How I Left My 9-5: Finances & Timing

This post is part of a series, How I Left My 9-5, that I’m creating with the hope that my experiences might help you take on a big life change, whether that’s switching careers or just generally stepping off the beaten path. In part one, I talked about the process of leaving my job and transitioning from employee to consultant to (currently) full-time blogger/student/life-seeker (how’s that for a job title?). I don’t have it all figured out, but every day I learn a little more.

Rose Garden

In describing the process of how I left my job in the Search Engine Optimization field, I mentioned that in the final months of my SEO consulting work, I maxed out my hours to make more money in seven months than in the entire previous year. Some people may have looked at my savings and thought that this wasn’t necessary – that I had enough of a cushion already – but I had to do this for my own sanity. In my mind, making at least as much money in January through July gave me the self-imposed “permission” I needed to take time off without feeling overly anxious and guilty. This is very much a personal decision, and when it comes to your own financial comfort zone, you may have a totally different scenario that works for you. This is simply my story.

Aaron and I have always been relatively frugal with regard to our spending. We spend the vast majority on rent (pricey in Boston and we agree that it’s worth it to us to pay more for a nice apartment in our preferred neighborhood). We’re also uncomfortable with having debt when it can be avoided, which is why we made it a priority to pay off our student loans and our car as soon as possible, allocating extra money there instead of for more fun things like travel. I was debt-free in June 2011, the day I turned twenty-seven (a birthday goal/present to myself), and Aaron paid off his much heftier student loans the following year in 2012. I wouldn’t have felt comfortable quitting my job otherwise, but again, this is a personal decision.

The next big piece of the puzzle was Aaron’s employment situation. He was let-go from his full-time job at the end of October 2012, which essentially gave him a giant kick in the butt to completely set out on his own. Aaron’s always had plenty of freelance clients at any one time, but he had founded a branding agency in Boston the previous year. Getting laid off, though scary, lit a fire for him to really ramp things up. However, as anyone who works or has worked in a creative industry knows, this is extremely challenging and the instability is stressful, to say the least. We were fortunate in that Aaron was able to bring home almost enough money to cover our bills beginning in November, and I took the rest out of my paychecks.

I should rewind a little and also note that when we were married in 2011, we began saving like crazy. The last year had involved two cross-country moves and periods of decreased income, and neither of us were thrilled with the state of our bank accounts. We decided that Aaron would use his income to pay our monthly expenses, and I would put as close to one hundred percent of my income as possible into a separate savings account – not connected to our checking. We had tried different saving strategies previously, like each of us putting $X away each month, but it wasn’t until we started living on one income that we were able to be really effective. This meant that when we wanted to go away for a long weekend or splurge on a new piece of furniture, we had to not only budget for it (and agree it was worth the cost), but I had to take the money out of our savings account if it wasn’t within Aaron’s income. And let me tell you, unless we’re buying something truly awesome, it pains me to see our savings decrease!

To this day, this is still our financial strategy, although my income right now (and I have to remind myself that this is temporary) is only a small fraction of what it used to be. Aaron’s, on the other hand, has thankfully ticked up over the months, and as of July of last year, he started making enough to comfortably cover our costs with a little extra for our current goal: saving enough to afford a down payment on a home. It was around this time that he also had contracts for at least six months’ worth of work, which again, if you work in a creative industry, is about as good as it gets.

So, six months of visibility for Aaron’s income, plus what I viewed as my five months’ of extra income, and dedicated house downpayment and “oh crap!” funds (the latter is a separate account with enough to cover almost a year’s worth of expenses at our current spending level, or whatever “oh crap!” moments we hopefully don’t experience). All of these things came together in late July last year, and in August, I took the leap and said “I quit! I quit! I quit!”, with Aaron enthusiastically onboard and me happy and nervous, but knowing I just needed to finally do it before I found a reason not to leave.

If you’re looking for it, there is always a reason to wait, save more, feel more stable, become more certain. But there comes a point when, as I remember reading somewhere, you have to jump and the net will appear. I like to create my own net in addition to this one that’s supposed to appear, just to be safe.

If there’s a particular aspect of how I left my job or how I’m working to change careers that you’d like to learn about, definitely let me know. I’m happy to share my experience, and I’d love to hear yours if you’ve found yourself in a similar quarter-life crisis breakthrough.


P.S. If you’ve discovered any helpful saving/budgeting strategies over the years, please share!