Susannah: We can’t all earn lots of money

Dear The Tank,

Ever since I graduated college with a degree in literature, I’ve watched my friends go on to successful careers in medicine, entrepreneurism, finance, and law. I’m stuck as an assistant manager at a used bookstore. Sure, I feel a lot of envy at times, but that’s just the beginning of my problems. They’re my friends, and I want to be with them, but they’re always inviting me on outings I just can’t afford—say a long weekend in Aspen or dinner at Le Bernardin or a trip to the Bahamas. How do I handle this without losing my friends?

—Susannah

Dear Susannah,

First you say you don’t have enough money. Then you say your friends are rich. Do you really not see the obvious opportunity in front of you? These people are your friends; they trust you.

I suspect a sense of diffidence—perhaps even an inferiority complex—has been holding you back. You need to overcome this, in order to change the course of your life.

Here’s what you do. Next time you’re over at their houses for a wine tasting or to admire their new art, look around. Note where the valuables are. Check out locks and alarms. Maybe happen upon the drawer where they keep their spare keys (hint: most people keep ’em in the kitchen). Don’t think of it as casing. You’re being observant.

Then the next time they propose some jaunt to Saint Tropez or wherever rich people go to marinate, instead of whining about it, do something. Pick out some dark clothes. Get a flashlight, a duffel with an over-the-shoulder strap, and some comfortable shoes. If you start to feel guilty, remember, you got better grades than these people. You deserve a little pecuniary recognition.

Let me know if you need any help liquidating assets. I know a guy.

I’m excited for you. This could be the start of a whole new career and a whole new life for you.

Good luck!

—The Tank

The Tank is inspired by Gracious Living Without Servants, the new novel by Wall Street Journal writer Brenda Cronin. Juliet, the heroine of that novel, makes all kinds of bad choices that end up making life way more interesting. Read the first chapter.