sounds like you're on a nice path now. We were in a similar situation several years ago making many of the same choices. One of the tactics that seemed to work and continues to work was "automate and envelope" You described a time when you had lower income and you adjusted your spending. You have 401ks, 403bs, etc. Do you have 529s, savings accounts for the kids, checking accounts for the kids, UTMA/UGMA accounts for the kids? I automate all these every month and encourage grandparents/aunts/uncles whatever to gift directly to my kids' 529s as part of their Christmas/birthday gifts....the relatives love the convenience and like the fact their contributing to the kids' education and/or savings. More automation of investment naturally leads to higher savings rate and then if you're like some people, you gradually adjust your spending lower to prevent yourself from going into debt. I thought enveloping was kind of hokey especially I like using CCs for the points, and I hate having change in my pocket because I always lose it. But, there is something about having to actually hand over cash to someone that gives you pause. One clicking is so easy, and the 5% back on the Target card makes you feel really good b/c you're "saving", but what is that really enticing you to do? If nothing else, enveloping gives you a different way to think about your money. Lets say you set a $20/month coffee budget. Normally, you hit starbucks, grab a super macchiato whatever (I drink black coffee so i don't even know the names) swipe your phone, get a bunch of stars and you're on your way. You do it over and over and over having no clue where that money ever went. Now, instead, you put that crisp $20 in an envelope and you're thinking, this $20 is only going to last a week if I get the fancy coffee OR, I could buy 8-9 tall pike place black coffees (better option) OR, I could buy two 20 oz bags at the store, brew my coffee every day at home and make it last most of the month. its painful and a bit tedious, but worthwhile nonetheless especially as your trying to come to grips on your spending.