My last house was paid off, but then I upgraded when I moved by accident (long story). Once my savings is at 1.5 years my goal is to then go gangbusters at my mortgage again and get it paid off. It is a really nice from a stress standpoint not having a mortgage.
I make more money than I ever did and drive around in a paid off Honda with my GF driving around in a paid off 7 year old Kia. I look at the toys others have and think, man, that would be fun…but not worth the stress debt/financial insecurity gives me.
For some reason people really have a bad case of financial FOMO, and it's been like that my whole career. I've had people try to explain how I should sacrifice my residential security do this or that because that's the way the market is going and I am missing out on a whole lotta bread. I can't even count the the number of guys and gals who tried to get me to cash out my home and invest in the market. When I explain that my home is not an investment vehicle, but someplace that covers my head and keeps my stuff dry, it's like watching a dog run into a sliding glass door. Of course, they hand wave it away saying "well, had you done what I said, you'd be ahead", well, maybe, but how many sleepless nights would I have had in all those years.
The same goes for health care. Every time someone starts in on it, it's well, if you are healthy.... Well, that's exactly what insurance is for, when you're not healthy, so pardon me if I don't play in that casino.
Career Changing:
Yea, I've seen it happen. Stuck my toe in that pool. It can work in some very, very limited circumstances. Maybe the situation is just so bad and you're so miserable with what you are doing there is really no alternative for your mental health.
But you have to be starkly realistic in your goals, the schools and the job prospects, and this is something we do a piss poor job of with people entering the job market, and it's 10x worse for those who want to change. People go on line, and they read stories about people who got scholarships, and good jobs and all the good stuff, when in most case those situations are either extreme outliers, they had additional, significant support or they're just plain fibbing. And this was 20 years ago, and now SM makes it even worse.
Everyone reads the forums at IWANNABEANXYZ.COM, and thinks they can pull up roots at 40, pay $300k for an degree, plus another $50-75k to prep because they've been out of school for 10 years, because ONE person actually made it work, because they had nice parents, a flush spouse, or got a scholarship because of an exceedingly unlikely set of circumstances. Oh, yea, there's the little detail of actually getting into school.
Are there people who can make it work? Sure, those people are generally already covered. Police/Fire/Military who put in their 20 and got a check coming every month. Spouse who makes some bread and can cover the roof over your head. Really nice parents. Maybe you sold a little business you started and now want to coast working for someone else. But the stark, cold facts are that if you are past 35, it almost never makes financial sense to make that jump. Yea, golden handcuffs suck, but that's the world we live in. If you're 35, you are just starting the upward trajectory of your earning power. Burn 3-4 years in school making less than zero, plus another 3-5 years at the bottom of the pay scale, probably working 60-80 hour weeks, and you've destroyed your earning curve. Oh, yea, you've got a couple of hundo in new debt, and you've missed out on the compounding on the money you could have saved.
In almost every case, it's far better to go learn welding, plumbing, electric, HVAC, some trade, apprentice two-three years (while getting paid!), take a fraction of the money you would have spent, and hang your own shingle. And now you're your own boss. Local kid did that with plumbing. Put in a couple of years, learned his trade, got his ticket, put some money into new gear and a new truck, spouse works the phone. Couple years in, it's all paid off, phone is ringing off the hook because he does good work, master of his own destiny.
It's heartbreaking to show the math to people. Some people don't care, press on, try to be the outlier, and that's awesome, as long as they go into it eyes wide open. Others are absolutely stunned about what a raw deal it can be. Others are really upset about the stark, in your face ageism that happens, today, at universities and other places lining up to take your dream money.