I'm mostly glad that we are (still) struggling to make ends meet. I'm worried that we won't be able to buy a house and save for retirement, but we're proud of being debt free (except for student loans) and I feel really good each month about saying "I can by this and this, but that will have to wait until next month". It's the second half of that sentence that makes me feel good.
My daughter gets a small allowance, which mostly she saves. We buy everything she needs and I make sure she has spending money (either from her allowance or I'll just supply it)--but despite that she herself has ample money she is SO worried about money all the time, and she hates parting with it! I love her dearly but I don't know how she came to be such a tight a$$! She's been that way since she was quite little. We aren't like that, neither are we the opposite, I'd say we used to spend a little more than we ought and now we are a lot better at saving--but still not unwilling to part with money like she is.
2009 Trek 7.2FX WSD, brooks Champion Flyer S, commuter bike