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

As always, Cheryl Strayed and Steve Almond give compassionate responses to these questions—but we have a few additional pieces of advice.

When Doing What You Love Doesn’t Pay: What Next?

The notion that the perfect book/sculpture/performance equals the perfect life stems from a deep-seated belief that if “you can be the ideal artist and be so in touch with your creativity, everything else will just fall into place,” says Clayman.

Sharp, Young Thing: How Do You Manage Someone Older Than You?

My mom called me the other day. “I have a new manager,” she explained, “and he’s younger than you.”

Appreciating Success, In 15 Second Increments

It’s easier, somehow, to kick myself for losing money years ago than to pat myself on the back for saving it last summer.

WWYD: My Parents Want My Hard-Earned Savings!

“Last week my dad approached me and said he and my mom want to retire to Florida and are looking at houses. They’re hoping my brother and I can each chip in $5,000 for the down payment.”

Ask the Grindstone: Job Reference Etiquette

Hi! I have a question for your Grindstone series: The etiquette with references.

In Which I Answer a Question About Marriage and Finances That ‘Call Your Girlfriend’ Asked Us in October

Call Your Girlfriend asked The Billfold if we can provide any additional advice to a person who wrote them a letter about a tricky financial situation.

The History of the Wooden Nickel

A Buffalo nickel is worth a pretty penny, should you find one these days.

Is Less Than a Year Too Soon to Switch Jobs?

We received the following questions below from Rosemary (not her real name), 29, who is working as a librarian in a medical context, but wants to make the switch to an academic library. She asked a question that many people worry about: Is it too soon to switch jobs?

Ask An Assertive Person: Being Social While Being Frugal

How on earth do I make and keep friends without spending a ton of money? I don’t want to turn down invites because I can’t afford another dinner out but I don’t want to be weird and not eat anything either.