How to pick gifts cover image of Kim excitedly opening her present

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Eight fun, easy, and scientifically-proven tips for how to pick gifts that you’ll be proud to give and they’ll truly treasure.

How to Give Great Gifts Like Socks


This morning, I couldn’t decide which socks to wear.

One pair, Kim’s mom gifted me for my birthday. The other, a Christmas present from my sister. Both brought happy memories of when I got them and the people who gave them to me.

I felt like I was choosing which gift, and which gift-giver, I liked most.

Then I had a thought that “knocked my socks off”:

These socks, the classic crappy present, were actually great gifts! I wear them all the time and whenever I do I’m thankful to the people who gave me them.

This realization plunged me into a deep dive. I read the psychology, experts’ advice, and online stories about gift-giving to rebuild my beliefs about how to pick gifts.

Here’s what I discovered: Eight unconventional strategies for how to pick gifts.

GIFT IDEA: Solve a friend’s problem by giving them a dog-sitting or dog-walking IOU.

1. Give Problem-Solvers

One of the biggest mistakes we make when buying gifts for others (and for ourselves) is thinking that giving more stuff makes people happier.

That’s backwards.

Happiness doesn’t come from adding positives. It comes from removing negatives.

So when it comes to how to pick gifts, find a problem in your recipient’s life and solve it with your generosity.

Examples:

  • Fix annoyances: Get their knives sharpened, buy them black-out blinds, or pay for a handyman to go to their house and fix up the little things like squeaky doors, broken light switches, and leaking sinks.
  • Boredom: Plan a party or outing with the gift recipient and friends. Blind taste tests are one of our favorites.
  • Prevent pain: If they complain about a sore neck, get them a session with a physical therapist or Alexander Technique lessons.
  • Assume responsibilities: Give them a gift certificate for a few days of petsitting or babysitting. (Warning: This will backfire if the gift recipient thinks you’re irresponsible.)
  • Outsource chores: Give them a gift certificate for home-delivered meals or home laundry service. Or get them merino wool so they rarely have to wash and iron in the first place.
  • Reduce environmental waste: Gift them Swedish dishcloths to use instead of paper towels, a Silpat baking mat to use instead of parchment paper, beeswax wrap to replace saran wrap, or a water filter to use instead of bottled water.

Warning

Don’t solve problems they don’t know they have!

Buying deodorant for a friend with bad B.O., breath mints for your stinky-breathed colleague, or a fat-loss plan for your wife who’s put on a few will backfire.

Ceramic workshop
GIFT IDEA: Rather than give her sister a coupon for a ceramic workshop, she planned a date and recruited friends. It was a hit.

2. Don’t Give them More Problems

People don’t like having to make decisions, so don’t pick a gift that makes them decide.

✗ Don’t Buy Gift Cards

When you buy someone a gift card, you’re giving them a problem by passing the decision-making burden to them.

Give cash if you have to. “Mo’ money, mo’ problems,” sure, but most people prefer those problems’ flexibility over having to make a decision.

✗ Don’t Gift Experiences Without a Date Attached

If you gift a massage or cooking lessons, schedule it, too. Even if the recipient’s forced to reschedule, they’re forced to do so. They don’t have to decide.

Better that than have your card/certificate to sit in the recipient’s wallet staring at them for months. When they see it they don’t think, “Oh yeah, Chris was so generous for gifting me that.” They think, “Uggh, right. I have to use this thing Chris gave me.”

Guy selling fynbos flowers
The bedazzlement factor of flashy gifts like flowers quickly fades.

3. Be Practical, Not Flashy

Our choices in gifts tend to be selfish. We want the glory of being great gift-givers, so we buy presents with a maximum bedazzlement factor. Flashy flowers, for example.

The problem is the flash fades away and the recipient’s left to deal with what’s left.

To be selfless, a better strategy for how to pick gifts is to buy practical presents that last. Plants, for example. You may get fewer bedazzlement benefits, but they get continuous rewards. Studies have found they outweigh the one-time hit of a flashy gift.

Examples:

  • A Swiss Army knife instead of jewelry.
  • A packable coat (like Kim and my favorite Patagonia Nano Puff) rather than some frilly fashion piece.
  • A deposit on a top-of-the-line blender rather a mediocre one paid in full.

How to Be a Good Giftee

Here’s how to make it easier for friends and family who worry about how to pick gifts for you.

  • Don’t say, “I don’t need anything.” If you really, truly don’t want a gift, say “Please don’t give me a gift.” Otherwise, think about it and tell them what you want.
  • Tell them exactly what you want even though it can feel selfish to send someone a wish list. Get over yourself. They’ll appreciate it.
  • Always be thankful. If it’s a bad gift, the person who gave it will know. It doesn’t help to openly express your disappointment.
Rob and Laura cutting into their wedding cake Kim made
GIFT EXAMPLE: Kim gave her friends exactly wanted they asked for for their wedding: this cake.

4. Don’t Be So Thoughtful

As gift-givers, we want to show off how well we know someone. But you know who knows the recipient even better than you?

The recipient!

So when they tell you what they want, don’t stupidly try to outsmart them.

Give them what they want!

It may feel thoughtless to you, but it doesn’t to them. According to surprising studies, gift recipients say the most thoughtful gifts are the ones they asked for.

Surfers in Imsouane in Morocco
GIFT EXAMPLE: Kim surprised me with a trip down the Moroccan coast together for my birthday.

5. Do This When They Say, “I Have Everything I Need”

Moms are especially famous for saying, “I have everything I need. Just having you with me for my birthday is enough.”

And we’re infamous for misinterpreting that as, “You better to be extra generous and creative with my gift to show me how much you love me, kiddo.” It’s not. Don’t buy her a new iPad she won’t be able to figure out how to play bridge on.

If you want to be extra generous, give her more of what she asked for:

YOU.

As Grant Sabatier says in a quote our friend Lindsay M shared with us, “Time is more valuable than money. You can always get more money, but you can’t get more time.”

If you feel compelled to spend money, too, plan quality time together over a nice dinner or a small trip, or by buying tickets to visit if you live in different cities.

Chris chopping up greens in a knife skills class
GIFT IDEA: Give something that keeps on giving like a top-of-the-line knife and a class on how to use it.

6. Give Gifts that Keep On Giving

“It’s the thought that counts,” may be somewhat true, but the thought only counts once. For gifts that keep counting up brownie points, seek sentimentality.

It’s not as hard as you think:

✓ Give Something Useful

Studies show that people value a useful item more if they receive it as a gift than if they buy it for themselves because novelty wears off but sentimentality doesn’t.

My aforementioned socks are a perfect example. Others are a printed collection of your favorite recipes, or a painting, print, or ceramic work to decorate their new apartment.

✓ Capture the Moment

Make the gift of an experience more sentimental by capturing the moment.

For example, if you buy an experience like a cooking class or a weekend away, make a photo album of it with Artifact Uprising. Or make a rap video, like we did to memorialize a family Thailand getaway we did to celebrate my mom’s 60th birthday:

For Extra Sentimentality

Keep in mind that sentimentality is extra important and impactful for gifts that celebrate a special life event like a wedding, graduation, or retirement (or pretirement?).

Studies find that physical items make better gifts than experiences for such occasions.

For Extra Extra Sentimentality

Personalize the gift.

That does NOT mean put your face or name anywhere near it. Put their initials on it. Maybe the date, too.

For example, Kim loves the ring her sister gave her for her 30th birthday. It was made by a Vancouver jeweler, features her birthstone, and has her initials and birth date engraved on the inside.

This type of personalization increases the uniqueness of the gift. Also, any time others ask about it, the recipient will remember you and the special occasion you celebrated together.

Boost Your Business With Gift Giving

Gift-giving consultant John Ruhlin’s quick and easy-to-read book, Giftology, makes a compelling case for using gifts as an effective and overlooked strategy to get more referrals, connect better with clients, and stand out from your competitors.

Here’s a taste of his strategic gift-giving advice on a podcast interview.

Kim painting watercolor
GIFT IDEA: Hand paint watercolor cards with a thoughtful letter to put the “present” in presentation.

7. Put the “Present” in Presentation

Even if what you’re giving isn’t particularly thoughtful (at least in your mind), you can make it extra special with how you give it.

A special presentation of your present elicits emotion and forms memories that attach to the gift to give it extra value.

Examples

  • A letter. Write a thoughtful letter full of sentiments that are corny in regular life but much-appreciated on special occasions.
  • Fun wrapping. Disguise a small gift in a giant package, make it a scavenger hunt, or wrap a gag gift and reveal the real one afterward.
Best men's shorts for travel, sports, and style cover image
GIFT IDEA: Buy the best like these Outlier shorts, one of the 3 best pairs of shorts Chris has ever worn.

8. Always Buy the Best

If you decide to buy someone a physical item rather than an experience, make sure it’s best in class.

If you can’t afford the best, pool together funds with other gift-givers, who’ll be grateful for the opportunity to pitch in and not have to think of a gift.

Or think smaller. Recipients will get more long-term value out of an exceptional small gift than an average big one.

Examples

Wrapping it up

Let’s recap the eight strategies for how to pick gifts:

  1. Give Problem-Solvers
  2. Don’t Give them More Problems
  3. Be Practical, Not Flashy
  4. Don’t Be So Thoughtful
  5. Do This When They Say, “I Have Everything I Need”
  6. Give Gifts that Keep On Giving
  7. Put the “Present” in Presentation
  8. Always Buy the Best

These should be enough to help you come up with a couple of great gift ideas. And if you have other strategies to share or questions, let us know in the comments.

Start Finding Your Own Gifts

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1 comment

  1. I LOVE THIS TOPIC. Thank you so much for curating an amazing podcast playlist over at Podyssey. I listen to all the episodes that you recommended and I have so much to say about this! I LOVE receiving experiences, and I HATE random gifts that take up space and are given with absolutely no intention in mind. I also agree in gifting consumables. If you’re one of my friends, then you know I LOVE gifting food because a.) it doesn’t take up space, b.) I know you will get value out of it (because you need to it!) and c.) food /feeding you is language of love. Also, I have a fear of receiving gifts (that are not food or experienced, lol). This is why I have never held a birthday party as an adult – because I didn’t want people to OBLIGED in giving me a gift. So here’s what I did for the past two years: I treated my friends to experiences paid on my behalf – so nobody would feel an obligation to pay for anything. I held a karaoke birthday party last year and a private dance party this year. Better than any gift I could have received. Lastly, thank you SO MUCH for telling us about the John Ruhlin book. More people need to learn how to say THANK YOU properly! This is why I always give referral gifts to people who refer me business.

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