Weekstart

The curse of productivity is that it's self-perpetuating. Respond to e-mails with lightning speed and you just get more replies. Demonstrate your reliability to others long enough, and they'll just bring you more shit to do. Develop productive routines and habits and—before you know it—your natural disposition will shift towards being done with things and away from actually doing things.

Left unconstrained, optimizing for a productive life can diminish the joys of living. Many of us who opt into the lifestyle of "staying on top of shit" do so, ostensibly, to maximize time for creative work, or for leisure, or for family. That's the spirit with which I first discovered Getting Things Done near the beginning of my career. And it really worked! I have no doubt I owe much of my success to adopting a clear productivity process, low-friction tools, and ruthless discipline.

But even for the handful among us who successfully find a productivity regime we can stick with, the technologies that both enabled remote work and unintentionally led to the disintegration of work-life boundaries have resulted in a situation where highly productive people often wind up cursed with the inability to turn it off. I had no problem forgetting about the hundreds of e-mails and things to do in 2009 when I would—get this—leave my computer at the office overnight. But once I started working from home, there was no longer a natural threshold through which to transition from being "productive" to being "unproductive". I doubt I am alone in this.

Depressingly, even after I retired and no longer had any job at all, I found myself continuing to be hyper-vigilant about checking e-mail, tackling todo after todo, and generally prioritizing productivity over whatever shit I claimed to want to do. I've been promising myself a hedonistic life of video games, vodka, and gummy bears since I was 19 years old. And yet, even though I have plenty of money, zero constraints on my time, and a backlog of thousands of games, here I am writing a fucking blog post instead of literally ever doing the one activity I set out to achieve before starting my career.

Moreover, when others look at me and how I go about getting shit done, and—rather than wanting to emulate it—they tend to walk away feeling grateful they're not as tightly-wound as I am. When I consider all the people in my life, it's starting to feel like there are essentially two classes of humans: people who never get shit done and people who never stop getting shit done.

This state of affairs was clearly suboptimal. That's why, last year, Becky and I adopted a bespoke weekly schedule that enables us to get things done without getting carried away. The key insight was, as usual, to implement a strict timebox. We call it "weekstart", and this is how it works.

What is a weekstart?

Weekstart kicks off Monday morning and ends with the dinner bell on Tuesday.

The big idea? Life is too short to work for a 2-day weekend by spending 5 days chained to the computer, obsessively checking e-mail and knocking out tasks with a robotic procedural mindset. Instead, we decided to try flipping the schedule on its head: what if we spent only 2 days each week clearing our e-mail inbox and living out of our todo backlog? The rest of the week may not magically become a blur of vodka and gummy bears, but it might open the door to feeling more free to pursue our professional and creative endeavors with a clear head while also having the benefit of syncing our schedules to enable spontaneous ideas and joint activities.

Here's all it is:

• Monday and Tuesday are our weekstart: We temporarily give our lives over to our e-mail inbox, our todo tracker, and the pile of shit we hate doing. We know this is the only time we've got for this shit, so we're both heads down and focused, and are mindful not to interrupt each other's flow.
• Tuesday's dinner doesn't start until we quit: Our closing ceremony—and our ticket to dinner—is to demonstrate to one another that our e-mail inbox is empty, our todo tracker's inbox (we use Things) is also clear, and all our scheduled todo items have been scheduled out to the subsequent Monday.
• Wednesday through Sunday are the week: the rest of our lives are spent living. This is where we pursue our passions. It's when I study Japanese and build apps. It's when Becky designs her strength-training program and broadens her horizons with things like bodybuilding. Quality time with each other is the top priority, so if one of us suggests hanging out, the other has no excuse but to drop what they're doing.

By far the hardest part of adopting weekstart is to become comfortable with the idea of declaring defeat every Tuesday evening. There's always still so much to be done! But the truth is that, whatever it is, it can wait. If it was truly urgent, we would have made time for it.

Good for you, you're unemployed

I hope that you have the clarity of mind to be taking all this with extreme skepticism, "great, so your productivity hack is to retire before 40," you ought to be thinking. And you'd be right! I'm not going to lie: financial security and early retirement are pretty great. But it's also given me firsthand evidence that the job wasn't what was chaining me to my desk: I did that to myself.

If you're:

• Required to show up at a workplace in person every day
• Have a calendar full of meetings you can't reschedule
• Lack basic control over when and how you do your work

Then I can't help you. But if you do anything that could be described as "knowledge work", can work remotely, and are engaged in a role that cares more about outcomes than attendance, then it might be worth chewing on the approach laid out above. Maybe give something like weekstart a try. Whatever particular system you adopt for yourself, whatever silly name you might give it, what matters is that you develop an appreciation for how liberating constraints can lead to better results than unstructured freedom. Just my two cents.

Okay, it's Wednesday at noon. I'm gonna go not get something done.