Four-day Orlando gathering marked two decades of independent research and commentary with a keynote address by Digger Cartwright, anniversary champagne toasts, and wide-ranging discussion of the economic, political, and institutional issues shaping the United States
Myrtle Beach, SC, Orlando, FL and Washington, D.C. January 2, 2024—Thinking Outside the Boxe has released the transcripts of the question-and-answer session from its 20th Annual Symposium, held December 28–31, 2023, in Orlando, Florida. The milestone gathering marked two decades of the organization’s annual symposium tradition, bringing together correspondents for several days of discussion, debate, reflection, and celebration. The 20th anniversary observance included a keynote address by Digger Cartwright, champagne toasts commemorating the Symposium’s history and the work of its correspondents, and the annual question-and-answer session examining some of the most consequential economic, political, legal, technological, and institutional issues confronting the United States.
Participants in the 2023 Annual Symposium included Thinking Outside the Boxe correspondents 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, along with Digger Cartwright. As in previous Symposiums, the question-and-answer session was designed to encourage independent analysis rather than produce a prescribed organizational position, allowing participants to approach common questions through their individual professional backgrounds, regional perspectives, and areas of expertise.
The 20th Annual Symposium discussion ranged across an unusually broad set of issues that had emerged or intensified during 2023. Participants examined the failures of Silicon Valley Bank and remaining gaps in bank supervision; regulation of artificial intelligence; the scale of border encounters under existing asylum law; the potential effects of generative AI on white-collar employment; industrial-policy subsidies; and the long-term fiscal burden of entitlement programs.
The discussion also addressed the increasing use of legal proceedings in American political conflict and the implications of lawfare for democratic norms, as well as the Middle East conflict and its implications for global energy markets. Other topics included viewpoint diversity within universities, the economic tradeoff between maintaining higher interest rates and allowing entrenched inflation, commercial real-estate financing in the aftermath of remote work, and the potential effects of digital currencies on traditional commercial banking.
Participants further considered the practical limits of economic and technological decoupling from China in critical industries, the relationship between public safety and the commercial viability of major American cities, and the growing concentration of regulatory power within independent federal agencies.
“Twenty years is a long time to keep asking difficult questions, particularly when the answers are not always fashionable,” said Digger Cartwright. “The Annual Symposium has never been about reaching an approved conclusion or asking our correspondents to speak with one voice. It has been about putting serious people in a room, asking serious questions, and allowing the argument to go wherever the evidence and experience take it. We raised a few glasses of champagne in Orlando to twenty years of doing exactly that—and, more importantly, to continuing the conversation.”
The Orlando gathering also provided an opportunity to reflect on the development of the Annual Symposium itself. What began as a forum for examining issues that often received limited or incomplete treatment in conventional public debate has developed over twenty annual gatherings into one of Thinking Outside the Boxe’s signature traditions. The anniversary keynote and champagne toasts recognized both that history and the organization’s continuing commitment to independent inquiry, open debate, and the willingness to challenge prevailing assumptions.
Thinking Outside the Boxe believes the value of the Symposium lies not in requiring its correspondents to agree, but in giving thoughtful people with different professional experiences and regional perspectives the opportunity to test ideas in conversation. The published transcripts preserve that exchange and provide readers with a record of how participants viewed the major questions of 2023 at the time they were being debated.
The transcript of the question-and-answer session from the 20th Annual Symposium is available at www.ThinkingOutsideTheBoxe.com.
About Thinking Outside the Boxe
Thinking Outside the Boxe is a private, independent research and commentary organization dedicated to examining politics, finance, economics, world affairs, law, public policy, and the conduct of institutions from perspectives often absent from conventional media and public debate. Through original research, commentary, symposiums, and contributions from a diverse group of correspondents, Thinking Outside the Boxe seeks to broaden the parameters of public knowledge, challenge prevailing assumptions, and encourage thoughtful debate on issues of national and international importance.
Thinking Outside the Boxe is independent of political party donors, universities, media organizations, and institutional orthodoxies. Its work reflects a continuing commitment to limited government, lawful borders, fiscal seriousness, open inquiry, constitutional principles, and the belief that a free people are best served when arguments are tested against evidence rather than restricted to an approved range of opinion. Its correspondents may disagree with one another, but they share a willingness to examine difficult questions, reach conclusions, and say what conventional institutions sometimes will not.
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