The Chautauqua Way: How a 150 years of Comprehensive Thinking Still Applies in the Age of AI

The bell tower on Chautauqua Lake, Chautauqua Institution

These are of us, they are with us,

All for the primal needed work, while the followers there in embryo

wait behind,

We to-day’s procession heading, we the route for travel clearing,

Pioneers! O Pioneers!

Pioneers! O Pioneers! “Leaves of Grass”, Walt Whitman

Life at Play

Recently, my partner and I have been starting our weekend mornings with what we call “pool dates.” It’s nothing fancy—our condominium has a pool and a large lounge area. The pool has a five foot maximum depth. It’s a leisure pool. And on these weekends, we, like our green anole and blue-tail skink friends, are its dedicated leisure lizards.

We normally bring breakfast and coffee, either from the house or the Starbucks nearby. We wave and say hello to any myriad of other folks visiting the pool that day, and settle into our routines. She makes a beeline for the pool, and I, because I spend so much time otherwise glued to a screen, open my local newspaper and indulge myself on the Sunday features.

The subtitle catches my eye first:

“In the age of AI, a growth mindset and continual learning are key.”

The article is a short but information-chocked piece about the necessity of upskilling and re-skilling in today's market. And the author is 100% right. Today's world is moving faster than it ever has. And while every generation can say that, the exponential increase in speed since the birth of the World Wide Web and then once again with the integration of AI services greatly out paces any other. So much so that according to the World Economic Forum’s 2023 Future of Jobs Report, “60% of workers will require training by 2027 to keep pace with evolving job demands.” That means additional training just to continue doing the same job. The article graciously offers free or affordable ways to close these gaps and create comprehensive skillsets (LinkedIn Learning, Coursera, Udemy, etc.) and warns that not embracing a growth mindset is a great way to get left behind. And they’re right. Especially in corporations and tech companies, the lack of AI literacy will be the equivalent of not knowing how to operate Microsoft Word.

But this “growth mindset” isn’t exactly new knowledge. Far from it, actually. I’m reminded of this as I read this article, trying to force myself to relax from a long week of full-time job hunting, portfolio building, and yep, you guessed it—upskilling. You see, recently, I was impacted by a global, company-wide layoff. And while my company treated me well on the way out—a layoff is still a layoff.

So I’ve had a lot of time to think. And to consider the things I’m grateful for. Pretty high on that list is Chautauqua.

Life in Art

I was fortunate enough to be the Managing Editor for Chautauqua during graduate school. Chautauqua is a joint-publication literary journal produced between UNC Wilmington & the Chautauqua Institution in upstate New York. In short, Chautauqua's mission is to encourage, foster, and facilitate lifelong learning for adults. Sounds familiar, huh?

The last time I was submitting job applications everywhere and constantly attending online tutorials and courses was 5 years ago. I had just graduated in the beginning of the pandemic shutdown and had just stepped down from the role that forced me to learn so many things simultaneously. Visual and print design. Contract management. Teaching and syllabus design. Copyright issues. Mentorship. Professional developmental editing. Online and social media engagement.

And here all I thought I’d be doing was reading and proofreading.

It was during this time that I learned the full “jack of all trades” proverb, probably from either Philip or Jill Gerard in their seemingly infinite wisdom. Like most things that are misquoted, this proverb means the opposite of what most people think. What we normally hear is:

"A jack of all trades is a master of none."

This is usually interpreted to refer to an individual as someone who can't commit to finishing a project or achieving a certain level of certification, i.e., someone who is unfocused. However, the full proverb reads:

"A jack of all trades is a master of none, but oftentimes better than a master of one."

The proverb is meant to educate and advise people that over specialization is a liability. It’s true. That doesn’t mean that true experts aren’t needed, it just means that they are niche roles, and therefore mercurial. Another adage comes to mind: Don’t put all your eggs in one basket.

We understand this in finance. You want a diversified portfolio to protect and capitalize on your investments and assets. In our professional and personal lives, we should strive for the same. The negative antonym for a “specialist” is a “generalist.” I say it’s negative because in my experience, its connotation is often equated to the terms “educated” vs “uneducated.” In reality, the generalist should be referred to as a Comprehensive Thinker. Because overspecialization—knowing just one thing, very well—means you’ve pigeonholed yourself into only being proficient in one task, and at a moment’s notice, that task, role, or field may become irrelevant. As can you—just like the article from the newspaper stated, and you don’t need a research statistic to know that. General or even advanced knowledge in multiple fields supports the ability to recognize and implement the integration of techno-economic advantages and ideas.²

Take the original sea farers (pirates or otherwise): you may be the best oarsman in the world. You can row for hours. Or the perfect helmsman. Your grip and precision, unmatched. As a cannoneer, nobody is faster than you and you never miss. All of these, essential to an early frigate or sloop. But they are all specialists. The generalist is the captain. The captain knows how to do all these things, or enough to figure it out—but the captain also knows how to navigate. How to alter or redraw maps. Knows that while wheat is scarce and highly desired in x location, it is so bountiful in y location that they throw it away.² The Comprehensive Thinker doesn’t just see moving parts, they see where to implement moving parts.

But let’s look at another, slightly more modern example, the pioneers. Anyone who is an avid outdoorsman, DIYer, or off-grid homesteader can relate to this. Or, for anyone who played simulators like Oregon Trail, or for the younger folks, Red Dead Redemption II, you’ll have a general understanding. The pioneers wandered off into the depths of an uncharted continent (by European standards) to settle homesteads. They had to know how to do everything they needed, because it was their job to build the infrastructure. They had to farm, hunt, cook, build houses and wagons, wagon wheels, and make clothes. They had to know how to dig root cellars (the original pantry/fridge combination), and survive the elements. Harsh winters. Dust storms. Tornadoes. They had to learn how to implement basic medicine, and yes, like Oregon Trail and RDR2, how to treat snake bites and dysentery.

And yet, even these pioneers, these youthful sinewy races that all the rest of us depend³, despite all their knowledge and know-how, wanted to know more. They had this thirst because if they did not recognize it before, their transcontinental trek through the untamed, unpaved, and utterly breathtaking danger of the American frontier taught them one thing: Knowledge is power, and power is knowledge.

Having the knowledge to problem solve was, literally, the most valuable thing you could have on the frontier. The only problem was, once these pioneers, these youthful western races³ settled, there was no time for additional education. They worked day in and day out, without much, if any, chance to expand their knowledge beyond their own experiences, let alone any sort of leisure time.

That is, until Chautauqua showed up with bells on in covered wagons one Sunday.

Life Lessons

The Chautauqua mission began in 1874 by training Sunday school teachers, but it quickly expanded to include educational, cultural, and recreational activities. Originally, they travelled in caravans not so unlike a circus, but instead of lions, clowns, sideshow attractions, and the like; they brought doctorate-level ministers, art and music instructors, writers, and teachers in multiple fields of study to deliver their mission to the rural communities of Reconstruction and Gilded Age America. Their mission was then and remains as such, to foster adult education and lifelong learning, truly improving everyone’s quality of life through the four pillars of the institution: Arts, Education, Recreation, and Religion.

The last pillar was the most important at the time, as it was generally frowned upon to take a day off from farming in the late 1800s for anything other than religious services and functions. Chautauqua provided the people of rural America with fresh and vibrant religious and recreational activities for merriment and health, gave lectures and hosted workshops on any number of subjects, and provided access to all manner of arts including music, painting, and pottery. As a religious entity, it was accepted and later, a highly anticipated event. Before they left, Chautauqua would collect subscribers to send books to. Oftentimes on these massive homestead ranches, women were the primary educators for children too young to work the fields. So with their educational mailing list, Chautauqua became known for contributing to women’s education (and more than likely, a direct influence on the suffrage movement).

150 years later, the Chautauqua pillars are still applicable today. All of them are designed to create well-rounded and healthy individuals and communities. A comprehensive health, which requires comprehensive knowledge.

We indulge ourselves in the arts for the emotional release, the adventure, the catharsis, for fun and for joy. To relax, to dream, to disconnect one side of the brain for a while. We do this every time we turn on Spotify, Netflix, or a Playstation. And for a country that likes to throw shade on arts degrees as much we do, we sure do love to consume it.

In recreation, the value in engaging in recreational activities well into adulthood is obvious: fostering new community relationships, healthy lifestyles, pickleball rivalries, or even weekend breakfast pool dates. “Decompressing” has become a common phrase for unplugging oneself from their work, and with as many sedentary jobs as there are now, we all need a little more exercise.

Then there’s education. We should always be learning. This doesn’t just apply to old-timey pioneers. When we do not challenge ourselves to learn, we become stagnant. I won’t claim to be an expert in this regard, but my advice is to just get out there and get after it. It doesn’t (necessarily) matter what it is. If you want to learn it, do it. If you need to pick up a new skill or build on an old one for that promotion, well, prioritize that. But the point is, you don’t have to enroll in another college course if you don’t want to (or can’t), there’s plenty of other avenues. Some were mentioned previously and a quick google search (or even AI chat) can provide more options that fit your budget and schedule. And whether you’re attending “Youtube University,” Codeacademy, or Harvard—keep a portfolio somewhere. If you’re in tech, keep a public Github. Alternatively, keep a website like Wix or Wordpress, or just something public. Put whatever you’re doing on it. Heck, you’re reading mine right now.

Professionally, refusing to learn new skills, market trends, or adapt is an excellent way to age your self out of a position. That fact has been true for more than a century. Look up the term “Renaissance Man.” It remains true, though the speed of which it occurs has only increased, and the only way to keep up is the path of lifelong learning.

Individually, as we age, if we do not engage our mind, it literally dulls itself. Far too many people retire and stop engaging themselves and find that they cannot operate simple new technology or have trouble keeping up with others in conversation.⁴ Some of this natural, but we can choose to prolong it and enhance the life we have by embracing lifelong learning. Now is the time to instill these healthy habits.

Looking at Chautauqua’s model, you might think something along the lines of, “Wow. That’s a really well-rounded lifestyle.” And you’d be right. But you’d also be looking at a comprehensive lifestyle developed by comprehensive thinkers. This is designed to create a healthy, happy life of fulfillment. You need leisure and recreation activities to keep the body active and to relieve stress. According to the National Institutes of Health, stress (especially chronic stress), is known to increase the chances of high-blood pressure, weakening the immune system, triggering inflammation, and alter hormones which can increase chances of cancer and other serious conditions such as cardiovascular disease, mental disorders, and sleep disturbances.⁵ In short you have to see the big picture, to think comprehensively to know that while the need to learn (and work) is essential, so is balance.

Now while I certainly don’t mind singing Chautauqua’s praises, and encourage you visit the institution in New York if you’re ever able (it’s not far from Niagara Falls, either), it’s not what I’m saying you should do. What I am saying is, that even though it not new knowledge that we need to continue to challenge ourselves to learn new things, to better ourselves first for ourselves, then our careers; it doesn’t mean that we don’t need a reminder from time to time. I’m seeing it firsthand in a rough job market balancing precariously on recession concerns, and I was upskilling before I was laid off.

In my opinion, there are three valuable skills that are paramount to any individual’s success, fulfillment, and security for the next couple decades or so:

AI Literacy: The ability to adequately use AI tools and recognize their use within reasonable expectations; this is also assuming you already have computer literacy, which is a foundation for this proficiency.

Critical Thinking Skills: The ability to consume information and make a logical and educated judgement about it. This is necessary in every aspect of life, from determining the best grocery deals to discerning which politician is saying one thing and then voting against that very same thing in Congress. In our careers, it’s the ability to look at our processes or products and see their faults and blindspots, and how to determine how we can make them better.

Traditional Literacy: The ultimate bedrock, you have to have this for literally every field of study. You have to be able to read. You have to read. If you can read, you can learn literally anything. Rocket science. Traditional Mandarin. Global trade economics. Advanced calculus and quantum physics. How to avoid dysentery in Oregon trail (and real life!). Reading more also immediately makes you a better writer, and if you need to know why you should be a better writer, just ask yourself how important personal and professional, or internal and external communication is.

As AI has shown, it’s not hard to write “correctly.” Writing well—well, that's another matter entirely.

Life of the Spirit

When I say reading is important, it really is important. But don’t hold unrealistic goals. You can’t just read textbooks. It gets boring and carries a heavy cognitive cost. A good investment, sure, but you can’t do it all the time. Read a magazine. A pulp fiction novel. A comic book. A biography of someone you think is cool. If you’re religious, pop out that sacred text for a devotion. It’s about rounded fulfillment. It’s about comprehensive learning. Comprehensive reading and comprehensive experiences are where your breakthroughs come from. They’ll arc through your brain like heat lightning and hang like cobwebs under moonlight. The integration of ideas and experiences are where innovation is born and the soil from which it thrives.

And speaking of integration, it's predicted that AI and small business models are the next big wave in the tech industry, potentially capturing as much as 37% of venture funding in the near future, according to CB Insights.⁶ For a while, in the professional corporate landscape, upskilling, re-skilling, broad-skilling were recommended, but not always necessary. But AI is here and it’s here to do the mundane work. It’s here to man the oars, and hold the helm. Now, it’s time for everyone to become captains. To think comprehensively. Metaphorically, we once again need people who know how to fair a horse, build wagon wheels, make butter, hunt, and to sew. To build structures for tornadoes and long winters. To treat dysentery.

Unsurprisingly, in the world of frontier technology, we need pioneers once again.

*All the sections in this article are modeled and named after the sections in the Chautauqua journal, each representing one of the pillars of the Chautauqua Institution.

Sources:

1. Hull, A. (2025, August 3). Future-proof your career. Star News, pp. 3C-3C.

2. Richard Buckminster Fuller. Operating Manual for the Spaceship Earth. New York, Simon & Schuster, 1969.

3. Whitman, Walt. Leaves of Grass (1) and Democratic Vistas, by Walt Whitman. [Introduction by Horace Traubel.]. 573, Everyman’s Library ed., London, JM Dent & Sons, 1912, pp. 194–197.

4. Publishing, Harvard Health. “How Aging Affects Focus.” Harvard Health, Harvard Medical School, 24 June 2021, http://www.health.harvard.edu/staying-healthy/how-aging-affects-focus .

5. Vignjević Petrinović, Sanja, et al. “Interplay between Stress and Cancer—a Focus on Inflammation.” Frontiers in Physiology, vol. 14, no. 1119095, 20 Mar. 2023, http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10067747/ , https://doi.org/10.3389/fphys.2023.1119095 .

6. CB Insights. “State of CVC 2024 Report.” CB Insights Research, CB Insights, 4 Feb. 2025, www.cbinsights.com/research/report/corporate-venture-capital-trends-2024/.