Estimation by day, year, and lifetime.

I’m about to get really fast-and-loose with my quote attribution here.

Recently someone shared a quote from someone else that ran to the effect of: “People overestimate what they can get done in a day, and underestimate what they can get done in a year.”

Only when I went to Google it, it came out as overestimating a year, underestimating a lifetime, and it might have come from Bill Gates, but by then it sort of ruined the moment. The point is: If, as I have said before, people are bad at planning things, why plan at all?

A friend and commenter recently linked me to some articles talking some articles on goal setting. Essentially, setting ambitious goals gets you further than setting attainable ones.

When I write my to-do list every morning, I put down everything I could to to achieve a truly terrific day’s worth of work. As I go through the day, I cross off tasks, and often re-write my list several times. Each time I re-write it, I make a more accurate list of priorities. I re-focus. I get more done.

I feel like the same thing happens when I write down goals for the year (or the quarter, or the month, or the week). Typically, I set forth an absurd list of aspirations and stretch goals. But with everything on paper, I can prioritize.

As the year goes on, the list inevitably shifts. One item which I thought would be super important a few months earlier now seems oddly dated. As in: why did I want to do that again? But others rise to prominence by virtue of their longevity. Writing, traveling, and languages remain constants on mine, and have done for the last decade.

Estimation is guesswork. You’re guessing about what you think you can do, what you think is important. But when you assess your guess work again and again, even though each individual guess doesn’t seem to get any better, cumulatively you learn a lot about yourself.