Why is gift giving so hard? Because of what it reveals about you.
When I was 16, my stepdad gave my mom a beautiful set of jewellery for Christmas.
Gold, diamonds. Clearly expensive.
But when my mom opened the present, I saw a deep sense of disappointment in her eyes that lingered for the rest of the evening.
I found her reaction puzzling. On one hand it felt unfair, on the other it felt justified.
It wasn’t until much later in my life that I understood why I felt this tension.
Fast forward 10 years, and I had spent about 5 years being a rootless nomad. I had seen the world, but my temporary experiences and shallow relationships started to wear on me. I felt a mile wide but an inch deep. I decided it was time to settle down and Lisbon was the location I chose.
This was a difficult time, because I realized that I wasn’t used to being a good friend people could rely on. Which created lots of discomfort that forced me to take a hard look at myself, and struggle against the itch to escape through travel.
After about a year of struggle, I was leaving to visit family in Norway and at the end of a going away dinner a friend pulled me aside and gave me a small plastic compass with a note saying, “To help you find your way back to Lisbon”.
On the surface, it was such a simple gift. But below the surface it showed an incredible level of perceptiveness and care. Not only did I feel seen, but I felt like there was someone who saw my weaknesses and was willing to be my friend regardless.
Lesson hidden in plain sight
This was what was missing in my stepdad’s gift to my mom. When she saw the jewellery, she saw a man who had not paid any attention to her and last minute over compensated by buying her something really expensive, hoping she wouldn’t notice.
My stepdad’s gift was expensive in terms of money, but cheap in terms of attention. My friend’s gift was cheap in terms of money, but expensive in terms of attention.
In other words, the value of a gift can be measured in how seen someone feels. And to truly see someone, you need to pay attention.
This gets to the heart of why gift giving is so hard.
Giving a gift places demands on us, and mercilessly punishes those that don’t pay attention by pointing a mirror back at us.
For someone weak, this can lead to avoidance and exuses. But for someone strong, it can be an invitation to grow and improve.
Gift giving is in this sense a spiritual endeavour, and as much of a gift to ourselves as the one receiving the gift.
Applying the principle to real life
Using this principle, let’s have a look at ways we can come up with great gifts that make people feel seen.
If we simply think of a gift as either seeing and acknowledging someone’s struggles, or giving them something that supports them in that endeavor, then any gift needs to start with identifying someone’s needs.
Our needs have multiple levels to it. There are surface level needs and then there are deeper needs. Below I’ve outlined a map of surface and deeper level needs, note that this map of needs is by no means a complete list or a particularly sophisticated one, but since the deeper sense and meaning of human existence is beyond the scope of this essay, this should suffice.
Our surface level needs are our physical and utilitarian needs:
Health – Having energy and vitality through eating, moving, and rest
Wealth – Having resources for long term sustenance and security
Then there are deeper needs that get at our ability to grow and develop as individuals:
Connection – Being part of a community of people that love you and accept you for who you truly are.
Purpose – Feeling like you are playing an impactful role in something larger than yourself.
Mastery – Feeling at the edge of your abilities and improving as you adapt to the challenges.
Autonomy – Feeling like you have the room to make decisions and be a master of your own life.
If you pick a person in your life you know intimately, you can probably pinpoint one or more of these that the person feels like they are falling short on. This is a good place to start when you think about gifts.
Below I’ve outlined some examples of gifts that you could give depending on the situation you find the person in.
Prompts and ideas
Surface needs
What does your friend enjoy but hasn’t fully realized themselves?
Ex: Your friend always gets the same tea while at your house, so you buy him a few packs for himself.
What’s a product someone uses that they haven’t splurged on the fancy version of yet?
Ex: Your friend journals every day with a plastic bic pen, so you buy him a nice refillable fountain pen.
What’s a problem someone has in their life that they have yet to recognize or fix?
Ex: Your friend has an old backpack they use every day but hasn’t yet replaced it.
What is some problem in their lives that always ends up at the bottom of the priority list because they have more important things to do?
Ex: Their garage is really messy, so you hire someone to come clean the garage for them.
Deeper needs
Are they feeling a lack of mastery in their life?
Your friend jumps between hobbies and projects but rarely sticks long enough to feel competent.
Gift idea: A high-quality beginner’s toolkit for one specific skill, plus a handwritten note saying “One thing. Done well.”
Your friend compares themselves to experts and feels behind.
Gift idea: A book or course focused only on fundamentals, with a note that says “You are allowed to be a beginner.”
Are they experiencing a lack of resources in their life?
Your friend is capable but always stretched thin, mentally and financially.
Gift idea: A prepaid service they already use, groceries, cleaning, software, anything that buys back time and bandwidth.
Your friend downplays their needs and never spends money on themselves.
Gift idea: A gift card with one clear rule written on it. This must be spent on you.
Are they feeling a lack of autonomy in their life?
Your friend feels trapped by obligations and expectations from others.
Gift idea: A solo experience. A night away, a day pass, or a travel voucher. No plans attached.
Your friend always adapts to others and rarely chooses for themselves.
Gift idea: A notebook titled “What I Want,” with the first page already filled out by you with permission to be selfish.
Are they feeling a lack of purpose in their life?
Your friend is successful but feels oddly empty about it.
Gift idea: A long-form letter naming the concrete impact they have had on you and others. And an encouragement to use their abilities in the service of others.
Your friend wants to make an impact but does not know where to aim.
Gift idea: A small, real responsibility tied to something meaningful. Mentoring, volunteering, or helping you build something real.
Know your limits
Gifts like these only work if they are grounded in real insight. You have to actually see the person. Guessing, projecting, or forcing meaning onto a gift will often land wrong or feel performative.
You also need to make sure that the person is willing to accept what it is that you are implying with your gift. Sometimes people can get offended or be sensitive about these things, because they point to things inside themselves they aren’t willing to look at.
The benefit of doing that through a gift rather than telling them, is that implied in the gift itself is a recognition that you truly care, so what might not be well received elsewhere can penetrate deeper because of the way it’s delivered.
If you are not sure what someone truly needs, don’t try to be clever. Go with a simple, surface-level gift but pair it with a sincere compliment or a clear signal that you care about the relationship and intend to show up for it. Showing that you see them matters more than being impressive.