Money makes the world go around

Someone I know who is better of financially than me said the other day that just because they live in a fancy house whilst I just rent a room in a shared house doesn't mean they are better off.
I get they were trying to make a point but my first thought was - well obviously it doesn't? And how little do they know about me to think that? Especially seeing the point I was trying to make to the person at the time.
I don't think I've ever said that how much I make is in anyway related to my level of happiness and more importantly I'm not unhappy.
Don't get me wrong, there is stuff which isn't great, but all in all I'm happy to be alive. There has been parts of my life such as when I was really sick with RA and there was no way of knowing if I would get thru it, were dying didn't seem like such a crappy option, but these days what do I have to complain about, I mean REALLY complain about? I got RA but its under control. I have a roof over my head & food on my table (which is more than many people can say). Good friends and lots of hobbies, I even currently have a nice job (even thou that looks like it wont be around for much longer, but that's a story for another time) and I am a smart & capable woman (modesty is not one of my virtues). Life could be a lot worse.

To me being happy is the most important thing to strive for in your life, because you aren't going to be around for all that long and you really can't take it with you when you go. Saying that thou, some peoples ultimate happiness is money, so go them I guess, but its not mine.

With my job currently being up in the air I need to find something else to do and the main thing I've been thinking is that I should find something I really enjoy. Problem is I'm not sure there is anything I can make a living out of. Ideas being living off my jewellery or open a café. With jewellery I could try and see if I crash and burn and then look for a job if I do (which I'm guessing I would because that must be so hard, to sell enough to make a living) but if I go for a cafe that's serious responsibility to take on, main risk being that if it does fail I end up in debt and as someone who literally don't owe anyone a penny, that's a really really scary thought. However I guess the main question is, lying on my death bed (sound dramatic doesn't it). What will I be the most upset about? Not trying to see if I could do it or trying and failing?