It's a good question, and one that I probably asked him on many multiple occasions. His answer was always multi-pronged, but the main points were approximately

It's a good question, and one that I probably asked him on many multiple occasions. His answer was always multi-pronged, but the main points were approximately (in order of importance, as I perceived it): 1) Law = Higher stress career. 2) Office vs Outdoors; he loved being outdoors every day, especially loved talking to people -- most everyone on his route knew him by name and he strongly believed in [perhaps incorrectly, as things have changed dramatically] in mail carriers being very 'customer/service oriented'. He loved talking to people, he'd bring mail up to elder-aged peoples homes every day and talk to them for a few minutes, etc. Perhaps a bit Mayberry-esque, even. ;) 3) Moral reasons; a general dislike of bureaucracy (though plenty of that at USPS, and more towards end of his career, which we heard about over dinner ~nightly!); generally a preference for meritocracy (his 'sorting speed' was N times faster than the 'baseline', he would tell us); an extreme disdain for "schmoozing" for lack of a better term. He never even took the bar exam, which actually surprises me a bit even today. As a young teenager I found it borderline insane, selfishly of course -- I can remember thinking "we'd be in the nicer neighborhood if Dad would just go be a lawyer!", and I remember wondering if my grandfather was upset by it but I was a bit surprised to not really get the impression that it was an issue. He also had owned & sold a bar in his 30s, had the only home we lived in my entire life paid off in his ~50s, the USPS insurance & pension plans were great, and we lived quite frugally -- so he was comfortable, he carried our own route so he was home 2x each day, the rotating schedule was nice to get Saturdays off occasionally, and he was off work by ~3-4PM every day (except near holiday times when they'd have 20ft of mail and tons of parcels). I actually believe he initially began carrying mail just as a summer job while in college, and then probably kept at it simply because it was fulfilling for him. He retired a bit early, with >2 years of PTO & Sick Leave time saved up; proceeded to get hip replacement surgery almost immediately -- likely somewhat attributable to walking up/down ~100 flights of stairs each for a nearby apartment complex on his route. Unfortunately he passed away just 6 weeks after retiring. The funeral procession had ~50 (ish) LLVs in it, and I think he'd have liked it. It made me smile, on what was an otherwise cold day both literally & figuratively speaking. :) I miss his advice tremendously, he was a very smart person and I often reflect on his decision to become a mailman, despite having a law degree. I have but a [honors!] GED, though more philosophically sometimes I wonder if more succinct & 'adventurous' job -- and a more frugal lifestyle -- might be more fulfilling. I respected his decision though, and as I've aged I definitely feel that I better understand it, as well.