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The New Rules of Gift Giving

It was awkward. The couch was sweaty. Probably because I was nervous. I don’t know. All I knew was it was uncomfortable.

We’d decided not to do gifts that holiday season.

It felt like a scene out of 20th century England. No one said anything directly, but their faces were judging us. We’d made a faux pas. People like the physical act of opening something. They like participating in the social ritual. We’d interrupted the natural order of the gifting tradition.

Except…it’s not natural. It’s invented by people like me.

For those who aren’t familiar, here’s how this works: PR companies and sales reps are on a rampage during the holidays to get their clients as much exposure as possible. So they email assault editors to get their products into magazines, newspapers, and whatever outlet they can score. The goal is to make one of the coveted “holiday gift lists.”

…Which is silly because people like me just make them up, like I did here for Inc this week: The 7 Perfect Books to Gift the Entrepreneur in Your Life.

You get to say “We’ve been featured in Forbes!” because you’re #7 on a list of 25 Cool Gifts For Your Sister and the logo goes on your website, your cachet goes up, and (presumably) you make more sales.

Voilà! Validated! You’re legit now.

It’s smart.

It does not, however, mean that these are legitimately good gifts. And if you’ve learned anything from reading my stuff, you know that most people producing content on the internet are full of poop.

Gift lists are supposed to be helpful. But how many times have you looked at pretty pictures of a lotion or candle and thought, “YES! That’s what I’ll get for my mom!”

Never times.

bedazzled candles

Don’t play dumb well-intentioned-great-aunt. You know no one wants these bedazzled candles.

None of us needs more stuff. We may want it, but we don’t need it. That said, we live in a culture that loses its GD mind every year around this time and if you don’t want to be considered an asshole, you need to find a way to give a non-shitty gift.

We talk a lot here at TSI about leaning into the discomfort of doing the hard thing. The holidays are a perfect opportunity to flex that muscle. For me, that means rewriting the rules of the obligatory gift-giving tradition.

Gifts are wonderful. But spending thousands of dollars on stuff you don’t want and people you don’t *really* like is the part I’ve got an issue with. If you’d like to join me in changing this tradition, here’s my first stab at the new rules:


RULE 1: Stop chasing new sh*t.

Peter Nygen, the founder of Essential Man, taught me this lesson. He tells his clients to value quality over trendiness and to buy things they’ll use for a decade. Which is the opposite of how I shop. I buy a lot of crap so you can say, “Ooooo cute necklace!” when I see you next week.

Entrepreneurs (good ones) tend to be romantics at heart and appreciate longevity, staying power, and quality. Which is why I like to gift them old books. But you can interpret this any way you want.

The “newest” thing isn’t necessarily better. Expand your options by looking beyond what’s on display for the holidays or on everyone’s “must have top 10” list.

Learn to use your own rubric for what you think is valuable.


RULE 2: Choose something meaningful over something cool

Earlier this year I was at Cafe Grumpy in Chelsea with my friend and Caveday co-founder, Jake Kahana. He handed me a book, presumably to keep. Only, I wasn’t allowed to keep it. The book was meant to be given away. I had to sign the front (where all those who’d read it before me had signed it as well) and then gift it to the next person.

It was one of the most creative and memorable gifts I’ve ever gotten. And a lovely symbol of the friendship we’d create thereafter.

“Oh, Margo, I’m not creative enough for this kind of stuff.”

First of all, yes you are. Second: You don’t have to be “creative” to do this. You just need to know something, anything, about the person you’re giving a gift to.

You think you need to “be creative” because it’s really difficult to buy stuff for people you aren’t close with or don’t know much about. Much easier to get the Coach keychain and call it a day.

But if we want to break these old habits of obligatory meaningless gifts, then we have to do the work of actually caring about the people we are gifting.

Or at least know a thing or two about them personally and what they would enjoy, value, or appreciate.


RULE 3: Write something thoughtful. 

Let me introduce you to Emily McDowell who will save you from greeting card embarrassment for the rest of your life. Besides being fantastically irreverent-yet-serious, her greeting cards leave plenty of room to actually write something that matters instead of “Happy Holidays, Love, Jane.”

The effort is not in spending $6 on the fancy Papyrus card (Though, yes, Shannon, they are pretty). The effort is in the words.


It’s a fantastic card. But you still need to write in it.

(If you’re worried you don’t have enough to say, you can write using large letters or big spaces between your lines, but goodness, say something). 

You don’t even need to pair this with a physical thing if you do this right. How often does someone get a real hand-written card?

One of the greatest gifts I’ve gotten came from, Robert Zeitlin, a founding member of my virtual co-working space and the man who is going to revolutionize how you think about parenting.

He sent me a hand-written note to say thank you. It would have been easy to send an email or just DM me on our private Slack channel. Instead, he took the time to immortalize how he felt and send it via snail mail. I’ve kept it ever since.


Making New Traditions

The pressure on the holidays is out of control. And it takes the fun out of the best time of year.

Yes, I’ve read that “love languages book” and I know some of you really light up around physical products. They mean something to you. And I’m not here to judge your love language. It’s the obligation for reciprocation (and the cost) that I’d like to call into question.

I can’t speak for your family, but I know for mine, we’re opting out this year. I love giving gifts randomly for no reason other than “Saw this…thought of you.” The way someone’s face lights up when you’ve thought of them for no good reason other than…you thought of them. That’s what makes gift giving gift giving (to me).

Whether you make a new tradition or not, is up to you. But recognize that you do have a choice. Make the holidays meaningful for you. Whatever that looks like. Don’t blindly follow tradition because you feel obliged. Do it because you genuinely love the traditions.

I’m not giving up latkes and dreidels for nothin.