Every morning, millions of people around the world wake up, get dressed, and go to their place of employment for 8+ hours. Some wear suits, while others wear shorts. They work with varying degrees of enthusiasm until it’s time to go home.

I was one of them – until a year ago.

My first job out of school was in the treasury department of a bank. I interned for three months while I was finishing up my last few credits before accepting a full time offer upon graduation. I was the stereotypical new graduate, fresh-faced and optimistic.

I worked there for a few years before following my boss and the rest of his team to another bank, where we were tasked with delivering a project of vital strategic importance. I was doing challenging work with great people and well compensated for it. Sounds ideal, right?

Fresh-faced graduate. Enjoys ties.

Unfortunately, there are some unavoidable realities of working for a large organization that have a tendency to wear you down over time. If you work at or have ever worked at one, you’ll know what I’m talking about. The immense stress that we were frequently under didn’t help. One subway ride home, I asked my boss how he had survived a decade of this. His reply: “If the other eight were anything like the last two, I wouldn’t be here right now.”

I didn’t ask what he meant by “here”.

Does not enjoy ties.

I knew I wanted out, but how? Rent and international travel aren’t cheap. The answer came in the form of prescient predictions during the 2016 US presidential election (with sizable wagers attached) and leveraged bets on a rising Dow when most were expecting a crash. The resulting war chest wasn’t quite FU money, but it did allow me to clean out my desk with a smile when my final contract expired in June 2018.

Flânerie Highlights

aimless idle behavior

flâ·ne·rie (Noun)

My physical health drastically improved. High stress and generous per diems had led to significant weight gain. Because buying new clothes to reflect this was too demoralizing, I wore the same tired black v-neck and camouflage cargo shorts to every social event – so much so that more than one person made it their Halloween costume that year!

But after I knew I would be leaving, I found the motivation to put down the (fifth) burger and hit the gym again, losing 30 lbs in six months. Yes, you read that right.

I traveled the world. With some help from Ricky at Prince of Travel, I put together a round-the-world itinerary, visiting nine countries – Netherlands, Germany, Austria, Slovenia, Croatia, Hungary, Turkey, Malaysia, and Singapore – that I’d never been to before.

The best part? Thanks to an abundance of Aeroplan miles, a vast majority of the flights were in business class. As a huge sucker for airline status, the champagne, lounges, and ancillary benefits (like skipping the hour-long Malaysian exit immigration line) were some of the best parts of the trip.

I moved to New York City for six months. It was in Singapore near the end of my travels that I crossed paths with some friends who were there for a wedding, one of whom mentioned that they were looking for a new roommate in the Big Apple. A few weeks later, I sent them a rent check (kidding, email money transfer) and moved in. It was the first time I’d ever moved to a new city independent of my parents, who were (thankfully) supportive.

Like many others that have made the NYC pilgrimage, I fell in love with the place and decided to split time between Toronto and New York (where I am at time of writing) this summer.

Welcome to New York, it’s been waitin’ for you. 

Most importantly, I regained curiosity. I once scoffed at the notion that “many people die at 25 and aren’t buried until 75”, thinking it did not apply to special butterflies like me. But one day, I woke up and realized that I had indeed died somewhere around 25, having stopped caring about growth.

Although you certainly don’t need to stop working to start living, so strong was my mental homeostasis that I needed a big change to shock myself out of the rut I had fallen into.

A year later, I’ve returned to my former curious self whose favorite questions were why and why not.


In a word, the benefits of unemployment boil down to freedom. More specifically:

I don’t have to wake up at a certain time. No one likes being forced to get up before they’re ready. However, more importantly, it also means I don’t have to go to bed by a certain time. If I’m having a good time with friends at the bar or in the middle of a great book, I’m not forced to choose between stopping early or sacrificing sleep.

That’s not to say I sleep in until noon every day, but I could if I wanted to.

I can live wherever I want. If you work a traditional job, you generally have to live where you work. When you don’t work, you can live wherever your budget and passport permit. If you’re still trudging through two feet of a snow/slush combination for several months every year, it’s because you chose to. I don’t think I’ll choose to do that this year.

I can be contrarian with my schedule.1You give up some of these benefits if you start dating someone who works a traditional job. Since most people are forced to schedule their day a certain way, I can save time and money by scheduling mine differently. I can fly on Tuesday or when a last-minute mistake fare pops up. The same gyms that are bursting at the seams during lunch or rush hour tend to be ghost towns around 10 AM/3 PM. The one near my last apartment even offered an off-peak membership at a significant discount.

I don’t have a commute. I’ve always hated commuting. I’ve never managed to turn it into enjoyment or productivity. When I was employed, I tried to live as close to the office as possible and took advantage of every work-from-home opportunity. Now my commute consists of bed to coffee machine to desk.


All things considered, the benefits are both fairly obvious and outweigh any negatives. But that doesn’t mean it’s all sunshine and rainbows. For example:

It’s easy to become a hermit. When I had an office to go to, I would be guaranteed some level of in-person social interaction. Since I like the people I worked with, this was a positive. Nowadays, if there’s food in the fridge, I can easily go days without stepping foot outside.2And when there isn’t, there’s always Seamless.

I have to create my own sense of meaning and purpose. Most people go straight from school to work, never finding themselves in a prolonged situation where they have to choose a purpose independently. That’s the situation I found myself in during the first few months of unemployment. Although I nominally told myself and others that I was working on several business ventures; truthfully, I was engaging in aimless idle behavior. Flânerie was both enjoyable in the moment and something I gained a lot from in retrospect, but not having a purpose I could articulate led to the occasional “what the fuck am I doing” panics.

Now that I have a better idea of where I want to go, what was once a drawback is slowly transforming into a benefit. But not having a predetermined purpose was definitely a drawback for most of the year.

People are envious. Envy is a basic part of our nature and nothing makes an unhappy employee more envious than someone who is happily unemployed. As the average person would rather not go to work, it is likely that most people I encounter will experience some degree of envy towards me. Consequently, they may be less willing to do me a solid or expect me to contribute more than someone else. Or both.

It took me a while to realize this for two reasons: 1) almost no one will ever admit it and 2) having made a concerted effort to avoid feeling envious of others, I had forgotten what a universal and fundamental emotion envy was.

To alleviate some of this envy, I like to remind people that…

No one deposits money in my bank account on a biweekly basis. Obvious drawback is obvious. However, landlords like renting to people who have steady paychecks from recognizable employers. Their (not incorrect) thinking is that an employee can lose their life savings at the craps table and still make rent. Conversely, I might have to fork over a significant number of rent payments in advance to provide a similar level of comfort. At least my credit is sterling.

What’s Next?

It’s been a good year. Frankly, it was so good that special effort was necessary to avoid sounding like a self-congratulatory jackass in every paragraph.3I don’t think I succeeded. The urge to delete everything was strong. Some things I’d like to focus on in the next 365 days or so:

I want to get a business off the ground. Unless I win the Powerball, the coffers will need replenishing at some point. And even if I do, I’d like to produce something of value rather than solely consume. A successful business would meet both of those goals.

I want to improve my physical fitness. I’ve fallen off the fitness bandwagon recently. Thankfully, I’ve managed to stave off the belly fat by keeping the diet in check, but I’ll need to rediscover the iron soon.

I want to write more. Between blogs and books, I already read quite a bit. However, it’s been some time since I wrote anything longer than a tweet. I’ll look to change that going forward, starting with this blog post.

I want to learn new skills. For the last few years, I’ve largely coasted on my existing skills and abilities, which is not sustainable in a fast-changing world. Adding skills, like WordPress, to my talent stack will increase my value.

I want to go traveling again. I still have enough Aeroplan miles to do another round-the-world trip. This time, I’d like to visit the UK, Spain, Portugal, Scandinavia, Russia, Japan, Korea, and Vietnam (to name a few). I would also like to spend more time in each country if possible. And to fly the entire trip in business class again, of course.

I know I wrote quite a bit on the benefits of unemployment, but there are days where I miss working with talented people on ambitious goals. I wouldn’t rule out returning to the workforce, even if only for a tour of duty.

Photo by Tegan Mierle