Our advice columnists have heard it all over the years—so we’re diving into the Pay Dirt archives to share classic letters with our readers. Submit your own questions about money here. (It’s anonymous!) 

Dear Pay Dirt,

I’m a woman in my mid-20s, and I recently graduated from college and am looking for my first “real” job. I am terrible with money, to an embarrassing degree. Once it’s in my account, I have to spend it. I’ve tried hiding it, using apps to put it in different accounts—it doesn’t matter. I grew up very poor, and now that I finally have access to a bit of money (I worked full-time through college), I’ve turned into a bit of a bon vivant.

Recently, I got about $3,000, which I had been planning on saving so I could move later this year. A month later, it’s all gone. Some of it did go to expenses, but most of it went to vacations, clothes, and going out. I also have a lot of credit card debt for this reason (although I’ve paid down about half of the original $8,000 total). I just don’t know how to stop spending. There is definitely some mental illness involved, which I’m working on (unfortunately, it’s not as easy as “here, take this pill”), but the general idea of budgeting makes me miserable. I get paid $1,400 on Fridays, and I usually have $200 left on Monday. I thought running out of money and having to ask people to borrow money and defaulting on a bunch of bills would be my “rock bottom” and encourage me to stop spending, but here I am, still shopping and eating out like it’s going out of style. How can I stop spending money the second it hits my account?

—Broke in Boston

Dear Broke In Boston,

A money script is a subconscious belief you have about your finances. It can be positive or negative, and it plays in your mind like background noise from a TV. This is what influences you when it comes to how you perceive, and act, with your money. If you grew up poor, your mind may associate money with lack. When something is scarce, you tend to either hoard the item or use it as fast as you can, because you never know if you will receive it again. So of course you’re making it rain with your paycheck. Your mind thinks you’ll never have money again.

I want you to sign up for a budgeting app that will track your spending for you. This suggestion isn’t to feel bad about yourself but instead to see where your money is going. When you can see exactly how you’re spending your funds, you can then assess what to do about it. You can’t make a budget or try to cut back without knowing what to cut back on. I also want you to make small money goals. You aren’t going to be in peak financial health by starting big, so try next week to make it to $300 on Monday instead of $200. Or try not to borrow money from anyone for one week. These small, actionable steps are what will get you going to where you want to be.

You also mentioned mental illness. You’re absolutely right when saying it’s not as easy as just taking a pill. I’m sure you know that therapy, a good diet, sleep, and exercise are all things that can also help, as well as taking time out for yourself and having a solid support system. Therapy can be expensive, but there are more affordable options now. You aren’t alone in your journey—I’m cheering for you.

—Athena Valentine

From: My Cat Needs $2,000 Dental Surgery. Should I Spend The Money To Keep Him Alive? (July 5th, 2021).

Please keep questions short (

Dear Pay Dirt,

Quite some time ago, a very close friend lived with me. She could not keep up with her rent, and it grew to a rather large sum. She paid here and there—small amounts—and she had to be asked for the money. The sum grew so large that I had to ask her to live elsewhere. She has never brought it up again and has never made any gesture of any monetary kind toward me. What would you do?

—Big-Hearted Dummy

Dear Big-Hearted,

I think it would be reasonable to ask for the money that she owes you, but understand that if she wasn’t able to pay it then, she may not be able to pay it now, either. So for your own sanity, you should probably assume and plan for the possibility that you never get that money back.

If you’re still friends, it may be useful to bring it up and then put the ball in her court. Mention that it’s been bothering you and that you’d like to know if or when she has plans to pay you back. Tell her you’re OK with a flexible timetable or a reduced amount, but the outstanding debt feels like a cloud hanging over your friendship and you’d feel better if there was a plan to resolve it. There’s a possibility that she may feel that because she lived with you a while ago the informal statute of limitations on repayment has passed. She may feel resentful about the ask. She may also have no idea that you’re still thinking about this. So you may want to start by reassuring her that you value the friendship and are sympathetic to any financial issues she may have. Give her a way out that doesn’t involve making her feel embarrassed or guilty about her previous inability to pay.

There’s also a possibility that even if you approach the issue compassionately and reasonably, she reacts badly and it damages the friendship further. But if you can’t even raise the issue with her, it’s likely that the friendship has weaknesses that have nothing to do with the money she owes you.

—Elizabeth Spiers

From: My Wife Spends Her Money On Hair And Nails, Leaving Me To Pay For Our Expenses. (July 7th, 2021).


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Dear Pay Dirt,
I am in my early 30s, married, with no possibility of children, working a six-figure job, and have no debt. I mentor a young woman who recently experienced some degree of familial rejection upon coming out to her family, but she doesn’t appear to have been cut off completely. She knows that if she ever needs anything, she can always come to me. She has never asked for money, but I am her emergency contact when she travels, she checks in with me to confirm everything is safe, etc. I’ve also made very clear to her that if she ever needs a place to stay, she will always have a place with us. I am currently thinking about making her a beneficiary of my life insurance.

Should I do that? If so, what do I need to look out for? Are there other steps that I can take to ensure that if anything ever happens to me, she doesn’t lose her safety net? However, I would also not like her to know that I’m doing this. I think of her like a sister, and I care a great deal and want to make sure she is provided for, but I also don’t want it to be known that I’m doing this, in case it doesn’t come to that (hopefully I will live a very long life and see her firmly established and thriving!).

—Wanting to Help

Greg Lavallee
My Son And His Cousin Look Exactly Alike. My Wife Can Never Know Why.
Read More

Dear Wanting to Help,

I think meeting with an estate attorney would be your best option with regards to planning for her well-being and identifying possible problems. (Your state bar association should have a referral service.) Putting her on a life insurance policy isn’t an issue, since you can list anyone as a beneficiary, but you should use this opportunity to make sure you and your spouse are on the same page. Unless a will is drawn up, your spouse is entitled to all your assets.

An estate attorney will go over options with you, so you feel comfortable no matter what should happen. Along with a will, you also should consider setting up an advance directive. (Everyone should!) She’s lucky to have you as her chosen family.

—A.V.

From: I Lost My High-Paying Job During The Pandemic. Now I Have $40,000 In Credit Card Debt. (July 12th, 2021).

Classic Prudie

I enrolled my two boys into an exclusive private school in our new hometown. At a school event I bumped into an attractive woman whom I didn’t recognize. She came by and asked if I remember her. It turns out that she was someone I bullied in high school. After that day I noticed other moms slowly avoiding me. I think she must have told them about how I used to bully her. Eventually my boys started coming home, crying and upset that other kids wouldn’t play with them. My younger son was not allowed to join a game of hockey during recess because another boy told him, “My mom says your mom is a b***h.” They are now openly being ridiculed and ostracized at school by their peers. I asked to meet my former classmate and apologized for bullying her as I was young and stupid, although I don’t much remember what I did. She smiled at me in a creepy way and said she went through therapy for what I put her through.

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