Thinking About Thinking Well

Garrett Smith
Conservative Pathways
11 min readMar 6, 2018

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Why the communities we inhabit matter for our thinking — for good or ill.

One of my favorite books published in 2017 was Alan Jacobs’ “How to Think.” There have been a considerable number of books on this subject throughout the past few years, but Jacobs has managed to write the only one I can recall that seems generally optimistic.

Jacobs himself notes that because these types of books detail the foibles of human thinking, most of them are pessimistic — some explicitly so. The title of Dan Ariely’s “Predictably Irrational” seems to suggest that something might be seriously wrong up there. But for eponymous pessimism, few can top David McRaney’s “You Are Not So Smart,” which I managed to lose while reading, funnily enough. Perhaps McRaney would consider this something of a confirmation of his thesis.

I learned something important from these sorts of books, and whatever that was has a great deal of power to explain other people’s behavior — but it did little to help me improve my own thinking. Reading about the Dunning-Kruger effect has helped me understand why elements of the Trump administration act like they do; it did not improve the accuracy of my estimations of how long it would take me to finish writing this article.

Learning about the defects in human thinking does not, in my experience, automatically render us somehow less vulnerable to those errors in ourselves.

This presents serious problems when talking about politics, particularly due to Trump’s tendency to substitute serious policy proposals with hot button bromides in the culture war. Most people trying to improve the way they think intuitively understand that we’re more vulnerable to errors in thinking when we’re emotionally invested in the outcome of whatever we’re thinking about, so culture war issues are particularly susceptible to bad and superficial reasoning. (This is a phenomenon called the backfire effect, and has been described memorably by The Oatmeal and David McRaney.)

However, the sort of cultural issues that substitute policy with emotion are also a reliable way to energize a political base. They accomplish this without requiring that anyone — including the speaker — understands detailed policy proposals. As a result, Trump talks about athletes kneeling for the national anthem rather than engaging in detailed discussion of the advantages or disadvantages of the Trans-Pacific Partnership. The excitement of the rallies and the energy that results is an apparently acceptable price to pay for the loss of clear thinking.

One result of this has been the degradation of political dialogue — not only of the topics that are being constantly pushed into the public sphere, but also in the way that they have been discussed. There’s a huge need for Jacob’s book, and it’s worth discussing some of his more important points, and, if possible, teasing out some of the implications.

The current discussion of the impact of identity politics provides a striking illustration of Jacobs’s observation that thinking, good or bad, is an intensely social activity.

Whether or not we realize it, the majority of the thinking that we do is done as part of a community.

The cliché that I should “think for myself” is, on a basic level, nearly as improbable as the popular entry in twitter bios: “thoughts are my own.” They’re probably not, if we’re being honest.

We grow up as part of communities, we learn to think in them, we take their identities as our own, and we are influenced by them even when we think that we are not. Whenever we change our mind on big issues — our political party, our religion, or our position on cultural issues— it’s likely because we are listening to people that are part of a different community.

My personal experience bears this out. I consider myself to be a conservative, and thus skeptical that the recent developments in the Republican party are in any way healthy, but I did not come to this conclusion by myself. I inherited both a tendency towards conservative politics and an aversion to cable news from my family, and so when I started deliberately paying attention to politics around 2005, it made sense to do it by reading books and subscribing to a magazine that seemed to publish the sort of authors that also wrote books.

I happened to subscribe to Commentary, and years later, this still seems a reasonable decision from the standpoint of thinking well — which, it’s important to note, has more to do with how we come to conclusions than the conclusions themselves. When Twitter became popular enough to be interesting, I started by following the writers that were associated with the magazine.

In retrospect, this was a deliberate attempt to become part of a specific community, which in turn shaped the way that I thought. Not only was I influenced by the opinions of op-ed writers and conservative essayists — the community of which I was a part made it more likely that I would see or hear more about news that supported their particular approach to thinking.

This isn’t in itself meant to be a justification of any specific political opinion, but rather an illustration that this approach only works well when it’s an attempt to join a community that’s actually thinking well.

All men may be created equal, but all communities are not, and we join specific communities because we think they are more appealing than alternative options, that they better in some way.

If I’m in a community that surrounds me with people who make an effort to be well read and informed about the past, and who use their knowledge to cite historical examples of political disagreements to support their arguments about current issues, then it’s likely that I’m going to value being well read even if I don’t agree with all of their conclusions. In time, I’ll probably decide that this is an effective way to argue, and I’ll come to respect people that have a command of historical examples.

Conversely, if I’m part of a community that is motivated to political involvement by anger and resentment, then I am likely to be angry and resentful as well, and it’s difficult to see how the quality of my thinking would be improved.

In both cases, though, thinking is being done in community, but that doesn’t mean that both ways of thinking are equally valid.

We intuitively make value judgments about communities all the time, simply because it’s not practical to continually evaluate every claim that we encounter. Most of us don’t reject conspiracy theories because we’ve conducted detailed examinations all the evidence behind them, but do so because prior experience has convinced us that that the communities that promulgate them are not worthy of our time.

Conversely, the communities that find such theories compelling have done so because they’ve decided that expert explanations are lacking in some way. Once you believe everyone outside your community is acting in bad faith, further evidence becomes evidence of a conspiracy.

Another word for this, of course, is bias, and Jacobs points out that if we think that the goal of thinking well is to eliminate bias entirely, we won’t be successful. Eliminating bias is neither realistic or particularly desirable. It may be biased for me to trust NASA to tell me whether or not we landed on the moon, but I don’t expect my thinking will improve if I’m not.

Fortunately, it may be easier for us to judge the health of communities than it is to constantly examine our own motivations. Learning about the Dunning-Kruger effect may be helpful when trying to understand the behavior of others; it’s less effective from keeping us from falling into the same traps. A similar principle is at work here. If it isn’t, then we’ve just substituted one difficult problem for another one.

So how do we judge communities well?

At this point, Jacobs wisely turns to C.S. Lewis’s 1944 lecture “The Inner Ring” for guidance. Lewis points out a phenomenon that most of us have almost certainly observed: In every human institution, there exist a series of “second or unwritten systems,” as Lewis puts it, that run parallel to the formal system or hierarchy.

This “inner ring” is composed — depending on the organization — of the leaders, the people that everyone wants to be like, the people everyone listens to or the people that are seen as being at the top of the social hierarchy.

The object is not to find a community in which an inner ring doesn’t exist. They’re ubiquitous. Lewis’ observation is that these are a natural part of human community, and while they aren’t necessarily evil, how they function can be used to judge a community.

What does it take to gain acceptance into the inner ring? Lewis points out that the desire for acceptance into the inner ring is one of the “is most skillful in making a man who is not yet a very bad man do very bad things.” Those that watch politics have seen numerous examples of this behavior, and it’s most common to see these events as only telling us about the character of the individual. This is an incomplete view — it also tells us something about the inner ring to which the individual is seeking inclusion.

What Lewis leaves unsaid is something that seems comparatively more rare: What if gaining acceptance requires you to be a better person? What if it requires you to do better things than you would have otherwise?

Jacobs, furthermore, points out that we can judge the health of a community by observing how members of the inner ring react to ideas that go against the prevailing orthodoxy: Are ideas met with honest discussion in good faith, or are they stifled? If the leaders of a community are unwilling to entertain other ideas, how can we expect that members of the community are thinking well?

When we’re judging a community in this way, though, we’re not trying to judge their thinking of the leaders directly. We’re judging the content of their character, and the implication of what Lewis and Jacobs are both arguing isn’t just that healthy communities are better in some sort of abstract moral sense (although that is true), but that the character that is exhibited by the leaders of those communities has a profound impact on thinking well.

This is why character matters.

Arguing for the importance of personal virtue seems hopelessly anachronistic in a post-Trump era, and even among religious members of the GOP, this is now an increasingly difficult concept to sell, as PRRI polling during the 2016 campaign indicated.

A terrifying sign of a profoundly unhealthy community.

I grew up in evangelical churches during President Bill Clinton’s impeachment, so from where I sit, the change seems clear and striking. What’s somewhat less clear if Trump is the cause of or the result of this swing. In either case, the resulting Trumpification of the GOP has resulted in a community that’s even less healthy than it was, although Trump’s ability to take over a political party doesn’t indicate that requisite levels of health existed prior to his arrival.

Some of the most salient criticism of the Trumpified GOP has come through a critique of the community that has resulted. Large swaths of Trump’s base has been fairly open about their motivation: They’re angry at liberals and resentful of elites — an attitude which, unmistakably, has been handed down from the inner ring of the movement.

This isn’t healthy.

The only way that it’s possible to equate resentment-based politics with the good of the country is if you’ve forgotten that your political opponents are also American citizens.

Being motivated by anger and resentment isn’t good for anyone, and the community that’s resulted doesn’t seem to be doing a lot of good thinking. They’ve also been unable to appeal to anyone outside of Trump’s base, thus does the “inner ring” force members of the community to act and support acts which are the precise opposite of its formal principles.

Trump also has, with the help of entities like Fox News, managed to construct a movement in which a belief in him and his abilities is not falsifiable. The president has been fairly open about this: “I could stand in the middle of Fifth Avenue and shoot someone, and I wouldn’t lose voters.”

For Trump’s base, it’s inconceivable to consider that the president doesn’t know exactly what he’s doing: Inexplicable changes in policy or bad PR decisions are the result of some undisclosed master plan; more conventional moments are similarly treated as evidence of his wisdom. Failures of the administration are taken as evidence that he’s being failed by establishment Republicans, and when those same establishment Republicans are able to pull off the rare legislative success in Congress, Trump’s base sees this as a result of his leadership.

It’s a virtual certainty that if Trump is found guilty of money laundering, or if Mueller uncovers evidence that members of Trump’s campaign were cooperating with Russian agents, there will be a certain percentage of Americans that conclude that an innocent man has been framed by the deep state. Additional evidence won’t serve to convict him in their minds, but it will only serve as evidence that the conspiracy was more extensive.

There’s a similar phenomenon among Trump’s base when talking about the president’s flexible policy positions. The president’s whimsical changes in policy positions doesn’t seem to phase his base. Taking up or abandoning principles, however, doesn’t seem likely to bother Trump. Perhaps the most unsettling aspect of this administration is something that we’ve seen both from Trump and from the inner ring of aides that he has cultivated: If your highest objective is to obtain personal power, then you have no other principles to betray.

All of this feels different from the community that has resulted from the conservative revolt against Trump.

My participation in this has been limited to watching and reading, but from what I’ve seen, the disagreements in the community demonstrate that there’s thinking going on. Members of this movement have an ability to critique the movement itself, and although I don’t think that insularity is much of a problem for those of us scattered throughout flyover country, perhaps it’s different in New York City. In any case, Brooks’ critique of the movement is at least possible, which is a good sign.

The people I’ve observed as part of this community seem to be motivated more by their belief in conservative principles than by the struggle for power or influence, if for no other reason that there’s comparatively little of it to be had. This is, after all, the opposition.

I’ve also observed a phenomenon of which I’m certain Jacobs would approve: The idea that, when confronted with new information, individuals are willing to change their mind. Jacobs discusses this concept of being “broken on the floor” as a better way of approaching debate: The goal isn’t to win the debate, but to arrive at the conclusion that is true. If that’s your approach — if you’re pursuing truth instead of competing at a game — then it’s necessary to be capable of losing when you’re wrong.

The odds of coming into adulthood with only correct beliefs is infinitesimally small, so we all need this skill. If you’ve never learned it, it’s not because you’ve always been right. It’s because you incapable of losing even when you’re wrong.

It’s not a perfect community, to be sure, but it’s something that resembles a healthy community, and I’ve been fortunate to be a part of it. My thinking has benefited as a result.

And here, perhaps, is why Jacobs’s optimism is warranted, or at least understandable: If thinking well, for Jacobs, is closely related to both cultivating personal virtue and seeking out and participating in healthy communities, then some of the worst foibles of human thinking can be at least partly ameliorated.

If this isn’t the only way to improve our thinking, it seems to be the most likely to work: We’re unlikely to truly listen to other points of view if we are not patient, unlikely to try to understand them without empathy, unlikely to admit our own errors without a healthy dose of humility and unlikely to see any of these virtues as admirable unless were are part of community that does.

We would do well to find communities where this is encouraged, and follow leaders that exemplify these traits and so encourage them in others. Our thinking will improve as a result.

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Garrett Smith
Conservative Pathways

Bibliophile. Theist. Conservative. Fan of the Oxford Comma. #NeverTrump for as long as it takes.