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4 gift-giving tips to give the perfect present this holiday



Headlines like “Oprah’s favorite things!” or “Tech gifts for gadget geeks!” have been popping up in your Amazon sidebar for weeks, all of America’s malls are playing “Jingle Bell Rock” on repeat, and your niece just sent you an email with the subject line “WISHLIST — ALL ITEMS HIGH PRIORITY.”

That’s right. It’s the holiday season.

And while some people get annoyed by the consumer-mania, I love this time of year because I LOVE buying holiday gifts for people. Watching their faces as they open up the perfect present — one I am totally confident they’ll love — that’s part of a Rich Life for me.

But I wasn’t always this in love with gift-giving. In my early 20s, I didn’t know how to give good gifts at all. I would literally say, “I suck at giving gifts,” and then walk into a party with a bottle of some random vodka, hand it over, and wipe my hands clean. (Notice how I created my own self-fulfilling prophecy by using that language.)

I also wondered why women seemed to be so much more thoughtful at picking good gifts and remembering to send them, when in reality I spent no time on it. I was looking for excuses to stay the way I was.

But then I realized: giving gifts is a skill. And just like any skill, I could improve. In this post, I’ll show you I did it, and the four lessons I’ve learned about how to give the perfect gift.

How to give the perfect holiday gift

Just like any skill, giving good gifts requires practice and opening yourself up to learning from others. When I realized that I could get better, I created a plan:

  • I read a ton of tips and books about gift-giving.
  • I sent out hundreds of holiday gifts to my friends and family over the next few years. And improved after seeing their reactions.
  • I even built a process with my assistant to systematize it. I made it a priority and it radically changed my personal and professional life.
  • Most of all, I started finding JOY in choosing a great gift and seeing their reaction.

After years of gift-giving, here are some of the lessons I learned.

Holiday gifts tip #1: If someone is really into something, DON’T BUY IT for them

I learned this lesson from Reddit and it blew my mind because it’s so counterintuitive. When you think of someone you want to buy a gift for, it’s easy to zoom in on the thing that defines them. For example, you know I love hot sauce. I live it, I breathe it, I go to the NYC Hot Sauce convention. Therefore, it’s natural to say, “Hey, let me go get this guy some hot sauce.”

WRONG — DO NOT BUY A GUY LIKE ME HOT SAUCE. I am already 500 steps ahead and you telling me “Hey, have you tried Tapatio” is like someone asking if I’ve ever had water.

For example, my friend Nick Gray is a tea connoisseur — I’m not going to buy him tea leaves, a tea set, or a tea subscription. He already knows everything about tea! Go one level deeper or one level laterally to pick a better gift.

Holiday gifts tip #2: Give people what they want, not what you “think they want” or need

The classic example is a mom asking her son what he wants, the son saying, “I dunno … maybe just an Amazon gift certificate,” and then the mom getting him a basket of olive oil and cheese (here’s an example). WTF.

If someone wants a gift certificate, get them a gift certificate. You can make it more of a special gift by the presentation and note you send (see more below).

Holiday gifts tip #3: Presentation matters

Again, most men suck at this, especially men in their 20s. They think walking into a holiday party and throwing someone a bottle of wine in a Rite Aid plastic bag is fine. It might be “fine,” but go the extra step, dude. Wrap it or get it wrapped. Write a quick note like this:

John — thanks for having me! I always appreciate when you throw your yearly holiday party. Last time, I loved the chicken and I met a new friend. Looking forward to today, – NAME

I’m not going to get into stationery because you aren’t ready for that.

The way you live life directly affects the way others see you — and how you see yourself. That means the way you look, the clothes you wear, the conversations you have, the gifts you give … it all matters. And you can control it.

Holiday gifts tip #4: Give the gift in front of others

Part of a good gift is letting the person signal that other people think about them. Have you ever been in a club and watched when someone orders bottle service? They have fireworks going off, lights, people dancing as they bring the bottles over. There’s value in theatrics.

If you’re not opening presents together during the holiday season, make a big show of the gift wherever you are — the person will love it.

(There is the rare person who hates the limelight. If you know this, adapt this advice.)

When it comes to good gifts, it’s not about the price

If you’ve been following us for a while, you may have a sub-savings account for the holidays or learned how to tap into hidden income or side gig to pay for those extra presents, but it’s not the money that matters when it comes to getting someone the perfect holiday gift.

You could just as easily handwrite a card that says something meaningful. Here’s an example:

Nicole and Jack — We always have a great time when we hang out. We’d love to take you to [dinner/movies/show you a new piece of art at the park that we love] in the new year. Are you free on January 5th or 6th? –  NAME and Your Partner’s Name

Think about what it would feel like to get a note like that. To feel appreciated and know others love your company. You don’t have to wait until the holidays, but now is a great time to start practicing and showing your family, friends, and colleagues how much you appreciate them.

Generosity is a huge part of my Rich Life, so I’ve tried to “dial in” and get deeper. I wanted to share what I’ve learned so far about giving good gifts, but I’m still improving.

So I’d love your help: What is the best gift you’ve ever received and what made it so great? Leave a comment and let me know. I look forward to hearing your stories!


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