I do not know how it all started but this cycle is very commercially driven. Buying a house (real estate agents), getting a mortgage (banks and brokers), getting a car (manufacturers and car dealers) or getting admitted into an expensive and prestigious school (commercialised education). As these things are highly valued by society, we try to acquire them so people will think that we are rich and intelligent. And then what? In the meantime, you change your lifestyle drastically. You try to cut your expenses to prioritise your mortgage. You stopped going to concerts. You stopped dining at your favourite restaurant every Saturday night. You don't travel because you think your money is better off putting into your mortgage. You even stopped getting your Starbucks coffee on the way to work to save $25 a week. You cut these small things that give you joy.
I realised that the more I care about what other people think, the more I'm not being true to my values. So one day I decided to stop worrying too much about what other people think.
Stuff it, I said.
Then, I focused on my goals and stayed true to my values of simplicity and frugality. I moved out of my three-bedroom house and rented it out instead. I moved into a small studio apartment near my workplace and also close to the city. I was able to go out more and catch up with friends often. Having a good and balanced social life is more important than mortgage. Having those small things like dining at your favourite restaurants and trying different cafes helped me maintain my joy.
In the end, you cannot bring your house or car with you on your death bed. All that you will think and feel at that point in time will be the love that you shared with all your friends and family.
All those times (not money) well spent.