Her Own Secret Santa

*This is a guest post by my dear friend Jeanne Sullivan. We were roomies at that badass writing retreat I had the privilege to attended in August. http://bookmama.com

Take it away Jeanne!

Just last Christmas I found myself on Christmas morning without presents under the tree.
We did our usual exchange with the family between my mom and sisters, but mine was a gift certificate that arrived via email. My kids, not yet of driving or earning ages, hadn’t contributed to the pile of wrapping under the tree. And my on again, off again relationship was off again. All that to say, I thought it wouldn’t bother me; I thought I didn’t care. I thought I wasn’t such a materialistic person. But when 2 pm came, my boys went to their dad’s house; and I had a good cry about it. Then I moved on.

Flash forward to February, and I’m laughing with my son at breakfast about how I’d ordered a flash drive for him at Christmas and forgotten about it. I’d come across it cleaning out my office the day before in a box with something I’d bought for myself: a Bamboo stylus I had been so excited about! Apparently, so excited that I completely forgot about it for two months while it was sitting in an Amazon box on top of my bookcase.

And just like that, the idea hit me.
If it was that easy for me to forget about the stylus, I bet I’d also forget about a new pair of boots, a sweater, and a brand new iPad.

Here was my plan: I’ll order myself a Christmas present every month between now and then. I’ll pay the extra $5 to have it wrapped and follow my son’s suggestion to lock them in the attic like I do their presents. I’ve had a smile under my hat about it ever since, part grin and part gratitude. You see, at other times in my life, I might have thought: “there’s no way this would happen again” or “I’m sure I’ll be in a relationship next year.” Or my favorite denial strategy:

“By next year, I’ll be so mature that not having presents under the tree won’t bother me at all.”

Those ways of thinking were for back then, when I wasn’t yet forty and cared a lot more about what other people think. Back when I wanted to be better than wanting a pile of presents under the tree. And, life might be short, so just in case, I decided to plan differently for this year.

Last February, I conceded that things could change: “Maybe I’ll be in a great relationship with a man who showers me with gifts by December 25th this year. Maybe I’ll cultivate a huge circle of friends who have nothing to do but think about their single sister’s supply under the tree. Maybe my kids will work all summer mowing lawns just to put a few gifts under the tree for mom.”

While I’m as optimistic, maybe even more so, than the next person – I sure am glad I took matters into my own hands. At this very moment, I have no shame in sharing that I have the MOST presents under the tree – ten to be exact. The final present to myself, from myself will arrive on December 23rd from Stitch Fix. This was, ahem, the same strategy I used for buying my own birthday present this year, and it worked out very well.

Vulnerability, like good wine, is always better with friends.

Won’t you to share your insights, fears, stories and dreams with me in the comments below?

Which holiday is hardest for you? What could you do to make sure it’s better this year, even if it seems silly or selfish?

Jeannie Sullivan

With a pocketful of entrepreneurial dreams, Jeannie left her VP corporate gig in the middle of the recession to launch her own consultancy. Within her first year, she was leveraging a revenue mix to bring home six figures annually doing work that she loves. Her coaching practice attracts professionals who are ready to create commerce on their own terms by starting a business, innovating their business strategy, or unleashing their true talents on the world. You can learn more about her at jeanniesullivan.com.