Productivity is dead. Long live Proactivity, Pt. 1

💭 Sprinting without losing your breath

The Optimizt is a newsletter about many things, but one thing it’s not about is productivity.

What I’ve learned from chatting with many of you is that you already know how to get things done. In fact, you’re so good at it that it can be a bit of a problem: You spend so much time and energy on work that there’s not much left for personal reflection, goal-setting, or hobbies.

That’s not your fault. You’re just trying your best to keep up in a system where your value is defined by your output.

When productivity is king, your priorities tend to be 1) learn how to run, 2) learn how to run faster, and 3) show others how fast you can run.

Missing from that list is choosing which direction to run, asking yourself why you’re going there, and considering whether you even like running. That’s how you end up with that hamster wheel feeling.

Don’t get me wrong: There’s definitely an argument for keeping your head down in your early career, working hard, and building momentum before you get too philosophical about what you want from life. But there’s also an argument that you don’t have to choose one or the other.

Instead of productivity, I think a lot about proactivity.

Proactivity puts the emphasis not on what you produce, but on where you’re going relative to your goals. Are you taking your life as seriously as you take your work? Are you standing strong against the big, scary problems? Are you looking beyond your task list to figure out where you’re headed?

Like a productivity system, a proactivity system helps you run faster — but it also makes room for you to ponder those questions at the same time.

What does a proactivity system look like in practice? Here’s part one of a look at mine.

Get SHIP done

In a sentence, what makes a proactivity system different from a basic to-do list is that it’s designed for task planning and prioritization, not just getting the current work done.

To add more detail, a proactivity system should have the following four qualities (which conveniently spell SHIP):

1. Strategic: The system should help you link long-term plans with short-term tasks, and make sure you’re doing them in the right order.

2. Humane: It should be flexible enough to account for fluctuating energy levels, unexpected events, and other facts of life that can derail the best-laid plans.

3. Iterative: It should evolve and improve over time to accommodate a person’s needs, not the other way around.

4. Predictable: It should organize the work into discrete chunks that are completed on a predefined schedule.

So, how does my system do all of that? I’ll give you the visuals in a second, but first, here’s what to look out for:

• Linked tasks, which allow me to connect long-term projects to daily steps, and a priority property make the system strategic.

• Effort points, where I mark how difficult I think a task will be, and reflection templates make the system humane.

• Reflection templates also make the system iterative.

• And sprints, which organize my work into weekly chunks with a regular deadline, make the system predictable.

And in the spirit of weekly chunks (yuck, what a weird phrase), today I’ll just describe sprints and effort points, and future editions will explain the rest.

First, a note: This is going to get deep in the weeds pretty quickly.

If you’re looking to adopt some or all of my system, I’d recommend copying my free proactivity system template and opening up the sprint and task databases to follow along more easily. If you want more hands-on guidance, just reply to this email!

If you just want to casually learn how I get things done, then feel free to read on, but this might not be the most engrossing read.

Now, let’s get started!

Life’s not a sprint, it’s a…series of them

It’s no coincidence that I call my weekly batch of tasks a “sprint.” The term is borrowed from Scrum, a task management framework usually used in engineering teams — but it also emphasizes that my system isn’t about slowing down. The idea is to move fast, but without sacrificing strategy and reflection.

As you can see here, I “run” a sprint each week, and each one measures three things:

1. The number of tasks I’ve committed to that week, and how many I’ve completed so far.

2. How many working hours I have that week, and how many hours I estimate that week’s work will require.

3. How many effort points I’ve assigned to myself that week, and how many I’ve completed so far.

Assigning effort points

You can think of effort points as a difficulty score that helps you tell apart the complex tasks from the quick ones, and mentally prepare to take them on.

Effort points are scored out of 100, and that’s also the amount I tend to complete in a week — so you can additionally think of them as a percentage of the sprint that I expect a task to require. For example, a task worth 25 points should take a quarter of the sprint to complete.

When new tasks naturally come up, I add them to my backlog and assign effort points and a priority. Then I can see how many points are on my backlog and get a sense of how many weeks it’ll take to complete them. That helps with predictability.

Effort points also help make the system more humane, because if I just pushed myself to finish 300 points in a week, it’s probably a good idea to commit to fewer points the following week to avoid burning out.

Setting up a new sprint

With my sprints database set up and effort points assigned, I can move onto my usual, 15-minute weekly planning session. First I set up that week’s sprint dates and number of available working hours.

Assigning tasks to the sprint

Then I scroll down to my task backlog and start assigning tasks to the sprint. I add as many of the highest-priority tasks as I can, paying attention to the total effort points so that I don’t overcommit relative to that week’s schedule and energy levels.

With those tasks added, I’m at 107.5 effort points, which is just right.

Writing subtasks

Once I’ve picked out my tasks, I can make them a bit more actionable by writing subtasks; finally, after all that planning, these are the concrete bits of work I’ll do each day.

For recurring tasks like writing this newsletter, the subtasks are pre-written, and all I have to do to add them to this sprint is press an “Add subtasks” button. For non-recurring tasks, I take a few minutes to think about how to make them as easy to tackle as possible, then write the subtasks.

Starting the work (finally!)

Finally, with all my subtasks written, I can pick out the first ones I’ll complete. I’ll do the same thing each day of the sprint, using my dwindling hours and remaining effort points as motivation to drive each task to completion.

Trust the process

Sprints and effort points are probably the most out-there aspects of my proactivity system. I mean, I’m literally an individual person using a system that entire engineering teams run on (not that I’m nearly as productive!).

But if you’ve been paying attention, then you know I love systems, and that they don’t make me any less human. While it took me years to land on this system, it takes less than an hour each week to maintain and gives me immeasurable value. (And I’m happy to set it up for you — just shoot me a reply!)

Combined with my “life areas” database, sprints and effort points give me a way to juggle several commitments while guaranteeing that a certain amount of work will get done each week.

But they don’t form a complete system on their own. They’re more focused on the “running fast” part, while linked tasks, prioritization, and reflection templates account for the “where and why to run” part. I’ll go deeper on those in the next issue or two.

The point of this series isn’t to claim that my system is the only way to live proactively, and certainly not that I’ve got everything figured out. My deeper desire is that as much as you invest in what you do, you also invest in how you do things.

That’s how you get off the hamster wheel — and there’s no better time than now.