How to Disrupt Gift-Giving When You’re Entrepreneur

gift giving

Ah, gift-giving season: It’s as American as football and apple pie. Or, in the parlance of startups, something so established that it’s ripe for disruption. That’s what I’m doing this year: disrupting my gifting circles and cycles. The same way we no longer stay at hotels (hi, airbnb) or rent a car (hello, Zipcar), we also don’t have to gift like we used to.

It’s a mindset that crystallized for me the first winter after I became an entrepreneur. Suddenly, I had neither the cash nor the energy. Why did I have to buy gifts for 30-plus people? At first, my new entrepreneur mindset went a little overboard and adopted a “screw it” mentality: I was over gifts: giving and receiving. Both came with pressure I didn’t have the bandwidth to handle. I had software to build and customers to woo!

Opting out wasn’t completely new for me. Throughout my 20s, I often skated by taking people to dinner or drinks in lieu of traditional gifts. Sometimes, it was laziness, but usually, it was a visceral reaction to loading more stuff on people. Instead, I tried to focus on experiences, like a ticket for my brother to come visit me in New York, or entry to a race that a friend and I could run together.

Then I married into a family of passionate gift givers and quickly realized I was in over my head. My solution was to throw money at the problem. I used my growing paycheck to “give good gifts.” The internet made it especially easy: With a few clicks, I could send wine, gourmet ice cream, and stockings full of novels. I ordered cashmere sweaters and hats and so many other…things. The gifts I’d felt drawn to, I loved giving. And the filler gifts — when no inspiration struck — felt like…filler. Expensive filler that gave me a financial hangover come January. Between us, my husband and I spent over $1,000 one year…to do what, exactly? Return home with $1,000 worth of things we didn’t particularly need or want?

I thought there was no way out, and that gift giving was what it took to keep the peace. And then I left my nice corporate career to launch my own company, and realized that I didn’t have to do anything. That was the first year I inadvertently tried disruption: cold turkey.

Here’s what happened.


It turns out that, for me, no gifts felt a little too much like the Grinch’s Christmas. But I wasn’t at all ready to go back to the “normal” gifting rules. While a few gifts enhanced my holiday spirit, it was the overwhelming number that left me feeling like there had to be a better way.

Plus, by opting out entirely, I felt like I was hurting some of my relationships. Some of the people I love thrive on gift giving (it’s even one of the five “love languages” that classify how people give and receive affection). So if I was going to disrupt the season of gifting in my own life, I was going to have to do it in a way that felt win-win for everyone. That’s what great disrupting technologies do, and it’d work for my personal life too.

So I planned my disruption carefully… I wasn’t anti-gifts, I simply wanted to give (and receive) gifts in a way that added the most joy and value to the season.

Here are the five strategies that work for me:

1. Shift out of gifting circles or traditions that aren’t emotionally necessary or part of your holiday. If possible, set up drinks or potluck instead, so you get to enjoy each other’s company. Even if you’ve been exchanging gifts with your neighbors since 2007, being an entrepreneur is a great “excuse” to shake things up and try something new.

2. Think “Secret Santa” for groups where gifts are important and part of the holiday celebration (i.e. family). Set up exchanges so everyone is gifting just one person. Put someone in charge to play matchmaker, or draw names out of a hat. Tip: Approach this quietly with the “leader” first (your mother-in-law, perhaps), since you might have to win over a few people and it can get political or emotional. But being an entrepreneur is a great excuse to suggest changing things up!

3. Gift and send cards throughout the year when the perfect idea alights. My best friend and I both run our own companies, and so she understands completely that sometimes the right present doesn’t come at the expected time. Instead, we gift when the moment fits, like the massage I treated her to the day after she ran the NYC marathon.

4. Make a go-to list of gifts you like to give. For me, it wasn’t just the financial aspect, but also the time. Now that Cyber Monday was on my own time — not my boss’s — I was even less inclined to surf the sales. (I’d rather use that time to share hot apple cider with friends, or take a holiday-song yoga class.) So I curated a list of affordable items that I love, and now turn to it whenever I need a gift. It includes fun, useful, and somewhat unique things, like my favorite wines, three months of Netflix (and a note to check out my favorite shows), a Sugarwish candy drop, the If book, or the planner that changed my life.

5. Don’t forget homemade treats! There’s a reason cookies are a cliché: They’re affordable, one-size-fits-all, and when they’re gone, they’re gone. To make a kitchen session fit your entrepreneur lifestyle, set aside a weekend morning to bake in large batches and give everyone on your list the same thing. And you can still be unique: Instead of piling on more sweets, try healthier options like homemade peanut butter, trail mix krispy treats, or tomato sauce.

6. And above all, give thanks with abandon. Any gift you receive — whether time, items, or experiences — becomes that much richer when it’s received with gracious thanks. Pull out the notecards (or try a service like Postable) and thank away. Regardless of where you stand on gifting, you’ll make people feel appreciated and loved.

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