You’re switching gears. Not everyone needs to be a rock star or actor or celebrity to be content in life. Nor are those universal goals, even in youth.
You cite Nintendo as losing the console wars… but they’re not even a combatant. People try to force them into that space, but Nintendo themselves has a philosophy completely divorced from that mindset, as much as analysts want to pigeonhole them into it. Their successes and failures both are completely on their own terms. They define their own success. Just as you should learn to do, it seems.
Your grandfather was missing the most important part of his analogy. Instead of coming late to that game of Monopoly… play something else. Or go outside and make up your own game. There’s a whole world outside of that little myopic den, even if it seems like it’s the center of your world growing up.