Why thoughtfulness demands sacrifice - a few thoughts across several days:

I: Compliments that actually matter

The best compliment I've received is "you’re great at using free time".

I valued that compliment in an especially sincere way because I often think about how I should spend my free time: What fills a vacuum, agentic growth, where freedom comes from, curate your space.

I was thoughtful about something, and someone noticed. The best compliments reflect something you've chosen to invest in.

Studies have found that children who are called smart perform worse on subsequent tests, while those praised for their hard work perform better. Why did I prefer the compliment I received over, say, a compliment about my appearance? It was a compliment about me applying myself, not an intrinsic trait or outcome. One is not born being “great at using free time”.

This has materially changed the way I compliment people, I compliment not the intrinsic trait or outcome but instead the applied behavior.

• I try not to call someone intelligent; I call them thoughtful. Thoughtfulness is them applying their intelligence.
• I try not to call someone athletic; I call them disciplined and hardworking. Process over outcome.
• I try not to compliment someone’s shoes, I’ll instead say they have great taste.

I pride myself on giving good compliments, and a good compliment is more than just complimenting applied behavior.

A great compliment cannot be about anyone else and it cannot have been spoken by anyone else.

It’s non-fungible: an action that can’t be swapped, traded, or generalized. They are one-of-one.
 

II: The non-fungible reach-out

I was discussing networking with other professionals my age. Someone asked the question:

“How do you choose who to respond to when people reach out for a coffee chat?”

Someone else spoke up:

“I just want to see a little bit of effort, just personalizing the invite a bit to show we have something in common.”

I agreed. Similar to compliments, a good reach-out message cannot be about anyone else and it cannot have been sent by anyone else.

Here we find that non-fungibility again, let’s call this the non-fungible principle.

One of the best messages I’ve received was after a brief conversation at a networking brunch, they sent:

“It was great meeting you at brunch! I've since read nearly all of your essays and have been really enjoying them. If you're willing, I'd love to have a chat. Cheers!”

This was a very thoughtful message, it is by no means an expectation I have, but because I mentioned it was a passion of mine at the event they spent the time to comment on a specific thing that cannot be about just anyone. By reading the essays, they had entered a smaller set, now sending a message that cannot have been sent by just anyone.

Admittedly, this is a bit hyperbolic. Others write essays, and others could have read my essays too, but the gesture remains rare.

Other messages, without a similar non-fungibility, come across as being less thoughtful, and so if I am to prioritize spending time with someone, I will choose the more “thoughtful” one every time.

Rather unsurprisingly, someone who strives to be thoughtful values the thoughtfulness of others; however, in that conversation everyone agreed that this was indeed their selection criteria. “A little bit of effort” matters.

III: Sacrifices on Valentine’s

The florist in my neighborhood was the busiest I’ve ever seen on Valentine’s Day. I’ve always felt a little strange about getting your partner flowers on Valentine’s Day. It’s not that I’m against getting someone flowers, it just feels unthoughtful to buy them on that day if you never buy flowers on other days. It’s going through the motions: it’s done by just about anybody for just about anyone else.

I had the honor of growing up in the presence of great relationships. My dad taught how to be loving and caring by example: I saw him leave hand-written poems hidden around the house; fly home early from work trips to surprise my mom; yes, get flowers; and much more.

It was never because the world was telling him to do those things. It was him making small, specific, gestures.

A non-specific gesture, like gifting cash, is not thoughtful, even if it’s appreciated.

Being thoughtful is not giving someone a portion from an overflowing bounty, instead it is a real sacrifice. A clear prioritization of someone over competing priorities.

To be thoughtful: to do something that could not be for just anyone else and could not be by just anybody else, means spending time and effort on this sole action. For this reason, being thoughtful is a Zahavian signal- something that requires a commitment of resources as a demonstration of the quality, like an engagement ring or a peacock's feathers.

The structure of the non-fungible principle, being “not for just anyone else and not by just anybody else” has the effect of domain restriction. It guarantees that your effort prioritizes them because, by definition, it could not apply to just anyone else. This signals that a sacrifice of some kind must have been made. The fact that it’s not by just anybody also signals that the thoughtfulness is not “outsourced,” but is instead driven entirely by you.

Thoughtfulness does not necessarily require a significant sacrifice. There are high-leverage ways to go about being thoughtful. When I was in high school, one of my best friends always seemed to know when I had tests or big events and would wish me luck or something of the sort.

It meant a lot to me. For him, he would just mark down in his calendar whenever I mentioned an event and would be reminded to ask about it later. It’s easy, but for a kid stressed about a test... it had an outsized impact.
 

IV: The cost of caring

Each of these examples: compliments, networking, relationships, gift giving, and friendship, all resonate as ones where thoughtfulness matters.

Thoughtfulness, the deliberate investment into a specific connection, is often met with commensurate investment by the counterparty. As you signal more and more investment (thoughtful acts), you pay attention to reciprocal investment to validate your belief about the relationship.

In many instances, there is a clear first player: the prospective hire, the smitten would-be-lover, the one seeking friendship. This is structural, for the other party to consider hiring, dating, or befriending someone requires that commensurate sacrifice to be made. The price to conduct an interview is higher than writing a tailored cover letter, be thoughtful first.

Thoughtfulness, for this reason, is not a specific set of actions, but instead it is by nature rivalrous (something that can only be used by one person at a time: if one person uses it, others can’t). In order to be specific, it must be specifically not what anyone can do for anyone else. Giving roses on Valentine’s Day is commoditized thoughtfulness, a standard cover letter is drab, more than anything else you want to signal a sacrifice of a unit of work.

A unit of work is the minimum amount of effort required to phase shift from one state to another (thoughtless → thoughtful).

Being thoughtful becomes a differentiator, a bid. A unit of work becomes a currency. This is why the non-fungible principle works, it demonstrates an intentional sacrifice for them and them alone.

Many may want that job, that partner, that friend, and so you are often needing to be thoughtful in rivalrous settings.

A rose on Valentine’s Day doesn’t feel thoughtful, not because it lacks kindness, but because it only meets expectations.

The market doesn’t move when a company announces a dividend that matches the last—because the news was already priced in.

So it’s not the gap between you and others that matters. It’s the gap between you and what was anticipated of you.

What everyone else does just tends to be a convenient stand-in for that expectation.

A hand-written card means more than a pre-filled hallmark even if all words written are identical. Hand-writing the card represents a unit of work being completed; it is a representation of thoughtfulness.

If one hopes to be thoughtful in a rivalrous setting, one needs to honestly demonstrate non-fungible gestures by spending a unit of work.

Units of work are not time bound or effort bound, and depending on the domain can vary in scale wildly, but if something matters, you do whatever it takes.
 

V: Sales is a battleground

Thoughtfulness scales through specificity, and nowhere is this more tested than in sales.

Sales is, by its very nature, a rivalrous domain. It is a game of limited attention, finite budgets, and constant competition. Multiple vendors want the same customer.

In these environments, the signal that breaks through is rarely the loudest. It is the most precise. It is the one that says: this was meant for you, and no one else. It is a gesture that cannot be mistaken for automation or routine. That is what makes sales so interesting in the context of thoughtfulness. It is a space where commoditized effort is common, and where genuine, specific sacrifice becomes all the more powerful.

Which brings us to automation, and its limits.

I co-founded and ran a go-to-market agency. We focused on automating and connecting sales (and marketing) channels and improving personalization.

Lots of tools exist to increase sales leverage, including AI SDRs (sales development representatives). These AI SDRs automate or augment parts of the outbound sales process (i.e. prospecting and outreach) by mimicking what a human SDR does, but at a greater scale and with less manual effort.

If hand writing a card yourself is honest, if I were to get someone else to write the card for me, this would be a dishonest signal of the unit of work.

There is plenty of room for AI in sales, and I have used it extensively myself; however, AI SDRs will not be replacing salespeople in the way some people tend to state.

If evaluating sales outreach requires thoughtfulness, using an AI SDR to reach out is the commoditized thoughtful act, it is flowers on Valentine’s Day. Already in sales there exists the notion to “lead with value,” and against the onslaught of AI slop, this value will be a demonstrated unit of work above and beyond what others do. It will be a sacrifice.

AI outbound could make a B2B dead internet. A wasteland of bots communicating only with bots. AI tools will supplement human efforts (clay.com supports sales teams by providing lots of “variables” to improve personalization) or you could make scheduling and responding more automatic; however, the rivalrous setting will require going above and beyond whatever the commoditized action becomes.

AI SDRs (or any other technology) will get arbitrarily good at solving whatever they can; always, tech will get competitors up to a frontier, and what will push a customer over the edge is differentiation beyond that established frontier.

In the short run, AI SDRs will work as dishonest signals of units of work, but people will wizen up eventually. They are a leverage multiplier.
 

VI: Fashion is earned

Fashion marks a departure from the non-fungible principle explored earlier. There is no specific recipient, no single person the gesture is “for.” And yet, it is deeply connected to the same idea: demonstrating thoughtfulness still demands a sacrifice. To care about how you present yourself, to develop taste, to iterate, and to experiment are all units of work.

Fashion, in many ways, is a very visible demonstration of thoughtfulness. Just like a handwritten card, a tailored outfit is a unit of work made visible. In that way, fashion is a Zahavian signal: its power lies in the difficulty of faking it.

There are many ways to “pay the price” for good fashion:

• You might have good taste, cultivated over years of visual exposure and iteration.
• You might have money, spent on stylists or premium brands.
• You might spend time hunting down thrifted pieces or experimenting at home.
• You might have skills like learning to sew, alter, or combine pieces yourself.
• Or you might use social capital: leaning on a stylish friend to lend their taste.

Fashion is a mountain with many ascents... and everyone climbs.

Stealing the poem is dishonest, yet stealing a style is often not. Not all thoughtfulness is evaluated the same way, because some domains are about the gesture, while others are about the result.

In fashion, a unit of work reigns supreme, and being thoughtful is the intrapersonal deployment of any unit of work. Thoughtfulness is not just about who you’re thinking about... it’s about what you’re choosing to care about.

Once everyone does the thing (trends, flowers, cold emails, LinkedIn posts), it no longer signals anything. The floor rises. This mimics economic inflation. Signals devalue over time. Once everyone has the “look” the style changes. The threshold for “thoughtful” moves as more people learn to fake it.

Fashion has no “end” because fashion needs to always reward those continuing to try.
 

VII: Thoughtfulness is a sacrifice

A thread revealed itself: thoughtfulness is spending a unit of yourself on someone or something else.

It is a sacrifice of time, attention, taste, creativity, or skill offered up as a gesture of sincerity. In a world where so much can be faked, outsourced, or automated, that gesture stands out more than ever.

The test of a thoughtful act is simple:

• Could this have been done by just about anyone else?
• Could this have been done for just about anyone else?

If the answer to either is yes, the signal is weaker. It may still be kind, but it is not personal. Not pointed. Not precise. And precision matters.

Real thoughtfulness is non-fungible.

The unit of work is the marginal effort, the deliberate detour, the part of you that didn’t need to be offered, but was. It’s not necessarily the costliest gesture in any traditional sense; it’s the most intentional one because intention is costly.

In rivalrous spaces, that intention is currency. Everyone wants something: the job, the sale, the partner, the friend, the moment. But attention is finite. The economy of thoughtfulness is zero-sum, so you bid a sacrifice.

AI, templates, norms, and trends all press against this. They flatten signals. They commoditize what once stood out. The thoughtful will always find new edges. New ways to show they care. New mediums where effort hasn’t been automated yet.

In a noisy world full of shortcuts, thoughtful sacrifices are one of the few things that still whisper:

“This was meant for you.”

Sacrifice thoughtfully and be thoughtful about being thoughtful.