It’s November 2009, the sun disappears early and the days are bitter cold. The world is still reeling from the great recession, and I’m feeding squirrels in my Toronto back yard. It was time to get a job.
By most measures I would be considered a veteran quitter. People generally go through life experiencing resignations to greener pastures, maybe a lay off or two, and eventually retirement. COVID definitely increased the number of quitters for the sake of quitting, but this was masked by the indelible subsidies and other means of making a living. I am the original quitter. Leaving without severance or a secure alternate form of income.
The squirrel feeding episode marked the end of my second tenure. This followed three years in management consulting, two of which were tolerable and highly educational, the third a harrowing, soul sucking experience.
Picture early 2009 in North America, companies going bankrupt left and right, and you’re a consultant charging exorbitant fees to advise some of these firms on how to stay afloat.
I generally have no issues with layoffs or ‘restructurings’, they are a necessary evil that every company experiences at some point. My issue was doing it on some one’s behalf for a handsome fee when it was quite clear what needed to be done. Maybe I was too altruistic, but this didn’t ‘align with my principles’ at the time, seriously affected my performance and caused me to leave. In hindsight I should have probably asked for a cut of the fees and not beat myself too much about it. That definitely would have gotten me fired though.
The first quittings happened way back in 2004. These were a bit more straightforward. I had spent four years in remote locations on drilling rigs. I had already saved up for an MBA, a down payment, and a mini slush fund. I was spending over twenty days a month in the middle of the ocean off the Brazilian coastline, and was facing a six-month deployment to the Amazon River to look for some good gas. I was told the rig was really nice, they served BBQ shrimp on Sundays! I did not want to do that and could afford to buy my own shrimp, so I quit without any job lined up. I tried, but it was kind of hard lining up interviews from the rig floor.
Both these quittings were followed by six months of rejuvenation and slightly frivolous yet controlled spending. Negative cash flow is not easy to stomach, but it’s kind of fun when its your own and you don’t have to ask for permission, it also gets forgotten and eventually replaced, on a long enough time frame.
My first quitting bought me an MBA and the opportunity to do something completely different with my life, and set the foundation for further self ejections down the road.
The second led to one of the best summers of my life, the summer of Sam, where I learned how to Golf (poorly), sail a small boat, ride a motorcycle, crash it and continue to ride, attend a dozen concerts and build up an everlasting hatred for PowerPoint and all its evils. It also led to a period of general stability, buying a house, not traveling and staying in the same city for almost seven years.
Today, I am three months into my third quitting. And this time it’s different.
I was pretty happy at my job and liked the company I worked for, I gave three months’ notice and left with no qualms or anger but with lots of good memories and a ton of good friends. The economy isn’t in a recession (yet) but it’s certainly in a very confused state. I have a decent plan of where I want to get to, and the last thing I’m anxious about is getting another job. This one wasn’t a quitting per se, more like a natural evolution to the next phase.
Let’s get to the point of this whole thing. A few people have asked me: what’s it like? what do you do with your time? Are you crazy?
So let me share some of the highlights with you. What really happens when you forgo stable employment and a recurring paycheck?
The good stuff first:
You sleep really well. I’m physically and mentally tired every night. This is a function of redeploying unproductive meeting and meaningless task time to more exercise and interesting undertakings. Talking to people, reading, learning new things, and weighing many different options, makes my brain hurt every day.
You have a lot more energy. Probably a result of better sleep, the general excitement of knowing I control my own destiny, and that I will only do the things I want to do.
Mealtime is real. Breakfast, lunch, and dinner. I have time to prepare them (or go out for them), sit down and enjoy them without worrying about rushing to my next call or meeting.
Priorities get re-prioritized. Without a salary dictating the inherent value of a task, you begin assigning value in a very different way. It becomes much easier to take a long view on something that was deemed irrelevant by your job but enjoyable, even if it has zero immediate payback (this article is a good example).
You have interesting conversations. People stop associating you with your position, they learn more about you and you about them, and you start discovering new things.
You don’t waste time on someone else’s problems. A typical ‘white collar’ structure has seven layers stacked seven people across multiplied by the number of products or services offered. No matter where you fit in the spectrum, there are roughly 49 people who directly impact your day. 5 of them will be brilliant, 5 will really suck, and the rest are somewhere in the middle. On any given day there’s a high likelihood that you’re cleaning up a big mess, trying to figure out how this new brilliant idea has anything to do with your job, or listening to people drone on about status updates because no one likes reading anymore (or all of the above). This all goes away, for better or worse, mostly for better.
You are continually surprised. Things start happening in places you least expect them to. You begin to realize the power of your network, the impact you’ve had on people, and the lengths they will go in offering their support and time. The reverse is also true.
And now the not so good:
Negative cash flow sucks. No matter how you look at it, spending from your savings never feels good, especially if you’re programmed like I am and believe disaster will strike at any moment. I have convinced myself that I’m investing in my soul and the payback is going to be huge.
Self motivation is hard. Artificial deadlines in corporations create urgency and false motivation. They provide a structure and a clear path, no matter how unenjoyable. Filling your days and assigning value to what truly matters can get subjective and downright frustrating, resulting in some roller coaster days where you just want to do nothing. The good news is you can do just that, nothing. Go for a walk, enjoy some nature, do something mindless, exercise, and reset for the next day.
You have to re-establish your relevance. A job and title offer you some kind of credence. People come to you for permission, advice, approval, favors, mostly because they have to but sometimes because they want to. That goes away when you lose the title, the flip side is that you find out what you’re truly good at and who your real friends are.
You miss the good people. Starting out on your own means leaving all the good friends behind. They are still there but they’re busy with their jobs and many deadlines. You no longer share the same physical space or have the common outside force that brings you together, whether you like it or not. It takes a lot more effort to find the time to reconnect, but when you do it’s much more meaningful.
Ultimately, I believe that the advantages of a self-directed resignation far outweigh the challenges. While this definitely isn’t for the faint of heart, everyone should experience it at least once, ideally with a severance package, and well before retirement.
It will prepare you for the inevitable, and the squirrels will thank you.