Jeff Shearer

It’s easy to see the library as a hassle. Who wants to wait around for weeks for a book to become available, then be bound by a two week period to read it? I know I used to hate this process. If I wasn’t ready to read that book, then I was forced to confront the shame of returning the book earlier (or the shame of late fees).

But the constraints of the library are really a gift. The gift of a deadline.

When you check out a book from the library the constraints aren’t negotiable, and you can almost find peace in that certainty. You don’t get that book to read someday. You have to start now.

You can do this same thing elsewhere in life to force action. But constraints for the sake of constraints don’t do much good. They have to carry weight. Perhaps a penalty for violating them. You might have the willpower to psyche yourself up to run every morning. But perhaps a better way to force your behavior is to sign up for a race. Once the deadline is there, you have no choice but to act.

I flew home from a trip on MLK Day and arrived to an airport in chaos. I usually take a Uber or Lyft home rather than park at the airport, but when I went to call a ride, the prices and wait times were astronomical, with a line of drivers stretched for miles around the airport.

I glanced over at the nearly empty line for a regular, boring taxi. It was as if it were invisible to the horde of people overflowing in the Uber waiting area.

I made it home faster than an Uber would have even been able to pick me up. Oh, and it was cheaper too.

It’s always worth pausing, taking a breath, and noticing when you’re engaging in a habit or pattern. Is what you’re doing truly the best course of action? Or are you just on autopilot, following the crowd?

One of my main hobbies this past year or two has been woodworking. Nothing too elaborate yet—mostly picture frames and boxes—but certainly something I now practice regularly.

As I was building a few frames recently, I decided to try a new, more challenging joint for bringing the frame pieces together: a mitered half-lap (see below):

This joint is more challenging than what I’d previously been using, and requires much more precision to get a clean and well-seated joint in the end. I should have spent a lot more time planning out the cuts and measurements. But instead, eager to get started, I charged ahead, rushing the cuts of the pieces of the frame, to predictably mediocre results.

Things got even worse when I was cutting the slot for the artwork with my router. The work splintered when I tried to remove too much material at once. The project was ruined, and it was time to start over. All because I was rushing.

It was a painful lesson in the value of patience and planning. Rushed work rarely pays off. Instead, it’s always worth overestimating the time and effort you’ll need.

I’m in a music rut. Every time I look through my Spotify library and recommendations, things just feel stale. The recommendation algorithm seems to be in a positive feedback loop, and now I’m just seeing more of the same.

Some days, it’s enough to convince yourself that there’s no new music out there you might like. It’s the dark side of overreliance on algorithms: since you get fed only what you like, you lose sight of any other universe other than the one manufactured for you (see also: any feed-based news/social media).

I’ve grown to dislike most algorithm-based recommendations, but music is one area where I’ve seen a tremendous amount of value, especially within Spotify. Over the years it’s introduced me to countless genres and artists I never would have explored otherwise. But knowing the tendency of these recommendations to get caught in a circuitous loop – sometimes you just need to blow it up and start fresh again.

Spotify, regrettably doesn’t make this easy – you basically have to start an entirely new account. Which seems a little ludicrous at first, but is it really? I may just try it.

There’s a great case to be made for doing the same on your social media – start fresh with the stuff you’re following and reading, and see where that new path leads you. Unfollow everything, then build it back up. See what you actually miss. You can spend your whole life consuming what you already like – but there’s a whole world of stuff that you love – you just haven’t discovered it yet.

On a busy week, or month, or year, it’s natural to crave some quiet, uninterrupted time to get things done. I always tell myself “if only I had a week alone to work on this, I’d make so much more progress”, as if an opportunity like that could only exist in a fantasy.

Yet I’m often handed exactly that, especially around the holidays with a lot of teams out on vacation, and the otherwise frenetic pace of the office at a standstill. It’s certainly a treat to get things done during these times, but I’m often disappointed by myself when I don’t make better use of the time. For a long time, I convinced myself that this was some failing of myself, or an ability to focus.

But more likely, it’s a symptom of an overly ambitious to-do list. I love a good list – it’s how I run much of my life. But I can always sense when I’ve gone a bit overboard with them. The threshold typically happens when I start trying to measure the amount of time I spend in each hour of the day. It helps to look at past to-do lists, and see how often my eyes were bigger than my stomach. It’s plain as day in hindsight, yet when planning the coming day or coming week, it’s quite hard to estimate. There’s no clean solution to this, other than continuing to give your best laid plans a haircut before proceeding. If you have three big tasks and two small ones to tackle today, give them an honest look. Which of those tasks is truly essential today? Can you get away with one big task, and those two small ones instead?

If you can negotiate with yourself to accept this deal, and underestimate your productivity, then you’re much less likely to be disappointed with your progress.

I’ve gone through countless pens in my life, never paying them much mind. My drawer is full of them, pens I’ve never use, pens I probably will never use.

But I started using a particular kind of pen a year or so ago for my journal and handwritten notes. The pen is pretty ordinary, with the one exception being that it’s fine-tipped, which makes writing satisfying.

I have two of them, and I’ve now had to refill the cartridges on them 6-7 times. I never do that. The idea of using all the ink in even one pen felt, frankly, impossible until now. But I write enough daily to go through ink surprisingly quickly. This pen I love. I use it every day, and it’s the perfect tool for me.

It’s amazing how much a difference a great tool can make. It makes me wonder where else in my work or life could be helped just by discovering better tools.

The first problem with good documentation is that no one wants to do it, so it never gets done.

The second problem is that once it’s made, no one remembers to refer to it. Since no one refers to it, no one wants to create it. And around we go.

If you want documentation to happen, you have to stop treating it as a side project, a second class citizen. Documentation should be a required step for shipping any new work.

A “depth year” is a year where you focus on enjoying what you already have, rather what’s new, novel, or happens to be a desire right now.

A depth year is a way of finally reading all those books already on your shelf. In my case, it’s also a way of revisiting favorite games, or finally playing the stuff I bought years ago, but never started.

Perhaps most importantly, a depth year lets you finding your way back to hobbies you’ve put down. It can help you get past the superficial dopamine hit of “new”, and digging for the deeper satisfaction had on the pursuit of mastery.

I’ve decided 2020 will be a year I experiment with a depth year, and here’s the rules I’m setting forth, posted here to keep myself accountable:

1. No new books. I’ve got a ton of stuff already on my shelves that I’ve been meaning to re-read, or I’ve never read before.
2. No new games. Similarly to books, there’s so much already in my library. Games I’ve wanted to revisit. And a massive backlog of unplayed games. It’s time I started making a dent.
3. No new hobbies – focus on what I already have on my plate: homebrewing and woodworking.

Given the phrasing of the rules above, you might consider this a year of “No”. But I don’t see it that way. If anything, setting constraints like this are liberating, as t hey give me clear guidance on exactly where to focus.

The more you build it up to a momentous, life changing occasion, the more likely you let yourself down with a failed resolution later. You can start making a positive change in your life any day of the year. No need to wait for tomorrow if today will do.

And speaking of resolutions: skip them. Focus on building the right habits instead. If you don’t know where to begin, read Atomic Habits. Easily the most valuable book I read all year.

“What is important is seldom urgent and what is urgent is seldom important.”

— Dwight D. Eisenhower

Increasingly I’ve realized that one trait that separates good leaders from the great is the ability to discern the important from the merely urgent.

Dwight Eisenhower had a great system for identifying the relationship between urgent and important work, and it’s a handy tool for looking at your work with objectivity to identify what truly matters.

But the first challenge, I think, is being able to truly discern what is actually important work. Many days, I can’t help but focus on the most urgent thing – the squeakiest wheel, the loudest person in the room. Yet as I’m doing the work, I can’t help but wonder if the work I’ve chosen to do is truly what matters most – and what I’m putting off by focusing on it instead.

My only method for identifying the important work is regularly looking at all the projects and tasks I’ve identified at once and mentally prioritizing them.

Of course, doing this requires you actually organize all your tasks in one place – a task easier said than done. But whether it’s a trello board, Jira issues, a whiteboard, or a boring old notebook – some method of cataloging everything of note is key to making this work.

From there, it’s important to look at the tasks with objectivity. So preferably, it’s best to do this exercise at the end of the week, or outside working hours, to avoid being influenced by the latest fire alarm to come across your desk.

It’s inevitable that some of your priorities will need to be the urgent ones, but this exercise helps ensure you sneak in some of the important work first.