Curiosity Exploration - An evolutionary approach to lifelong learning

Updated: Aug 17


Like many of us, I was born curious. My parents told me stories of my natural and intensive curiosity. How I relentlessly asked questions when I was young. My parents were loving and caring people, but even they had limits as to how much of the day they could spend answering my questions. Finally and probably out of desperation, they bought me a set of “Tell Me Why” books. I remember spending hours with these wonderful books, asking and answering my own questions. For me, “Tell Me Why” was my first Google. My initial approach to exploring the world.

Today, I am an insatiable and broad reader. I genuinely enjoy reading different topics. Even during the pandemic, when travel is limited, I find I can travel the universe and across time, on the wings of a good book. Rene Descartes’ saying rings true for me,

“The reading of all good books is like a conversation with the finest minds of past centuries.”

This article shares my approach to fulfilling my curiosity. The article starts with my background and personality, to help you understand my motivation. Then, I share the technical approach used to satisfy my curiosity. I’m sharing a curiosity-enablement method that works for me. I hope that my approach will be helpful to you, as you make your own curiosity exploration journey.

This article is presented with the following sections:


Curiosity Exploration Approach

Curiosity Exploration Method


Notes- Examples and musings for Curiosity Exploration

By way of background, I am an academically trained economist. My educational background includes Mathematics, Finance, and Economics. Not long ago, a friend of mine (a Ph.D. Economist), explained to me the difference between a data scientist and an economist. He said the data scientist wants to understand HOW different data are related and drive some predictive outcome. The economist is similar in the desire to use data, except, the economist’s passion is for WHY certain outcomes occur. That was the day I truly understood why I like economics!

From a personality standpoint, I am a dot connector. In the language of the Meyers-Briggs personality type, I skew toward the “Intuitive” as opposed to a “Sensor.” This means, among other things, I am very comfortable with the counterfactual. I can easily move between topics and utilize partially complete information to forecast the future. I see the future as dimensionally available. By our choices today, we have the ability to influence future outcomes and our place in those outcomes. By connecting the dots, I enjoy taking seemingly disparate topics, bringing them together, and driving unique “why” insight. The following is an example that “connects the dots” between math, science, economics, and investments.

I like learning about chaos theory and fractal geometry. This includes the understanding of how fractals relate to nature, like fluid dynamics or the biology of trees. There is a short leap to physics and how fractals relate to inertia, momentum energy, entropy, and the atomic dependence of nature. From there, the analog to financial markets is powerful, where fractal geometry can help explain the uncertainty associated with quickly changing financial markets. Especially, as the market transitions from a lower volume, low inertia, low entropy state to a higher volume, high inertia, high entropy state. This is especially true in a phase change analog, similar to the physical phase change transition from ice to water. Ultimately, securities price volatility is better explained by fractal geometry than the overly simple variation models described by traditional statistics, like standard deviation. Thinkers like Benoit Mandelbrot will be hailed as one of the geniuses that figured this out, once the rest of the world catches up in about 50 to 100 years!

So, what did I do as a result of these connected dots? It has informed my overall investment approach in terms of risk-taking and time frames, to name just a few investment considerations. Please see my Investment Thoughts For My Children article for a summary. The evolution of my investment approach is based on both theory and practice. In general, I regularly experiment with a number of different curiosity exploration approaches. For me, it has evolved based on both theory and experiment. The following section describes my general approach.

So what is my approach to learning? How do I feed my “always-on” curiosity engine?

Curiosity Exploration Approach

First of all, I am a big fan of the Kindle and eReaders in general. I understand this is controversial for book purists. Many accomplished people prefer paper books. N. N. Taleb comes to mind as a paper book purist, he has many valid reasons….just different than mine.

The next section describes the stepwise creative method to my curiosity enablement. This is accomplished via reading, thinking, connecting the dots, writing, editing, experimenting, and practicing. It is an evolutionary process that can be described as a heuristic learning spiral (please see the graphic). My approach to learning is facilitated via a biological evolution-like model, including trial, error-correcting, and action updating processes. The learning spiral uses reasoning associated with both Deduction (like theory development) and Induction (like theory testing and updating via practice and experience.)

I am reminded that understanding “why” (causation) requires doing. It is hard to understand “why” only through observation (correlation). See my 4/26/21 note regarding the Ladder of Causation. My experience suggests curiosity fulfillment is a balance of theorizing and doing. Physicist Heinz Pagels said:

“The relationship between theory and experiment is like a dance in which sometimes one partner leads and sometimes the other.”

Curiosity Exploration Method

The following provides the step-by-step method for my curiosity exploration process. This has been evolving throughout my life, especially as new technologies become available.

  1. Utilize the Kindle to collect and read books and articles of interest. The Kindle is very light, easy to carry if you are a business traveler (as I was before the pandemic). Books of interest vary, based on my fancy or current interest. Sometimes I cluster reading books around a particular topic, sometimes I jump to a different topic not visited in a while. Also, I will load articles and other PDFs onto my Kindle. In this section “books” are referring to a broader set of information resources, including books, research papers, podcast transcripts, etc.

  2. Most important, as a dot connector, is having ready access to my entire library. The speed at which I can cross-reference is very helpful to draw connections between my thoughts and ideas found in different books. Sometimes a “connected thought picture” is ephemeral, so checking references while the connected thought is “front of mind” is helpful. Sometimes a dot connection occurs from a catalyst. An good example of this occurred as a result of the January 2021 attack on the U.S. Capitol. This article was catalyzed by the attack. The article almost wrote itself, I was more like the vessel. Sometimes a dot connection is made out of the blue. Perhaps, this occurred after my subconscious had been working on a problem. My subconscious does not give any forewarning for when it will provide a solution. So having my thinking tools at hand is very helpful. (The Notes section references Alexander Hamilton’s related approach to engaging his subconscious)

  3. I manage my thinking at the idea level, not the book level. As such, I view books as nodes in an information web to support ideas, not as a stand-alone entity. The Kindle facilitates accessing this web of ideas.

  4. I am a book curator. I am very careful only to read books that meet my broad but picky needs. I am also quick to “fire” a book if I discover it is not what I expected. For example, I am a big fan of Yuval Harari and his books Sapiens and Homo Deus. As such, I expected his book 21 Lessons for the 21st Century to be just as good. It wasn’t for me. I found some of his lessons to be simplistic and not researched as deeply as I expected. As such, I stopped reading the book about 20% of the way through.

  5. I find annotation much easier in a Kindle. An annotation is like a dot generated from some previous idea and maybe the starting point for a dot that will ultimately get connected to future ideas. If I am really into a book, I have been known to create 100s of annotations. Some of these annotations will find their way into articles as described later in this article.

  6. I use OCR-based automation apps as a way to efficiently capture annotation or related reference “dots” and to make them available for the articles. Naturally, I make sure all captured information is properly attributed.

  7. I write articles on an ongoing basis. I keep these articles organized in my cloud google drive account. I have thousands of entries. Some are a paragraph long, some are 10+ pages. Each article grows organically, as I learn and connect the dots between topics. What is important here is that I do not get too hung up on initial article length or quality, I just put my thoughts down or refer to ideas. Over time, though, I find ideas naturally grow in their own way and at their own pace. I do spend more time editing as my ideas crystalize. However and to emphasize, this is a natural process, nothing that is forced. I can leave topics for years and then find my way back to them. Or, sometimes I will get intensely interested in a topic and I will spend more immediate time thinking, writing, and editing.

  8. I do have a paper book library. I rarely read the paper version and prefer reading the same book on my Kindle. A good question would be, “well Jeff, then why the heck do you have a paper book library?” This is because: a) I see a finished book as a bit of a trophy, like an accomplishment worthy of some bookshelf recognition. b) I like books aesthetically. They make me feel good when I’m in my office. They are like good friends that I care to be around c) I keep extra books as gifts for others. d) As a hobby, I enjoy shopping for books at thrift shops and online used booksellers. Happiness is finding a good hardback at a deeply discounted price! (Yes, admittedly, I’m a practicing Econ geek.)

  9. I do keep a spreadsheet inventory of all my books. This has been made pretty easy by apps, library APIs, and ISBN code scanners. This way, if I’m at a bookstore, I know whether I already own the book. See the attached file at the bottom of this article for the latest inventory.

  10. Based on my learning, I will generally develop experiments to confirm an idea. One example is work I and several collaborators are doing on improving the college decision for high school students. Please see my article for more information: The College Decision - Framework and tools for investing in your future. I appreciate climbing the learning spiral with both induction and deduction.


Curiosity exploration is one of life's great pleasures, along with faith, family, and friends. Beyond our formal education, curiosity exploration is an expression of lifelong learning. (see the 12/20/20 note) My belief is, rarely are people born to do some specific grand pursuit. Much more likely, by following persistent curiosity exploration, we will receive both great pleasure and personal fulfillment. Curiosity enables us to adapt to our environment and to provide for our society. And, maybe, the grand pursuit will find us as our curiosity is revealed!

The approach and method described here is one I found organically that works for me; my personality, my comfort with technology, my skills, and my interests. I encourage you to consider your approach to curiosity exploration. It is truly one of life’s greatest gifts.

Notes - Examples and musings for Curiosity Exploration


I am in the process of standing up a website called “The Curiosity Vine.” This will be an idea incubator to engage others in curiosity exploration and to share relevant writings. I have some students at JMU helping with this project. This George Dyson quote from his book Darwin Among The Machines seems fitting for the Curiosity Vine project - “Human creativity is the recombination of ideas.”


A passage about Thomas Hobbes written by John Aubrey. Perhaps this approach to curiosity exploration is very Hobbesian?! Imagine if Hobbes had access to the cloud!

“He walked much and contemplated, and he had in the head of his Staffe a pen and inke-horn, carried always a Note-book in his pocket, and as soon as a notion darted, he presently entered it into his Booke, or els he should perhaps have lost it.” - John Aubrey about Thomas Hobbes

Similarly, David Epstein wrote of Charles Darwin in Range:

“He cut up their letters (from other science people) to paste peices of informaton in his own notebooks, in which ’ideas tumbled over each other in a seemingly chaotic fashion.’”


For me, education is a multi-faceted process. I see people sometimes conflate these facets. As a way of explanation, there are 2 major segments for the educational process:

  1. Formal education - this provides the base organization process of the brain. This trains the brain how to learn and is usually provided earlier in our life. In fact, the information that is provided via formal education is more exemplary as an aid to the heuristic process.

  2. On-going education - this is the process of increasing knowledge and its application. While the brain improves its ability to learn after the first segment, the primary purpose of segment 2 is mental expansion via knowledge acquisition and practice. This is the process of learning throughout one's life.

I find it interesting, in most societies, much more emphasis is put on the first than second segment. As the speed of technology change accelerates, more emphasis on segment 2 seems warranted.

The value of 3rd party teachers varies and depends on a person's learning style. For me, I tend to learn best as an autodidact. As such, my ongoing education comes mostly through self-driven study and practice. I do believe 3rd party teachers are most important in the first segment. I see the value of quality teachers related to child motivation during the initial Formal Education step. The confidence to learn, the love of learning, and the discipline to learn are most important. With that motivation, an individual can be a successful learner within both segments. My wife is a tutor and life coach. While Patti is very smart, her strength is not teaching rote knowledge. She has an amazing ability to inspire learning confidence, love, and discipline in her students.


Alexander Hamilton was known to be a brilliant autodidact. One who lived his life in a consistent state of learning.

Following is a passage from Chernow’s Hamilton biography. Truly a great example of intelligence and collective learning.

“Hamilton developed ingenious ways to wring words from himself. One method was to walk the floor as he formed sentences in his head. William Sullivan left an excellent vignette of Hamilton’s intense method of composition.
‘One who knew his habits of study said of him that when he had a serious object to accomplish, his practice was to reflect on it previously. And when he had gone through this labor, he retired to sleep, without regard to the hour of the night, and, having slept six or seven hours, he rose and having taken strong coffee, seated himself at his table, where he would remain six, seven, or eight hours. And the product of his rapid pen required little correction for the press.’” - Ron Chernow about Alexander Hamilton

Hamilton had an impressive understanding of his own neurobiology. The importance of sleep as a cognitive processing bridge from intensive introversion to intensive extroversion.


Judea Pearl, in The Book Of Why does a nice job of describing the importance of causation in terms of a ladder. Causality needs to get to at least the second rung of the causation ladder, whereas correlation is only at the first rung.


I have come to see Sal Khan and the Khan Academy as a great ally in curiosity enablement. His book, The One World Schoolhouse, Education Reimagined is a nice presentation of his ideas. He and his organization have done a great service to changing our outdated education system. His goals for Khan Academy are on point:

“I hoped to help students see the connections, the progression, between one lesson and the next; to hone their intuitions so that mere information, absorbed one concept at a time, could develop into true mastery of a subject.”


Johannes Kepler, the great astrophysics of the 14th and 15th centuries, is an archetypical curiosity exploration example. His approach inspires. The following is a quote from David Epstein’s book Range:

His fastidious documentation of every meandering path his brain blazed is one of the great records of a mind undergoing creative transformation. It is a truism to say that Kepler thought outside the box. But what he really did, whenever he was stuck, was to think entirely outside the domain. He left a brightly lit trail of his favorite tools for doing that, the ones that allowed him to cast outside upon wisdom his peers simply accepted.

Jeff's Book Collection 8_15_21
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Your Personal Finance Journey Guide:

Core Concepts

1. Our Brain Model

2. Curiosity Exploration - An evolutionary approach to lifelong learning

3. Changing Our Mind

4. Information curation in a world drowning in data noise

Making the money!

5. Career choices - They kept asking about what I wanted to do with my life, but what if I don't know? - Part 1

6. Career choices - They kept asking about what I wanted to do with my life, but what if I don't know? - Part 2

7. Career success - Success Pillars - Maximizing luck with an adaptable mindset to reach your goals!

8. Career choices - Do I need to be a Data Scientist in an AI-enabled world?

9. Career choices - Diamonds In The Rough - A perspective on making high impact college hires

Spending the money!

10. Budgeting - Budgeting like a stoic

11. Car Buying - Auto buying and financing thoughts from a Behavioral Economist, a Banker, and a Dad

12. College choice - The College Decision - Framework and tools for investing in your future

13. College choice - College Success!

14. College choice - How to make money in Student Lending

15. Event spending - Wedding and event planning guiding principle

Investing the money!

16. Investment thoughts for my children

17. Anatomy of a "pump and dump" scheme

18. The Time Value of Money Benefits the Young

19. How Would You Short The Internet?

Pulling it together!

20. Capstone - The Stoic’s Arbitrage: A survival guide for modern consumer finance products

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