Orlando, FL and Washington, D.C. January 2, 2024—The office of Digger Cartwright has released the transcript of Mr. Cartwright’s speech delivered at Thinking Outside the Boxe’s 20th Annual Symposium, held December 28–31, 2023, in Orlando, Florida.
The transcript of Mr. Cartwright’s speech follows.
Good evening. Thank you all for being here. It is good to see so many familiar faces.
Twenty years. I have been thinking about those two words since we arrived in Orlando. Twenty years is long enough for an annual gathering to stop being an experiment and become a tradition. It is long enough to forget some of the arguments we were absolutely certain mattered at the time, and long enough to discover that a few of the questions we thought we had settled were not settled at all.
It is also long enough to accumulate a lot of opinions. And, in the case of Thinking Outside the Boxe, quite a few disagreements.
That may be the part I am proudest of. Because the purpose of this organization was never to get a room full of intelligent people together and discover how much they agreed with one another. We could have saved ourselves the airfare. The purpose was to create a place where the argument could continue.
Thinking Outside the Boxe was founded on a fairly simple proposition: conventional coverage is often incomplete, conventional wisdom is frequently provisional, and a free people require something broader than the approved range of conversation.
That proposition sounded reasonable twenty years ago. It sounds considerably more important tonight.
From the beginning, we believed there were ideas, questions, interpretations, and conclusions that deserved an audience even when they were not fashionable, institutionally convenient, or especially welcome. We believed there was value in asking what had been left out of the story. We believed there was value in asking who benefited from the accepted explanation. We believed there was value in examining the incentives behind institutions rather than merely repeating the language institutions used to describe themselves.
Most of all, we believed that adults should be trusted with arguments. Not slogans. Not approved conclusions. Arguments. That has remained the animating spirit of Thinking Outside the Boxe for twenty years.
We did not begin with a promise that we would always be right. Anyone who promises that should immediately be regarded with suspicion. We began with the promise that we would be willing to ask. And then we would be willing to argue. And then, occasionally, we would be willing to admit that somebody else in the room had made the better argument.
Occasionally. Let us not get carried away on the anniversary.
But that matters. A serious intellectual institution cannot be afraid of disagreement. It cannot be afraid of conclusions either.
There is a peculiar modern fashion in which institutions sometimes confuse intellectual seriousness with an unwillingness to reach a judgment. Every question becomes complicated. Every conclusion requires seventeen qualifications. Every observation disappears into a fog of “on the one hand” and “on the other hand” until nobody is responsible for saying what he actually thinks.
That has never been our approach.
Independence, as we have understood it, does not mean emptiness. It does not mean standing in the middle of every road because the middle appears safer.
It means refusing to subcontract the conclusion. Not to a television network. Not to a newspaper. Not to a political party. Not to a university. Not to an administration. Not to a donor. Not to a professional guild. Not to whatever collection of credentialed people happens to have declared that a particular question has been settled this week.
Independence is a method. And sometimes it is an expensive method, because independent thought has an irritating habit of disappointing everybody eventually.
If you think independently long enough, you will say something your friends wish you had not said. If you never do, you may be loyal. You may be disciplined. You may even be useful. But I am not certain you are independent.
Thinking Outside the Boxe has tried to remain independent in the only way that finally matters: no political party owns the work, and no election retires our obligation to examine evidence, incentives, costs, consequences, and the long interests of a constitutional people.
That does not mean we lack convictions. We have always had convictions.
Limited government matters. Fiscal seriousness matters. Lawful borders matter. Constitutional restraint matters. Open inquiry matters. Personal responsibility matters. The ability of ordinary people to make decisions about their own lives without being treated as a problem for experts to manage matters. And the idea that the citizen is sovereign—not merely a customer of government, not a ward of government, and certainly not an inconvenience to government—matters.
Those convictions give Thinking Outside the Boxe a character. They should never give every correspondent the same voice. There is a difference.
Over twenty years, one of the most important lessons of this Symposium has been that people can begin with many of the same first principles and still arrive at a question through very different doors.
Someone who has spent his life around manufacturing sees incentives differently from someone who has spent hers around courts. Someone who deals with budgets sees a policy differently from someone who deals with the people who must implement it. Someone in Arizona sees Washington differently from someone in Michigan. Someone in California sees growth, housing, regulation, and capital through a different window from someone in North Carolina.
That is useful. In fact, it is essential.
Our correspondents do not exist to provide regional decoration to a predetermined conclusion. They bring experience into the argument. They know things because they have lived around them. They have watched regulations leave Washington as paragraphs and arrive somewhere else as costs. They have watched policies that sounded elegant in conference rooms collide with payrolls, permits, supply chains, court calendars, insurance markets, classrooms, banks, farms, ports, factories, and families.
That distance between the announced policy and the lived result has always interested us. It ought to interest everyone.
Tonight, as we mark this twentieth Symposium, I want to recognize the correspondents who have joined us here in Orlando—from Prescott Valley, Arizona; Orange County, California; Gastonia, North Carolina; Wheeling, West Virginia; Bismarck, North Dakota; Myrtle Beach, South Carolina; Sydney, Australia; Sheffield, Jamaica; Knoxville, Tennessee; Long Island, New York; Tyler, Texas; Cheyenne, Wyoming; Dayton, Ohio; Clermont, Florida; Owatonna, Minnesota; Las Vegas, Nevada; Jacksonville, Florida; and Novi, Michigan.
Thank you for bringing your experience into this room. Thank you for arguing. Thank you for occasionally disagreeing with me. I emphasize occasionally. And thank you for understanding something fundamental about the Symposium: the point is not to win every exchange. The point is to leave the question better examined than we found it.
But if we are going to celebrate twenty years honestly, we should go back to the beginning.
Robert M. Clinger III is here with us tonight. Mr. Clinger founded Thinking Outside the Boxe. And I want to say something to him directly. Robbie, none of us would be sitting in this room tonight if you had not first decided that there ought to be a room like this.
Before there were twenty Annual Symposiums, before there were correspondents from across the country, before there were transcripts and archives and years of arguments preserved for somebody else to read, there was an idea.
You had that idea. You believed there ought to be a place willing to ask the question the room had agreed not to ask—and then follow the answer wherever the evidence led.
That became Thinking Outside the Boxe.
Founding something is different from merely having a good idea. People have good ideas every day. Most of them disappear somewhere between lunch and Monday morning.
A founder decides the idea should have a life. He gives it structure. He gives it continuity. He keeps it alive when it is still too small to have momentum of its own. And if he is fortunate—and perhaps if he has done the job properly—there comes a day when the institution develops traditions, voices, memories, and a history larger than the first moment in which he imagined it.
Robbie, this room is part of that history. This twentieth Annual Symposium is part of that history. Every correspondent who has sat at this table is part of that history. Every argument that remains on the record, including the ones we would probably phrase differently today, is part of that history. Twenty years later, the wager you made has a record. And those of us who came later have had the privilege of working on the foundation you laid.
But Mr. Clinger did not build that early foundation alone. There was another man in those conversations. Sebastian G. Peréy. And this twentieth anniversary cannot be complete without talking about him.
Long before most of us entered this story, Robbie and Sebastian talked on benches around Myrtle Beach about business, money, economics, life, and the things people are supposed to understand but somehow nobody ever teaches them.
I have always liked that image. Two men on a bench. No television studio. No university seminar. No panel moderator reminding them that they have thirty seconds remaining. Just conversation. Question. Answer. Another question. Disagreement. Experience. A lesson. And then another conversation later.
There is something almost elemental about it, because underneath everything Thinking Outside the Boxe later became, that is still what we do. We put people together. We ask the question. We let the answer go where it goes.
Sebastian spent his career in finance and economics, but describing him only by profession misses something important. He was a teacher. Not necessarily because he stood at the front of a classroom. Because if you sat on a bench with him long enough and listened, sooner or later you were going to learn something.
He helped give Thinking Outside the Boxe much of its character: clear-eyed, unsentimental, and unwilling to tell people what they wanted to hear simply because hearing it would make the conversation easier. Tell people what they need to hear, not what they want to hear.
There is a great deal of Thinking Outside the Boxe in that sentence. Maybe almost all of it.
I first attended the Symposium in 2007. So I did not stand at the absolute beginning of this twenty-year road. Robbie and Sebastian did.
I inherited conversations that had already begun. And one of the privileges of coming into something that already has a foundation is discovering the people whose thinking is built into the walls even when their names are not written on every page.
Sebastian was one of those people. He died in July 2011. He did not get to see this twentieth Symposium. He did not get to sit in this room and see what Thinking Outside the Boxe became. He did not get to watch the circle grow from those bench conversations into correspondents in cities and towns across the country, into Annual Symposiums and Champagne Summits, into an archive of arguments stretching across two decades.
I wish he had.
Two years after we lost him, I wrote Conversations on the Bench as a tribute to Sebastian and to the two men whose conversations helped build Thinking Outside the Boxe.
There was a reason to put those conversations into a book. Institutions usually preserve their official history. Dates. Announcements. Programs. Names.
But the real origin of an institution is often harder to preserve because it lives in conversations. It lives in habits. It lives in the standards people teach one another without ever writing them into a charter. Conversations on the Bench was an attempt to preserve some of that.
And there was another way Sebastian’s name remained connected to what mattered to him. After his death, Thinking Outside the Boxe established an endowed scholarship in his name at Coastal Carolina University for students studying economics.
I think he would have appreciated that. Not a monument. A student. Someone else learning. Someone else asking questions. Someone else getting a chance to decide where he or she intends to go. That seems right. And so tonight there is joy in reaching twenty, but there is also an empty chair in the history.
Milestones do that. They make you count what endured. They also make you remember who did not get to see the count reach twenty. Sebastian belongs in this room tonight.
Not sentimentally. Historically. Intellectually. Personally.
Because Mr. Clinger founded Thinking Outside the Boxe, and Sebastian helped him build the character that made the institution worth preserving. One gave the idea a home. Together, they gave it habits of mind. Those habits survived. We are sitting inside them tonight.
So Robbie, thank you. For beginning it. For sustaining it. For giving the rest of us something to inherit. And Sebastian—wherever one believes old arguments go after the people making them have left the bench—this twentieth one belongs partly to you.
Now, anniversaries invite nostalgia. I am suspicious of nostalgia. Memory has an excellent editing department. It removes the boring meetings, the wrong predictions, the ideas that went nowhere, the arguments that lasted too long, and the moments when everyone in the room was tired and somebody should have ordered dinner two hours earlier.
What remains is a highlight reel. That is not history.
The history of Thinking Outside the Boxe is messier and more useful than that.
It is twenty years of questions. Questions about politics. Questions about money. Questions about institutions. Questions about the economy. Questions about war and peace. Questions about constitutional government. Questions about technology. Questions about whether expert institutions actually possess the expertise they claim. Questions about whether markets are being allowed to work. Questions about whether governments understand the costs of the policies they impose. Questions about whether journalism is describing events or arranging them into narratives. Questions about whether the public is being informed, persuaded, managed, or occasionally all three at the same time.
And through all of those questions runs another one: What are we missing?
That may be the most important question an independent organization can ask.
Not, “What does our side say?” Not, “What is everybody talking about?” Not even, “What is the conventional answer?” What are we missing?
Because history has a brutal sense of humor about consensus. The idea everybody knows to be true today can become the idea nobody remembers believing tomorrow.
Institutions are not immune to that. Credentialed people are not immune to that. Experts are not immune to that. Neither are we.
The cure is not to distrust expertise. The cure is to distrust intellectual monopoly.
There is a difference.
Expertise deserves respect when it explains, demonstrates, predicts, revises, and exposes itself to challenge. It becomes something else when it demands deference as a substitute for evidence. That distinction has become increasingly important over these twenty years.
We now live in an environment with more information than any civilization in history could have imagined, and yet remarkably little agreement about what information can be trusted.
That sounds like a paradox. It is not.
Information and trust are different products. We have solved the scarcity problem for the first. We have not solved it for the second.
And when trust becomes scarce, institutions often make the mistake of demanding more of it. Trust us. Trust the experts. Trust the process. Trust the intelligence community. Trust the prosecutor. Trust the corporation. Trust the university. Trust the algorithm. Trust the platform. Trust the fact-checker.
Perhaps.
But trust is not a command. Trust is an output. It is produced by consistency, transparency, competence, humility, accountability, and the willingness to explain yourself to people who do not already agree with you.
Once an institution begins treating questions as evidence of bad faith, the institution begins spending trust faster than it earns it. That is not healthy for the institution. It is certainly not healthy for the republic.
And this year—2023—has given us no shortage of examples of questions that deserve more than an approved answer.
At this Symposium, we have talked about the failure of Silicon Valley Bank and what that episode says about supervision, risk, and the ability of regulators to see vulnerabilities before everyone else sees them at once.
We have talked about artificial intelligence—not simply whether it is impressive, because obviously it is, but what happens when the technology begins changing professional work, regulation, education, employment, information, and eventually the relationship between expertise and machines.
We have talked about the border and the asylum system, not as an abstraction but as a question of law, incentives, sovereignty, capacity, and whether rules that cannot be enforced remain rules in any meaningful sense.
We have talked about industrial policy and subsidies. We have talked about entitlement obligations and the fiscal promises one generation makes to another. We have talked about interest rates and inflation, and the uncomfortable reality that sometimes there is no painless policy available—only different distributions of pain. We have talked about commercial real estate in a world in which work itself has changed location.
We have talked about digital currencies and what they could mean for banks.
We have talked about China and critical technologies and the difference between announcing decoupling and actually rebuilding the capacity that decoupling would require.
We have talked about public safety and the commercial viability of cities.
We have talked about universities and viewpoint diversity.
We have talked about independent agencies and how much governing power can accumulate in institutions increasingly distant from direct electoral accountability.
We have talked about war in the Middle East and the consequences conflict can carry into energy markets and the wider world.
And, yes, we have talked about lawfare. We have talked about what happens when legal institutions enter the political arena and political actors enter the legal arena until it becomes difficult to determine where one ends and the other begins.
These are not small subjects. They do not fit neatly into a party platform. They are connected by a recurring question about power.
Who has it? Who checks it? Who pays for its mistakes? Who benefits from its exercise? Who bears the cost? What happens when the institution is wrong? And can the rule being defended today survive when somebody else controls the institution tomorrow?
That last question deserves more attention than it receives.
One of the easiest things in politics is to defend power when your friends are exercising it. One of the easiest things in law is to discover procedural flexibility when the defendant is somebody you dislike. One of the easiest things in economics is to support a subsidy when the recipient is an industry you consider important. One of the easiest things in regulation is to tolerate discretion when you trust the regulator.
The test comes later.
Would you give the same power to the people you oppose? Would you accept the same discretion when somebody else holds the pen? Would you accept the same rule if your business were regulated by it? Would you accept the same speech restriction if your opinion were unpopular? Would you accept the same prosecutorial theory if your preferred candidate were standing in the dock? Would you accept the same executive authority if the other party controlled the White House?
That is not cynicism. That is constitutional hygiene.
The founders of republican government understood something we periodically forget: institutions have to be designed for human beings as they actually are, not as we wish our preferred officials would be.
People have interests. People have ambitions. People have factions. People rationalize. People convince themselves that an extraordinary measure is necessary because the present situation is extraordinary. And then the next extraordinary situation arrives carrying the precedent from the first. That is how temporary powers become permanent institutions. That is why rules matter most when they are inconvenient.
Anyone can support due process for a friend. Anyone can support free speech for an opinion he shares. Anyone can oppose executive power when the other party controls the executive. Anyone can discover fiscal discipline when the other coalition proposes the spending.
The useful principles are the ones that cost you something. That is one of the things Thinking Outside the Boxe must continue to insist upon.
We should be willing to ask whether our own preferred policies survive the same tests we apply to somebody else’s. We should be willing to say that an institution we generally support has exceeded its proper role. We should be willing to say that a politician we generally support is wrong. We should be willing to say that a politician we generally oppose is right about a particular issue.
Otherwise we are not thinking outside anything. We are simply changing boxes. That is not independence. It is relocation.
There is another responsibility that comes with twenty years. We have to be willing to remember our own mistakes. An institution that publishes for long enough will eventually create an archive of opinions that seemed considerably wiser at publication than they do years later.
Good. Keep the archive. Do not hide it. Intellectual credibility does not come from pretending you have never been wrong. It comes from being able to explain what you believed, why you believed it, what changed, and what you learned.
That is another reason the transcripts of these Symposiums matter. A transcript is different from a retrospective essay. A retrospective knows what happened next. A transcript does not. It preserves people thinking in real time. That has value.
Years from now, somebody ought to be able to read what we said here in Orlando and judge us fairly—not by whether every prediction came true, but by whether the reasoning was serious, whether the assumptions were visible, whether the questions were worth asking, and whether we had the courage to reach conclusions without pretending certainty where none existed.
That is a much harder standard than simply being provocative. Provocation is easy. You can provoke people accidentally. You can provoke people stupidly. You can provoke people by saying something outrageous and waiting for the attention.
Thinking Outside the Boxe has never existed merely to be contrarian. Contrarianism is dependence with the sign reversed.
If the establishment says north and you automatically say south, the establishment is still choosing your direction. Independent thought requires more discipline than that.
Sometimes the conventional answer is correct. Sometimes the experts know what they are talking about. Sometimes an institution performs exactly as it should. Sometimes the unfashionable answer is unfashionable because it is wrong.
Our obligation is not to disagree. Our obligation is to examine. And then, having examined, to say what we think.
That seems simple. It is becoming rarer.
Part of the reason is fear. Not necessarily dramatic fear. Ordinary professional fear. Fear of losing access. Fear of losing standing. Fear of being called irresponsible. Fear of saying the wrong thing in a meeting. Fear of being associated with the wrong person. Fear that a sentence will be removed from its argument and displayed to an audience that has no interest in the argument. Fear that one opinion will become a permanent digital label.
Modern institutions have become extremely sophisticated at enforcing conformity without ever issuing an order. Nobody has to tell you what not to say if everybody understands what saying it will cost. That is precisely why independent institutions remain important.
Someone has to be willing to host the argument. Someone has to be willing to publish the unpopular paragraph. Someone has to be willing to say that the emperor’s new clothes have a supply-chain problem. Someone has to be willing to tell a room full of experts that the model has forgotten the human being standing outside the model. Someone has to be willing to say that there are costs hidden behind the word “free.” Someone has to be willing to ask whether compassion without capacity becomes cruelty by another route. Someone has to be willing to ask whether regulation written to solve yesterday’s scandal creates tomorrow’s concentration. Someone has to be willing to ask whether a legal tool we celebrate today becomes something we fear after an election. Someone has to keep the argument open.
That is what I hope Thinking Outside the Boxe has done for twenty years.
Not perfectly. Not always elegantly. Certainly not quietly. But persistently. And persistence matters. Institutions are built by repetition.
You publish again. You gather again. You ask another question. You bring another correspondent into the conversation. You revisit an old issue after the facts change. You discover that something dismissed five years earlier has become conventional wisdom. You discover that something everyone believed five years earlier has quietly disappeared.
And then you gather again. That is how twenty years happens. Not all at once. One argument at a time. One Symposium at a time. One question at a time.
Which brings us to the next twenty. I have no idea what the twentieth anniversary of the twentieth anniversary will look like. If someone here tonight claims to know what the world will look like in 2043, do not give him control of your money.
But there are a few things I think we can say. Technology will change faster than institutions know how to regulate it. Government will continue promising more than budgets comfortably support. Political movements will continue discovering constitutional principles when those principles are useful and forgetting them when they are inconvenient.
Experts will continue being necessary. Experts will continue being wrong. Markets will continue surprising planners. Planners will continue being surprised. Human beings will remain human beings. That last one is the safest forecast of the evening. And because human beings will remain human beings, the need for independent inquiry will remain.
We will need people willing to distinguish information from wisdom. We will need people willing to distinguish expertise from authority. We will need people willing to distinguish compassion from policy effectiveness. We will need people willing to distinguish a legal outcome from a just institution. We will need people willing to distinguish economic growth on a spreadsheet from prosperity experienced by families. We will need people willing to distinguish political victory from constitutional health. And we will need people willing to disagree without treating disagreement as evidence of moral contamination.
That last requirement may prove the hardest. A republic cannot function if every argument becomes a question of whether the other person is permitted to speak. Self-government requires a certain confidence in one another. Not agreement. Confidence. Confidence that the citizen can hear something objectionable without collapsing. Confidence that a bad argument can be answered. Confidence that a good argument does not become bad because an unpopular person makes it. Confidence that disagreement does not require exile. Confidence that truth does not need protection from questions. If Thinking Outside the Boxe contributes anything to the next twenty years, I hope it contributes to that confidence.
Keep more than one correspondent in the room. That phrase matters to me. It does not mean every idea deserves equal weight. It does not mean every fact is negotiable. It does not mean we manufacture disagreement where there is none. It means we resist the temptation to mistake consensus for proof. It means we understand that the person asking the inconvenient question may be the person keeping the institution honest. It means disagreement is not a design flaw. Sometimes it is the safety system.
So when we leave Orlando and return to wherever we came from, I hope we carry something more than the memory of a twentieth anniversary. I hope we carry an obligation. An obligation to remain curious when certainty is easier. An obligation to remain skeptical when deference is rewarded. An obligation to remain fair when partisanship would be more satisfying. An obligation to notice costs that have been moved off somebody else’s spreadsheet. An obligation to ask whether our principles survive a change of names. An obligation to remember that institutions exist for people—not people for institutions. And an obligation to keep the public argument open.
That was the idea twenty years ago. It remains the idea tonight. Thinking Outside the Boxe does not exist to elect a party. It does not exist to soothe a faction. It does not exist to provide intellectual decoration for conclusions somebody else has already reached.
It exists because a public argument can be closed in many ways. It can be closed by government. It can be closed by corporations. It can be closed by universities. It can be closed by professional associations. It can be closed by media institutions. It can be closed by algorithms. It can be closed by fear. It can even be closed by exhaustion—when reasonable people finally decide it is easier to say nothing.
Our job is to keep it open. Not because every argument is equally good. Because arguments have to be made before they can be tested.
Twenty years ago, Mr. Clinger made the wager that there ought to be a place for those arguments. Sebastian Peréy helped give that place its character. Tonight, twenty years later, the fact that all of us are sitting here is part of the answer to whether that wager was worth making.
It was.
And now, after twenty Annual Symposiums, I am going to violate one of our usual rules and suggest that there is at least one subject on which we can safely reach consensus.
Champagne.
There are moments for analysis. There are moments for footnotes. There are moments for minority opinions. And there are moments when reasonable people should recognize that they have been arguing for twenty years and have earned a glass. So I would like to ask everyone to raise one.
First, to Robert M. Clinger III. The founder. The man who decided twenty years ago that Thinking Outside the Boxe ought to exist. Robbie, everyone in this room tonight is here because you first created the room. Every Symposium followed the first one. Every correspondent followed the decision that there should be correspondents. Every argument followed the decision that the argument was worth having. You laid the foundation. We have simply had the privilege of building on it. To Robbie.
And to Sebastian G. Peréy. His friend. His partner in those early conversations. A man of finance and economics, but more importantly a teacher to the people fortunate enough to sit beside him and listen. Sebastian did not live to see the twentieth Annual Symposium. But he helped shape the institution that reached it. His name lives in a scholarship that helps another generation study economics. His voice survives in the lessons remembered in Conversations on the Bench. And his habit of telling people what they needed to hear rather than what they wanted to hear remains part of the character of this organization. So to Sebastian.
To those who begin things.
And to those who help give those things their character.
To the correspondents who have joined us over these twenty years.
To the people who have challenged us.
To the people who have disagreed with us.
To the people who read the work precisely because they wanted an argument they were not getting somewhere else.
To our correspondents from all across this great country and from all over the world who are here for this twentieth Symposium.
To the questions we answered well.
To the questions we answered badly.
To the questions we are still arguing about.
And especially to the questions nobody has thought to ask yet.
May Thinking Outside the Boxe remain independent enough to be inconvenient, disciplined enough to be credible, curious enough to reconsider, confident enough to conclude, and stubborn enough to keep the argument open.
To those who founded it.
To those who shaped it.
To those who carried it.
To those we remember.
To twenty years.
And to the next twenty.
God bless you all, and God bless the United States of America.
Transcript as delivered. Any departures from the prepared text are noted in brackets.
