He's a compelling storyteller and it's a good story, but there's always something about this kind of inspiration-core that wears on me, which is partly where those mixed feelings about linking to Neistat comes from. (He also repeatedly leaps to the defense of famous YouTube dudes who act badly, but that's a conversation for another time.)

My initial reaction was similar to yours: If you don't achieve some goal you set for yourself years ago, that's perfectly fine. You're not a failure. You can let it go. As Hank Green said in his XOXO 2014 talk, "You have no obligation to your former self."

Also, who has the resources to hire an Olympic marathon coach to train you for two years, just to shave off three seconds from your marathon time!? This is an incredibly weird thing for someone to do who isn't a professional runner! Don't beat yourself up about it. You're doing great.

I would say: always question your dreams. Why is this the goal? What will this goal provide to me? Once I pass this goal, how am I different? How am I the same? There's a term, "demand avoidance," for the "I'll show you" tendency, which is inherently reactionary rather than proactive. It's almost like a revenge instinct, particularly in those who have suffered a traumatic event, as Casey has. So, if you're going to have a goal and dedicate a huge swath of your life & time to it, understand why you have it. Make sure that the time you spend on it absolutely could not have been better spent elsewhere.

You have to admire his persistence in the face of repeated failures. Not many people would do that.

Whether you persist in chasing down the impossible dream or change course to chase another dream, the importance is the process. You should have fun and be inspired in the pursuit of it. I'll add that you shouldn't make other people in your life miserable doing it. I give him credit for not putting the dream above family and work. (I'll also give his wife credit for looking after the kids when he was pounding the pavement for hours and hours!)

Personal moonshots can be just as important as societal ones.

From afar, it seems to me that Casey has accomplished a lot — and I appreciate him bringing us along on this journey.

I've been fortunate enough to accomplish many of my lifelong goals, but at a certain point realized it doesn't really move the needle that much on feelings of Personal Satisfaction. I think that's just my internal wiring.

I'd be curious to hear how this specific thing felt for Casey. He's done many things that he's set out to do, but this had evaded him for a long time. I wonder how it feels different than other things he's done — like have a family, become an incredibly popular YouTuber, have an HBO show, create a tech company, et cetera.

I think Casey's accomplishment is magnificent. And one that almost any runner would be very proud of.

But the Tucson Marathon where he broke his record is widely known to be a very fast course that predominately runs downhill. It appears on many lists of "fast courses to break your PR."

Again, I'm not trying to throw shade here. Bravo, Casey! But if this is about shaving two minutes off a New York Marathon time, and achieving some 20 year long impossible goal, one way to do it is to go to a course that's known for giving out personal records.

I’ve always told my kids, there’s a difference between quitting and stopping. Push yourself not to quit, but never be afraid to stop.