December 21, 1992
[Chappaqua] A day of cheerful puttering about amongst my stuff. Tallied up twelve months’ worth of credit-card statements, that sort of thing.
I’ve got so much money it hardly seems real. It’s so much more than I need. The awful thing is, now that I have it, I feel the urge to keep it.
It’s good that I’m doing this train game. I should spend the money and not worry about it. The conservative impulse, at this point, is not my friend. If I’m not prepared to roll the dice now, when I’m young and on top of the world and the cash is rolling in, when will I ever be?
I know myself well enough to know that whatever happens, it won’t be my excesses I’ll regret, it’ll be the things I held myself back from doing. In all my life I’ve never yet given a present so lavish, or made a gesture so expansive, or indulged a pleasure so recklessly that I regretted it later. Whereas there are so many things I look back on now and think: That was one of the high points, that moment will never come again, why did I hold back?
I know it’s possible to err in the other direction too, to screw up your life by not thinking of the future. I just don’t think I’m nearly there yet…

