How to Deal With Awkward Money Questions Over the Holidays
Talking about your finances with folks requires tact and the right timing. But throw in some eggnog and a dinner table packed with extended family, and any hope for a reasonably civilized conversation about money goes right out the window. Depending on your family dynamics and your financial situation, heading home for the holidays means preparing to field some majorly awkward money questions. Consider it a cross-examination where the courtroom is the dinner table, and the jury includes a great aunt, a distant cousin, and some in-laws. Any good lawyer would advise you to prep before you take the stand, so consider us your counsel on all holiday money talk. We've compiled an assortment of awkward questions you might have to field this holiday, along with some tactful ways to answer—or deflect—them.
Is that a real job?
Whether you're one of the 37 million freelancers, starting your own business, working in the creative arts, navigating the startup world, or doing anything that your relatives might not consider conventional employment, the answer is always YES. Because that is the truth and because you shouldn't have to defend your chosen career and the goals you're striving everyday to meet. It's important when faced with this question that you answer confidently, if not for their sake, for your own.
When Jacqueline Whitmore, founder of The Protocol School of Palm Beach and author of the book Poised for Success, was starting her own business, she had to deal with this line of questioning over the holidays. "My answer back then was the first thing that came out of my mouth which was, 'I have a real job.' That's all I said. Sometimes that's the best answer," Whitmore tells Time. If you're worried you'll come off as defensive, Whitmore offers another tactic. Try saying: "I am doing what I love, and you know what they say, 'when you do what you love, the money will follow.'"
How much are you making?
File this question under one you never have to answer directly, unless you really want to. Your income is your business, and unless you're asking for financial help, you are entitled to keep your business to yourself—especially at the dinner table surrounded by distant relatives.
Wisebread's Emily Guy Birken suggests responding to the question playfully —"for instance, by saying "Half of what I'm worth, I'd say," or by placing your pinky against your mouth and intoning 'One million dollars!'" Then, feel free to change the subject. ("So, what's the secret ingredient that makes this stuffing so delicious?")
You're still living in that place?
Here's one you might get from a parent or sibling. Whether they're prompting a discussion about your investment strategy or pressuring you into home ownership, the question may be well-meaning, but it's also dripping with judgment and condescension—and that's no way to begin a productive financial conversation.
One tactic is to shut it down with a simple, "Yes, and I'm still very happy there, thanks." But if you really want to address the elephant in the room, state your case. There are plenty of solid reasons millions of millennials are choosing to rent their homes rather than buy—from a volatile housing market to lowered insurance costs.
"Be honest with your parents, laying out the ways in which renting is a better fit for you right now and how much better off your finances are as a result," suggests Learnvest's Marianne Hayes. "A big mortgage payment may have meant not being able to afford your plane ticket home, for example." If they won't listen to your reasoning, maybe they'll listen to Warren Buffett who believes the best investment you can make is in yourself.
Why don't you hire your cousin/invest in her company?
Yeah, this one is really awkward. One of your relatives is playing job recruiter, or worse, you're confronted directly by a relative who wants you to invest your hard-earned cash into a business that doesn't seem financially sound.
There's nothing wrong with helping out a family-member in need, but the holiday table isn't the best place for financial matchmaking. If your cousin needs a job, you can respond by saying you'll be happy to help in any way you can, but that you're not in a position to make hiring decisions at this time. Feel free to ask him to send you his resume in the new year, and add that you'll be happy to pass it along or keep your ear out for opportunities that might be the right fit.
If you're being hit up for a financial investment you're not comfortable making, you can be a bit more direct. "Instead of saying you have anything against the product or her method of doing business, just blame your budget," suggests Refinery29's money expert Priya Malani. "If it's not entirely true, think of it as a white lie for the greater good: 'I'd love to but it's not really in my budget right now. Thanks anyway!'"
Can I borrow some money?
The answer to this question all depends on who's asking. Is it a parent or sibling? Is it someone you trust with financial decisions? Is their need dire? And most importantly, are you flush enough to meet their requests?
"If you're able to take on the responsibility, pinpoint how much you're comfortable offering," writes Learnvest's Hayes. "In other words, lend only what you can afford to part with. From there, establish a clear payoff timeline and put the agreement in writing."
Still, Hayes suggests listening to your instincts before you jump into any agreement. "If the idea of loaning cash to little bro makes you uncomfortable, trust your gut," she writes. "Politely saying that you can't afford it right now is better than a ruined relationship down the line."
When are you going to find a stable partner?
This one is a doozy. You may be dating someone who isn't as financially stable as your family would like. Even if it's an issue you've grappled with in your relationship, it's not healthy or fair for your family to interfere with your romantic choices—financially or otherwise—unless you're soliciting their advice. Being too defensive can open a can of worms, and take the conversation further down a road you'd rather not go. Try citing a positive career shift your partner has recently made or touting an achievement you're proud of them for. Then, change the subject as fast as you possibly can.
Any other awkward question we haven't covered yet...
You may not be able to predict what you'll be hit with before the holidays, but you'll know an awkward question when it lands.
"If it's uncomfortable for you, it's probably uncomfortable for everyone in the room," Bethany Palmer of TheMoneyCouple tells USNewsandWorldReport. Do yourself and everyone else a favor and follow her blanket suggestion for shifting the conversation. Try saying this: "That's an interesting question – let's talk about it later?" Then, ask about dessert. Better yet, ask if you can replenish anyone's wine glasses. A glass or two more, and they might forget all about it.
Looking for a job? In addition to encountering those annoying never-ending job interviews you may find yourself face-to-face with an artificial intelligence bot.
Companies worldwide increasingly use artificial intelligence tools and analytics in employment decision-making – from parsing through resumes and screening candidates to automated assessments and digital interviews. But recent studies claim that AI does more harm than good.
While AI screening tools were developed to save companies time and money, they’ve been criticized for placing women and people of color at a disadvantage. The problem is that many companies lack appreciable diversity in their data set, making it impossible for an algorithm to know how people from underrepresented groups have performed in the past. As a result, the algorithm will be biased toward the data available and compare future candidates to that archetype.
The City’s Automated Employment Decision Tools (AEDT) law is designed to offset the potential misuse of AI and protect job candidates against discrimination. It was enforced on July 5th, 2023 in New York City - with other cities and states expected to gradually follow suit. Employers must now inform applicants when and how they encounter AI. Furthermore, companies have to commission a third-party audit of the AI software used, and publish a summary of the results to prove that their systems aren’t racist or sexist. Job applicants are able to request information regarding what data is collected and analyzed by the AI. Violations of the law can result in fines of up to $1,500.
Replacing Human Hiring Decisions
However, should a job applicant want to opt-out of such impersonal judgement by a bot, the new law's scope is quite limited.
While the law specifies that instructions for requesting an alternative selection process must be included in the AI screening disclosure, companies aren't actually required to use other screening methods. Not to mention that the law only applies to AI in hiring and not any other employment decisions. It also wouldn't apply if the AI, for example, flags candidates with relevant experience, but a human then reviews all applications, making the ultimate hiring decision.
Some civil rights advocates and public interest groups argue that the law isn’t extensive enough and that it’s even unenforceable. On the other hand, businesses say that it’s impractical, costly, and burdensome, and that independent audits aren’t feasible.
Responsible use of AI in hiring
Although this law may be a good first attempt to assign more regulatory guardrails around AI, it remains to be seen if it ensures the responsible use of AI in hiring processes. At the end of the day, perhaps recruiting talent should remain a human-made decision.
The good news is that AI can help companies without harming potential job candidates in many ways – such as connecting new employees with internal organizational information and company benefits during onboarding. Or helping employees to do their jobs more effectively rather than replacing them.
The world of travel is not the same as it was two years ago. From the surge in "revenge travel" to the TikTok-inspired itineraries that make the most random destinations suddenly the most popular, there's so much about traveling that's out of your control.
What you can control — to some extent — is how much you pay for it.
According to CNBC, “Between dining out and taking trips, Americans are now spending an average of $765 more a month compared with last year when much of the country was shut down due to the coronavirus pandemic, according to the MassMutual Consumer Spending & Saving Index … Young adults, in particular, are determined to make up for lost time. Millennials and Gen Z, who reported feeling the financial impact from the rise in reopenings and social gatherings, said they are shelling out $1,016 more a month, on average, than they did during the summer of 2020. MassMutual polled 1,000 U.S. adults from July 21 to 28.”
While some are okay with making up for lost time by gleefully spending all their money, not everyone has the desire to blow up their budgets on trips. Yet, the allure of travel still calls. Thus, the appeal of travel hacking.
Travel hacking has been around as long as credit card rewards have. But during the pandemic, travel hacking gurus found unprecedented fame on TikTok and Instagram. With time to learn about the points and miles community, suddenly people were planning for future travel using tips and tricks gleaned from experts sharing their knowledge on social media.
Though it might sound complex, anyone with a fair credit score can enter the travel hacking game. Here’s how:
What Is Travel Hacking?
Travel hacking is using reward points and miles from airlines, hotels, and credit cards towards free or heavily discounted travel. This ranges from opening a number of credit cards for the reward bonuses, optimizing your normal spending in order to max out your points per shopping category, and leveraging loyalty and status for awesome perks.
To a lot of people, the term “travel hacking” can sound shady. The “hacking” scares people off. Is it illegal? Is it a scam? Can you get punished for opening too many cards? Will you ruin your credit score? The answer to all of these concerns is no.
There’s no hidden trick to travel hacking. It’s not a game of risk or cheating, it’s a game of research and planning.
Travel Hacking 101
Most commonly, travel hacking hinges on the points you can get from certain travel credit cards. Credit cards aren’t merely a way to manage cash flow. Many offer rewards programs that give you points for each purpose. These points can then be repurposed to pay for part or all of a trip.
Different networks have different systems, but most can be transferred to a range of partners. Top credit cards are with Chase, Amex, Citi, and Capital One. Simply accumulate points on your credit card, then you have the option to transfer those points to airlines, hotels, and more — for free.
When learning travel hacking, The best tip is to go backward. Don’t just open popular cards with high bonuses. Identify where you want to go, then find out what actions to take. Which airlines travel there? Which cards’ points can be transferred to that airline? Where do you want to stay? Which hotels can you book with points? Once you’ve planned out your dream vacation, see how many points you need. Then strategize for the best way to nab them.
Choose which cards are right for you, then start stockpiling those points towards free travel.
One way to quickly amass points is to take advantage of sign-up bonuses. Many credit cards use sign-up bonuses to entice users. And if you play smart, just one or two sign-up bonuses can account for one entire flight cost. However, there’s one catch: you must meet a minimum spend requirement to qualify for the bonus.
The best way to approach this is to funnel all of your regular expenses through those credit cards to chip away at the minimum spending. Pro tip: open your card right before you need to make a lot of purchases. The holidays are a good time to open a card so the cost of festivities ends up working for you.
And remember: it’s key to always pay off your monthly credit card balance before the due date! The benefits of those points are useless if you go into debt to accrue them.
And here’s a hack for you newbie travel hackers out there — be sure to manage your money and keep track of how much you’re spending for that bonus with the MeetCleo app.
MeetCleo is the personal finance tool that’s actually fun to use. Taking control of your money while “earning” free travel using your credit cards? Finances have never been more fun.
There’s all this talk about solo travel. And for good reason — no wasting precious time waiting for others to get their act together, take the plans out of the group chat and actually buy the tickets. Going solo, you can be spontaneous. You can plan your trips according to your precise tastes. You can hop on any flight and fly awayyyyyy.
But what if each time you flew you’d get a free ticket? That’s what you get with the Southwest Companion Pass.
Award status, upgrades, lounge access — there are many perks in the frequent flier game. But one of the coveted holy grails is the Southwest Companion Pass.
What is the Southwest Companion Pass?
The Companion Pass is part of Southwest’s Rapid Rewards program. You get to choose one person to be your “companion,” and they fly with you for free (plus some taxes and fees) on every flight. That’s right. Two for the price of one. That’s half off each ticket if you split it! Whether you’re flying with a partner, family member, friend, or anyone else, they can tag along for free.
And it gets better: once you earn the pass, you can reap the rewards for that full calendar year … AND the next. That’s why people go mad trying to earn a companion pass during the early months of the year. The sooner you qualify, the longer you can use it.
There are also no blackout dates. There are no limits. And if you didn’t purchase the ticket (think: work travel, your companion, or a generous benefactor), there are no restrictions! As long as you’re the one on the plane, your companion can also … be on the plane.
You can also switch out your designated companion 3x a year. So, no need to stay in a relationship simply to get the most out of your companion pass! Ghost and fly away — with a whole new companion!
If this sounds too good to be true — it’s not. But there is one small catch. It’s kinda tough to earn this mega reward.
How to qualify for the Southwest Companion Pass?
You can qualify for the pass in one of two ways:
- Fly 100 qualifying one-way flights
- Earn 135,000 qualifying points in a calendar year.
Clearly, this is no small feat — especially if you’re trying to qualify ASAP.
So how do you actually earn the Southwest Companion Pass?
Don’t worry, there’s a path to earning this amazing reward without climbing on 100 flights or spending an exorbitant amount of money.
Earning 135K reward points may seem completely impossible, but it’s easier than it sounds. Simply sign up for a Southwest Credit Card and turn those spending habits into a rapid rewards account. Through the Rewards Priority Credit Card, earn points when using local transit and commuting, plus score major points and miles whenever you spend.
Stay with me here. This is not some scheme to get you into credit card debt. Many airline cards come with potential savings, giantic rewards, awarding you points, and cashback with every purchase you make that can be redeemed for travel. And often they can come with passive sign-up bonuses. If you spend a specific amount of money within a certain timeframe of opening the card, you can be in for a windfall of points.
Now that’s where the companion pass comes in:
- Southwest Rapid Rewards Premier
- Southwest Rapid Rewards Plus Credit Card
- Southwest Priority Credit Card
- Southwest Rapid Rewards Premier Business Credit Card
- Southwest Performance Business Credit Card
Southwest has three personal cards and a business card. Each of these cards offers rewards between 30K-80K points. In the past, people could open two cards and get a bonus that granted enough points to almost meet the minimum. However, with new restrictions on personal cards, you can only get one bonus every 24 months. Boo!
However, this doesn’t apply to business cards. If you’re eligible, have good credit, and not likely to spiral into insane credit card debt, you can open a business card and a personal card, and accrue 100K+ points. The Rapid Rewards Priority Credit Card will get you points after you spend money in no time.
Now to earn the rest of them.
The secret to gaining these credit card points is to plan your card sign-ups around big purchases. Just before a recent move, I opened a card . . . and the rewards came rolling in — a small balm to ease the pain of how exorbitant moving can be.
Put everyday spend — especially big purchases or bulk items — on your Southwest credit card and watch your award points quickly add up. Typically, you earn 1 point per $1 spent on your Southwest card and 2 points per $1 on actual Southwest purchases.
But there are other ways to earn points, including:
- Flying Southwest: Booking travel on Southwest earns more points. The cost of this travel will be worth it with your companion pass
- Shopping from Rapid Rewards Partners: Purchases with Southwest’s “Home & Lifestyle” and “Shop and Dine” Partners also earn Companion Pass qualifying points. While you shouldn’t make gratuitous purchases, browse Southwest’s partners to see if you could earn extra points for items you'd be purchasing anyway. All this, simply from enrolling in their Dining Program and shopping with their partners.
So there you have it! And since it’s almost Spring, get to earning and soon you’ll be flying two for the price of one!