Bezos mentioned this idea elsewhere, but I think he's using it as a framework to evaluate present decisions in absence of external pressures that typically cloud judgement. When you think with a long enough time horizon, some of the external 'trappings' of success (money, prestige, status, pride, security, etc) seem to fall away.

Before Amazon, he was a VP at DE Shaw. You can argue that if he stayed at his hedge fund job, he'd have enough money to buy all the material possessions he has now. I doubt he'd drive a different car, live in a different house, etc.

Its easy to risk it all, when you have nothing to lose. But he had pretty much everything to lose. I think most people at that point would look around, realize they're richer than most of their friends, and stay at their jobs.

If you think ahead to when you're on your deathbed, you're back at a point in your life where you have nothing to lose. You won't care about external pressures. You will have wished to have invested your time on matters that improved your quality of life with compounding interest. I'd like to believe that Jeff Bezos isn't just happier today for choosing to start Amazon- as he gets older, it will only make him that much more content.

I smiled when I came across that line because I frequently use it--even down to the 80-year old number.

It helps put things in perspective, especially with respect to fear. We fear so many things and not do it. And yet, a lot of the fear is just imaginary--something the 80 year old you can see looking back but the current you cannot.

So I ask myself "what would the 80 year old me think of it?" and if it says to do it, I try to do it.

Example: you want to take a temporary crappy job to get back to your feet but you're afraid friends will see you working there and lose respect.

Present me: afraid I'll lose my friends, ego hit

80-year old me: proud I followed my dream!

Now I totally understand if this doesn't work for you and don't expect it to work for everyone or even most people. But I just thought I'd provide some background on how people who do use this to motivate themselves are using it.

I think it's (hopefully) just a dramatic way of pointing out that and how all of your days have added up to something, instead of being random disconnected bits. Of course they are adding up as you go, too, they don't just suddenly sum up at the end.

I think it's because many of us believe there is life after death, and being able to reflect positively about your mortal life when at its end is a good sign that you're off to a good start for the next!