We have a very similar upbringing I think JR, I also feel guilty when I spend money on myself - and I would never ever think to hire a cleaner. The guy you met was interacting with life with his schema and has what I term 'posh person confidence' - often imbued from private school education and parental role modelling where your time is valuable. My time is valuable too.

I would never think to hire anyone to do something I could do myself. If I can walk, I won't take a bus. I often make the cheapest choice, no longer out of necessity but out of habit. I've lived in London for over a decade and I can count on one hand the number of times I have taken a cab. The roots of this run very deep and it's taken me a fair bit of time to work out what was me and what was upbringing and to make peace with some of the things I like about myself and some of the things I don't. I am industrious, I work hard - but I didn't like that I used to be nice. I am no longer nice. I used to think that good and nice were the same thing - and they aren't.

I don't want to work harder doing things I don't enjoy for things I don't really want. This is a trap I've seen lots of both posh and nice people fall into. Instead, I keep my costs low and I live the sort of life I enjoy. What is of most benefit to you is whatever you determine it to be. If you haven't read it/listened to it - I can recommend 'The Chimp Paradox' and 'Path Through the Jungle' as books worth listening to about how thought patterns come to arise and what we can do about them. I found it very helpful

As it happens, we all have to enjoy the short moments of chaos between two interludes of infinite nothingness - there is no right answer, there is only spectrum. :o)