"Darren makes $5k+ as a keynote speaker per gig and he did say that the $5k is not for the 30-min or hour he speaks - it is for the thousands of hours he put in"That reminds me of this story by Chuang Tzu:
Cook Ting was cutting up an ox for Lord Wen-hui.
At every touch of his hand,
every heave of his shoulder,
every move of his feet,
every thrust of his knee,
the ox came apart with a zip.
He slithered the knife along with a zing,
and all was in perfect rhythm,
as though he were performing
the dance of the Mulberry Grove
or keeping time to the Ching-shou music.
"Ah, this is marvelous!" said Lord Wen-hui.
"Imagine skill reaching such heights!"
Cook Ting laid down his knife and replied,
"What I care about is the Way,
which goes beyond skill.
"When I first began cutting up oxen,
all I could see was the ox itself.
After three years I no longer saw the whole ox.
And now -- now I go at it by spirit
and don’t look with my eyes.
Perception and understanding have come to a stop
and spirit moves where it wants.
"I go along with the natural makeup,
strike in the big hollows,
guide the knife through the big openings,
and follow things as they are.
So I never touch the smallest ligament or tendon,
much less a main joint.
"A good cook changes his knife once a year,
because he cuts.
A mediocre cook changes his knife once a month,
because he hacks.
I’ve had this knife of mine for nineteen years
and I’ve cut up thousands of oxen with it,
and yet the blade is still as newly sharpened.
"There are spaces between the joints,
and the blade of the knife has really no thickness.
If you insert what has no thickness into such spaces,
then there’s plenty of room,
more than enough for the blade to play about in.
That’s why after nineteen years
the blade of my knife is still as newly sharpened.
"However, whenever I come to a complicated place,
I size up the difficulties,
tell myself to watch out and be careful,
keep my eyes on what I’m doing,
work very slowly,
and move the knife with the greatest subtlety,
until -- flop!
the whole thing comes apart
like a clod of earth crumbling to the ground.
"I stand there holding the knife and look all around me,
completely satisfied and reluctant to move on,
and then I wipe off the knife and put it away."
"Excellent!" said Lord Wen-hui.
"I have heard the words of Cook Ting
and learned how to care for life!"
Of course, despite this, the butcher is still going to make $10 an hour, not $5k+ like Darren LaCroix. So I think it's a bit of an oversimplification for Darren and Louis CK to claim they get paid so much simply because they've put in the time and became skilled at what they do.
Some professions, (like entertainers, businesspeople, sports stars) are simply much more valued in this society than others. And even in the valued professions, the odds are you could easily work your ass off for decades and fail because of the tremendous competition -- there's no shortage of kids who want to be rock stars or play in the NFL... very few actually make it, despite putting in the time.