Getting Less Worse at Gift Giving

We’re about eight weeks past the holiday season here in early February. And as with every year, at least for me, having it in the rearview mirror makes the next one feel about as far away as the moon.

But it’s not. It’ll be here again before you know it. And between now and next Christmas or Hanukkah, there are plenty of other occasions where you’ll need to give a gift - and that gift can either make someone’s day or fall flat.

And that’s great. Because here’s the thing: giving a great gift is an awesome feeling. It’s a chance to show care for the people around you and make them feel seen. Delivering a really good one is way better than receiving one.

Somewhere along the way there’s a natural sea change toward giving rather than receiving - something that would have shocked eight-year-old me, right up there with really loving Brussels sprouts and unironically liking jazz.

I’m not, however, a naturally great gift giver.

You know the type. The Shaun White–Sidney Crosby–Mikaela Shiffrin wunderkinds of gift giving. The kind of person who falls out of bed and effortlessly delivers beautifully wrapped gifts that cut straight to the emotional heart of the person receiving them.

Luckily, gift giving can be improved with effort and intention. You can work hard, listen closely, and get better at it. Which, I guess, means you can become the Jimmy Butler of gift giving? Struggling to land this sports metaphor. He broke late, we’ll go with Jimmy.

I’ve mentioned in the past how much I like the Getting Things Done system for organizing work. One of its core ideas is simple: capture things the moment they occur to you, then process them later into reminders, calendars, or tasks you can actually act on.

It’s probably not a shock that I used this as the foundation for my own system.

What that boils down to is this: throughout the year, whenever I run into something interesting, think of a good gift for someone, or discover a store that might be useful later, I write it down. Immediately. One list. One place. With a note about who it might be for and why.

I do this because I don’t trust myself to remember these things later, and I don’t scatter them across multiple apps or notebooks. Everything goes in the same place.

On top of that, I set reminders far enough ahead of birthdays, holidays, anniversaries, and Valentine’s Day that I actually have time to procure something nice. No panic-buying. No frantic shipping cutoffs. Just time to find something that’s actually good.

Once I put this system in place, something interesting happened: I got better at listening.

When friends or loved ones casually mention things they like or need, I became more likely to notice. Maybe because I knew it wouldn’t get lost. Knowing I had a place to store the idea made me more willing to capture it in the first place.

Over time, this created a large Rolodex of gifts to choose from. I can sort by person and “shop” from a curated list instead of scrambling for a gift card at the last second.

From here, it helps me to remember my rough gift hierarchy - or simple gift pyramid, if you will. The higher up the pyramid you go, the better the gift tends to be. If you can check off more than one of these, you’re in great shape.

The best gifts are ones that:

• create an experience they can have or share with you
• are made by you
• upgrade something they’d never prioritize for themselves

Experience gifts sit at the top for me. Giving someone the chance to do something they love - or something they wouldn’t normally splurge on - is hard to beat. Think about the friend who loves Formula 1 and gets a gift card to go race high-end go-karts. Photos and a memory are better than things that will collect dust on shelves or hang unused in closets.

Next, for me, things made by you always stand out.

I’m not some incredible artist, but there are things in my wheelhouse I know I can make. And it doesn’t have to be “art.” Most of my custom gifts involve Affinity Designer (pay-once Photoshop) and custom-ordered stickers, shirts, high-quality prints that are framed, coasters that reference an inside joke, etc.

The internet makes it absurdly easy to order small runs of custom items now - almost to the point where listing examples feels unnecessary. Use it to your advantage.

The rule here is not to underestimate the power of something you made. Even technically “bad” art - if it’s thoughtful and clearly made with care - can be exceptional. Time and intention beat perfection almost every time.

Finally, with upgrades, you’re showing that you’re seeing your friend or family and thinking about them in a caring way - noticing where their life could be a little better or easier, but where they’ve never bothered to spend the money.

A recent example: my parents had used the same serrated bread knife for my entire life. I believe it came as part of a wedding knife set. It worked, technically - but it worked a lot better in 2004, if we’re being honest.

Upgrading it never felt like a priority because it did technically cut bread. So for Christmas, I bought them a really nice bread knife. It turned their small annoyance into a genuinely nice daily experience.

Some people might roll their eyes at that, but spotting these minor friction points and using gifts as an excuse to fix them is one of my favorite kinds of giving. It’s also one of my favorite kinds of gifts to receive, which makes it easier to justify doing it for others.

Finally, if you’ve got another minute, here are some quick hitters - small practices that punch above their weight:

• I wrap every gift the same way: plain brown paper, tied with twine (sometimes changed up for the season) into a simple bow. It’s cheap, reminds people of how items used to be wrapped at department stores, looks good, and I’ll never run out of it.
• I buy multiple cards anytime I find a store with ones I really like. Birthday, thank-you, baby, congratulations. Having a small stash saves a surprising amount of time and effort. You’ll use them. I promise.
• I use online postcard sites (like Postable) to send one-off cards for birthdays and special occasions. It couldn’t be easier to be thoughtful.
• If you want to go one step further, buy a printer and make your own cards. Use Affinity or whatever you’re comfortable with. It’s easier than it sounds, and it makes even simple notes feel personal.

Ok, now that it’s all down on paper - what did I miss? What rungs on the gift pyramid are we missing?

Let me know at joeyplunkett[at]gmail.com.