There's a distinction between "saving money", as in putting it in a savings account, having a nest egg. That is clearly a good thing. The other, which is what the OP is about, is "saving money", as in paying less for things. This is rarely a good investment in terms of the time/happiness/convenience/actual money saved trade-off. A somewhat extreme example is clipping coupons - the cognitive load of planning around saving a few cents on butter is simply not worth it for most people (and also, there's the subtle bias in altering your behaviour to take advantage of an offer). Another saying in the same vein is "penny-wise, pound-foolish".

I know someone who carefully plans and then spreads the weekly shopping trip between up to five different grocery stores -- and also complains that they have too little time. I and several others have tried connecting the dots for them, but it's clearly become an obsession (and needless to say, it's not like they track their spending and saving on this -- just assumes that they are saving loads).

Obviously, there are things that make sense. Of course you should shop around and negotiate for big-ticket items. It might well make sense to alternate weekly shopping trips between two different stores with different strengths (one might be good for fresh produce, but expensive for staples and household goods etc).

> For most people on HN I'm not so sure, most roles have a ceiling that is very difficult to get above without [...] starting your own business

Hacking on a side project is one of the things you could do once you stop spending hours saving dollars.

But, the point is, time is a strictly limited resource. Money has steeply diminishing returns around those ceilings. Stop wasting time saving small amounts of money and spend it getting the most out of your time (whether that's working on your revenue streams, or doing any of a number of activities that makes you happy).