‘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.

“So! Do You Have Any Questions For Me?”

Acing a job interview isn’t merely about being able to reply, in a sensible and capable-seeming way, to questions. It’s also about posing sensible and capable-seeming questions yourself.

How To Retire Early Without Being A Millionaire

The math says I’ll be able to quit for good shortly after I turn 40, about fourteen years from now.

“Don’t Say You’re Sorry”: Advice On Firing People From Time & J. Crew

It’s usually awkward when the news reports that you’re outsourcing American union jobs to Manilla. It’s even more awkward when you’re caught telling your managers to refuse to apologize.

A Good Candidate For A Loan

Will studies like these only give lenders another reason to direct their efforts away from the less fortunate?

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.”

Five Fixes For Next Year’s Taxes

Having a large return can be fun, but it also means that you loaned the government your money interest-free for a whole year.

The Myers-Briggs Personality Type That Makes The Most Bank

When it comes to financial success, extroverts are king of the world.

How To Make Leftovers Into A Meal

You can fancy it up further with those herbs that you bought a bunch of for that one recipe and left in your fridge to silently judge you every time you open the door.

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.

When Do I Tell My Boss That I’m Applying to Other Jobs?

Job searching while you have a job is a tricky thing to navigate. While it doesn’t feel good to be dishonest with your coworkers, you also don’t want them to think you’ve checked out—especially if you end up being there a while! The sad and uncomfortable truth is that it’s quite normal to have a period of deception while you hunt for other jobs and fake doctors appointments while you interview.

Getting Funded While Female

Olen advises women to swagger more, even if we have to fake it; be more resilient and less dispirited by the word “no”; and make use of our networks.

Which Siblings Would You Like To Cut Out Of Your Parent’s Will?

No one who writes to an advice column asking, “Should I hire a lawyer and have both my mother’s and my grandparents’ wills revised?” is living a blameless and sunshiny life.

Repair or Replace: The Smartphone Conundrum

A couple of hours without my phone? If only the repair guy worked while I slept, like elves in a fairy tale.

Would You Ever Tell a Friend That They Were Making Bad Financial Decisions?

It seems obviously inappropriate to gang up on a coworker and stage a finance intervention about personal purchases, but what if the person were a close friend or family member? Have you ever told someone close to you that they were making bad financial decisions? Would you ever?