Stop Overthinking Kindness
Wanna make someone’s day? It’s really not that hard.
I had a call last Thursday with a former boss. We keep in touch. He’s only a few years older than I, tickling his mid-30s, yet he hunches about with the energy and attitude of a late Gen-X accountant who just wants to go home, pet his dog, eat leftover meatloaf, and be in bed by nine. Only he’s a picky eater, so I doubt he’d touch meatloaf. I mean this all endearingly.
He shared the past few weeks had been difficult. A friend of his, from high school, had taken his own life.
There is nothing good to say to this. Meaning there are no sentences that can leave our mouths, enter another’s ears, sink into their heart, and patch up this hole. Yet we very much feel pressure to say something perfect, something salving. I think more often than not what really strikes in these moments is the impulse to remove the discomfort of something so heavy suddenly placed at our feet. That’s okay to admit. Most of us are not inherently skilled — and were certainly never taught — how to just sit with deep messy feelings. Ours or others’.
The world is stupid, stupefying, disturbing. Though within its maze most of us sincerely do not inflict abject harm at scale.
Most of us carve out our little corners that will constitute our lives, balance a lot of responsibilities, feel a lot of competing pressures, but put one foot in front of the other in order to try our best every day. We all carry around a rough draft sense of self. The pages will get crinkled.
The world is stupid, stupefying, maddening. We can make this dumpster dive less stinky for one another. We really can.
Several suggestions anyone can do — literally anyone — right now, without actually a whole lot of money or effort, to make someone’s [insert timestamp here].
1. Create a calendar noting important but not obvious dates.
A friend of yours having surgery? Doctorate-earning anniversary of a sibling? An older relative finally, finally, taking that vacation they’ve sermonized about for years?
It’s easy to remember the traditional milestones. Birthdays, anniversaries, all the run-of-the-mill annual calendar gemstones. These days are important, but I guarantee there’s a buffet of more individualized, more personal dates carrying great meaning tucked inside all us. Acknowledging those dates is profound.
2. Surprise a loved one with dinner from a food truck. A good food truck.
Yes, a food truck. Why a food truck? Food trucks are perhaps the last independent bastion left in the otherwise sprawling M&A fiefdoms being erected and funded (largely) by private equity portfolio overlords. The restaurant industry is not unique in facing a top-heavy consolidation squeeze. But it is a real issue, and it hurts the lil’ guys, and you can actually do something directly to help.
Also, food trucks are notoriously inexpensive. You get affordable yummy food. You support an actually local business. You feed a loved one. Booyah!
3. Run errands for someone.
Fun fact: Sisyphus was not pushing up a boulder. In the original text, Sisyphus was doomed by the gods to unload and load a dishwasher. Ha, relatable!
Do a chore or run an errand you know makes a loved one want to rip their hair out. That’s basically all of them, so you will not want for choice. For instance, if someone came over and folded my laundry, I would cry.
4. Leave an anonymous thank-you note.
I’m not reaching when I say we’re all impatient, and impatience is a hallmark of self-centeredness, and the self-help books should get credit for indicating gratitude as one potent antidote against this vicious cycle. Write out a thank you to someone, for something specific, and mean it. There is power in a lone sticky note. An affirmation scribbled on a restaurant receipt. Smile as you hear they’ve hung it on their fridge.
5. Compliment a stranger NON-SEXUALLY. I said NON-SEXUALLY, you dirty dogs.
Compliments are not calculus, though the aforementioned self-help books do not get credit for commodifying something as simple as the exchange of a few sweet words.
Non-sexual stranger compliments are just intention meets presentation. You have no ulterior motive, no transactional wish. You speak with calm, cheer, and warmth. You move on.
Months ago a guy behind me in line at a coffee shop tapped me on the shoulder and told me I had nice hair. He said he hoped that wasn’t weird. He smiled, a genuine smile. He then waved, walked away. Myself and a few women around me took in the moment, appreciating how fundamentally unscuzzy that whole exchange went. Clearly it makes an impact. I’m writing about it now.
6. Just message someone to say you’re thinking of them.
Verbatim. That’s all you have to say. Hey! Just wanted you to know I’m thinking about you. Embellish with another line or two should you wish, but don’t overthink it. These words become ropes to clutch when we need a reminder of our mooring.
7. Share a song you think someone would enjoy.
I think of high school days when I used to burn CDs for friends. Friends who’d pop those puppies into their parents’ Honda Civic’s CD player as we rode to and from cross country practice, to impromptu grab Kopps frozen custard, to drive around just for the private intimacy of driving around, feeling small and silly, feeling you might start shaking right there in your seat cause you’re so content, so alive, and in the moment. Music has this singular power. Share it.
8. Practice remembering & bringing up inside jokes.
I fell down a rabbit hole the other day reading up on the pros and cons to certain flavors of humor. Self deprecation, for example, can signal someone has poor self image but also a natural proclivity for creating social cohesion. Pick your perception poison, I guess.
Inside jokes give a nod and a wink. They’re an invisible hand squeeze wrapped in laughter. What you’re really saying is this: That moment we shared mattered to me. You matter to me.
9. Practice asking people thoughtful questions.
First, please. Don’t go paying for yet another snake-oil-masked-as-self-help course sold by an ex-McKinsey consultant turned entrepreneur turned life “guru.” In his podcast, he promises if you just memorize these five conversational tricks, you can make friends and network with anyone and woo the princess and rule the world.
Just start by paying attention.
Most of us can tell the difference between the earnest questioner — the curious, relational questioner — and the perfunctory one. Most of us appreciate being listened to. Really, deeply listened to.
10. Send someone a bouquet of flowers.
Bonus points if the recipient is a man. Fun fact: Men like flowers! (Translation — humans are human!!!) The vast majority of them will not receive their first bouquet until…wait for it…their funeral.
11. Offer help with a task or to-do.
When you care to know someone well, you tend to discern what parts of adulting bring them the most stress. Stress then hang glides into procrastination, procrastination into anxiety. The dance shimmies and tizzies on.
My partner knows I’m a worm who gets in her silly worm head about talking on the phone, so he places restaurant orders, calls businesses to check event bookings, confirm times. I know my older sister, with two young kiddos plus a two-week-old newborn, barely has time to get dressed in the morning, so I went over last weekend to fold laundry. No pressure to go overboard here. Keep it small, keep it earnest.
Consider doing any and all of these things, in some form, for yourself.
Self compassion is a muscle, not a mail order. You have it within you but you must choose to work it. It will strain sometimes. You’ll wake up sore. You have to reinforce its mind-body loop, and it will likely take a lifetime.
This all begins by truly noticing — not judging, not organizing, just noticing — how absolutely god fucking awful you speak to yourself. Self-questioning, anxiousness, shame, guilt, fear. These are most of our default settings. That brain of yours is simply not a nice place. Slowly, painfully, it can be re-trained. I swear to you, it can be re-trained.
There’s a lot of negative goop mucking the wheels of the world. It’s easy to find and read and write about negative goop. Endlessly. Exhaustingly. I do it, and will probably keep doing it, too.
For my own sanity, I want to get better at marinating in the lighter things. The whimsical. The nostalgic. The connective. The silly. The soft. Not in order to play into the sweaty hands of toxic positivity, but to functionally romanticize my life and the life of those around me.
Real romanticization requires you to integrate dark and light. To train your hands to swirl these things on the palette, noting how each becomes necessary to bring out the truest form of the other. You most genuinely and fully admire a flower once you see it growing amongst weeds.
It is now the young side of a fresh month, and across it I’m going to try doing everything on this list. Probably just once, maybe more.
If you’re up for it — don’t squirm away now! — try one or two yourself. This next part I mean earnestly: Let me know how it goes. Seriously! Drop a DM. Share the tale. Describe how it felt, what comes next. Consider it a digital bouquet. It smells kinda nice, doesn’t it?
-Amy 🎱
Another very nice article. I know I've said it before, but you have this great voice, and I always look forward to your latest. You probably would cry if I folded your laundry, though. I've had more than one person suggest, forcefully, that doing the washing was enough, just please please take it out of the dryer and leave it in a pile!
Love this list. So simple, so thoughtful, so helpful 😊🙏