There are two types of hard work. It’s important to recognise which you are engaged in.
Sisyphean tasks are hard and pointless. You can work your very hardest from here until eternity and end up no closer to your goal. People like them because it feels like you’re doing something and they’re pretty straight forward.
Herculean labours are also hard, but working is correlated with progress. If you need to slay the Stymphalian Birds, then working a bit harder to kill some more birds is probably a reasonable plan.
Mountain climbing is a herculean task. You have to work real hard, and the more effort you put in, the closer you are to the goal. Climbing a slippery mountain with no gear that you are guaranteed to slide back down is sisyphean and you should probably stop doing it.
Historically, many of our most relevant tasks were herculean — running, farming, and even certain intellectual problems just need to be thought about endlessly until they untangle. As such, we default to using the difficulty of a task as a rough heuristic for its value.
Hercules is an introspective Sisyphus
Some of Hercules’ tasks appeared sisyphean at first. When he went to work cutting off the heads of the hydra only to see them grow back, he could have either 1) given up or 2) continued working real hard to cut off heads. Neither leads to success.
Instead, he reflected on his process and recruited an executive assistant to take a torch to the neck stumps before they could re-grow. Similarly, when he needed to clean the Aegean stables, he saw the enchanted cattle were producing dung faster than he could possibly clean it, and so he put on his earthworks hat and redirected a couple nearby rivers through the stables.
If Sisyphus was in this position, it sounds like he would have grumpily spent eternity shovelling dung. I haven’t been down to Hades to examine the circumstances in detail, but I feel like the real lesson of Sisyphus is that sometimes you should slow down and reconsider whether all this hard work is accomplishing anything.
So in conclusion
Sisyphus wasn’t doomed. He was a sucker, happy to play the victim card and work hard on the obvious task instead of figuring out how to re-frame it into something he could make real progress on.
Lots of startup work is sisyphean until you take the initiative to change that. Then you’re living large, Hercules style.
PS. Sisyphus perhaps should have thought to build an elaborate pulley system like in Fitzcarraldo. He could have used the damned as labourers. He evidently watched too little Werner Herzog: