Good theme. Being a Navy sailor, my first thought was Jimmy Buffett and the sea. So I would choose any Jimmy Buffett tune with two of my favorite philosophical (vs partying) tunes.
I know not many people actually listen to them all, so I'll C&P some of the lyrics to a fave that most over 40 people can relate to, "A Pirate Looks at 40". The other Buffett philosophy song, "He Went to Paris" is a true story based on an old man who left the States for Europe, found his dream, then lost it all in the War there, and returned. Great song. Not posting lyrics to that one. It has to be heard.
So here's a few lines from "A Pirate Looks at 40". I'll just link to "He Went to Paris" without lyrics.
A Pirate Looks at 40
Mother, mother ocean, I have heard you call
Wanted to sail upon your waters
Since I was three feet tall
You've seen it all, you've seen it all
Watch the men who rode you
Switch from sails to steam
And in your belly you hold the treasure
That few have ever seen, most of them dreams
Most of them dreams
Yes, I am a pirate, two hundred years too late
The cannons don't thunder there's nothing to plunder
I'm an over forty victim of fate
Arriving too late, arriving too late
I've done a bit of smugglin'
Yes, I've run my share of grass
I made enough money to buy Miami
But I pissed it away so fast
Never meant to last, never meant to last...
"He Went to Paris"
If I was going to have a tombstone (I won't) the last line of this song would be my epitaph:
"Some it was magic, some of it tragic, but I had a good life all the way"