David Foster Wallace would have turned 50 today. With that in mind, below is a fascinating letter he wrote at 33 years of age, to Don DeLillo — an award-winning author and playwright for whom Wallace held a great deal of respect. With Infinite Jest written and soon to be published (to huge acclaim), Wallace was faced with a problem: although the quality of his writing was improving, he was having less fun in the process.

“His concern was always what it is to be a human being—that is, how to be an actual person, someone whose life is informed by values and principles, instead of just an especially shrewd kind of self-preserving animal.”