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How to find the right gift, every single time

7 steps to becoming a more thoughtful gift giver.

Sean Johnson
Sean Johnson
4 min read
How to find the right gift, every single time

Like most of us I’ve been turning my attention to the holidays. And one of the big tasks is gift giving.

Gifting well is an art. An art I’ve spent considerable time over the years working on improving. An art I think is incredibly valuable to learn how to do well.

The right gift tells people that you see them. That you know who they are and what they value. That the relationship matters to you.

It’s worth getting right.

As with many other areas of my life, the suggestions I’m about to share will probably look insane to some of you. This is a process that works well for me.

I feel like the structure doesn’t make it any less personal - I feel like it makes it more so. And while you might not adopt it whole cloth, hopefully something will be useful for you.

Start with gratitude.

For each person on your list, start with a moment of reflection.

Think about how grateful you feel that they are in your life. Give consideration to the specific reasons you get joy out of that relationship. What specifically they do to bring value to your life.

This accomplishes multiple things.

  • It often can jog your memory and give you some ideas.
  • In the craziness of the holiday season, it can be a really nice reminder that gift giving isn’t something to stress out about. It’s an opportunity to show people love them. It should be fun and soul-giving.

Spend a couple minutes on each person. Even better - write those notes down.

Speaking of…

Create profiles of your people

This is where I’m going to lose you.

For each person create a profile. Use the gratitude exercise as the beginning. But also write down the things they care about. The concerns they’ve had over the last year. The hobbies they’ve picked up. The interests they’ve wanted to get back into but haven’t for whatever reason.

Anything you can think of that would be potential fodder for ideas should go in here.

This profile should become a living document. It will serve you well year one. But if you get in the habit of updating it throughout the year, it will become even more valuable, not just for gift giving but for the health of your overall relationships.

What you’re doing without realizing it is creating the beginnings of a personal CRM system. Even if it’s just a bunch of notes (it is for me - I use Evernote), it can be incredibly powerful.

Having a mechanism to track this stuff probably sounds sterile. But I completely disagree. If coupled with a review at some cadence, it makes you a better friend, not a worse one.

Review at some cadence

As many of you know, I’m a huge proponent of Getting Things Done (or GTD). One of the main concepts is this idea of review.

In order for you to have a system for personal effectiveness that you genuinely trust, you need to review your system regularly. This is typically a weekly cadence for adherents, myself included.

I track my stuff in Omnifocus, and have a weekly review project set to repeat every Sunday.

While my review is primarily about the tasks and projects I have going on at any given time, one of the tasks in my weekly review process is “Review personal CRM”. This links to my Evernote notebook with my notes.

Doing this keeps the people who matter to me in my mind at least once a week. It’s super helpful in general for reminding myself to reach out. But it also allows me to do the next step of my process, which is…

“Curate” all year

As of this writing I’m about 80% done with my gifts for the year. This is possible because I don’t just shop during the holiday season. In fact, I don’t really “shop” in the typical sense at all. Instead I curate.

I have an Evernote notebook called “Cool Shit”. And throughout the year I add to it. Source material comes from any number of places:

  • An interesting recommendation from a friend over dinner.
  • A recommendation from a podcast I listened to.
  • Sites I visit regularly.
  • Ads that target me (the DTC boom and targeted Instagram ads have been awesome for this.)

I typically just add this stuff the notebook. But often, as a result of my personal CRM and my review cadence, a product appears that I know would be perfect for someone on my list. When that happens I go ahead and buy it.

The result is less stress during this time of the year, and gifts that I know will resonate with people because they were surfaced organically.

Track who you gave what to, when.

Sometimes you find something that would work for multiple people. Or you find something that was relevant to one person one year, and suddenly relevant to another person another year. And obviously you want to avoid giving someone something (or something similar) twice.

In order to take advantage of this, you should track who you get what for.

I have notes in Evernote with my shopping list for each person. Christmas 2019, 2018, etc. When I kick off the holidays, typically the day after Thanksgiving, I make sure to review my old lists.

Schedule a kick-off.

The day after Thanksgiving is usually the perfect day to start this process. My process looks like this:

  • Grab leftovers and a bottle of wine.
  • Sit down with my laptop.
  • Review my personal CRM. Feel gratitude. Update as necessary.
  • Open my Christmas 20XX note. Add names to the list of who I’m shopping for if they weren’t already on there.
  • Review the stuff I’ve already purchased for folks. Think about if anyone else on the list would be interested.
  • Go through my old lists. See if there’s anything I did previously that might be a good fit this year for someone.
  • Review my Cool Shit notebook. Look for anything interesting.
  • Go through my holiday gift guides list. Read through any magazines I purchased the week prior.

Create a list of holiday gift guides you trust.

There are certain sites and magazines I’ve grown to trust as sources of good ideas. Some of my favorites include:

  • Esquire
  • Food 52
  • Bon Appetit
  • Real Simple
  • NY Times
  • New York Post
  • GOOP
  • Bespoke Post
  • TRNK
  • Cupofjo
  • Cool Material
  • Kottke
  • One Piece
  • Tools and Toys
  • Blue Ribbon

Giving gifts can be joyful and painless

Gift giving doesn't have to be stressful. By framing it around gratitude, and following a process throughout the year as you go about your life, you can find meaningful, awesome gifts for everyone you care about.

I'd love to hear how you use this process. Send me a note on Twitter if you found this helpful!

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