Multiple problems here:
- He was earning "low six-figures", yet he wasn't saving. This wasn't a one-time mistake; it was an ongoing, decades-in-the-making decision. At that salary rate, he could've saved plenty.
- When the economy had a downturn, he dipped into his savings to "maintain his lifestyle" rather than cutting back.
- Between Social Security and a small pension, he has $1800/month. With a paid-for house and frugal habits, a single person should be able to live on that. He says he's working these jobs to allow for savings and "extras" like the theater, plane tickets and vacations.