Why your plans never go quite as... planned

Today I woke up feeling good. Darn good.

I sensed it—I was on. This was going to be one of those writing marathon days. I was going to hit the 10,000 word mark in one single afternoon.

I was going to be Lebron James in game 7 of the 2016 NBA Finals. Nothing was gonna stop me.

So I made a smoothie, drank a bigboy-sized cup of coffee, and got to work.

For the first hour, I was on fire. Words were just spraying out of me.

Hour two, I still had it. I was weaving a rich tapestry of nouns and verbs.

Hour three… I started to lag a little bit. I needed to take a break; a long break.

So I listened to a podcast or two and watched some interviews on YouTube. There’s nothing quite like an episode (or three) of EconTalk to soothe the soul.

Then I drank some more coffee, made another smoothie, and… sat around

My brain was just… fried. Over the next few hours, I was able to get two, maybe two and a half, more hours of writing in. But I wasn’t game 7 Lebron anymore. I was pre-retirement Kobe Bryant. I was a joke.

My A-game had turned to B-game and C-game… it was ugly.

I’d like to say that this was a rare occurrence. But I fell victim to a common beast that haunts each and every one of us: The Planning Fallacy.

My dewy-eyed morning optimism caused me to dramatically overestimate my abilities, and underestimate how long it would take me to complete my writing task.

“When will you learn, silly Jason?”

You see, that’s the crazy thing. The Planning Fallacy is a curse upon each of our minds. It prevents us from learning from our foolish ways. No matter how many times we underestimate the task in front of us, we will still continue to pound our chests and look down on each challenge that comes our way in the future. But the challenges we face will always have the last laugh.

In other words: this fallacy is part of the structure of our brains. He's the bad tenant we can never evict.

All we can do is remember that he’s there, somewhere in the building—messing up our plans and setting us up for bitter disappointment.

But I don't want to end this email on a depressing note, so I will say this. When I was a product manager, I always used to multiply all of my initial estimates of how long a feature would take to to build by 1.5x to 2x. When I did that, I was almost always dead-on. So, maybe there is hope after all. You just have to remember to systematically revise your initial guesstimates.

-Jason

Jason Hreha