If he's smart he'll stay in his current well-paying secure job. If he's stupid he'll trade his $100k a year job (that he feels is boring) for a pilot job that is more boring, unstable, lacks progression, and doesn't pay enough to support his family.
If you really care about this guy, you need to talk him out of piloting as a profession.
If you really care about this guy, you need to talk him out of piloting as a profession.