To plan, or not to plan?

Planning is a hammer, but not everything is a nail

Your Five-Year Plan is a newsletter about embracing life’s profound uncertainty.

Maybe your own plans went up in flames; maybe you’re considering a big, scary leap. This is your trusty companion while you’re writing the next life chapter.

Welcome to the conversation—and to the adventure that unfolds when your plans go sideways. This is letter #21. ✨

To plan, or not to plan?

The intricately-planned Sagrada Familia, captured on Kodak Portra 400 film

If you participate in the Overplanner Industrial Complex, that cottage industry of spiral-bound goal planners and bullet journaling influencers, you know that many of us wear the label “planner” like a badge of honor.

No shame in that—I certainly did!

Planning every aspect of my existence was a security blanket I thought would shelter me from life’s profound uncertainty; you know how that turned out.

Facing the unknown required me to imagine a life without planning as its organizing principle, and quit the bad habit of overplanning my days, weeks, and years.

But living a less plan-centric life doesn’t mean never making another plan. It means knowing when it’s an appropriate tool for the job at hand.

As I’ll argue below, planning is a useful tactic in the following scenarios:

• ✅ When plans are a source of freedom, not constraint.

• ✅ When plans are flexible enough to account for chaos.

• ✅ When your planning timeframe is appropriately short.

• ✅ When you’re coordinating lots of moving parts.

✅ Plans are useful when they’re a source of freedom, not constraint.

Here’s a typical summer vacation scene. You’ve just shuffled through customs after an exhausting trans-Atlantic flight, and are (virtually) hailing an Uber to escort you into the center of an unfamiliar city.

Now imagine this: you don’t know what destination to tap into the app…because you haven’t made hotel reservations.

This is the textbook problem that plans exist to solve.

There’s very little upside to being spontaneous with certain foundational aspects of your vacation, right? Finding yourself in a strange place, tired and hungry with nowhere to go isn’t a recipe for adventure (for most people, at least). It’s a recipe for an argument with your equally cranky travel companions.

In a recent episode of his podcast, author Cal Newport touched on this idea when he said, “It’s very difficult to keep breathing room in your life if you can’t control the stuff that’s taking away the air.”

Plans become a constraint—and threaten to overtake the possibility of magic or discovery—when we go too many steps further. When, in addition to booking our lodging and researching attractions we’d love to visit, we make hour-by-hour itineraries that leave zero room for serendipity.

Here’s one of my favorite memories from a trip to Turkey: I walked past a group playing backgammon, and one of the participants motioned me over to join. I had no idea how to play, but somehow we hopped over the language barrier by communicating through hand signals, encouraging smiles, and nods.

If I’d been rushing off to my next planned destination, too busy to sit down and play, my plans would’ve entered the zone of constraint—and I’d have lost a meaningful opportunity for connection.

✅ Plans are useful when they’re flexible enough to account for chaos.

Nathan Fielder is, hands down, my favorite comedian. (If you’re a fan of Nathan For You, congratulations, we’re now best friends.)

In his HBO series The Rehearsal, Fielder coaches people through high-stakes conversations and experiences, grasping at certainty by walking them through increasingly elaborate maps of how the future might unfold.

Below is the decision tree he creates to prepare for one such moment:

Nathan Fielder’s decision tree in “The Rehearsal,” via HBO

We know this is absurd, which is precisely why it’s funny.

Our lives are full of unpredictable variables—let’s call them Chaos Agents. Their existence is inescapable; there’s a chaos baseline we’re all subject to.

Some of our lives contain more Chaos Agents than others, and not all Chaos Agents are created equal. Sure, there’s a level of unpredictability baked into life with my eight-year-old cat Cammy—requiring unplanned vet visits and schedule adjustments—but if she were an eight-year-old human, that unpredictability would be next-level.

The more Chaos Agents our life contains, and the more unpredictable each Chaos Agent is, the more often we’ll have to adjust our plans. When those plans are flexible, that helps them bend instead of shatter.

✅ Plans are useful when your timeframe is appropriately short.

The phrase “five-year plan” is used frequently and with very little irony, but the title of this newsletter is squarely tongue-in-cheek.

Chaos Agents ensure that our plans change at unpredictable intervals. Occasionally, those changes alter our life’s trajectory. So to make meaningful plans, we have to shorten our timeframe.

Forget about your five-year plan. Maybe you can plan your week. With enough Chaos Agents making mischief, maybe you can only plan your day…or, in the case of harried new parents, the next fifteen minutes.

It’s entirely normal to have goals you want to accomplish in five years, like starting a business or buying a house. And you can, responsibly and consistently, take actions that build toward those objectives.

But you should complete those actions knowing that, five years from now, it’s possible you’ll want something entirely different, for reasons you can’t begin to understand today.

✅ Planning is useful when you’re coordinating lots of moving parts.

Dwight D. Eisenhower understood this when he said, “Plans are worthless, but planning is everything.” This paradox is relevant when you’re coordinating lots of people or tackling a complicated project.

In these cases, you’re working within a system comprised entirely of Chaos Agents, and that requires plenty of flexibility (see: “plans are worthless”). But when Plan A inevitably goes up in flames, you still need a way to conduct the chaos orchestra (see: “planning is everything”).

In this scenario—a common occurrence at your workplace, I’d guess—planning is a reasonable and effective approach.

But is it the best way to approach the majority of your off-hours?

It sure isn’t, because planning was never meant to be a way of life. It’s a tactic best deployed under specific conditions. It shouldn’t be a mindset, a lifestyle, or a personality trait.

So let’s relegate planning to the moments where it’s most appropriate, and start experimenting with new approaches the rest of the time.

💬 What do you think?

I’m curious to hear from you. Would you make any changes to the list above? In your experience, when does planning feel freeing, and when does it become limiting?

Had your own plan-in-flames experience? Taking a leap into the unknown? I’d love to hear more. Just hit “reply” to get in touch, or introduce yourself here.

Warmly,
Maddie