‘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.

“Say Yes First, Figure It Out Later”: Top 10 Pieces Of Advice From Entrepreneurs

“Eliminate the word “just” from your vocabulary—as in “Just checking on this!” You’ll immediately feel more confident.”

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.

Do Whatever You Want With Your Discretionary Income

I know the “give up your coffee habit, become a millionaire” storyline is trite, but: Do I need to give this up?

One Ring To Rule Them All … And Bind Them

1) what do we owe our friends and family in exchange for an unprompted, generous expression of goodwill; and 2) how important are engagement rings to a proposal, anyway?

What Do We Pay For Vs What Do We Ask For

When do you ask your friends or family to help you move rather than hire movers? Only when you’re in early-to-mid twenties? And/or only when you’re seriously broke, or you seriously don’t care if something gets broken?

A Father/Daughter Duo Answers Your Questions: What Career Path Should I Take?

Dear Meghan and her Dad,

Hope you’re both well. I’m a 26-year-old woman with an MA in art history. Before graduating in May of 2013 I had a job lined up, and it sounded like a dream job at the time. So for the last year I’ve been working as a researcher at the art museum in my home city, part-time, no benefits, doing what I care about despite its relative unimportance in the big picture. I had a second (retail) job for several months to make ends meet, and then two months in my boyfriend moved in and I quit the other job, because the two of us combined made enough money, and also because the retail job was exactly what you’d expect it to be like.

On Success vs. Striving

Lionel Shriver writes for the Guardian about how the years she spent getting rejected were, in retrospect, really happy. It’s an interesting meditation on what happiness IS really, anyway, and a good reminder to enjoy the PROCESS, the challenges you’re facing, the various purposes you have in your life right now, instead of focusing on specific achievements. After all, an achievement is exciting for a day or so, and then what?