Why is Gratitude So Hard?
Spoiler: For similar reasons to why "just stop being depressed" is not actionable advice.

In the past few years, psychological research has consistently shown that feeling gratitude is quite good for you. Both in terms of physical and emotional wellbeing, the cultivation of gratitude and thankfulness seems to have measurable and significant benefits. You may have heard of the concept of a gratitude journal, which is designed to facilitate making this cultivation habitual. The fact that such an aid must exist, however, draws one’s attention to how challenging an “attitude of gratitude” can be to maintain. I believe it is a fair observation that most people find it difficult to feel grateful for various aspects of their lives. (I am quite guilty of this.) Note that I am distinguishing the feeling of gratitude and the expression of gratitude. Clearly the latter does not require the former, as when we open a disappointing present, thank a deity for our lives without feeling particularly happy to be alive, or begrudgingly admit to ourselves that compared to starving African children or Chinese sweatshop workers, our existences don’t seem incredibly unpleasant. “In the grand scheme of things,” we say, “I guess I have a lot to be thankful for.” We just need perspective, right?
Maybe not. In our globally interconnected world, we have no shortage of people we can point to whose lives are unimaginably worse than our own. Never before have the people of the world had as much perspective as we do now. But relying on this perspective to foster gratitude tends to feel awfully hollow. If it truly were just a matter of perspective to keep ourselves grounded and content with our lives, ours would be the most grateful and tranquil society in the history of the world. Perhaps it is, but this would be an empty compliment. So what is it that makes truly feeling gratitude so hard, even for people who, realistically speaking, have an abundance of things to be thankful for?
(If the idea that you have a lot to be thankful for makes you bristle, we’ll get to that later.)
1. Our mirrors are too far away.
I would wager that, if forced to choose, most people would spare the life of their pet rather than the life of some random, far-away person whom they would assuredly never meet. Much has been written on how distance, both physical and psychological, alters our internal moral calculus in ways that we acknowledge to be irrational or even monstrous, most notably by philosopher Peter Singer in his thought experiment of the Drowning Child. Consider, for example, how many of the products we consume come from literal or effective slavery. Perhaps Nike or Apple will find themselves the subject of an unflattering investigation, again. They will, unerringly, profess to have been unaware of the horrid conditions that their manufacturers subject their workers to, and give reassurance (to domestic consumers) that they don’t stand behind such atrocities. They will promise to “investigate” how their shoes [PDF] and tech are produced, and then nothing will change because the populace will get bored and the media will move on. Those who pay even a modicum of attention to how corporations work will see through the charade, but will keep buying the products anyway. Most people will briefly feel bad for the slaves, but not long or deeply enough to bother changing their behavior. The least compassionate among us may openly declare that sweatshops are a good thing, actually.
Is this really a good reason to condemn first-world consumers? Yes. But it’s also a poignant indicator of how our psychology works. Sweatshop slaves are simply too far away, too far removed from our daily lives, to elicit any sort of visceral concern. Those of us with functioning empathy do truly care, but this caring comes to us at an intellectual, deliberative level. We motivate ourselves to care in spite of the vast distance, in spite of our unwillingness to forego bloodstained sneakers or gadgets whose chips contain metals mined by young children. This caring is obviously distinct from the sort elicited by issues and people closer to home. A news article about a serial puppy rapist two cities away will immediately enrage us without the need for conscious thought acknowledging that these actions appear to be objectionable. But yet another article about a popular brand manufacturing products using slavery in a distant land just doesn’t have the same punch even when the atrocity involved is far greater in magnitude and scope. A kitten murderer two houses down makes me mad and shocks me. A multibillion-dollar corporation exploiting East Asian children just makes me disappointed and has long since stopped shocking me.
All of this is to explain that the perspective we gain from examining the less fortunate yet more distant is qualitatively different from that which we gain by comparing ourselves to others nearby, whose lives are, compared to the global have-nots, essentially exactly the same as ours. In other words, somebody far away whose life is much worse doesn’t motivate people as much as somebody nearby whose life is not nearly as worse. Suppose I am forced to work through my lunch break. This is displeasing to me. Am I cheered up more by comparing myself to an indistinct and unknown sweatshop worker, or by comparing myself to my coworker John who just found out he’s been mandated to work an extra shift? Rationally speaking, the knowledge that I am fortunate enough to have been born in my own country should cause me to fall to my knees and weep in elation, as many Americans demand, but the most I can muster is a twinge of guilt and an uncommitted recognition that “it could be worse.” But giving John a smirk and conciliatory slap on the back on my way out the door makes me feel grateful. See you bright and early, John!
Ultimately, the most powerful mirrors in our world, into whom we can gaze and come away with a deepened perspective of our own good fortune, and the most effective mirrors, the kind that actually make us feel appreciation for our fortune, are not the same mirrors. Our psychology prevents us, barring concerted effort, from learning very much from the teachers who have the most to tell us. Gratitude may be a matter of perspective, but more perspective does not mean more gratitude.
2. Being fortunate is uncomfortable.
Assume for a moment that, like myself, you are an incredibly popular, attractive, and charismatic basketball star who has just led your team to victory, and that you’ve been invited to make some comments on the matter. I posit that it would be nonsensical, even incoherent, for you to state that you are grateful for your victory.
This is because when you really think about it, that would just be shorthand for expressing gratitude for things outside of your direct control: your genetic predisposition to athleticism; your parents’ encouragement early on; the fact that you weren’t born in an unstable country; the fact that your family was wealthy enough that you could spend your free time practicing rather than going to a job to help pay bills. These are all elements of your good fortune that you could have done absolutely nothing to earn. Meanwhile, your victory, in and of itself, is just something you did under your own power. If this distinction seems irrelevant to you, try to conceive of how much sense it would make to be thankful for your victory without being thankful for any of the elements I just listed. To be thankful for something you’ve done but not for the conditions that made it possible would defy logic. Picture the omnipotent Christian God, who creates the world and sees that it is good. Would God, the “unmoved mover” and “first cause,” be thankful for his own action? Surely not; to be thankful implies the significance of something beyond one’s own agency. If something was accomplished entirely through your own will with nothing left to chance, there is nothing left to feel grateful for. You’re not thankful that you put the ball through the hoop; you’re thankful that you had the ability to do it in the first place.
Western culture, especially in the United States, is incredibly individualistic. Furthermore, people do not tend to enjoy acknowledging that they were not solely responsible for their successes. Many Americans in particular are unwilling to recognize that luck plays any role at all, a phenomenon demonstrated quite bizarrely in discussions featuring poor people denigrating other poor people for lacking the work ethic ostensibly possessed by the people responsible for keeping them poor. To acknowledge that luck plays a partial, if not overwhelmingly significant, role in our lives is to acknowledge exactly how much our destinies are beyond our own control. The fact that so much of our health, wealth, and quality of life is due to good fortune is discomforting, which is why I think so many people opt to implicitly condemn themselves for supposed weakness of character over admitting to themselves that they just aren’t as lucky as they’d prefer. And as we’ve established, practicing gratitude is all about recognizing luck. To purposefully cultivate thankfulness is to look your fortune in the face, just as it is and without reservation, and declare that it is good. It’s hard to feel gratitude because doing so forces you to confront an uncomfortable truth: most of the good things in your life exist only by chance.
This way of examining gratitude leads the astute reader to the next hurdle. If gratitude is to look at your fortune and declare that it is good, what if you aren’t actually thrilled with what you see?
3. Gratitude feels like complacency.
Most of the time, exhortations to be thankful are used as a bludgeon against discontent. We are chastised for complaining and told that we ought to be grateful for what we have because, as discussed above, there are many out there with significantly worse lives than ours. To cultivate gratitude is presented as a means of stifling our negativity, rather than as a way of growing our positivity. It is used to instill shame for the sin of having so much but being hungry for more. To a certain extent this approach has merit; negativity in excess of what is constructive can cloud our judgement and trap us in a mire of unproductive rage against a world that cares not for our wellbeing. But negativity can be productive. It’s difficult to grow without a clear vision of how and in what ways we intend for this growth to occur. We’ll never make beneficial changes to our lives if we’re not permitted to reflect on what changes we’d like to see. The impoverished worker will never seize an opportunity to get a better job if he’s been shamed out of looking for how his life could be made better.
Utilizing gratitude as an obstacle to reflection is just perspective weaponized, used against oneself to hurt and hinder rather than to help and heal. After being conditioned since childhood, as many have been, to see gratitude in this “never complain” sort of way, it can be difficult to reframe it. Gratitude, properly conceived, does not indicate settling, or holding back one’s negativity toward life. Being grateful for your job (because at least you’re not homeless) doesn’t mean you can’t look for a better one. Being grateful for your country (because at least you weren’t born in Somalia) doesn’t invalidate your thoughts about how it should be better. Bottling up your pain and rage for the sake of fulfilling an obligation to recognize how much other people’s lives suck is not healthy or productive. You can be thankful and unsatisfied at the same time, but, far too often, the invitation to be grateful is used as an admonishment.
Gratitude, and all of its accompanying benefits, need not elude us as much as it tends to. The problem is that the way most people think of gratitude characterizes it as an obligation or a tool for beating down discontent. Feeling grateful for what you have doesn’t mean you have to stop recognizing your needs or desires that aren’t being met, and there is no gratitude quota you must fill to avoid being a bad person. The way we talk about gratitude is often not very constructive or conducive to realizing its psychological benefits. For the reasons I listed above, cultivating gratitude and making a habit of feeling thankful is likely to be quite challenging, but it’s cheaper than therapy!

I love your writing, Matthew. I was a little lost in this piece, I have to admit. Have you written your perspective of optimism versus pessimism? I'd love to read that.