Dear It’s Complicated: Money Stress Is Sucking the Fun Out of the Holidays. Help!

Michael Taylor — It’s Complicated

Dear It’s Complicated: The holidays are coming up, and I’m already stressing out! My extended family has a variety of income levels and situations—from a wealthy single aunt to my cousin’s family of four trying to make ends meet on one modest salary. I’m a freelancer, so some years my partner and I have more money to spare than others. All this makes gift giving a minefield of difficult decisions. Should I spend more to match my aunt’s taste? Give my cousin practical gift cards instead of toys for the kids? During flush years, is it OK to spend more lavishly to make up for times when I’ve given smaller trinkets?

Opening gifts together is a part of our holiday tradition that I used to cherish, but now dread as our big family grows. I know it’s the thought that counts, but now I’m overthinking this! Are there any strategies that will help release this present-pressure?


I love your question because it gives me an opportunity to humblebrag—or maybe just outright brag—about the proudest family moment of my own life. In my 20s, I found myself in this nearly exact situation, and I came up with a solution that was both self-serving and holiday-tastic. I was doing well and doing good. (It’s almost like that’s a theme I’ve heard here before. Anyway.)

Fair warning: Implementing your own version of this vision will take effort and organizing, not to mention some emotional bravery on your part, but the rewards are worth it.

My story: In my third year of college I had no money and was dreading the approaching holidays. My older brother and sister were already married, employed, and able to afford pretty nice presents for family members. With great in-laws comes great responsibility, so I also felt the added pressure to provide not just gifts for my nuclear family but for the expanding crew with whom I’d be spending Christmas. And I couldn’t afford anything without going into debt. But I had two big ideas.

My proposal, which I typed up and distributed to everyone in the family in the weeks before Thanksgiving, was to change the game.

“Forthwith!” (OK, so I didn’t actually type “forthwith,” but it was implied in my tone.) “The Taylors will be each assigned a single family member for whom they are permitted to purchase a gift from a store.”

“In addition,” I wrote, “each family member will be assigned a single other member, to whom they are expected to present a ‘non-material gift.’”

“Non-material gift,” meant that the second gift could not be paid for at a store. You had to make it by hand. In later years (we ended up adopting my plan for about a decade) the “non-material” gift was renamed the “spiritual” gift, and my whole idea was dubbed “Spiritual Christmas.”

Also, I figured allowing for one “material,” or store-bought, gift was a nice nod to the traditional American values of massive consumption for the holidays. I wanted us to be enlightened, but not force us to be, like, too enlightened.

Finally, I asked family members to stick strictly to the plan and not make additional gifts beyond the ones assigned. This was key to not undermining the Spiritual Christmas plan. I even suggested no gifts between spouses if they weren’t assigned, although I didn’t have an enforcement mechanism there.

So, what happened next? We had the best Christmases ever. My sister wrote a poem for my mom. My brother-in-law built a wooden CD holder for my dad. There was a handmade crossword puzzle. fresh-baked bread accompanied by recipes, a playlist of bluesy music with a note exploring personal experiences with bouts of depression, and a three-dimensional Scrabble board art piece. My mom gifted a needlepoint rug she had worked on for years to complete. My brother wrote an incredibly moving passage for my dad comparing him to a high-end bottle of scotch that beats anything anyone will ever say at his funeral someday. Tears.

So. Many. Tears.

The inevitable crying portion of spiritual gift giving became the highlight for me. I loved Christmas because, for the first time, it became an opportunity to express the feelings my WASPy family would never dream of saying out loud in any other context.

The postscript to my family’s spiritual Christmas celebrations is that once the next generation came along—first my nieces and nephews and then my own kids—we reverted to the materialism of every other red-blooded American family. At this point we all could more or less afford the wasteful spending, and maybe partly didn’t want to freak out the younger generation with our tear-streaked faces on Christmas morning. I will say, however, that I’ve gone back to dreading Christmas each year, so you can see where my own preferences lie.

Anyway, I’m a finance guy, and you asked a pretty straightforward financial advice question, and I answered by basically saying you should change the holiday game away from money to begin enjoying the season again. I believe that deeply.

Do you wish I had answered in a more traditional manner, weighing the pros and cons of gift cards and spending variable amounts depending on the year’s earnings? I mean, I could do that, but my heart wouldn’t be in it and you’d remain incredibly stressed, as I was. I once solved your problem in my own life, and no other solution even comes close.