Keep raking

It’s that time of year. The air is getting crisp. The days are getting short. And any number of leaves are gently cascading to the ground. Like they do, every year. And so, as you reach for that rake to ensure your rain soaked sewer drains and yards are clear, I thought I’d touch upon something that’s always struck me about the act of raking leaves—and how it applies to startups and founders and entrepreneurship.

WTF? I know, I know. You’re checking that you’re at the correct URL. You’re probably thinking you accidentally stumbled upon a Medium post. But bear with me, if you will.

Keep raking

I’ve always found the act of raking leaves both extremely cathartic and unendingly frustrating. Much like running a startup.

So maybe this is an allegory. Or a parable. Or an analogy. Or simply an observation. Or an expository writing exercise.

I don’t know. I’m not an English Maj… oh. Crap. But I digress. Where were we? Oh yes…

Here you have a project. And a tool for completing that project. A clear objective. And the opportunity to attack the problem firsthand.

“What could be easier or more straightforward?” you quietly delude yourself. “I’ve got a rake. Which is way better than a leaf blower. And I’ve got all of these leaves. Easy.”

And so you start in, attacking this obvious opportunity with a tool that seems especially well suited for the job.

And you rake. And rake. And rake. And rake.

After a time—and with a hearty sense of accomplishment and satisfaction—you glance at the massive piles of leaves you’ve managed to rake together. Clearly delineating your progress from area to area. Clearly conquering this opportunity that seemed so obvious.

But then you look back at where you’ve been. And what do you see?

You see the same thing you saw when you started the entire process. Leaves everywhere. It’s as if you’d never been there. As if you’d never even weakly swung that rake in the direction of the yard.

But you’ve done all this work. You’ve created all these piles. You’ve spent all of this time.

Keep raking.

Now, it’s not really fun. Or satisfying. You’re covering ground you’ve already covered. And there is a breeze. And more leaves are falling. And it’s starting to rain. And you’re just building more and more piles. Maybe you should just give up and do this another day.

Keep raking.

And so you go over the same ground. Again and again. And you’re still seeing progress with the piles you’re creating. But your back is starting to hurt a bit. As are your hands. And you’re kind of cold. And this seems completely thankless.

Keep raking.

But then something happens. And it’s almost unnoticeable at first. But then it dawns on you.

That patch of ground. That swath of grass. The one that you’ve raked innumerable times today.

It’s still visible.

There are absolutely no leaves on it. And it’s small. But you’re drawn to it. Struck, as it were, by this odd sense of accomplishment. And satisfaction. You’re making progress. This is working. It’s small. And seemingly insignificant. But it’s progress.

And so you sit there. Staring at that patch of ground rather smugly. Proud of yourself. And your small patch of accomplishment. And then you quickly glance up to see if there is anyone else within earshot who can share in your moment of victory.

There isn’t. Keep raking.

Suddenly, you’re not so tired. Or cold. And so you keep at it. And that patch of ground grows. And fewer leaves fall. And you’re making progress.

You take brief breaks to survey your progress. But you keep at it. Raking and piling leaves and clearing huge swaths of ground.

And a few leaves fall in areas you’ve already cleared. But now it seems easy to wander over and bring them into the nearest pile. Enjoyable even. And satisfying.

And then you’ve reached the edge. And everything is piled.

“Almost done,” your annual flare-up of naiveté tells you.

And so you start collecting your piles of leaves. Pushing as many as you can into each of the swollen bags. Or into the wheelbarrow to hustle them over to the compost pile.

Either way, the repetitive hoisting of those wet masses of organic material begins to take its toll.

But you still feel a sense of accomplishment. And you feel as if you’re nearing your goal. Again, with a sense of satisfaction, you pause. And look back.

Only to notice. Notice that—now strewn across your previously leaf free pristine domain—there are a whole bunch of leaves—probably an entire bag’s worth—that have escaped from piles. Or blown from the wheelbarrow. Or fallen out of bags. Or gently drifted down from another tree.

Keep raking. Always. Keep raking.

Don’t give up. Keep raking.

  1. this was a really beautiful piece Rick, thanks for sharing and re-inspiring us all. Like you tend to do or something

  2. “your annual flare-up of naiveté” is so hilarious. And so spot on. Nice piece.

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