What a great thread...
Sooo, I decided last year that I needed a change after 16 years in the corporate world, eaking out my hiking time between work & travel. I am married with one little toddler (see my avatar), a mortgage, etc. After a ton of obsessing last fall, I decided to make the change to become a teacher. One of the primary reasons was a dream of more trail time - aided and abetted by attending the BPL wilderness skills course last July in Montana. ;-)
So, my wife and I did a deal where if I saved $100K, I could quit the high paying gig and she would support my return to school. The $100K would cover the cost of returning to school AND would be a high enough hurdle to make sure that I really wanted to do it. So I did it, and in January, with $100K in my bank account, I quit the big job (senior marketing manager at an insurance company) and went back to school.
The problem is, the transition is HARD! I'm doing MORE work now than I was before, including teaching SAT prep at the weekends to get as much teaching experience as I can, going to school four nights a week to get my MA in Teaching (at Sacred Heart University in Connecticut), and doing a part time consulting job during the week to pay the major household bills.
Because of all this, my hiking has been restricted to day hikes - my first overnight will be next month, and I was only able to schedule it because it will give me college credit (LNT backcountry master educator). In addition, my gear-buying habits have had to change... in the short term, at least, I do not have a gear budget for this year. I won't be the BPL Nano tarp this year...
I am able to sustain myself because I am looking forward to finishing with school, getting a good full time teaching position, and teaching high school kids about ultralight! Thankfully, since I am going to be a high school math teacher, full time jobs are fairly plentiful (at least they are in Connecticut public schools)... in addition, my wife is supportive, my toddler loves that I go to school (just like her) and keeps asking me if we do circle time and show-and-tell at my school.
So, here's my advice: if it is in your heart to change, do it... BUT, go into it with your eyes OPEN. It is HARD. So, you better make sure you can sustain your new career choice after the challenges of the transition! You will need a fully supportive family (maybe do a deal like the one my wife & I did - set a goal for yourself BEFORE you start the transition). You need to be able to devote time and energy to get yourself to your destination. You need to focus on the long game, because the transition might hurt your short game!
Good luck to you... and feel free to drop me a PM if you'd like to chat more! Take care.