Good chance he was relating experiences as they relate to what you were
about to do in your flying career. I do the same thing. Not to impress
young pilots with my daring-do, but to pass on the experience I got the
hard way.
I've done more stupid things and made more mistakes than any room full
of a hundred pilots or more. Fortunately I learned from those mistakes
before one killed me.
I've logged more than 13,000 hours in the lowest reaches of the
airspace system in both airplanes and helicopters, and another 9-10,000
hours at in the safer altitudes. The areas of most danger are those
down low.
Cheers
Selway Kid