The absurdity of over-optimizing

someone using a smart phone

TIL a new productivity strategy: Micro-tasking.

Whenever you have a free moment, do something productive.

  • Clear out some iMessages.
  • Pay your cell phone bill.
  • Queue up 3 tweets.

It’s the key to feeling in control. And on top of things.

Plot twist. I’m totally kidding. This is an absurd strategy.

But the feeling of needing to squeeze in one more thing is a very real one.

And if you’re stuck in a cycle of over-optimization, here are 5 questions to ask yourself.

Productivity culture always asks a flawed question: “HOW can I get more out of an activity?”

But it fails to ask the WHY.

1. Why do I fear being ordinary?

This question sends chills down the spines of high-performers.

High-performers want to be seen.

You want to be celebrated.

You want to be recognized.

You, my dear high-performer, derive your self-worth, from achievement.

Because being “ordinary” means losing the game of life.

But who do you lose to?

Ordinary is a relative game.

Perhaps, you find me accomplished.

(Questionable 😉)

But an academic, a Billionaire and pro surfer might look at me and say: “Meh.”

And at the end of our days, we’re ordinary.

We’re dust.

Just specks in this infinitesimal universe.

2. Why can’t I take a walk without headphones?

I know. We need to be always listening to podcasts.

Podcasts on AI.

Podcasts on parenting.

Podcasts on audience building.


Well since you fear being ordinary, then “Game On.”

Bring on the micro-tasking. Bring on the hyper-optimization.

Learning is how you stay relevant. It’s how you win.

And once again, it’s how you fight the insurmountable tide. There’ll always be more to do.

And even if you do it all – whatever that means – you’ll probably still be paralyzed by your own mortality.

3. Am I playing the right game?

Now as your chase continues to be relevant, you find a game and try to win it.

Go for partner at a law firm.

Managing Director on Wall Street.

YouTuber with 1 million subscribers.

After all, that is how you defeat “Ordinary” and get all the accolades.

But close your eyes and think about that future.

Do you want to own the successful version of that career?

Yes, the Wall Street financier does have 2 homes, 3 cars and sends their kids to $80,000 private schools.

But they’re also tethered to email.

They numb themselves to sleep with alcohol.

They haven’t focused on their health in 20 years.

You can win the game – but make sure you actually want the trophy.

4. Who gets my best energy?

The promise of productivity is a better life.

And your family and loved ones are the key recipients of this better life.

Do you show up with love? Presence? Levity?

Do you show up with a serious case of Intoxicating Joy?

If the answer is no, something is wrong in the optimization.

What’s the point of banging through 72 items on a to-do list if you’re just gonna be a grumpy parent?

5. What makes me come alive?

An obsession with productivity leads to the Deferred Life Plan.

You’re trading some time, work and mind space today – for the promise of a better tomorrow.

And there’s nothing wrong with delayed gratification.

We all need to balance the requirements of today with the dreams of tomorrow.

But we can’t delay the feeling of aliveness.

(And don’t tell me that “once you get promoted, you’ll focus your efforts on aliveness.”)

Aliveness is that delicious cocktail of purpose, love, energy and enthusiasm.

You can’t find it in a podcast.

You can’t find it on your resume.

And you can’t find it in your bank account.

And guess what’s the opposite of aliveness?

Feeling dead inside.

Thankfully aliveness doesn’t come from money.

And it certainly won’t come from squeezing in one more task.

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