‘Dear Sugar’ Answers Questions About Money, Family, and Class

I have been a Dear Sugar fan ever since I did one of those “why doesn’t he love me” Google searches and found myself on The Rumpus. (Never ask Google why he doesn’t love you. I mean, it was a net win for me because I discovered Cheryl Strayed, but… Google is not going to be able to answer that question.)

If you have not read Dear Sugar, consider it a gift I have given to you, and set aside a few hours to go through Cheryl Strayed’s compassionate, thoughtful advice column.

If you have read Dear Sugar, you might already know that Strayed and Steve Almond (the voice of Sugar before Strayed took on the column) have recently launched a Dear Sugar podcast, where they continue to answer reader questions but in podcast form.

This week’s episode was about money.

The first letter came from a young woman who is pursuing a career as a theater director and writer. She feels like a “rich asshole” (her words) because her wealthy parents have helped fund many of her opportunities and experiences, including allowing her to live rent-free in a Manhattan condo “which they insist they bought for themselves because they want to spend more time near me and my brother when they retire, but I suspect they really bought it for me.”

She asks Strayed and Almond how she can feel like she’s earned her success. She makes it clear that she has always worked, but she is also able to take on different kinds of jobs because she does not have to pay her own bills — and, of course, that freedom has propelled the success that she does not yet feel she has earned.

Strayed and Almond suggest that the writer move out of her parents’ condo and begin supporting herself. Cut off the parents and see what you can achieve on your own.

This is the sort of advice that sounds like the beginning of a Hollywood movie where the writer/director is the protagonist and the parents are just two ancillary characters who live in the background. I am going to bet that the parents feel like they’re protagonists in their story too, and in fact they may view life as an ensemble piece starring themselves and their children. A daughter rejecting their gift of a Manhattan condo is going to cause problems.

The best-case scenario is a weekly “but we don’t understand” call where the daughter continues to reiterate that she’s doing just fine on her own and that lots of people live in tiny apartments with roommates and survive. The worst-case scenario is some kind of estrangement. (The daughter also says that her family is from “a small country” where her parents currently still live, which means there might be some cultural issues in play as well. Not every culture insists that success can only come after familial and financial independence.)

I am curious about your advice to this person, because the only advice I have is “keep working as hard as you can” and “do everything you can to share opportunities with others.” Also, as you begin to earn more money, start taking over the cost of living.

“The cost of living” is the subject of the second Dear Sugar letter in the podcast; a single mother worries that she is going to go bankrupt because she cannot stop spending money. Almond immediately diagnoses her with a spending addiction and suggests Debtors’ Anonymous, but I feel like it might be more complicated — and more simple — than that: the amount of money she’s bringing in is probably not enough to cover her basic expenses.

Here’s what this letter writer says she spends her money on: private school for her children, extracurriculars for her children, lattes for herself, and dinners out when she is too tired to cook. She notes that she drives a very old car and lives in less-than-optimal housing. Both Almond and Strayed talk about how she’s spending to fill a hole, and sure, we’ve all bought that latte because we feel sad and want to give ourselves a treat, but it’s not like this woman writes about coming home with shoes she never wears or spending money on items she never even takes out of the bag. There are spending addictions and there are people who just can’t get ahead, and this single mother seems like she’s in the latter category.

I feel like we should send this woman a copy of Helaine Olen’s Pound Foolish, and help her understand that it isn’t the lattes or even the takeout that is the problem here; it’s the entire system, along with the concept of the middle class. She writes that she feels like her children deserve a particular type of life, and that’s probably also part of the issue here; the Standard vs. Deluxe parenting costs that Ester wrote about this morning, for example.

As to her immediate financial situation: she might need to take her children out of private school, she might need to take a look at her child support arrangements, or she might need to ask her parents for support if they are willing and financially stable. Sure, laying off the lattes will put another $20 in her pocket at the end of the month, and that’ll help with the utilities. But this is a big-picture problem, not an individual purchase problem.

What do you think? What advice would you give the young woman living in Manhattan and the single mother fearing bankruptcy?