I was entirely unprepared to quit my last job even though I figured out how I could anyway. You can rely on the same luck, and you may be similarly successful, but you could instead perform a simple mental exercise in advance and save yourself the anxiety. This exercise is what I call “Saving for the Sunniest of Days”.

I Always Had a Dream, but Never Saved for It

If you asked me in 2009 when I graduated university and joined IBM full time what my career ambitions were, the list would have included running my own business. In fact, that ambition was present when I got my first real job as a co-op with the Eclipse Foundation in 2006. It is difficult to understand even in hindsight why I took no financial steps towards realizing that idea.

My spending habits over my short career with large and medium corporations grew in lockstep with my paycheques. I never went into debt, somewhat miraculously, not in the least because I never bought anything more expensive than $5000. But I also never saved a penny, except for when I had a year to pay back that same $5000 interest-free. I proved to myself then that I could easily save for a goal if the exact monthly amount went out of my chequing account into a savings account automatically. I never saw it – and I never missed it. The rest of my paycheque I spent without a care.

Canadians among you are likely to ask, “What about RRSPs?” From the moment I began making money, the nebulous notion of RRSPs was continuously present, which I linked to the highly unlikely event of retirement. I say unlikely because I both have trouble imagining myself living long enough to make use of the benefit, and, if I happen to accidentally, don’t see myself stopping to actively generate income. This all to say that I never saved for RRSPs above the employer match contribution percentage, and even then only because “you should never leave free money on the table” as per my father.

The thing I never could do was save for the sake of saving. The admonition to save for a rainy day did not resonate with me one bit. I wish someone told me from the start that it didn’t have to be that way.

Then I Jumped Anyway

When I got word of the impending re-org at my last job, I was on vacation in Spain. Even without many of the details, I felt strongly that this was my opportunity to leave and think about starting my own company. As alluded to in my last post, I feel strongly about little without data. This was an exception; as I remember, it was a super-sunny day in Granada.

A bit of an aside: it turns out I knew 2 years earlier as you can see from the piece of paper penned in September 2011 in the picture above. I meant a different startup with a different team, but my timing was remarkable: travelabulous was incorporated on November 12, 2013.

I was out of a job a couple of days after coming back. I did it because it felt right, not because I knew how exactly I was going to feed myself in the coming months. I’m particularly fortunate that Canada has an Employment Insurance program that supports unemployed people. Otherwise, I would have had to borrow money to make it. I had to adjust my lifestyle to match the 60% decrease in my income – fortunately, my spending turned out to correlate with my income on the way down as well. It was almost painless, accounted for largely by increased frequency of home cooking, decreased alcohol intake, and minimum travel and fashion expenses. I also cannot thank my family enough for keeping their jobs and supporting me through this time.

And that’s what I want you to think about. The inputs to my financial wellbeing over the last 10 months were largely uncontrolled by me, dependent on government and family support. Looking back, I am grateful to have had access to both. I have no regrets about jumping when I did. But I do wish that when I still had the capacity to save some of my income, I had realized that you don’t have to save only for falling on hard times or retiring. Instead, you can plan for your dream. Instead, you can decide to save for freedom.

For me, freedom is almost a year of making no money, working for sweat equity to get a startup off the ground. What’s your freedom? How can you save for it now?