The Rambling Man: Advice on Trying to Make a Living and Doing the Best You Can

AdviceHello! Remember me? I used to write rambling, opinionated screeds for the Billfold, mostly about small cities and racism and socialism and sousaphones. Then, some months ago, I stopped. Last weekend, Ester came to visit me with her family and asked me why I’d stopped (I don’t think that was the sole purpose of the visit, but maybe).

“I am playing the euphonium a lot lately,” I explained. “I only have so much creative energy in me.” That was only partly true.

A few days later, on Facebook, Ester asked a general question about whether sandwiches should come with side dishes, and I found myself moved to put aside my work, my euphonium, and practically all my other concerns to pound out three paragraphs on that important issue. And I realized that I had stopped writing not simply for lack of creative energy, but because I had run out of issues pertinent to the Billfold’s frank take on personal finance to serve as jumping-off points for my opinionated screeds. It is easy to see most of the world’s problems as soluble through a combination of socialism, divorce, and brass instruments, but harder to keep finding new and interesting ways to expound that philosophy to a broad audience.

Ester’s sandwich question shook me from my torpor. I realized the world was full of marginally important questions — many of them tangentially related to money and finance — just crying out for breathless, curmudgeonly answers. So I proposed to Ester and Mike that I write an advice column. Not expert advice. Not necessarily sensitive advice. Just rambling, opinionated advice that might be amusing, on matters obliquely connected with money. They said OK.

So, dear readers, send me your questions. Not questions about refinancing a mortgage or buying a new car or saving for retirement, mind you, because I am useless in such matters and will give you lousy answers (don’t buy a house, don’t buy a new car, plan to work till you die). Rather, send me queries about the moral acceptability of sandwich prices; about the ethical implications of using toothpaste to hide nail holes and get back your security deposit; about whether you should categorically reject potential mates who buy only brand-name cereal.

I have said in the past that there is only one answer to all the advice column questions ever. I was probably right when I said that, but I will endeavor to prove myself wrong.


Editor’s note: To preserve anonymity, in case that is required, please direct all emails to, subject line: Rambling Man; Ester will forward them to Josh. 



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