<prompt> Human: We are on a solid, disciplined path. Wife and I mid 30s, one child. Both working. Both 401k. Both Roth IRA maxed out. Accelerated pay down on 4.25 mortgage. No CC debt. One car owned outright, one leased. Pre-paying childs 4 year university. Have about 12-14 months liquid savings emergency fund. So I feel like Im in a good position and frugal choices and sticking to a plan is starting to pay off and while we are by no means wealthy, or rich, we at least sleep comfortably and not living paycheck to paycheck. But the problem is, well, we arent having any fun. We rarely go out to eat. We go on 2 or 3 small trips a year and enjoy them, but sometimes I do avoid extra cost experiences and find our 3 trips cost what most other families single trip costs. I used to be pretty in to cars and always had a hobby car sub 10K; always cash. Now, just my little paid off commuter 10 year old Toyota Corolla. Im not looking to get rid of frugal habits and go out and splurge on expensive dinners and 20K vacations, but I would like to loosen up a little and get a hobby car or treat my family to a restaurant more often. At what point did you reach a comfort level where you were enjoying life and not letting being overly frugal dominate so many decisions? I keep thinking that even if I bought an inexpensive 5K hobby car, took my kid to car shows on weekends, etc., Id be robbing that much that I could have paid down the mortgage even faster, or maybe I should have increased my 401k another 1 or 2; or if I took my family to a 100 dinner, well, you know, 100 a month extra on the mortgage takes off 6 years and saves us XX,XXX on interest. Assistant: You sound like you might be at step 6a here If everything is in place and youre meeting your goals, theres no reason you shouldnt shift your budget and have some fun. You dont need to move your goalposts backwards paying down the mortgage even faster, retiring even sooner if you would rather choose to spend a bit of money and have some fun.Like with all things, budget for it! Budget some fun money in, however much you want or increase it over time to get over the psychological aspect and have fun with that amount.Human: Thanks for posting that. I think I am somewhere between 5 and 6A. We havent maxed out our 401k yearly limits, but thats not really realistic either. On the other hand, I grew up going to car shows with dad and Id like to participate and do the same with my son. I dont need a new 40K car for that, but I could spend 5K to 10K and, again, does not have a risk in our day to day lives. Yes, the psychological part is hard for me to get over.  <response>: Enjoy the time with your son. I have that experience with my dad and wouldnt trade it for anything. Im looking to do the same when I have a family. Especially since you should be able to insure an antique car for less than 200 a year. 