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The holiday office party, where cringe meets opportunity

It's the season that makes legal advisers cringe and work gossips thrive: Office holiday parties are back … and maybe more awkward than before. This year, the festivities unfold as major companies are enforcing return-to-office mandates and the congeniality many of us shared with coworkers pre-COVID doesn’t feel the same. So what’s the best approach to the office party?

awkward holiday party

In a recent survey, 95% of 18-to-34 year old participants said that holiday parties boost engagement. That can be true for elder millennials, too, if we can move past our collective cringe. These gatherings aren’t just about lukewarm catering and small talk. They’re strategic moments disguised as social ones. At the holiday party you can:

  1. Get face time beyond the screen: You spend all day Slacking, emailing, and Teams-ing — this is your shot to connect as actual humans.

  2. Shift the narrative: A party can reset dynamics. That colleague you thought hated you? Turns out they’re just bad at emojis.

  3. Show off the un-Googleable: Whether you’re schmoozing with leadership or calmly, competently putting out a Sterno fire, you have a chance to showcase those soft skills that don’t show up in the decks you build.  

Important: Stay long enough to make an impression, but not long enough to make headlines. After all, you’re likely going to be seeing a lot of these folks in the New Year. 

Quietly hiding the karaoke mic, Anna Davies, writer


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Quick Hits

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Q&A: Avoiding Debt-cember

Q: We always overspend on the holidays, and it's always on stuff like extras at the grocery store, stocking stuffers, Santa meet and greets …. little things that add up to hundreds of dollars. Advice for staying on track and still having room for spontaneity?

— Watching my holiday spirit compete with my self-control

headshot of Kerry Keihn
Featured Expert

Kerry Keihn

Partner and Financial Advisor at Earth Equity Advisors

Here’s the hard truth about the holidays: most of us are feeling stretched thin — financially, emotionally, all of it. Acknowledging that? It’s not just OK; it’s freeing. The problem is, we dive headfirst into the frenzy without asking the bigger question: “Does this actually match the kind of holiday we want?” asks Kerry Keihn, partner and financial advisor at Earth Equity Advisors in Asheville, NC. “Before making a purchase, consider whether it aligns with your values and enhances your holiday experience.” (Related: Steal These Money Tips to Cut Down on Holiday Costs)

This also means rallying your family and friends. Still haven’t set plans? It’s time to send the WhatsApp: White Elephant or Secret Santa, here we come. Set price caps. Brainstorm themes. Keep it creative but doable. (Related: Entitled Friend Doesn’t Understand the Point of White Elephant Exchanges)

One more thing: Stay realistic. A $25 reindeer cocktail or three-figure wreath will catch your eye. And guess what? That’s fine. Keihn recommends building a “spontaneity fund” into your holiday budget so you can lean into those small indulgences guilt-free. Because what would the holidays be without at least one overpriced snow globe on the mantle? 

overpriced ornaments on a holiday tree

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Wealth Builder

An online shopping hack that's all about location

What it is: Using a VPN to shop online

screenshot of VPN

Why we love it: There’s a TikTok hack gaining traction: Use a virtual private network (VPN) to browse from another location, and you might see lower prices. In practice, mileage may vary, but I once scored $40 off an expensive gift by using a VPN to shop as if I were in Canada instead of the US. Here’s why: retailers and travel companies (hotels are especially guilty) use “algorithmic pricing,” which adjusts prices based on factors like your location. A VPN hides your location and lets you browse as if you’re somewhere else, and could potentially unlock better deals. Curious? Here’s a guide to the best VPNs available.

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Not a stretch to say that Cyber Monday is our Super Bowl. So we put together a cheat sheet of all the sales worth your time and money. (And it's alphabetized.)


It's the smartest time to pick up bigger-ticket items, like this multiuse storage cabinet and nice-looking desk chair from Wayfair.

Psst…love our recs? Follow @skimmshopping on Instagram for more products, gifts, and services that are actually worth the hype (and the price tag).

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millennial spending meme