#MerryMoney: Have the Awkward Holiday Money Chat

This is the first in a three-part series called #MerryMoney, about the different strategies I’m using to keep my holiday spending under control. They aren’t rocket science, and honestly, if you’re a spending-and-saving guru, they might seem totally basic! But if you’re looking for ways to get through the season without having to tap into your TFSA to do it, you’re in the right place.


Christmas is a time for family, and the simultaneous best and sometimes-most-infuriating part of families is that they’re made up of individuals, all of whom will probably have a slightly different take on what gift-giving at the holidays should look like.

Unless you’ve had six years to work up to a no-spend holiday, a la Our Next Life, you’re probably going to be spending some money this Christmas / Hannukah / whatever.

But just like any other time of the year, I’m a big fan of being upfront about your budget. Now, maybe Nanna doesn’t want to hear about your savings rate or your astronomical cell phone bill, and I bet your cousin Sally couldn’t care less either. That doesn’t mean there aren’t ways to introduce the idea of spending less that they wouldn’t want to hear about.

Think less

“I have no money please help”

and more

“Here’s a really fun way we can both save some money this holiday season.”

Here’s a framework I’ve uh… totally never used to get my way with family members and friends.

Not ever.

And bonus: it totally un-awkwards the entire conversation, because if you follow it? You aren’t even talking about your budget in the first place.

Step One: Customize Your Message

Your first step in having a conversation that will save your holiday budget is to make it more about them and less about you. To do that, you need to know what else they would like, other than an expensive gift.

Luckily, you probably know every single person on your potential-gift list really well. Why’s that lucky? Well, you’re in the know about what this person values beyond just a pile of material goods.

If it’s older family members – think parents and grandparents – time with you is probably high up on their list! If it’s your friends, I bet you can think of at least one low-cost-and-awesome activity you like to do together.

Plus, you can pitch it as a win-win: if you’re suggesting an alternate gift plan, you can make it a two-sided affair.

For example, instead of sending long-distance friends a present in the mail, maybe you suggest that the two of you schedule a Skype date to try the same bottle of wine and catch up instead. You just saved SO much on postage, and so did they! (Caveat: if they’re a wine snob this is not your best option.)

Step Two: Set Yourself Up to Win

So you’ve got this killer idea of how you and your friend / loved one / Mom / human you know can save money and celebrate the holidays together at the same time. Before you pitch them on it, there’s a tiny bit of really easy planning you should do.

Ask yourself two things:

  1. How does this person like to connect with you? Are you two more iMessages and emojis, or face-to-face chats?  Maybe your grandmother likes to FaceTime with you as much as mine does. Whatever the answer is, that’s the method you should use to pitch your idea.
  2. What’s the best timing for them? This includes both what times and days are low-stress for them, and when they tend to do their holiday shopping.

For the time-and-day question, here’s an example. My work days are usually super stressful around this time of year, so sending me a text asking if we can try something new for the holidays this year? Not the best strategy, especially because you’ll probably be met with radio silence for 8 hours. That’s awkward.

Setting up a quick Skype chat in the evening on a Tuesday, however? A totally different story.

As for when they like to do their shopping, if they’re a super-early-bird shopper, you might be too late to suggest a mutually beneficial arrangement this year. Your gift is probably sitting in their closet already. That doesn’t mean you can’t get creative and pitch something else! It’s just something to consider before you initiate the chat.

If they’re no early bird? You’re all set!

Step Three: Deliver a Can’t-Miss Pitch

If you’ve got the first two steps down, this is the easy part. You’re walking in to this absolutely-not-awkward conversation armed with…

  • a killer idea for a budget-friendly holiday celebration you know they’ll love, and
  • a perfectly timed chat that works for them, in the method they like to connect with you.

At this point, you really can’t lose, and it’s time to just turn on the charm and have the conversation. If you’re really still stuck, here are a few ideas to kickstart your creative juices.

  • If it’s your significant other, why not suggest gifting each other an experience instead of things this year? I may or may not have suggested my boyfriend and I go get certified on the library’s laser cutter as a date night. It’s not technically our Christmas plan, but man oh man are we excited for it! (Plus, it’s free.)
  • If it’s your grandmother, why not suggest spending an afternoon having her teach you how to make those amazing cinnamon rolls she makes every year? You bring the ingredients, she brings the mad baking skills.
  • If it’s your best friend, why not suggest a lunch date at that new restaurant you’ve both been hearing so much about – or, if they’re long distance, a Skype date where you both try out a new bottle of wine in your respective locations?
  • If it’s your extended family, try floating the idea of a Secret Santa for the adults. It might be too late to implement this year, but you know when everyone’s really receptive to new ideas? After Grandpa’s liberally spiked egg nog on Christmas Eve, or Grandma’s special recipe* gin and tonics.

*The recipe is more gin.

So that’s my basic framework for having the awkward holiday money chat with your friends and family. Trust me when I say that if you follow it – as I have to stellar effect, my Christmas budget is so manageable – it’s not awkward at all, especially because your budget never even has to come up.

And in the meantime, your January bank accounts will thank you.

Have you had successful conversations with friends or family about spending less around the holidays? I’d love to hear how they went, and what strategies worked for you! And PS. If you’re a blogger and you want to share any #MerryMoney advice, send your posts my way here or on Twitter and I’ll link them at the start of next week’s posts!