5 Steps to Choose a Thoughtful Gift (with ideas!)

April 12, 2019 10 min read

1 Comment

Every month, we need to put a category in our personal budget for gifts. There is always an event or occasion that is calling for a gift: Christmas, anniversary, birthdays, retirements, graduation, sympathy, gratitude, and on. And, like most people, we want to make the gifts that we give count! So how do we choose a thoughtful gift that will be meaningful to the recipient?

Giving a gift is, of course, a subjective exercise; there is no perfect formula that will help you reach the “perfect gift”. However, there are certain questions you can ask that will help you choose a thoughtful gift:

  • Does the gift make the person feel known?
  • Does the gift represent a story or have a story behind it?
  • Does the gift bring a sense of connection?
  • Why is the gift being given? (context & occasion)
  • What more can the gift give?

Let’s look at these questions, some common gift-giving mistakes, and, finally, some thoughtful gift ideas!


Our definition for a thoughtful gifts is admittedly going to be broad! Every great gift does not have to have all of these elements but it will at least have a combination of them.

Here are five questions to ask yourself when trying to pick a thoughtful gift:

1. Does this gift make the person feel known?

The fundamental makeup of every person is that they want to be known. Everyone wants to know that someone understands who they are and what makes them tick. This is why personality assessments & identifications (like the Enneagram, Myers-Briggs Typing Indicator, Introvert/Extravert) are so popular. We do not need to be known by everyone, and, of course, we all have different levels of who we let into our inner circle.

However, this does not change the fact that everyone has a need to be known by someone.

This leads into the first question in giving a thoughtful gift: Will it be a gift that makes the recipient of the gift feel known?

A thoughtful gift needs to speak to the recipient’s values, what they think is important, what they enjoy and, essentially, who they are as a person. Often, we do not know the important values of the people with whom we spend the most time! Whether it be a coworker, a family member, or a friend, even the ones close to us can be a mystery. The most difficult aspect of this is that people do not always share their deepest desires, and only hint to what is meaningful to them; so, we must investigate deeper by asking great questions.

Illustration by Anne To.

Really start to ask great questions and listen carefully to their responses. What do they spend their time doing? Do they volunteer? Do they have old passions that they have let grow cold? If they could plan an entire day for themselves, what would they do? What is their story? Where have they come from and where are they going?

As they give answers, listen for ways that you can help facilitate the answers to those questions. If your gift answers these questions — even to a fraction —, you are on your way to giving a thoughtful gift.

Some of the best thoughtful gifts will resound with: Yes! This speaks to what I care about!

2. Does the gift represent a story, or have a story behind it?

Every person’s life is a story. We have come from some place, and are headed forward towards a destination. Similarly, every gift has a story. It has come from some place, with the intention of fulfilling some purpose.

When the story of the person and the story of the gift converge it will make the individual sing.

Their story

You can choose a gift that is reminiscent of something from your gift recipient’s history: a memory, an interest, a hobby, a comment mentioned in a conversation. There are significant moments in the past of a person’s life, and when the gift matches up with that event it is fantastic. For my parents’ 40th wedding anniversary, my sister sourced & framed a poster from the event where they first met — an amazing gift that speaks to the story of their lives. Great job, sis!

Our story

Or, you can choose a gift that reminds your recipient of your story together. Maybe a memento of a shared experience, maybe a common interest, maybe a reference to an in-joke that you’ve laughed over together. A meaningful, memorable gift less often creates a story and more often amplifies a relationship, connection, or story that exists already.

The story of the gift

Sometimes, a gift is excellent because it has a story in itself.

A gift having a backstory is one reason that Fair Trade items have become so popular. There is not only a gift to be enjoyed, but there is a story behind the gift. Was this gift made by a woman who has overcome difficulties in her life? Does this beautiful item also help someone have a beautiful life? Wow!

This is also why handmade or homemade gifts are great gifts. Or, when great lengths (or quirky wild goose chases) to procure a gift often adds extra meaning to the recipient.

In the same way that I might love a pair of shoes because they fit well and I got an amazing deal, there is a bonus when a story goes into the gift itself.


3. Does the gift create, deepen, or bring a sense of connection?

As we touched on above, a great gift will always make the person feel known. But, there is also another inherent need for people, especially in the context of a relational interaction like gift-giving: a need & desire for connection outside of ourselves.

Back to handmade/homemade gifts — this is another reason they can be so meaningful. There is a connection that a handmade gift gives the recipient, far beyond just the use of it. If I can imagine and picture where and how the gift was made, it will give me a greater connection to the gift itself. There is a certain relationship we have with the goods we interact with, and to know where it comes from just increases the depth of this connection.

But, even if the gift is not made by the giver, there can be deep meaning in the way, where, and by whom it was made. In a world where we are so far removed from the origins of what we use — whether it be food, shoes, or cars — it is powerful to know the story of how a gift came to be!

Does the gift offer a sense of belonging to the global community? Did the gift’s production help to create jobs locally? Was the business started by a young entrepreneur that your gift recipient might find inspiring?

Or, back to your shared story, does the gift deepen the connection between you, the gift-giver, and your gift recipient?

My dad is notorious in our extended family for his need to eat ice cream every day when he’s on vacation. As a middle-class, baby boomer in his late 60s/70s, he doesn’t “need” much for gifts, so I began giving him ice cream or taking him out for a scoop around town to celebrate birthdays, Christmas, & Father’s Day. We even planned a tour of a local gelato factory for his 70th birthday! This has been a fun way to connect together and also connect with our city by exploring the local food scene (though, admittedly, in a very ice cream-centric way!)

4. Why is the gift being given? (Context & Occasion)

There are a myriad of different occasions to share gifts. Of course, there are a few key occasions that are very common: Christmas, birthday, baby, wedding, and anniversary. However, people also give gifts for graduation, retirement, sympathy or bereavement, painful struggle(s) like infertility or cancer, minor “holidays” (Mother’s Day, Valentine’s Day, Easter baskets), housewarming, thanks, or friendship to name a few.

The reason or occasion needs to be taken into consideration, along with the person to whom you are giving the gift. What might be appropriate as a Christmas gift may not work for a sympathy gift: “Hey, sorry about your loss, here is that camera you have always wanted!”

The context that the gift is being given will likely shape what type of gift is best to give.

A housewarming or houseguest gift, for instance, may be related to the home or food & drink that they might enjoy.

5. Will the gift “give more” (beyond the transaction of the gift-giving)?

Gifts that give more may be assumed to be only the category of ‘gifts that give back’ (charity-related, ethical, one-for-one models, etc.). These often make fabulous gifts, but this is a limited view of the whole concept.

“Gifts that give back”, traditionally, mean gifts that also give to someone else in addition to the gift recipient. Examples would be giving a goat through a charity catalogue, or money towards a water well; also, products that use a one-for-one model that gives the same item you’ve bought (shoes, glasses) to someone in need). There are also a growing number of businesses that create jobs for marginal communities to produce their product.

These kinds of gifts can be truly thoughtful for a recipient with a social conscience or someone who says they have no need or desire for gifts.

A straight donation to charity in someone’s name can also make a very meaningful gift, especially if there is a cause that is important or resonant to your gift recipient. But, as gift-givers, it feel great to have something tangible to give as well as the spirit behind it, which is why many of these social enterprise models have taken off.

But, “gifts that give more” can also be gifts that enable someone to grow in a certain area or have an experience that will enlarge them as a person.
It is very thoughtful to give a gift of an art lesson, or a cooking class, or a pair of running shoes towards that 10k run that your friend has always wanted to try.

These gifts are great at helping someone launch themselves into an activity or path that they have wanted to try or an old passion that they would like to rekindle.

Gifts that give more are gifts that continue to give into the future, creating a fuller person and world!



• It's Not About You

In giving a gift, the key thing to remember is that it is all about the other person.

This is great advice in... just about every area in life, but we've all seen it in public speaking, or training in a workplace. So often people set up a talk or event and they make it too much about themselves! The talk feels, to the recipient, boring, irrelevant, or simply not engaging of the subject. This can often be a mistake in gift giving, too!

Don't pick something just because you like it; think about whether it will resound with your gift recipient first & foremost

For older gift-givers, offering a present to someone younger, it is really easy to fall into the thought-pattern of "I really liked this when I was younger..." or "This reminds me of my XYZ memory from my teenaged years." 🙅‍♀️ Wrong parameters!

This may be a good place to start, but private preferences & memories are not enough to ensure a good, thoughtful gift!

• Money is not the issue (but don't cut corners)

It’s great having young kids to remind you of this. They do not know how much something costs, they just want what they want. For my son’s 5th birthday, all he wanted from me was one of those foam #1 fingers that you would get at a sporting event — in this case it was from our local NHL team. For us, it only cost $6 but he loved it so much because it reminded him of going to the hockey games together with his siblings and dad.

On the other side of the spectrum, spending more does not guarantee a meaningful gift. I received for my 30th birthday a $130 gift card from some friends to a spa/salon. But, the truth is I really am not a spa person, and I couldn’t seem to get around to booking a service. To my shame, the gift card has literally sat around our house for 5 years!! In this case, the kindness & effort (& expense) of the gift-giving was there — they truly were trying to be considerate & thoughtful —, but the object of the gift just didn’t land.

Now, when you are giving a retirement gift etc. we cannot get away with giving a $6 gift, and that is okay. One great lens through which to look when giving higher priced gifts is:

Abundance vs. Extravagance

By abundance, I mean that it is great to shower someone with a great gift that may cost a lot or that is beyond what they might ever buy for themselves. Abundance can communicate that the gift recipient is special, and worthy of extra treatment.

But extravagance can be excess simply for its own sake. I remember an old ad where an ‘expert’ was saying that an iPad would make a great stocking stuffer. An iPad! Come on, there are not many people who get an iPad as a stocking stuffer... I get socks and oranges. The attitude that considers a $400 item as a stocking stuffer is a mindset of extravagance.

A well-priced, quality product will communicate just what I want: a care for my gift recipient, and a desire for them to feel known & appreciated with the present I am giving.

Ideas for Thoughtful Gifts

Now, let's get to some ideas for gifts. There are so many great ideas out there! 

  • Cookbooks, cooking/baking supplies, interesting/specialty ingredients, skills courses, an excellent knife, wine pairings (based on the advice of a sommelier) or a wine-of-the-month club
  • Books, bookstore gift card, book-of-the-month club, a commitment to a regular date to discuss books
  • Coffee or tea subscription; specialty roasting or brewing gear; a handmade or locally purchased mug; a mug that references a book, movie, or place with a meaningful story to your gift recipient
  • Introduce a new hobby with supplies (e.g. knitting needles & yarn), a tutorial class (e.g. "How to Screenprint a T-Shirt"), a starter kit, or a how-to book 
  • Photography supplies, courses, or the gift of time & location for a special shoot 

Gifts with their own story:
  • Antiques
  • Social enterprise, fair trade, or ethically produced goods, like our kantha quilts
  • Family heirlooms

Splurge on something built to last:
  • A briefcase / leather bag or purse
  • Le Creuset pot (or similar)
  • Special tool like a knife or axe, or a leather case for a tool or item
  • Custom-made: Furniture, blanket, household item

  • Cook a meal
  • Offer to babysit
  • Bake a treat
  • Commit to change the oil, rotate the tires, take the knifes to be sharpened, wash the windows, hire a housecleaner, etc. etc. (taking the load off of pesky chores)

  • Printed photos, framed photos, or a photo book
  • Custom art: a creative, commissioned family portrait; a custom watercolor of a childhood or long-time home
  • A handmade item from a piece of wood, collection of rocks, or found items like seashells from a vacation or a special place


This is a beginning list, but I am happy to add to it! Leave a comment below if you have a fantastic idea or category to add.

1 Response

Angela Waterford
Angela Waterford

August 26, 2019

It’s true that a gift that makes one feel known will be a really great gift for someone to receive, especially on their birthday. I think I’ll buy my friend a gift from a one-stop-shop gift store since I always end up finding the things that she likes in those kinds of establishments. There may be a gift that has her name on it, so I might try giving that to her on her birthday. https://commercestreetmarket.com/

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