Chasing Dreams

Mathias in the van while traveling across Canada.
Traveling with kids

Freedom. Independence. What so many people chase after these days is something very few actually succeed in attaining. The dream of working for yourself or from home, unfettered by a commute and a cubicle, has been perpetuated by those trying to make money off other people’s dreams.

We have wasted so much time and money chasing the dream too. It has led to a pause in a career that in the end we’re returning to anyway having come to the realization that what we had was far more liberating than the reality of independence. The things we were striving for, more time together as a family and living our life the way we wanted to, were more achievable while working for others. Here are some of the lessons we learned.

Money doesn’t grow on trees

When we made the switch from a steady job to working for ourselves it was exciting at first. It’s always exciting to start something new, especially if you are making money from your own hard work and ingenuity. Unfortunately, the source of the money can dry up very quickly as you lose clients, the novelty of your product wears off, and/or people realize that they are paying far too much for something based on the “buy local, handmade, organic” fads. In the end people prefer to pay Walmart prices, especially when they don’t actually need something. Unfortunately, if you are not Walmart, you can’t afford to charge Walmart prices. If you want independence you need a solid, unalterable income, or a sizable (think of how much you blow through per month plus expenses associated with starting a new venture) nest egg to cover your expenses for the first couple of years until your income is secure.

Make a (real) plan

“We can do this, everything will be fine. People pay $X for this.” is not a plan. People may pay $X for whatever you may be trying to sell to support your new lifestyle, but will enough people pay it. If you make handcrafted furniture, yes, some people may pay $1800 for a table and another $200 per chair. Yes, you may be able to pound that out in double-quick-time. One of the things we learned is that if you can’t sell it, there’s no point in making/growing it. The business/marketing side of things is more important than the creation of something. Your kids can’t eat a dining table that’s sitting in your workshop hoping to be sold.

Time is valuable

What we had wanted to do: spend more time together as a family, became unachievable as we tried to grow our business. Trying to make your own money to support your family and yourself takes a lot of time. My wife is the marketing person of the two of us. She was on her phone/computer from the time we woke up until well after I went to bed sometimes. I had the easy part: production, transportation, etc. Even when I was writing cheques, paying cash, dealing with the government bureaucracy sometimes, dealing with some suppliers and customers, she was still overworked, and we had very little meaningful time together or with the kids. We had no vacations, no weekends off.

Employers pay for lifestyles far easier

With kids there are so many things that you don’t think of. With four of them medical and dental bills mount very quickly, especially when one of them likes to smash his teeth on walls and others. It costs as much to pay for medical/dental insurance as it does to just pay the bill when it comes. Vacation pay; you don’t get that working for yourself. Pension contributions: gone. Stable pay cheque: gone. The security of knowing how your life is funded: gone.


Everything comes down to money. In the end, what we wanted was unattainable. We saw all these TV shows and YouTubers who were living the dream. What they don’t show you is all the different things that need to come together to make that possible. The years of hard work, the broken marriages, eating rice and beans, unstable environments for children. Hard work is one thing, hard work that doesn’t pay enough is another matter. We were working harder for less benefit.

So now, I’m going back to what secures my children’s futures, pays well, gives benefits, and gives us plenty of paid holidays and vacation days to do what we want to do. Yes there are aspects of normal employment that we may not like: uniforms, regulations, having to listen to someone who is lazy telling you that you don’t work hard enough… but in the end, it is worth it.

Published by jrdobbin

I am a father of four, married for eight years. I live and play in Alberta, Canada.

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