Labour Day holiday in the creaky, musty comfort of a Depression-Era cabin. Dusk over Georgian Bay, cloudy and violet. Wind-bent Cedars and Pines. Motor boat engine buzz. The slash of wake against rock. Crickets. And finally a silence shared with an old friend and a good book.

In Canada, the Labour Day weekend is summer’s last hurrah, before school and work resume in earnest. I return to work too, on Tuesday. But unlike most folks my weekend has lasted three-plus years rather than three days. That’s right, I’ve not had an honest-to-goodness real job since April 1, 2010. No joke.

I wish I could tell you why that happened, but I can’t yet. What’s easier is describing what it’s been like to be work-free for so long.

It’s been awesome and awful. Glorious and humiliating. Living well above and well below my potential, all at the same time.

First, the glory. If you have the time, health, money and freedom to do as you please, here’s what you do (if you’re me): cross the Pacific by ship and Eurasia by train all in one go, help friends in need, take college courses, volunteer, coach kids and adults in community sport, write a blog, complete an Ironman. I won’t have to worry about not having pursued big dreams or done some good, and that’s a great feeling.

These were all worthwhile risks. But I did not plan to go off-road for this long and it gnawed at me – not finding the right job, not working (with limited exceptions), drawing down savings, not building my career. Add to that being in my thirties living with my parents for no real traumatic reason over 1.5 years, and you’ve got someone not fully at ease with life.

So what have I learned?

Sometimes you suck – get over it: did I really think I would make it to middle-age without failing dismally at something important? Anyway, the key point for me is to get better at job transitions. I’m far better at networking and positioning now than I was when this started. 

While failing at something, keep succeeding at other things: just because you’re in a rut, it doesn’t mean you have to wallow in it. You’re more than a job title – use your abilities where they can help others. It will be recognized, and gives you a pretty darn good reason to get up in the morning.

I have remarkable parents: Judgement-free support and love is an awesome thing to experience. Not once did they question my return into their home or how long it has taken to sort myself out. Never. I can appreciate this now in a way I probably would not have as a younger person. A child can’t possibly repay parental devotion in full, but he can learn from example.

So what’s next? Sometime in the coming months, I’ll join the rest of the normal working world complaining about commutes, colleagues, paycheques and work-life imbalances. But not just yet.