Why do authors (and editors, for that matter) find it so hard to talk about how much money they make—or don’t make?

In this Slate article, Laura Miller unpacks some of more compelling anecdotes from the authors who contributed to a new book, Scratch: Writers, Money and the Art of Making A Living. Probably the most jaw-dropping story belongs to Cheryl Strayed, the author of Wild, the voice behind the popular “Dear Sugar” advice column, and someone I suspect we’d all agree is probably a literary one-percenter.

So consider how surprising it was to hear her confess, in the middle of her book tour behind Wild, this to her husband: “My book is on the New York Times best-seller list right now and we do not have any money in our checking account.”

What follows is her confession that a) she didn’t make much money before Wild; b) her husband, a documentary filmmaker, wasn’t exactly the family breadwinner; and c) they decided consciously to avoid getting jobs and instead coast on credit-card debt to keep their artistic dreams front and center. Oh, and d) they decided to have two kids in the midst of all that.

Strayed doesn’t get defensive about any of this. She just tells what happened. Along the way, we learn that when you get a $400,000 advance for a book, you don’t just get a check for $400,000. You get it in three or four payments over a number of years, and you get it net after your agent takes their cut, and what you do get, gets taxed at at least 33 percent.

But it doesn’t take a close reading between the lines to see, or say, that Strayed made some dumb decisions. I know, because I’ve made some of those same decisions as an editor, and I’d definitely say they were dumb.

A lot of my self-esteem comes from the fact that I started my business from scratch and have built it into an (almost) self-sustaining enterprise for seven years now. I like my “have laptop, will travel” lifestyle, especially after many years of working an inflexible schedule—nights and weekends, with Monday-Tuesday weekends—as a newspaper copy editor. I love the freedom too much to take on anything that takes away from it beyond the occasional temp job, but that freedom comes at a high price.

I often say that “The only thing consistent about my work is the inconsistency.” I also often say, “Cash flow is my God; I shall not want.” Only, I want. A lot. So I do dumb things like:

• Go without health insurance. I find it easier to pay the tax penalty, and pay out of pocket for health issues when they arise. (And I got burned on this recently when I suffered an illness during the last holiday season and ruined that season by paying more than $1,500 in urgent-care and emergency-room costs.) Dumb, dumb, dumb.
• Run up credit-card debt. This wasn’t as dumb as it seemed because it helped me rebuild my credit from dumb decisions I’d made before I went into business for myself, and I was doing well keeping pace and then some with my monthly payments. It also financed working travel that was important to me. And it worked until … well, it didn’t. Once in a while, I have a crappy month. Or two. Or three. And suddenly I can’t even make the minimum payments because of poor cash flow, and seeing much of that cash flow into the hands of urgent-care clinics and emergency-room doctors. Late payments = loss of credit points I'd worked so hard to build back up. Dumb, dumb, dumb.
• Being weak in the face of my spending vices. I equivocate mightily on this by telling myself that I don’t spend money on what most people spend lots of money on: home improvement, electronics, non-working vacations, new cars, etc. So what do I spend money on? I like to eat out a lot. Like, twice a day. If not more. I’m a single guy living in a rented room, working for myself and by myself. I like catching the energizing current or ambient humanity while eating a pub burger or a plate of artery-hardening pasta. I like eating hearty breakfasts in the roadside diners of America and pretending I’m a noir character who got thrown off the hay truck just before noon. Doesn’t seem like much until I see I’ve spent $300 a week on meals out and have $78.14 left in my checking account. Dumb, dumb dumb.

Dumb. But real. But still dumb.

Isn’t it better to talk about this than to be embarrassed about how much we struggle—or worse, pretend to be embarrassed by how much we don’t struggle? I think so.

Then again, what do I know? Except that someday I hope to be as dumb as Cheryl Strayed.