Young wrote the song in 1965, the same period in which he produced "The Rent Is Always Due
," "Don't Pity Me Babe," and "Nowadays Clancy Can't Even Sing." The common thread running through all of these songs is a deep pessimism and world-weariness that doesn't seem to fit Young's then-20 years. There's a reason for this.
At that period in his life Young was dealing with a lot of rejection and failure. It was a sad, wandering time that followed the breakup of his Toronto band named 4 To Go. The group started with high hopes but never even played a show. They practiced and tried to find an in, but the Toronto music scene was "locked up" as Young told John Einarson in Don't Be Denied
. He'd been going hard, trying to make it as a musician for some time, and the failure hurt. It's easy to imagine him projecting himself into that disillusioned old man lecturing the paper vendor about life's futility.