Well, Billfold, you’ve finally compelled me to get over my annoyance with your new commenting format. It took 1000 clicks to read the 10 comments on this post, but I did it! And my impression is that people are using the co-worker’s candor as a cudgel. I’m not saying that he has an entirely healthy relationship to gambling, but it’s really weird to read comments that suggest the only reason someone would have a second job in 21st century America is because he has a gambling problem. It’s even weirder to read those comments on a financial site where people talk about gigs, hustles, making the most of our money, and all the ways in which our family cirumstances can shape how far our money goes. The man mentioned a (now ex-) wife, a son in jail, another adult son who needed help getting an apartment, and so on. Surely you can imagine that working in the magazine industry in NYC doesn’t allow a person to atend to all of the financial responsibilities that come with that kind of family setup? Again, the gambling doesn’t seem to help, but the logic in these comments seems to be that anyone with a second job must be hiding some vice. And of course no one here really thinks that, because I’m sure a lot of folks here have side gigs/hustles of their own. It’s interesting how a man outside of the standard Billfold demographic can be diagnosed, judged, and dismissed in ways that I don’t usually see happen with other interview subjects here.