My Friend Accidentally Let Me In On His Big Secret. I Think I Should Tell the Authorities.

Pay Dirt is Slate’s money advice column. Have a question? Send it to the columnists here. (It’s anonymous!)

Dear Pay Dirt,

Last year a close friend sought my advice on something, and inadvertently revealed they’d basically stopped paying income taxes a few years ago. What had once been their cash-based “side hustle”—coaching individuals in a high-cost sport—on top of their full-time job had turned into their full-time job since the pandemic. They’re basically being paid cash by clients and not reporting any of it to the government. I urged them to report it and pay income and Social Security tax, but they demurred.

Do I have an obligation to report them to the IRS? Their behavior is wrong, but it’s not like they’re some billionaire tax cheat, and many coaches in this sport do this. Is it unethical NOT to report them? Should I tell them I feel an obligation to report before doing so, to give them a chance to right their wrong?

—Torments of a Tortured Tax Tattler

Dear TTTT,

I understand your concern and that you have strong convictions about, well, tax evasion. At the same time, this is more of an ethical dilemma for your friend than it is for you. You could try to explain to your friend that it might be in their best interest to report this income—lots of surprises can pop up when you try to work around the tax system. For one, they’re missing out on deductions they could claim for running a business if only their business were legitimate in the eyes of the IRS. But most importantly, if they get caught dodging taxes, they could face hefty penalties. This happens to people all the time, and it leaves a lot of folks in massive debt—sometimes even financial ruin.

The bottom line is, if your friend wants to have a serious business, the first step is to pay their taxes and keep everything aboveboard. I would try talking to them one more time. Then I would leave it up to them to decide what they want to do. If you still feel conflicted and want to report them, that’s your right, but at least be honest about it. Give them a chance to do the right thing.

Dear Pay Dirt,

I am a staunchly anti-capitalist college kid. But the thing is, I’m secretly kind of rich. I have a trust fund with over $800,000 in it, and am set to inherit more. I sincerely do not need, or want, to keep this much money. I can’t see any reason to hoard wealth while there are people who can’t afford to even feed themselves. And altruism aside, I don’t even know what I’d do with this amount of money—I don’t want kids or a romantic partner, and my most lavish dreams include having an apartment with a decent kitchen someday.

I currently don’t have full access to my fund, but once I do, I want to figure out a way to distribute most of it to people or causes who need it more than I do. My problem is, I have literally no clue how to start a project like that, or what that project would even look like. How can I start getting my excess wealth to people who need it?

—Trust Fund Baby

Dear Baby,

That’s certainly a large chunk of money to inherit, especially at your age. But in the context of retirement goals—and how much you’ll need to live on for the remainder of your life, depending on when you want to retire—it’s not as much as you might think. Retirement is probably not something that’s on your mind right now, but many people don’t think about it until it’s too late to save. They end up playing catch-up just so they can keep up with the expenses in their older years. This can make life very difficult down the road. You’re in a prime position to make sure you don’t have to worry about that while still giving money to those in need. In fact, these two goals don’t have to be mutually exclusive.

To get a rough idea of what you’ll need to retire, consider the kind of work you want to do after college and what your income might look like. Then plug your expected living expenses into an online calculator and play around with the numbers to see how much money you’ll need to retire later in life.

Having at least some of that money saved now can free up your time, energy, and income in the future. You can then use that time, energy, and future income on things that matter to you, like volunteering, donating regularly to charities, working at nonprofits—whatever feels good to you. What’s more, “hoarding” some of that money in investment accounts means that the money will grow, which means there will be more of it to give away to the organizations that you see fit. As a “staunch anti-capitalist,” you might be opposed to investing in certain companies, but you can look into socially responsible investing. There’s also something called donor-advised funds (DAFs), which are sort of like investment accounts for donating to charities.

Your crucial next step? Search for a certified financial planner. They can give you more information on all of this, and tailor it to your specific budget, goals, and ideals. They can walk you through all of the factors to consider, help you come up with a plan, and even help you search for charities or organizations you want to support. Just make sure your planner is certified with the CFP Board, which means they’ve taken a fiduciary oath to act in your best interest and aren’t allowed to sell you financial products. Happy saving—and happy giving!

Dear Pay Dirt,

My husband and I have been married for almost 15 years and have three young children together. About a year and a half ago, I was offered an opportunity to go into consulting, a move that tripled my income for a limited period of time, but also involved more expenses related to starting and managing a small business. Even with those expenses, the extra income has allowed us to travel, replace things easily when they break, and save enough money to (almost) pay for a needed addition to our home. My husband worked in a hospital, and in December, he and I discussed him quitting his job and beginning to work per diem so that we would have more control over his schedule. We would have to give up his employer-sponsored health insurance, but I was OK-ish with having to fork over $20,000 to pay out of pocket for our family of five if it meant more flexibility and quality family time. Working per diem would also mean that he would still be able to contribute to household finances, though I agreed I would contribute more. (As it stood, he was paying 33 percent of household expenses, and I was paying 66 percent.)

Just before Christmas, he quit his job, but for some reason, he did not transition to per diem. He blamed it on his boss and her not liking him, but he did not follow up on anything with HR until his term date, and by then it was too late. At this point, he has not been working for almost three months, has applied for zero jobs, and instead has been “working on his podcast” most days. The podcast is pulling in about $1,000 a month, but he uses that money for equipment and platform fees. None of that money is every offered to support the family, or even his own personal expenses.

In addition, after he quit, he said he would be the stay-at-home dad, and yet I often have to drag him back to the family on weekends and in the evening and remind him to make dinner. In the first month, I was contacted by each of my children’s schools noting that they had been tardy to school a lot in the last month. Twice he forgot to pick up my son at preschool, and I got called from the school asking if anyone was coming. He still has student loans and I bought him a car in cash last year. He thinks his podcast is a viable business, but he spends every dollar he brings in and has never in our time together saved more than a few thousand dollars. I calculated the increased cost for this move to be at about $80,000 a year. This means that in the last three months, I’ve gone from easily saving money and feeling well compensated for my work and proud I can support my family in building generational wealth to resentful and pissed off at what I see as my selfish, immature husband roadblocking the way to our financial security and any chance of retirement down the line. How do I get him to see how his choices are hurting us in the long run?

—Girlboss Conned by My Own Spouse?

Dear Conned,

Being a stay-at-home parent is a lot of work, so I don’t want to be too hard on your husband. But it sounds like he needs some help with the whole “parenting” part of the equation. Which is one way of saying: You’re right, he needs to step up.

That said, it sounds like your family is in limbo in many ways. You both had some big work and lifestyle changes, and your husband might have realized he wants to do something entirely different with his career. Chances are, all of this happened quite fast and neither of you has had time to figure out what your new life looks like. I’m confident you can work out the details, but right now they might feel a bit nebulous. Living in a transitory space can feel uncertain, and that uncertainty makes it hard to commit to doing anything. Put simply, the dynamics and priorities of your family have changed, so it’s time to address those changes. From there, you can work out the details.

What do those details look like? First, it’s not acceptable for your husband to (repeatedly!) forget to pick up the kids from school. How can he prevent this from happening again? It’s cool that he’s doing something new, but maybe he needs to set specific work hours to dedicate to his podcast. He needs to establish a schedule as a stay-at-home parent. But also, there’s the financial issue—you didn’t agree to fund his career pivot. If he sees the podcast as a legitimate business, then he needs a budget. And that means spending any income the business generates on needs—like quarterly taxes, health insurance, retirement savings—before he spends it on things like travel or new equipment. If the income isn’t cutting it, maybe it’s time for him to pick up other work to supplement this hobby or return to his old job with a plan for eventually pivoting into a new career. For your part, could you increase your retirement savings and let him know he’ll have to make up the difference in take-home pay? This could encourage your husband to reel in the spending while making you a little less resentful.

The details will vary, but clearly, some rules need to be established. It sounds like you’ve tried, but big changes like this are often messy. It takes a lot of work to reestablish what your new dynamics and household duties will be. And you can’t do that work until you each have a clear idea of where you stand with your individual goals and shared priorities. Once you get on the same page, I hope it’ll be easier to set those expectations—and keep them.

—Kristin

I have a friend who’s always been a little cheap with shared checks. If I throw my card down for ease and let people Venmo me, he’ll pay me, like, a conservative estimate of his portion (often short of the real total) and also not take tax or tip into account. I always kind of forget about this until he does it again. A few months ago, it came to a head.