If it’s the last thing you could do…

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Last night I put together my to-do list for the next morning. It read:

  • landing page for sports leagues
  • landing page for gaming
  • landing page for financial institutions
  • send today’s manual drip emails
  • add some content about payouts and MassPay to the About page
  • add some “how to” stuff to dwolla.com/businesses

That’s the order I had it in.

I showed my list to a coworker this morning. She asked me “which of these would you do if it were the last thing you could do?”

Her question made me laugh, and then shrug awkwardly, and then feel stupid.

Turns out my list was completely in the wrong order. I had prioritized it based on some stupid combination of difficulty and perceived payoff. I also grouped similar things together for no apparent reason.

Why did I prioritize like this? And why do I keep telling myself I’m a good multitasker when I’m actually terrible?

Turns out, if it was the last thing I could do, I would do the 5th thing on the list. After that was done, if the next thing I did was again the last thing I could do, I would do the last thing on the list.

My original list was almost in perfect reverse order.

Then I thought about my personal life.

I’ve often found myself doing smaller, easier tasks first when it comes to my personal life – whether it’s my life’s ambitions or a simple weekend to-do list. But why would a logical human being do that to himself when he knows that there are only 24 hours in a day and he’ll only be on this planet for 82 years?

I think the answer is that we’re emotional creatures that think irrationally. We have a harder time imagining how we will feel in a year from now than the way we’ll feel in an hour or a day. So we set our sites on the more immediate feeling of gratification. Not because it’s better for us in the long run, but because it feels more real.

Our emotional selves are self-sabotaging our own happiness.

Which feels better – accomplishing more things or accomplishing less things?

More things, right? But what do we actually achieve by doing more things in favor of the most important thing? What truly makes a difference in the long run – making progress on stuff that matters, or finishing a bunch of small stuff that no one will remember?

Which approach will make you happier?

What would happen if you tried starting with the big stuff today? Fuck the little stuff. Stop doing the little stuff. See what happens. Make progress on the big stuff now. Pick the thing that you’d do right now if it was the last thing you could do, and do it.

The litte stuff will wait for you. It will be there after you finish the big stuff.

How long will the big stuff wait for you?

Here are some things I think may stop you from trying this, and why they are wrong:

“When I start with the easy stuff, it snowballs. Then I ride that feeling of productivity into the sunset knocking off bigger and bigger things until it’s all done.”

Sounds great. But how many times has this actually worked for you? How many times do you find yourself at the end of the day feeling lousy because you didn’t get around to even starting that big project, or maybe you started but you didn’t make enough progress to get that feeling of achievement? If you’re thinking “yeah that happens to me but I’m embarrassed to even admit it to myself because it feels sinful to even think it because God or my boss will read my mind and discover that I’m not as much of a powerhouse executor that I’ve led them all to believe I am,” then it might be time to start living up to the reputation you’ve created for yourself. It’s not too late. Try it. They’ll all think you suddenly kicked it up a notch and somehow became even more productive than they thought you were. There’s no risk in trying it if these are the thoughts you’re having.

“It looks like I’ve done more if I knock out 5 small/medium things in a day instead of just 1 thing”

If you can trick your boss that easily, go work for someone else. He/She is enabling you to suck at life.

“All that small stuff distracts me. If I knock those out first, I can focus on the big thing.”

You’re procrastinating. I bet you’re stuck in your inbox all day, making sure those emails get responded to so you can go “focus.” You’re letting the “latest and loudest” dictate your day. Stop it.

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