What Day is It? Reflecting on One Year Without a 9–5
Last year I left my corporate job after working with the same company in the finance industry for the previous decade. I’ve remained unemployed since, and continue to receive the same, inevitable question from friends and family, “What the hell are you doing these days?”
Why Did I Leave?
Near the end of 2018, I hit a wall. I was in a job that was contributing to frequently spiked levels of cortisol. Anxiety and preoccupation with work were overwhelming and ever-present. Pressure was building.
And so, one day, after a particularly stressful afternoon, without much thought, I told my manager I was leaving.
We negotiated I would stay on a few additional months to help finish up some projects. Although I was itching to wrap up my tenure, identifying an end date provided some relief and helped ensure a more graceful exit.
It also gave me some breathing room to determine my next steps.
The fear of losing a steady paycheque soon prompted me to seek other roles within the company, even after HR and I had agreed to an end date. After all, what I wanted was an escape from my current position, more than I wanted out of the company itself. Sure, I romanticized about leaving the corporate world altogether, but that was wishful thinking.
A life raft soon emerged in the form of a wonderful, former manager. I was offered a six-month contract with the potential for extension. I would be free from my anxiety-inducing role, and importantly, still be earning a paycheque. A reasonable and practical outcome, if not the exact one I may have secretly wanted.
Half a year later, fortunately or unfortunately, the extension didn’t occur. I completed my contract and parted ways amicably.
Now I was unemployed.
What Have I Been Doing?
Daniel Vassallo, who wrote a viral article last year on intrinsic motivation and his experience leaving a high paying position at Amazon, coined the phrase ‘portfolio of small bets’. As I understand it, it’s a collection of low-risk experiments that may or may not pan out in terms of generating future revenue. This contrasts to a typical self-employment journey that may start with massive debt and the pursuit of a single idea for several years, with no certainty of success. The following covers the bulk of what I’ve been up to recently and is heavily inspired from Mr. Vassallo’s strategy.
Playing Artisan
I set out on a sunny afternoon on my very last day of work, giddy, smiling cheek to cheek. Whatever worries I had about leaving my job were soon drowned out with the sheer excitement of a new beginning.
I had to do something, anything, to start building momentum for a self-employed future.
I immediately headed for Canadian Tire where I knew they had a sale on canoe paddles. I filled my cart and started sanding and painting them that day. Soon, my decorative, artisan paddle company, Project Sawdust, was born.
The experiment has been a blast. The work is painstaking, but I enjoy it. It’s been incredibly rewarding seeing my paddles hanging in other people’s homes, and even a hotel and a brewery.
Project Sawdust continues to evolve everyday. Recently I began making wall mounts, and not just for paddles, but surfboards, snowboards, wakeboards, and even an axe.
To date, I’ve sold a modest 70 paddles and 50 mounts. If Project Sawdust ceases to sell anything else, I’ll still consider it a success.
Nerding Out
Over the past year I’ve been dabbling in software and programming languages I’d been curious about in the past. Nothing too deep, at least not yet.
Initially, Adobe Illustrator became my focus. I needed a logo for Project Sawdust, so it was a great opportunity to learn the fundamentals of Illustrator at the same time. This even led to some graphic design business, where I commissioned a logo for a local Pilates studio.
I later jumped into Python, often recommended as an appropriate first-time programming language. I’ve enjoyed learning it, but it’s been tough. I completed the University of Michigan’s’ Python for Everybody Specialization and built myself a little Twitter bot along the way. I have some ideas brewing for some more advanced projects, but first I want to hone my skills further.
Getting Swole
My garage gym has seen a lot of use over the past twelve months. Lifting has been a growing passion of mine, and one that I receive a lot of questions about from friends and family.
Fitness is something I love, and an industry I would love to work in. So, to plant that seed:
- I obtained the ACTION Personal Trainer Certification;
- Began sharing more videos of my training on social media;
- Started writing about fitness at Salt & Iron;
- Created training programs that are available on Gumroad;
- Began training friends and family.
It’s a start. I’m doing what I normally do, but I happen to be recording and documenting it now. At the very best, I earn some credibility among friends and family as an authority in the fitness space. At the very worst, I wasted some time setting up a tripod, practicing my writing, and enjoying lifting with friends.
Staying Connected to Wall Street
I spent the last decade in Finance and worked very hard to obtain the coveted Chartered Financial Analyst (CFA) designation. In many respects, this designation has defined me in recent years. Although I continue to explore domains outside of Finance, I’m in no rush to shed this identity.
To this end, I’ve recently begun freelancing as a Financial Analyst and Contributor with the Lead-Lag Report. This work will help keep me relevant in the Finance space, and more importantly, help pay the bills.
What About that Cash Money?
I left work with a reasonable buffer of savings, conservatively enough to cover eighteen months of living expenses, with no additional income. The circumstances of my departure from my employer, however, also allowed me to obtain employment insurance, a welcome added buffer. And a somewhat unexpected source of cash came from the sale of our rental property earlier this year.
My experiments in self-employment, too, have begun to net a small income. Freelancing, and a modest sum generated from Project Sawdust, are hopefully just the beginning of a successful self-employment journey. That’s the whole point of this, after all.
And of course, my incredibly supportive spouse continues to work as a successful high school teacher.
I’m incredibly fortunate, to say the least.
How’s Life?
Life has been slow and wonderful. Lots of cooking and walking. Time spent with family. Fulfilling and absorbing work. Long, enjoyable sessions in the garage gym, followed by well deserved BBQs and saunas. Spur of the moment day trips to Perth, or Merrickville, with a packed cooler and swim trunks. Sunset drives while sipping coffee, listening to a favourite podcast.
It’s been pure bliss. No more anxiety-ridden Sunday nights dreading the start of the week.
What’s My End Goal?
To keep experimenting and iterating. Identifying what I enjoy, and what has the potential to earn income. All the while ruthlessly discarding activities that don’t meet these criteria.
I want to fill my day doing meaningful work, helping others, creating things, writing, painting, and, lifting. Lots of lifting.
It’s not that I don’t want to work. Far from it. I’ve been more productive these past twelve months than ever before. There’s nothing I appreciate more than the satisfaction that comes from a hard day’s work.
No, it’s not that I don’t want to work. It’s just that I want to work for myself, on my own terms.
Connect with me on Twitter at @salt_n_iron
My portfolio can be found at https://jesseoberoi.com
