The Realities of Living the Dream

Updated: Jun 17, 2019

I have wanted to work for myself for many years now. It took me a long time to work out what that looked like, but I never stopped seeking it. First I worked out how to minimise my costs — I built a tiny house. Then I worked out where I was going to park it — on my friend’s property in a town I have always wanted to live in. And last, but not least, I found remote work that allowed me to work fewer hours from my new home town, often on a schedule that suited me.

Sounds like I have it made, right? Two quotes come to mind.

“Be careful what you wish for.” 
“Every lifestyle has its problems, it's just a matter of which problems you are willing to solve” Mark Manson, The Subtle Art of Not Giving a Fuck.

On paper, I am living my dream. And people will look at me with disgust, wishing they could work fewer hours and fit in lots of flying, mountain bike riding, hiking etc. And even as I write this I wonder what the hell I have to complain about. Well, all of this comes with caveats.

I work for a start-up remotely from Sydney. Start-ups do not have a lot of cash so I had to slash my usual hourly rate by 25%. The understanding was that I would get about 20 hours of work per work. Some weeks its more like 10, some weeks its more like 30 but on average its around 20. Ideally, I would have got more work over winter when there was less to entertain me outside.. but that’s when I got the least amount of work. Looks like my summer off is not going to happen. But hey, who’s going to complain when it means I can do so much more of my hobbies? 

Overall, I can convince myself everything is sweet. But weaning yourself off your old habits is hard. For example, I needed to reduce my costs. Living in a tiny house that I own, paying minimal rent for the land with very few utilities is low cost. What doesn’t change in line with the new living conditions is insurance. There’s income insurance, health insurance, car insurance, contents insurance and house insurance (though smaller). I should point out that I am moving from an income where I didn’t have to worry too much about how much these things cost, to an income where it all matters. 

Income insurance is pretty much a luxury that only the more wealthy of us even consider. The problem is that you have been convinced that you should pay for income insurance because “God forbid, what if??” and that worry stays with you even once you decide you need to cut costs. Income insurance was the first on the cutting block. You start picturing what will happen if you break yourself mountain biking. You won’t be able to live in the tiny house because you won’t be able to get into bed in the loft. Then you worry how you will afford to live somewhere else? Will your “paid-by-the-hour” job wait for you to mend? The truth is that the only way I managed to wean myself off income insurance was to procrastinate when my credit card expired until it was no longer an option!

I have since been able to cancel the income insurance, downgrade the health insurance (it’s still way too expensive), benefit from lower home insurance, and put up with the high price of car insurance. It still a constant battle of conscience — am I doing the right thing? Kind of has to be now, because thats the only way the sums add up.

The other difficult thing has been motivation to work those hours I have been given. I knew before I started working remotely that I’d miss the social interaction of an office. What I didn’t realise was also how easy an office makes it to get work done. There’s very few other distractions, other than occasionally checking social media — but you know other people might be watching so you tend to minimise it. Even on an off-day I reckon it was easier to get more done than working from home. I charge by the hour now, so its not that I skive and bill for skiving. Its that I tend to have so much more to do before I start my time tracker for billable work. Sometimes I just don’t know where the time went.

Well I guess the truth is that the time goes into all the side-projects I have time for. I get involved in my local community, in my sporting community, in the tiny house community. I get out there on the bike and make new friends, discover new trails. Hike more of my backyard. I do fit a lot more in, but it just feels so… inefficient.

I guess what I am talking about is this residual feeling that you are not working hard enough, being efficient enough. It’s constantly at the back of your mind, giving yourself a hard time when actually you are doing ok. You are living the life you strived for — the hard part is allowing it to happen and realising that this is ok. I really didn’t think that was going to be a problem!

Back to Mark Manson’s quote from his awesome book. You think that you want the lifestyle where you have no problems. The reality is that it doesn’t exist. Every lifestyle has its problems — it comes down to which problems are you willing to solve? I wasn’t willing to solve the “How can I afford my own place in Sydney whilst taking enough time off to fit in all my hobbies?” problem. I am willing to solve the “How can I find enough work to afford a European summer next year” problem.

In winter the problem was how to entertain myself with limited indoor space and a fairly hostile outdoors environment. I learned to walk in the rain, I went snowboarding (although that clashed with the reduced income since ski resort entry is super expensive) and I hunted down a bit more work. In summer the problem is likely to be about how I can balance the increased number of work hours coming my way with all that the outdoors is calling me to.

Honestly, there is no perfect lifestyle. Your ideal lifestyle is the one where you are ok with tackling all the problems that lifestyle comes with. I’m still adjusting to my lifestyle. I have no regrets but I am surprised at how much adjustment is needed. The Journey into Tiny is looking to be a longer-term project 😊


© 2019 by Lilliput Living. 

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