"If checking boxes doesn't make you happy, don't do it."
What I'm asking is whether checking boxes really makes anyone happy. I mean, truly happy.
Don't get me wrong; I went through a lengthy box-checking phase that lasted about 20 years. Checking a given box made me happy only until the next box appeared on the horizon. The whole thing seemed like a cosmic treadmill.
I think there's something admirable in the sheer work ethic and determination required to check the top boxes. But at the same time, I wonder whether that effort couldn't be spent on something more worthwhile -- such as defining oneself on one's own terms, rather than by a weird chiaroscuro of ideals hit and missed.
I'd say it's like a video game. Keep trying to beat the current level and move to the next one. Why do people play video games? For the challenge and to pass time. Well, same here. What's the alternative? "Defining oneself on one's own terms" sounds nice but doesn't mean anything really. I'm not riding the treadmill myself but I'd take it any time over existential boredom.
Defining oneself has the consequence to set your own goals instead of only following the goals of others (you might join other people's quests, but you're now free to not do so without falling into existential boredom). You switch from external to internal motivation. That means very much.
One way to set goals is to avoid setting any goal that you think reaching will make you happier than you are right now.
Sound crazy? The idea is that "I'll be happy when"-type goals tend to be the kind that are most often misguided. They are often aimed at pleasing or impressing others or measuring up to external expectations - parents, society, peers, etc.
Conversely, the goals that you just choose because you choose them, tend to be much more rewarding in the end.
With total focus and attention, minimal ego involvement, and no expectation of reward or outcome, the process becomes the reward and happiness is the result.
Life is what you make of it. If checking boxes doesn't make you happy, don't do it.