Why Planning Less May Be a Better Plan

Disclaimer: this post contains affiliate links. If you click on them and buy the products, I’ll get a cut of the profit. I promise they’re good products!

Story time!

I embarked on my productivity porn addiction back around 2013, when I discovered David Allen’s Getting Things Done (GTD). After skimming a bootleg version of his book on my tiny iPhone, I reckoned I had found the secret to life!

In short, the goal of GTD is to offload all chores, plans, and to-do lists to a filing cabinet, to free your mind from the burden of remembering everything. Instead of never getting to large projects, you break all projects down into a series of smaller actions, listed on a piece of paper for you. Each day, you get a bunch of those next-actions in front of you and complete them.

Instead of using your mind as your to-do list, you can now use your mind to be creative while still getting everything done.

That’s it. Mind like water.

(Before you true believers out there pillory me, yes there’s more to it. Like, the machine that prints out labels for all the file folders.)

I got obsessed, bought two beat up filing cabinets, and filled them with file folders for everything in my life.

And I just couldn’t keep up.

I’ve since tried a few ways to approximate Allen’s write-out-all-steps approach, and sometimes have made a bit of progress. But I could never quite make it take off.

The part that filled me with guilt and failure, was that I just couldn’t bring myself to take every project and break it up into action chunks. While dealing with this guilt, and getting some things done half-assed, I kept wondering if maybe there was another way.

Then, a few days ago, it hit me. There is another way!

In this article, I’ll describe this other way, which is more like mathematical induction than exhaustive introspection. And, I think both you and I will become happier and more productive in the end.

Enjoy Failure

I’m reading a book called Fail Fast, Fail Often, by John Krumboltz and Ryan Babineaux. Their strategy so far feels a little like a learned faith. They studied the happiness and success of over a bajillion people, and have come to the conclusion that the most successful and happy among us act first, and plan rarely.

Most of us are the opposite – we plan always, act never. The authors instead found that it’s through trying new things and failing, that people encounter the most opportunities for growth and success. Those of us that plan out all our actions before taking the first step tend to blame everyone for our failures, while the fault really lies in our lack of action.

It is by fearlessly blasting toward little failures that we learn, and at the same time experience life in a way that the planners could no.

The behavioral therapy these authors suggest are 1. follow your curiosity, and 2. if you feel like doing something, figure out how to fail at it as soon as possible.

But how do I know if my curiosity is leading me in the right direction? And, if I fail a bunch of times, won’t I just go broke and lose my house?

To answer these questions, we need a little bit of mathematics.

Calculus!

I know you failed calculus long ago (so did I!), and there’s no way some dry subject like this can help with human psychology.

But it can. Give it a minute.

Think about power lines hung from electric poles. They hang in a conspicuous “U” shape called a catenary. It turns out that every chain, rope, bridge, string of lights, whatever, suspended between two points, will hang in that same shape. It’s pretty easy to do experiments to investigate this shape. For example, get a chain necklace, or just a length of chain, and hold it between your hands. That U is the catenary.

If you get a friend’s help, you can demonstrate something surprising about the catenary. While you hold the chain, have your friend pinch the chain somewhere else gently, so the chain stays pretty still. Now, you let go of the string on that end. The rest of the chain will remain in the identical catenary shape.

If you follow this experiment all the way down to the smallest bit of chain, the shape continues to remain.

German mathematician Gottfried Leibniz discovered that the shape goes all the way to the smallest conceivable length of chain, of length zero. He called that smallest length the infinitesimal. That infinitesimal can’t be a straight line, but must be some shape that represents the catenary’s curvature.

Leibniz showed a surprising relationship between that infinitesimal and the full catenary curve. He invented a new math called integration, where all those infinitesimals can be added together to form the entire, beautiful catenary curve.

In other words, the smallest bit of action, constructed properly and repeated over and over, is sufficient to recreate the full goal of the curve.

The challenge Leibniz and his collaborators, like Johann Bernoulli, faced, was to create a new mathematics to both describe this minimum-maximum relationship, but also to discover the relationship for new types of curves. This mathematics is today called “Calculus”, and it is crucial for understanding all areas of physics.

Tiny Actions, Giant Results

We can apply the laws of infinitesimal calculus to our own lives. I call this “trust the process”.

The way this works is by identifying certain behaviors that tend to aim towards success, and then practicing those behaviors even when they lead to failure. And when failure strikes, learn from it.

In fact, Krumboltz and Babineaux stress that failure, itself, should be a daily behavior!

The authors pack their short book with examples of people who apparently bumble into wild success. For example, Jack Dorsey, the founder of Twitter (now X). Dorsey got interested in the network problem of dispatch – like, selecting the best cops to get to the scene most efficiently. He got hired to a company to work on their dispatch software, and the company soon went bust at the end of the 1990s. Instead of jumping back into programming, Dorsey went and dabbled at massage therapy, botanical illustration, babysitting, and fashion design. Several years later, while working as a programmer again for a podcasting company that was on the verge of bankruptcy, he pitched the idea that would become Twitter. The rest is history.

Krumboltz and Babineaux show, from various angles, that trying new things and failing is not only a great path toward success, but an efficient path. Instead of pinning your hopes of success on some future goal that you might never get to, you spend your time doing little experiments and learning from them.

They suggest a few ground rules for picking an action to take, so you’re not just failing for failure’s sake. Here are the ones I thought most important, found in the chapter called “Think Big, Act Small”:

1. Keep it specific

Don’t pick something vague, like “start writing better”. It needs to be something that happens at a point, like “send a sales email to a bunch of my friends and family this afternoon”.

2. Keep it easy

Instead of trying to bench press 500 pounds right now, and getting discouraged, try benching 50 pounds instead.

3. Keep it fun

Cutting off a finger is not fun, though it’s probably pretty easy and specific. Do something that will make you smile instead.

4. Keep it immediate

If the action occurs way in the future, like planning to hit up a networking conference two months from now, you’ll have too much time to talk yourself out of it. And, that’s two months wasted not taking any other risks! Pick something you can do today.

5. Keep it cheap

The point here is that the only hurdle should be fear. You don’t want to stick your life savings into something that might pay out in a year. It needs to be something that, if it results in failure, doesn’t set you back at all but rather provides some form of lesson.

6. Keep it real

“Think about the good things that happened yesterday” doesn’t count. The action has to be something that will move your life forward, like “show my coworker my productivity side project and get his feedback.” Or, “send my most recent article to ADDitude magazine and see if they’ll publish it”.

7. Keep it social

This was the “ah ha” step for me, since I tend to be on the bashful side. A key to success is to be seen and heard by others. Remember, ultimately, other people give you money and other valuables. These things do NOT grow on trees in your own personal garden. Showing your little project to someone else will provide some form of feedback, and may open a door to a new experience or opportunity.

Trust the Process

That cycle of “act small – fail – learn” may sound somewhat awful. Like some kind of tedious homework assignment that never ends. But here’s the surprising bit Krumboltz and Babineaux drive home: this process actually builds happiness along the way.

When you manage to take just one tiny, low-risk step driven by curiosity, you get a little jolt of confidence. That confidence delivers its own ounce of joy. And that little spark of joy? It creates momentum, making you want to try the next small thing. Suddenly, each tiny step you take – even the ones that end in a “teaching failure” – has the power to make you happier right now.

Sure, trusting that these small, sometimes fumbling steps will eventually lead somewhere worthwhile might feel like a leap of faith. But isn’t it more realistic, more attainable, than rigidly following a complex set of rules towards some vague future state that might contain happiness?

So, what can you do today that could lead to a teaching failure?

If you liked this article, please leave a comment below, share it with someone you know, and get on my email list!