-week (I despise Tim Ferriss and every ounce of the bullshit that he is selling people. I don’t say that lightly). Self-employment means that every day is like scratching up a wall, and that wall is yourself. You have to decide what comes next. What the best course of action is. You can work 18 hour days for weeks making products for a three day craft fair. You can sit at that craft fair for three days with cigarette smoke swirling around you and loud bands blaring across the street and another vendor coming over to scream at you intermittently and then you walk away from those three days with $310 in your pocket. Minus the Square fee. Minus the tire replacement from the drive up and back and up and back and up and back. Minus gas for those 200 miles. Minus food because you were too busy to pack two meals times three days. Minus sales tax. Minus income tax. Minus self-employment tax.

Who wants to go halvsies on a package of Orbit? I’ll bring the coupon.

Then there’s the tiny house.

Building a tiny house is not picturesque. It sucks. Anyone who tells you differently is either balls-out lying, wants to sell you an e-course, or has had their memory genuinely clouded by a combination of time, nostalgia, and hindsight. Every fucking bit of building a tiny house sucks, and if you’re not careful, it becomes a sacred cow on wheels, a cow you genuflect to daily with blood sacrifice from your bank account and saline tears from your eyeballs and sweat glands.

Then there’s the part of my life that I don’t talk about because I think it’s boring. It’s the part that looks just like yours.

Our car needed over 1k of repairs this week. We got screwed royally by a shop that received great reviews and recommendations. We took our perfectly functioning car in for needed maintenance, and drove away with brakes that don’t work properly. Casey drove it back and was told it must be a coincidence and that the car rolling four feet after braking to a complete stop didn’t seem “that bad.” As of this moment, I don’t know what we’re going to do about it. It’s not just the money. It’s literally “We’ve seen every independent mechanic in town and been screwed at all of them. What in the hell do we do now?” My dad says our car issues are a first world problem. I don’t entirely agree with him. Being in a city where having a car is mandatory, when it’s how you get to the store and to clients and jobs and money, when you’re in a system that pretty much presents no other way…I don’t see that as a first world problem. I think FWPs are things that any person, anywhere could absolutely be living without at any time, but they’re complaining about having to deal with it. “Oh, I snapped another pair of my Gucci heels today!” “The barista never gets the temperature right on my drink order” or my favorite FWP meme: “I broke my iPad…by dropping my iPhone on it.”

I digress.

Ah, the joys of alternative living. Breaking the mold! Stepping outside the box! Living your best life! Simplify, simplify, simplify! I even found myself earlier thinking “If only we had decided to build a teardrop trailer that could be pulled by bicycles. Then our lives would actually be simple and better.” Again with those dreams. This is what I’ve realized: I don’t know if “the simple life” is even real. I don’t think it is. Even if you own one shirt, a bike, a backpack, and a pair of shoes, life is never simple. Anyone who tries to sell the simple life to you for either money or page views is, well, selling it to you. Never, ever forget that.

I have so many dreams. London, Stockholm, Copenhagen. Then the fantasy stops. Money must still be made in Copenhagen. No car, but rent and everything else is much more expensive. You’ve left all of your friends and must make new ones. You still have a chronic illness, it’s the end of your cycle and your fatigue is rapidly returning like a dust storm waiting to settle into every muscle and bone in your body. Also, fall is coming. The sun just left. This is Copenhagen, so you’ll see it again sometime next July.

I said above that living differently has a price. But that’s not fair. All living has a price. I want to stop selling the notion that there is a way to live that doesn’t.

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9 Responses to Tell the Truth, Tell the Truth, Tell the Truth: What It’s Really Like To Be Self-Employed and Building a Tiny House.

  1. Fluffykira says:

    I really really really appreciate this post. I’ve been watching with interest as you both follow your dreams. Your positivity and enthusiasm is infectious, and at the same time I know that I’m far too scared (for some of the reasons you mention in this post) to chuck some of my stability with the way everyone else lives. That doesn’t mean I don’t abhor debt and want it gone as fast as possible, but it does mean that right now I find my passion outside my job, and keep the job to pay the bills and not have to pound the pavement every day. I guess what I’m saying is that I admire both you and Casey for everything you are doing, and I also appreciate the honesty that “living the dream” isn’t always fun or easy.

    • iamchesapeake says:

      And I really, really, really thank you for commenting. I think your setup is perfect, especially with your need for stability. I agree about the debt, and I’d definitely recommend checking out Mr. Money Mustache. He kept a “regular” job for a short time (5 years or so) and he and his wife piled away money, saving and investing 70%+ of their take-home pay each month and are now financially independent in their 30s. This means that they don’t have to work if they don’t want to, but they still do here and there because they like it. It’s like having a 60+ year emergency fund. Here’s a great starter post:
      It’s what Casey and I are working towards, we just have a bit of an uphill battle being self-employed. The momentum is changing there, but it’s been a ton of work to get to that point. I’d recommend to anyone wanting stability and more certainty to stay patient with your desk job, pay off debt, and squirrel away as much as possible in investments. Build up that 60+year emergency fund.

  2. Chandelle says:

    Thanks for letting me know about this post. This is amazingly important stuff and I’m so happy to see someone being truthful about the grind of this life. I experienced it, too, when we were living as a family in four in 300 square feet with no bedroom doors or electricity. From the outside, it might look bucolic, but on the inside… well, like said in your comment, I cried a lot. Thank you!

    • Chandelle says:

      Lots of typos in there, sorry!

    • iamchesapeake says:

      Thank you for stopping by! (I didn’t notice any typos). I really enjoyed your post on living in 300 sf with your husband and two kids. It was refreshing and honest and it’s really sorely lacking in the online environment. I’m really glad I decided to write about all of this publicly. I was “saving” it until I had my shit worked out but that really helps no one. Especially since then it’s all too easy to edit or forget what it was *really* like. Nostalgia filter and all that.

  3. Zoe says:

    I couldn’t agree more. I often trawl the internet and get cross with myself for not having as perfect a life as is presented online – but you’re right. Life is ups and downs and living the best way you know how to muddle through. And that’s ok. Zoe x

    • iamchesapeake says:

      You know, it’s like the new marketing. Ads on TV don’t make me want to buy stuff anymore, and I even find myself saying “Why do people fall for this cheesy crap?” But then I go online and “buy” into other people’s lives almost instantly. It’s insidious and insane. I hopped on over to your blog and I really like it! :-D

  4. steamboat28 says:

    I needed this so badly right now. I’m in the early stages of my own tiny house adventure, mostly out of necessity, and it’s really easy to romanticize something so little and cute. I’m starting to get a little scared; roping off the dimensions and seeing how the entire construction can fit inside the room I’m typing from is mostly terrifying.

    It seems odd to say, but I’m glad to know it doesn’t magically get better. It’ll help me keep focus.

    • iamchesapeake says:

      I totally get it, and I’m happy that this helps you get perspective. Glad to hear there’s another non-magical thinker out there who is comforted by honesty rather than just sunshine and platitudes. Thanks for commenting and good luck with your build! Your realistic expectations in the beginning will take you far.

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