My mother always gives me useless gifts instead of cash.

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Dear Pay Dirt,

Growing up, my parents favored my little brother, and they didn’t do much to hide it. After a lot of pain and therapy, I’ve gotten over it (for the most part) and assume I will always be second best. About five years ago, my parents came to some realizations about their behavior. While they still mentally prefer my brother, I think they’re trying to make it up to me…but what they’re doing is creating more problems.

My mom is always asking me what my spouse and I need. Honestly, cash: 529 contributions, day care costs, a mortgage payment, etc. But, since I misused some birthday money when I was 8 and my mom still brings it up today in very embarrassing ways, she doesn’t want to give me money directly. She and my dad want to pay for things we need on our behalf. (They’ve given my brother checks with no strings attached, so it’s personal.) With certain things, like the 529, that was fine. But it’s more hassle than it’s worth for others like the mortgage. I wish they’d give us money, but then my mom will label me spoiled and wasteful because she doesn’t trust me to tell her the “real” price of things.

Even though we are a six-figure income household, my parents are still convinced I’m trying to steal from them despite the fact that she is offering to help us. (My mother thinks I’m lying about how much our West Coast mortgage is, and she insists day care costs haven’t gone up in 30 years.) Instead, she buys crap for my family via Target and Amazon that we don’t need. During the last two Christmases, I spent most of my time making Goodwill runs and hiding the endless supply of kitsch and toys from my kids because they don’t need more stuff! Now it’s starting up again. Neither one of my parents spend that much time with my family so they don’t know what my kids like anyway. I’ve got a pile of packages on my front porch right now that I’ll have to unbox, go through, rebox, and drive to Goodwill. I’m guessing there’s no way to stop this since neither one of my parents will listen to what we need. Am I destined to this wasteful cycle EVERY holiday season until they die? It seems like they want to assuage their guilt somehow, but they don’t really believe what they did was wrong.

—No Money, More Problems

Dear No Money, More Problems,

I am so curious—what wild thing did you “misspend” on when you were 8 years old that your mother still holds a grudge over?! Did you go out and buy a round for everyone in the local pub with your birthday money? Your mother’s unwillingness to consider you have changed since the second grade might be linked to her disbelief that child care costs have increased in the past 30 years. Her thinking doesn’t show she has changed since favoring your brother. In fact, it seems she’s still stuck far in the past.

After witnessing the comment battlefield after I mentioned the deadweight loss of Christmas, I have learned one cannot convince certain people of the greater efficiency of cash gifts. If you can’t convince your mother to contribute to the 529s instead of presents, you need to redirect her “gift” purchases into items your family will value and use. She’s likely at a loss for what your kids want since she spends little time with them. Create a wishlist (on Target and Amazon, places she is already shopping) for items you would find a helpful addition to the household. Make sure there are several things at the same price points as the stuff she is already shipping to your house and that there are toys your kids will like.

Tell her you’ve created a wishlist to make it easier for her to help out since she’s been “so generous.” Mention that the kids are getting older, and their tastes are changing (something she clearly struggled to grasp is possible) so you thought this was easier. If she fails to adjust her behavior within a year, adopt a stronger tactic. Send an email out to all the family members ahead of the holidays saying: “Kat and Min are lucky to have many toys, and our cupboards are overflowing. This year, we’re asking family and friends to give [one meaningful gift, a contribution to their 529s, etc.] instead.” A blanket announcement might make your mom feel less singled out.

If your mother still can’t take a hint, see if you can set her up to pay directly to your child care provider instead. While it’s less efficient than a blank check, she’ll see how big the bill really is and that you aren’t lying about the cost. As your kids get older, you can suggest concrete opportunities for your parents to pay directly for their grandkids (like summer camp, dance lessons, or tutoring) to take the pressure off your budget without adding more boxes of kitsch to your doorstep.

Dear Pay Dirt,

My youngest sibling recently graduated college, with what I would call a not-insurmountable (but not small to a not yet full-time employed English major) amount of debt. I’m at a place in my life where I am comfortable financially—my job pays well, I have few expenses, and have been able to set aside half of my paycheck every week in addition to contributing to my IRA, a few savings accounts, and a property investment.

Our grandparents always instilled in us the value of a good education, and in honor of the person who paid for my grandfather to attend university so many years ago have contributed to each grandchild’s post-high school pursuits generously (they helped me pay off my own very small college debts in a short timeframe about 10 years ago). I’d like to continue the tradition, starting with my brother.

I believe I can reasonably afford to gift him about $25,000. Some loans are in his name, others under my mother’s. What’s the best way to go about contributing such a large chunk of change? Are there any tax issues or other fees likely to cause him problems from a windfall like this? I want to make things easier for him, and not cause any financial trouble in the long term. We’re Colorado residents if that helps.

—Hoping to Pay It Forward

Dear Hoping,

What a generous sibling you are. I would wait to give any money toward federal loans as a gift until after student loan repayments are set to resume on June 30, 2023.* By then we should have better information on whether the Supreme Court allows Biden’s loan forgiveness plan to proceed. Feel free to tackle any private loans ahead of that date, though.

You needn’t worry about your gift affecting your brother’s taxes. Giving the money without expecting anything in return is a gift and never taxable to the recipient, only the gifter. (And since this is money for debt and not household expenses, your brother does not risk classification as your dependent on taxes.) The only special tax consideration would be your brother’s eligibility for certain student credits like the American Opportunity Tax Credit, which does not apply here since this is already the tax year following his graduation.

The cleanest way to pay these loans would be to get your brother and mother to add you as an authorized payer with student loan servicers, and you can pay the loans directly. This avoids any risk of your brother or mother “losing” the funds on the way to Navient.

Otherwise, you needn’t file a gift tax form if you pay less than $17,000 (in 2023) on the loans in either your mother’s or your brother’s name per year. You can straddle the payments across a calendar year if you need to give more than $17,000 to one person’s loans. However, even if you need to file gift tax form 709, you would only owe gift taxes if your estate exceeds $12.92 million.

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Dear Pay Dirt, 

I live in New Jersey, a state with a high cost of living. I work for a company that pays mediocre wages but large, twice-a-year bonuses based on project and client success (think: making $68,000 a year in wages and $8,000 twice a year in bonuses). Because bonuses are taxed so much more highly than regular income, this compensation package doesn’t go as far as it would if it were all paid in wages. I currently make the maximum contribution to my 401(k), with a small employer match. Is it possible to pay lower taxes on these bonuses if I were able to direct them specifically to retirement funds? If so, is that worth it? I’m looking to leave my job, but that may not be possible in the current market. What can I do to get the most out of my money in a place where I’m paying $1,700 a month for rent and trying to save for a house and retirement someday?

—Big Bonuses, Big Drawbacks

Dear Big Bonuses,

Believe it or not, bonuses don’t have special tax rates just because they are a bonus. They are taxed as ordinary wages when you file your taxes in April, but sometimes the way that employers calculate withholding for bonuses can push you into a temporarily higher tax bracket for that paycheck. While you might get more withheld than your usual paycheck, you will only owe whatever the appropriate marginal rate is for your total income when you file your taxes the following April. So, rest assured, there isn’t a special bonus tax rate, simply a higher withholding.

That being said, bonuses are an excellent way to shore up your retirement accounts. You can often ask your employer to redirect a higher percentage of your bonuses to your pre-tax retirement account—even 100 percent—as long as you don’t exceed the annual contribution limit for your retirement plan. But be aware that some employers will match your retirement contributions per paycheck rather than for the entire year. Contributing your full bonus in a lump sum and skipping out on retirement contributions in your regular paychecks could cause you to lose out on some matches. Check with your HR department about how your matches are calculated and ask about upping the percentage of your bonus you contribute to retirement.

If you still want to lower your taxable income, consider other tax-advantaged accounts like Health Savings Account or a Traditional IRA to sock away your bonus. But don’t stress about the higher “bonus” tax withholding—it’s all an illusion.

Dear Pay Dirt,

I’m 32 and recently ended the defining romantic relationship of my adult life up until now. My ex grew up well-off and has substantial familial financial support; meanwhile, I grew up working class and clawed myself into financial stability. We split expenses and while I’ve always made more money, on the balance, they have far greater resources.

In 2020, I started a pandemic-related job that paid me well, but the stress of the job led to kind-of-unchecked spending. While I ALSO used that job to create a safety net, my spending habits got way broader than they should have been, which was enabled by a cheap mortgage I shared with my ex and the ability to live within my means essentially on autopilot. I started an expensive hobby, and because I was working so many hours, spent a lot of money on takeout and other conveniences. I’m still making that income but I no longer need the conveniences as I now have a more predictable job; it’s a matter of habit changes that must happen for me to maintain financial wellness. No more takeout, goodbye to spending on hobbies without planning for it, so long subscriptions (I already canceled just about all of my non-essential subscriptions—I’ll add back in something if I really miss it).

We’re still in the process of deciding what to do with the house we own together (Do we sell or does my ex buy me out?), but in the interim, I’m moving out. In our city, it costs MUCH more on a monthly basis to rent versus own, and I will now be spending 37 percent of my income between rent and (expected) utilities. It’s doable, but I need to dramatically reign in my spending and begin saving more. I no longer have my ex to rely on if I’m in a bind. Add to that the expense of moving and replacing many of the things we previously owned together and I’m in a much worse-off position than I was a month ago. (Yes, we’re talking to a lawyer, an accountant, a realtor, and a mortgage broker about the fair distribution of assets from the house; we were never married.)

My emergency fund (about three months of income) remains intact, but I need to build back to where I was pre-breakup, and likely considerably more as I can’t rely on a partner for emergency support. I can’t expect money to come from the house for a while so it’s up to me to make good choices. But, I’m finding that I don’t know how to make these kinds of immediately necessary changes at the speed with which they must be adopted. How do I create a sense of control overnight and stop spending like I have money?

—Ex-Pensive Problems

Dear Ex-Pensive Problems,

You’re in a better position than you likely feel right now. A major breakup is, of course, going to make you feel unmoored. But you’ve got a lot going for your situation: You already recognize that your current spending can’t continue post-breakup. You have an emergency fund, even if it’s less substantial than you’ve hoped. Plus, you’re already working with your ex and the appropriate professionals to ensure you get a fair allocation of joint assets.

When your life changes dramatically, it can often be easier to make changes to your budget than if you’re stuck in the same old daily routine. You have the opportunity to build new habits in a different environment and create brand-new brain grooves. Since you want to build up your financial cushion now that you don’t have your ex to fall back on, you need to do a full audit of your finances.

Beyond knowing that you need to “spend less” on hobbies and takeout, you need to know precisely how much less. Find a quiet time to sit down and create a budget for your new life—including your new housing expenses, a category for increasing your emergency fund, and some money for the fun stuff. Getting an idea of your new baseline will help determine if you need to spend 10 percent less on the fun stuff or 80 percent less.

To create an immediate sense of control, utilize a zero-based budget where every single dollar has a job. For many people, a cash-based envelope budgeting system helps them resist overspending. (I’m the opposite, I track everything I spend on my card to the penny, but I swear dollar bills grow wings and fly out of my pocket—I use YNAB instead for my zero-based budget.) To build habits in your new environment, create an enjoyable ritual of checking in with your budget—pour yourself a nice beverage, light a candle, and check in with your budget every week or month. Regular check-ins will allow you to adjust before you get too off the tracks.

And while I’m not recommending you live like a broke college student in your 30s, finding an affordable furnished room to rent or a sublet might be a great option in the short term. It would allow you to focus on increasing your savings before drastically increasing your rent. A furnished place also will enable you to postpone replacing certain shared household items until you get your house payout. Good luck creating your new independent financial story!

—Lillian

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Correction, Jan. 3, 2023: This article originally misstated that student loan payments were to resume on June 30, 2022. It’s June 30, 2023.