field notes

The longest weekend

Now that I’ve quit my day job, what do I do all day?

As I recently left my job in engineering so that I could roam around the world and focus full-time on writing and other projects, this week marks the beginning of what I’ve been calling, tongue-in-cheek, “the longest weekend.”

I wanted to give you a simple update about what I’m working on, but I realized I couldn’t properly do that without explaining, in large part, my system for structuring my time. And I couldn’t properly do that without explaining why it’s important for me to have a system in place.

Disclaimer: Like I said, I only recently transitioned from full-time jobbing to full-time not-jobbing, so I don’t know yet how things will go and thus can’t speak from the perspective of, “here’s something that definitely worked well for me,” but only from the perspective of, “here’s the way I’m doing things right now, I don’t know how it will go, but maybe you will find something interesting or valuable in it.”

Why have a system?

My friend Nick and I were talking about what it takes to be ready to quit your day job, and I realized as I was saying it out loud, that money–having enough savings–is only the first and most obvious thing you need.

Another thing, which is at least as hard, is that you should be pretty confident that you’ll know what to do with your time and attention, when no one is putting meetings on your calendar and no one is asking you to get anything done. And pretty confident that you’ll be able to stay motivated, even if no one else is excited about the things you do get done. Not just for a day, but for weeks, months–maybe years.

Because they’re less obvious, I feel like people might be more likely to fail due to those factors, and not due to running out of money. I’ve seen many times the old advice, “don’t quit your day job,” and how the giver of advice learned the hard way: maybe he quit his job to pursue a passion, but a short while later he finds himself sleeping till 2pm every day and wasting all day on the internet, never changing out of pajamas, etc. So he goes back to having a day job, deciding that he needs that structure after all, and it’s better to do passion stuff on the side.

Having your job be the source of your sense of purpose, usefulness, motivation, validation, your daily to-do list (and those little hits of dopamine satisfaction that come with checking things off the list) is a psychological dependency, like any other. It’s an addiction, and a powerful one. (That doesn’t mean I think it’s necessarily bad for everyone, by the way. We probably all have some addictions that aren’t doing us harm.) As with any powerful addiction, I would be hesitant to quit cold turkey with no preparation, to discard the whole setup that my nervous system has structured its life around for years, without an alternate support system already in place. So I made one.

The first step is to answer a pretty important question:

Awareness: Do you know where your time goes?

As a gauge of whether you know enough about your own patterns to be prepared to quit your day job, I think you should know the answers to some basic questions about how you spend your time. Here are some examples of questions I would feel uncomfortable if I couldn’t answer (in order from easiest to hardest):

How long does it typically take you to go grocery shopping? This question is about simple time awareness.

How long does it take you to “sign off” from work? In other words, how long is it from the time you leave work (or stop working), to the time you begin your next real activity (like make dinner, watch tv, call friends/family, read a book, etc)? This time interval includes transition-y things like commuting, checking last Slack messages or social media, going through your mail, changing clothes, feeding your pets, and whatever else. (For some people, this may include the entire time until you fall asleep (I’ve been there too), but I hope that’s not the case!) This question is about your awareness of your process for context-switching.

If you sit down to work on something you’re really motivated to work on, how long does it take you to get in the zone (assuming you make it into the zone)? How long before you feel the urge to take a break? When you take a break, how long of a break works best for you, and what’s the best thing to do during your break? What’s the maximum amount of time you can work on this type of thing in a single day? These questions are about your ability to cultivate flow.

If you try to sit down to work on something you’re really NOT motivated to work on, what happens? This question is about your awareness of how you handle psychological resistance.

And finally, literally what your new life would look like: how long could you staycation (go without a job and without travelling) before getting bored? What would you be doing with your day after, say, 2 weeks? 2 months? 6 months?

Preparation: How do I know my own answers to those questions?

Nearly four years ago, I started the practice of planning out my day, at the beginning of the day, as well as logging how I spent my time the day before. At the time I had read Cal Newport’s book Deep Work, and this is the one thing I kept from it, and it’s made the biggest difference out of any practice I’ve tried, in the awareness and control I have of my time. First because it gives me data on how I actually spend my time, how much time each activity takes, and how that compares to my initial estimates. Second because when I plan out my day, especially with more informed estimates, I can quickly see if it already looks unrealistic. This practice takes me about 20 minutes each morning.

At the beginning of this year, I started also logging how many hours I spend doing the things I want to be doing (e.g. reading, writing, learning languages), and setting monthly targets. While I had a full-time job, I was pretty lenient about this (“try not to log any zero-hour days” being the general policy), but now that all of my time is available, I’m getting more specific with the categories, and ramping up the targets. I log this as part of the practice I described above. It adds like 1 minute to the process. On the first of each month, I spend about half an hour getting the totals for the previous month and setting the new month’s targets.

I also simulated the post-job life every chance I got: for the past 2-3 years, every vacation of 1, or 2, or 3 weeks, and every Sunday, I was actually working most of the time, but on my own projects. So I don’t know exactly how it will go after the 3-4 week mark, but I do know how I prefer to spend a day.

All this may make it sound like I’m hyper-obsessed with productivity. In fact, it’s almost the opposite: I’m generally of the “80/20” mentality; I like to do the minimum configuration that will make the most difference. An ideal, fully productive day for me includes plenty of time for lying on the couch daydreaming, with the cats sitting on top of me, watching the rain outside my window, and sometimes dozing off while reading a book. I just account for that in the time I allocate for reading, so that I can still make accurate estimates.

Plus, I’m nerdy and I find it relaxing to count things, so I don’t find it stressful to keep logs and totals.

By the way, just two books, Deep Work (mentioned above) by Cal Newport and Make Time, by Jake Knapp and John Zeratsky, contain all the specific tactics that I use for time management. Other than that, it’s all self-knowledge developed over years of trying stuff out.

Containers, projects, and code names

I have a number of projects going on. Each project fills what I call a container, which is just shorthand for a time block, a frequency, and a priority level. For example, the container named “p1” is, at the moment, defined as something I work on for a full block (2-5 hours), as many days of the week as possible (frequency), and which has the highest priority. Anything I’m working on that matches these criteria is my p1 project. Those criteria may change over time, and that’s okay. I can also switch what container each project is in.

As far as I can remember, I’ve never heard of this container thing from any other source. I made it up the other day while I was trying to remember all my projects. The benefit of containers is that I can slot them into my day without getting distracted by the details of specific projects, and I can think in shorthand like, “Did I spend enough time on p1 this month?” Other benefits include making the priority explicit, as well as only keeping a limited number of containers at once: if I ever get up to, say, p6, I’ll know things are getting out of hand.

Each of my projects has a code name. This is just a unique identifier that references a specific project, without boxing it in too much. What I mean by “boxing it in” is that for example, if I had a project that I thought was going to be a book about spiders, I wouldn’t want to call it “my book about spiders,” because that would leave no room for the thing to evolve into something other than a book, or evolve into something that’s not mainly about spiders.

For me, a project is just an unplanned walk. A good code name should be just enough to evoke the spirit of the walk, without determining the exact route.

Current containers and projects

Finally, now that you have the context for it to mean anything to you, here are my current containers and projects:

p1: 2-5 hours, as many days of the week as possible (hopefully 3-5 days per week when I get rolling). p1 is currently a project code-named safe passage, which is a writing project I’m not ready to talk about in detail yet.

p2: 1 hour, every day of the week. p2 is a project code-named a cup of tea, a language-learning project you can see a bit more about on my now page.

p3: 2-5 hours, 1-2 days per week. p3 is poste italiane, that is, writing for this blog and newsletter.

Friday project: 4-6 hours every Friday. An ideal Friday project checks as many of the following boxes as possible: visual art, coding, open source, and interdisciplinary. My current Friday project is code-named the map is not the territory, and involves ancient poetry and JavaScript.

There’s of course a lot more stuff that’s not projects, like journaling, binge-watching tv, running, riding my bike, climbing, wandering around town, catching up with friends, and so on.

In conclusion

A routine that works well for you is basically a superpower. You do have to build it yourself, but then it pays off every day, forever.