It’s been more than a year since I left the working world so I figured I should write something about my experience. To make it a little more useful I’ve structured this as a sort of guide for others. Over the last year I've seen more and more friends and colleagues leave their jobs without another one lined up - the great resignation is real. So to those who have already done it, I commend you and hope that this provides a little direction. And to those who are on the fence, maybe this will make the decision a little easier one way or the other. But before going any further we have to acknowledge the insane privilege of being able to leave a job to take some time off. Very few people have the opportunity to do such a thing. Unencumbered time is the ultimate luxury good. So if you are able to do it, the most important thing to remember is to be grateful. Take a step back every so often to recognize how fortunate you are, and try to pay it forward in some way. With that being said, here’s some thoughts that have stuck with me over the past year.

Three reasons why you should quit your job

Knowing why you want to take some time off is important because there will definitely be moments where you ask yourself if it was the right decision. My "why" was mostly the first two reasons. The third is something I’ve noticed over time and is not something I was anticipating at the start.

  • To do an uncomfortable thing - In America, land where people take (and are given) some of the least vacation on Earth, to wholesale stop working is to go against the prevailing current in a big way. If you’re also in the young professional class then there’s even more pressure to constantly be striving for ever more. To say no to the rat-race is hard. You have to muster up some resolve to make the jump. See it as an opportunity to put yourself in an unfamiliar position and experience all the feelings that come with it. For that alone it’s worth doing.
  • To stick your head out of the sand - The other effect of our 24/7 work culture is that it leaves very little room to get a sense of perspective. There are just 64 hours between 5pm on Friday and 9am the following Monday. 80,000 hours is an organization focused on answering how you can best spend the namesake 80,000 hours that constitute a typical career. As they frame it, if you’re willing to spend 6 minutes discussing where to go for a 2 hour dinner, then you should be willing to spend up to 4,000 hours or approximately 6 months thinking about your career choice - and that’s not even including everything that life involves outside of work. You can try to do this while keeping a job, but it’s the continuous expanse of time afforded by not having one that’s critical. You’re more likely to end up where you want to be if you stick your head up everyone once in a while and figure out where you’ve been and where you’re going.
  • To meet your real self - I still vividly remember a poster from my 6th grade English classroom which said “Character is who you are when no one is watching”. It’s a great quote and in many ways quitting your job is a similar test. Once you lose the routine and financial support of work your natural tendencies are quickly revealed. Unstructured time might be a dream come true or it might be a waking nightmare. Dipping into your savings might be tolerable or it might be a constant source of anxiety. Defining your identity in every introduction without referring to a job might be a fun game or it might be paralyzing when meeting new people. This process of self-discovery helps breakdown illusions and reveals what makes you tick. As an example, I thought I would have made a lot more art by now but it just hasn’t happened. Work disconnects you from yourself not only because of the mental energy it demands, but also because of how many raw hours of the day it endlessly consumes.

Three learnings I’ve had since leaving my job

My own time off has mostly focused on mapping out where I might want to go in the future. And that’s reflected in what I’ve learned during this past year. If you choose to spend your time with a different intention then these learnings might not be as applicable. The first two learnings relate to the paradox of choice while the last one is more about my own state of mind.

  • Optionality is intoxicating - You can wake up everyday and dream of a totally different future for yourself. One day that could be becoming an open source investigative journalist and another day it could be getting a master’s degree in public policy. When you have very few hard obligations, imagining each of these possibilities is quite thrilling. In many ways it’s more exciting to make plans for each different path than it is to actually pick one and start working towards turning it into a reality. Committing to one single area of focus has definitely been one of the bigger challenges I’ve struggled with. Even now I’m still juggling at least 2 different ideas for what to pursue. I’ve been trying to internalize the following quote ever since I found it a few years ago but haven’t got there just yet. “Anytime you have to make a choice between two (or more) things it'll feel like a loss. This loss is not regret, or an omen to change your mind, its sadness of the road not traveled. You have to accept now that you will not be able to travel down every road” ~ Anonymous
  • There will never be a right answer - I’ve also come to terms with the realization that there is no objectively correct answer for which direction to go with your life or career. We live in a time where you can justify making any kind of pivot at any possible point. If you wake up tomorrow and decide you want to become a doctor you will find a way to rationalize that decision. Because ultimately the only thing that matters is how bad you want it. Asking others for advice or making a pro and con list helps a little, but in the end it’s a subjective thing that comes from digging deep within yourself. It takes a certain amount of self-honesty to know whether the path you’re choosing is what you really want or just something you’ve convinced yourself to think you want.
  • The stress isn’t acute, it’s somewhat chronic - The benefit of leaving your job is that the anxiety around an urgent request that must be done by lunchtime or the dread of a contentious meeting with an executive who just doesn’t get it immediately vanishes. The ability to go to sleep and wake up without the fear of all the typical work stressors is marvelous. The drawback however is that without the structure of a work day, it’s hard to know when to stop thinking about future plans or what needs to get done. There’s always this background noise of your brain calculating whether or not your time is being spent as efficiently as possible. It’s your own savings that support you so leisure time can feel like a disservice to yourself. To live with this low-grade stress all the time is definitely something that takes some getting used to, especially if you’re a productivity minded person like myself.

Three pieces of advice for once you’ve quit

I’ve used the word structure a few times in this post because its presence and absence will greatly impact what you experience starting on the first Monday where you have nothing scheduled. I can’t tell you exactly what to do if you quit your job, but I do have some thoughts on how you can shape your time.

  • BYOE - Build your own environment - The space you occupy, the people you hang out with, and the content you consume will all take on a heightened importance once you leave your job. Without the rigid routine of work your mind is able to roam far and wide. And that’s a good thing. But the surface area it has to wander is something you need to be intentional about. There was a time last year before the election where I followed a bunch of right wing twitter accounts just to see “both sides” arguments. It materially affected my mood on a weekly basis. As soon as I unfollowed those accounts I got back a considerable amount of mental energy. Similarly, moving to a new apartment with more sunlight has made spending time at home so much more satisfying compared to the past. Take the time to carefully curate your surroundings across the dimensions that matter to you. It’s exciting and will increase the chances that you accomplish whatever goals you have.
  • Find someone to shame you - You’ll need to create some kind of accountability system for yourself. I try to semi-regularly check in with a number of people who I’ve met over the last year who are on a similar journey. You can only give the same update so many times before it’s too embarrassing and you’re forced to make real progress. We are social creatures and peer pressure can be a useful thing. In an ideal world you could fuel yourself on intrinsic motivation alone but I’ve found that having at least some extrinsic motivation goes a long way. The additional benefit of checking in with other people who are also taking time off is that you might make some friends. There’s a shared understanding that’s easy to bond over. Because again, intentionally hopping off the hamster wheel of American work culture is still kind of a wild thing to do. And even if your goal is to explicitly not think about how you spend your time, it still might be helpful to talk to someone about how that effort is going.
  • Look to the past to find the future - One exercise I did early on was to make a list of interests, experiences, and memories from childhood onwards that stuck out to me. This ranged from toys that I liked as a kid to volunteering efforts I found meaningful as an adult in San Francisco. Within those formative episodes you might find direction for what to do with your time off and what to do after. You are the sum of all your past experiences. They compound into the present whether you like it or not so you might as well study them to see if there’s anything worth noting. Looking back can also help you understand your reactions to new things you encounter. As an example, I remember reading a lot of Tom Clancy novels as a kid and can now very clearly see how that has led to my fascination with cybersecurity as it relates to protecting the electrical grid. It all comes back in one way or another. So make a list even if it’s to just dismiss those experiences as irrelevant to your current state of mind. This is another way to bring some order to the experience of having unending free time.

I’ve learned a lot about myself this past year. The jobless journey isn’t over just yet but there’s much more clarity and direction today compared to twelve months ago. The content of my weekly “Things to do” list has markedly changed as I’ve tried to heed my own advice. Hopefully this post can serve as a point of reference for anyone who’s thinking about or has already started down a similar path. And again as I said in the very beginning, it’s a very privileged thing to take time off and you should always be mindful of that. If I had to do it all over again, I only wish I’d figured out some of my own learnings faster, but I’d still choose to take the time off without a doubt. It’s probably one of the best decisions I’ve made no matter where the journey ends up.