The PLAN

The PLAN

Part One

Principles

Consider the next few chapters your entrance to Oz. The transformative principles of The PLAN will take you from the black-and-white binary of the self-help industry to the Technicolor dreamland of being a Lazy Genius. I can’t wait for this section to help you see your time in a brand-new way.

Now, there’s a chance you think you already know what I’m going to say. If you’re familiar with either me or self-help books in general, you might make assumptions about these principles—thinking that you know them, are fine without them, and can just skip to the strategies. I’ve done that myself when reading books like this. When you’re well versed in the language of productivity, principles are just the page fillers before you get to the good stuff.

Except when it comes to The PLAN.

These principles will surprise you. In fact, writing this book felt like opening Mary Poppins’s carpetbag—every time I reached inside, I pulled out something else magical that I didn’t know was there. The PLAN’s principles will go down differently. I promise.

We desperately need a new approach for managing our time, and that begins with a new way to see. The PLAN is your lens.

1. The Real Reason Planning Is Hard

I grew up going to the mall.

If you’re of an age where you’re not sure what a mall is, now is a good time to tell you that I’m in perimenopause, I’ve never downloaded TikTok, and I didn’t have a cellphone until I was seventeen. Not because my parents were strict but because people didn’t have them yet. Consider yourself generationally warned.

Back to the mall. I loved spending time there as a kid. The mall is where I got my ears pierced, where I awkwardly hung out with a boy I liked, where I ate a truckload of Cinnabons, and where I learned to confidently walk past Victoria’s Secret without looking or breaking stride.

But my favorite thing about the mall was the “You Are Here” map. Holy moly, I still love that thing. Not only do you have the stores organized by category on a giant screen, but you also have a beautiful red dot that tells you exactly where you are.

You can see everything, and you can see yourself.

Chances are you’d like that for your life, too. Wouldn’t it be amazing to see everything at a glance so you can quickly chart a route to an imagined future where life is beautiful and under control?

That’s probably why you keep buying planners.

A planner is the closest thing we have to a “You Are Here” map, to that bird’s-eye view. You want your day, week, month, quarter, year, to-do lists, tracking bubbles, words of gratitude, meal plans, and five-year goals all available at a glance.

You get your next new planner and spend hours setting it up, answering questions about what you want to accomplish and what habits you want to begin, and maybe even trying your hand at a doodle or two. Once you’re done, you let out a deep, gratified sigh. There it is! There’s everything at once! Life is going to be better now!

But then, much to your chagrin, life happens again, and you can’t keep up with your plan. You manage what you can for as long as you can, biding your time until the next opportunity to reset and see everything at once—the beginning of summer, the school year, January—and you repeat.

I bet you’ve been repeating for a long time, yet you’re still drowning. Why?

“Everything at once” is the problem, not the solution.

“Everything at once” is the problem, not the solution.

“Everything at once” is why you push your palms against your eyeballs multiple times a day. “Everything at once” is why you doomscroll in the bathroom, hoping no one notices you’re gone. (They will.) “Everything at once” is why you listen to an audiobook while cooking dinner while helping somebody with homework while wearing microfiber socks because somebody on the internet said it was like sweeping.

“Everything at once” is not how we’re meant to live.

Before you lose hope, let me be the Robin Williams to your Matt Damon and tell you that it’s not your fault. It’s not your fault. It’s not your fault.

You are not the reason you’re drowning. You are not the reason “everything at once” doesn’t work. You are not the reason time-management principles aren’t sticking.

The reason is far beyond you.

The System Is Rigged

Let’s sit crisscross-applesauce and do a little History Corner.

Remember the Industrial Revolution? America quickly went from “Whoa, coal!” to “OMG, gas is amazing!” to “Have you heard about this electricity thing?” The West got bigger and better and, consequently, went cuckoo for productivity. This guy’s factory had to beat that guy’s factory, and he did that by making stuff faster than the other guy did.

When the digital revolution happened, it gave us more than computers and AOL Instant Messenger. We were given the promise of more time. Technology would create efficient production for us, freeing us to do other, presumably more enjoyable, things. Amazing!

However, that digital revolution happened so fast that we never disentangled ourselves from the Industrial Revolution’s culture of productivity. Unfortunately for us, that same technology incidentally made the productivity obsession worse.

It makes me think of that scene in Sabrina when Harrison Ford (Linus) and Julia Ormond (Sabrina) take a helicopter to board a private jet to fly to Martha’s Vineyard for the day. Once they’re buckled into their plush seats, Linus immediately begins working, looking at nothing but the reports in front of him.

Sabrina, frustrated by his indifference to the present moment, asks, “Don’t you ever look out the window?”

“I don’t have time.”

“What about all that time we saved taking the helicopter?”

He awkwardly pauses. “I’m storing it up.”

“No, you’re not,” she replies.

And we’re not either.

In fact, the obsession with productivity is so deeply woven into our culture that we live in a productivity-industrial complex. Even though I did not thrive in any form of social studies class, allow me to explain what that means.

An industrial complex is essentially when an industry is in a feedback loop with some element in society. The public and private sectors become so intertwined that separating them is almost impossible, and that connection is often at odds with what’s best for society itself.

Let’s take weddings as an example. The U.S. wedding industry was worth over $70 billion in 2023, with the average wedding costing just shy of thirty grand. I’m not knocking anyone’s choices, and if you want an all-out wedding, enjoy it. But what if the wedding industry began pushing the idea that smaller, simpler, less expensive weddings were great, that you didn’t need to follow the trends, think about Instagram-worthy elements, or be impressive in any way? If that idea took root, people would spend less, and the industry would suffer. So even though it might be collectively better for folks to have whatever wedding they like, the wedding industry cannot encourage that. Therefore, we will continue to have magazines, blogs, and social media telling us what kind of wedding we should want. That’s a wedding-industrial complex.

Another example is the prison-industrial complex. Many are championing reform in the judicial system, which would lead to fewer people in prisons. However, the U.S. prison industry makes over $10 billion a year, and incarcerated individuals in the prison system generate revenue from goods and services on top of that.3 So even though justice reform and prison reform would be beneficial for society, the prison-industrial complex makes them extremely difficult because of how deeply entwined the justice system is with industry.

The same has happened with productivity.