The challenge with how we measure our life

One of the biggest challenges with designing a good life for ourselves is that the stuff we measure our days, weeks, and even months with is not how we measure our life as a whole.

The stuff we measure our life with – living with integrity or building a few deep relationships with people we care about for example – come with no awards, no vanity metrics, no promotions, and no recognition. And, just in case that wasn’t hard enough, there are often minimal signs of progress for long periods of time.

On the flip side, most of the stuff that seems to loom large and feature so prominently in the near future (e.g. work/career milestones or fun side projects) seem to matter for the longest time… until they don’t.

It is the classic urgency vs. importance prioritization problem. And, as is the case with most things, it is much easier to talk about thinking long term/balancing the short and long term than it is to actually do it.

PS: This is much like building good products. The foreseeable future seems more important than it is.

Work hard now so you can have it easy later

“Work hard now so you can have it easy later.”

The problem with that idea is that it places overdue importance on some arbitrary milestone – a certain promotion or some net worth number.

As long as we’re focused on solving problems that matter, we are never set. We don’t ever get to rest easy.

But, with some luck and accumulated privilege, putting in the work now does make it easier to create the sort of optionality that enables us to direct that hard work onto areas that feel less like work and more like play.

The law of painful progress

I had a realization when I was learning how to play the guitar – if my practice sessions didn’t have me wincing in pain, I wasn’t making enough progress.

This realization served me well in the 8 months I took lessons as I made faster progress than I had initially expected. The results were evident too – weeks when my practice sessions were more painful always yielded more progress.

The law applies to every skill, of course. The more we feel the pain, the more we’re likely making progress. There is no painless progress.