Educated Guesses A Blog Full of Guesses

How I went from wanting to be a writer to absolutely knowing that I am one


There are three things that have helped me make the transition from wanting to be a writer to absolutely knowing that I am one.

1) An ongoing and honest pursuit of self-discovery through self-awareness

2) Using the results of my self-discovery to develop good habits

3) Remembering the advice I gave my 25 year old son Wynton when he was 8 and applying it to myself as a writer.

The first two helped me to hone my craft as a writer, while the third actually sealed my fate of actually being one.


For as long as I can remember I always sought to better understand what it is about me that make me, me. There are certain behaviors that reach back to my childhood that can be attributed to some of my successes as well as my shortcomings.

I have suspected for a while that I was on the Autism Spectrum. Looking back at my childhood, I exhibited some behaviors and idiosyncrasies that would lead someone today to suspect that their child may be on the Spectrum. These include – rocking back and forth, usually in a rocking chair to soothe myself, banging my head against the couch when I was really young, collecting and categorizing things and an obsession with things like numbers and Snoopy.

I understand from my parents that I stopped banging my head against the couch when I was about five. However, I still regularly rock in a rocking chair to soothe myself. I’m still obsessed with numbers – my undergraduate degree is in Economics with a Minor in Actuarial Math. And, my daily uniform of choice is jeans and a Snoopy.  Seriously, all I wear are Snoopy T-shirts.  My bitmoji even wears Snoopy T-shirts, but that’s an entirely different topic that may be the subject of a future article.

Autism Spectrum
I have taken several of the Autism Spectrum tests that I found on the Internet to see just where I might land on the Spectrum. I have scored as low as a 25 and as high as a 30, which puts me very close to being in the inconclusive zone. “The test is not a means for making a diagnosis, however, and many who score above 32 and even meet the diagnostic criteria for mild autism or Asperger’s report no difficulty functioning in their everyday lives.”

I realize that these tests aren’t scientific and being on the Autism Spectrum is not that cut and dried, but going through this process and reading about it has made me realize that there are things about me, my personality and my behavior that are at the very least Spectrum-like.

And I’m absolutely fine with that. As a matter of fact I embrace it.

16 Personalities
Another tool that I came across in my journey of self-discovery was the personality test from This is a variation on the Myers-Briggs test which I took nearly 30 years ago. I remember being an INTP back then and a few months ago I took the test again online and got the exact same result.

The site labels the INTP personality as “The Logician”. The summary of the personality type is spooky because it describes me to a T.

“The INTP personality type is fairly rare, making up only three percent of the population, which is definitely a good thing for them, as there’s nothing they’d be more unhappy about than being “common”. INTPs pride themselves on their inventiveness and creativity, their unique perspective and vigorous intellect.

[INTPs] may appear to drift about in an unending daydream, but [their] thought process is unceasing, and their minds buzz with ideas from the moment they wake up. This constant thinking can have the effect of making them look pensive and detached, as they are often conducting full-fledged debates in their own heads, but really INTPs are quite relaxed and friendly when they are with people they know, or who share their interests.

However, this can be replaced by overwhelming shyness when INTP personalities are among unfamiliar faces, and friendly banter can quickly become combative if they believe their logical conclusions or theories are being criticized.”

The site also lists famous people who have the 16 different personality types. One of the notable INTPs listed is my friend, mentor and fellow writer, Stanley Crouch.

A Circuitous Career Path
In hindsight, this knowledge has helped me to make sense of my circuitous career path.

  • Actuarial Assistant – Providian, Louisville, KY
  • Non-Profit Educational Executive – Lincoln Foundation, Louisville, KY
  • Non-Profit/Arts CFO – Jazz at Lincoln Center, NYC
  • Non-Profit/Arts Producer – Jazz at Lincoln Center, NYC
  • Non-Profit/Arts CEO – August Wilson Center, Pittsburgh, PA
  • Artist Manager/Consultant – GuessWorks, Inc (self-employed)

Throughout my career, I have been able to successfully ride the wave on the continuum that exists between the forests and the trees, or even the leaves for that matter. I’ve enjoyed trying to master both the aerial view as well as the cellular view of things.

I actually attribute this to more of a compulsion than a motivation or desire.  I am very often driven by the need to not only know, but to make connections between knowledge, understanding and hopefully wisdom – the forest, the trees and the ecosystem, if you will.

This compulsion eventually led me to writing as a way to get the thoughts swirling around in my head out into the world. I started writing outside of academic obligation in the early 90’s. I got my first piece published in 1994. Since then, I’ve had several pieces published in various publications. Most of them are opinion pieces spurred on by that compulsive process.

I’ve also co-written a screenplay over a crazy three day weekend where my co-writer and I nearly killed each other. Thankfully we both emerged pretty much unscathed with the first full draft of a screenplay as a memento.

I got bit by the theatre bug as I sat in the long shadow of the spirit of the late Pulitzer Prize winning playwright when I was CEO of the August Wilson Center in Pittsburgh. I wrote three plays over the two-years that I was there. One is a full length play that I obsessively banged out from start to finish in another three day marathon session, but this time I only fought with myself.  I’ve written several short stories and am in the middle of a novel that is a fictionalized version of my late mother’s life – she was a Native Hawaiian born on a leper colony.

The thing that all of these writing projects have in common is that they all came to life when the compulsion muses came knocking, almost always without an invitation or a reservation.

For all of that, I can honestly say that I’ve never really taken writing very seriously. What I didn’t realize until recently was that my I wasn’t managing my writing as much as it was managing me through periodic bursts of creative compulsion and obsession.

This revelation came about 3 months ago when I decided to placed my writing alongside a couple of my other proclivities that I eventually honed into habits.

Developing Good Habits

Shortly after graduating from high school, I became a reverse addict. I stopped eating red meat in 1986. I was inspired by my sister Mary who gave it up for lent that year and was completely convinced after eating an entire bag of breaded steak fingers that put me in a gastrointestinal coma for 2 days.

I gave up alcohol in 1988 when my then fiancé and now wife of 28 years, Cheryl threatened to call off our engagement if I didn’t abstain from drinking – her father suffered from alcoholism. For about 8 years starting in 2000, water was the only beverage that I consumed, no soda, no juice, no milk, only water.

Raw Veganism
I became a vegetarian in the mid 2000’s and took the next step to becoming vegan in 2011. After three year, on July 3, 2014, I weighed in at 207.6 pounds.  I couldn’t believe that I weighed that much. How was this possible. I was vegan!

At that point I decided to take a drastic next step in my dietary lifestyle.  I heeded the wise counsel of my friend and new found health sensei, Doug who was a raw vegan. I took the plunge. My goal was to get down to at least 179.9.  To aid the shedding of the nearly 30 pounds that I wanted to lose, I rode my bike for at least 20 miles a day for over two months. On September 18th I weighed in at 178.8.  Mission accomplished!

So I stopped riding my bike and began to try to maintain my weight by living a healthy raw vegan lifestyle. Over the next four years that lifestyle has taught me invaluable lessons in discipline. I learned how to harness my obsessiveness into healthy habits.

10,000 Steps a Day
Along the way, I replaced bike riding with walking. I set a goal of walking at least 10,000 steps a day for at least a year. I’m happy to say that I reached that goal, albeit with an asterisk. One day I had a little under 9,900 steps. I actually thought that I had reached the goal and took off my tracker to charge it only to find out the next day that I was a little over 100 steps shy. That one stuck in my crawl space for a long time, but I eventually got over it – I think.

To help me to stay on track, I decided to walk for at least an hour every morning. The development of this habit has been beyond beneficial to me in so many ways besides physical health. My walks allow me to clear my mind every morning. They give me a productive and disciplined way to facilitate and harness the “unceasing [thought process that buzzes through the minds of INTPs like me] from the moment [we] wake up.”

This eventually paid dividends in my writing. I’ve come up with many of the ideas that ended up in published pieces during my morning walks.  However, what I later realized was that my writing was not really being facilitated by a regular process or habit but instead it still relied heavily on the compulsion muses.

The problem was that I didn’t have their number, they always found me and when they did they usually kidnapped me for a period of time, forcing me to neglect nearly everything else until they were through with me.  Thankfully, they often left me with a publishable piece. If I’m honest with myself – and I have developed a habit of doing so – I don’t like the quid pro quo.  It’s just too random, unpredictable and ultimately time-consuming at inopportune times.

Journaling Fail
Two years ago I tried journaling to try to bring some order to my writing process. The problem was that the compulsion muses didn’t cooperate so after less than two weeks I just gave up. So I was left to their random whims until about 3 months ago when I finally got fed up and decided to take matters into my own hands.

My Current Situation
After four years, I’m still  vegan and significantly raw. My weight fluctuates between 180 and 183 pounds. I still walk mostly every morning. The difference is that I don’t obsess over my diet and walking like I did when I first got started. They’ve become healthy habits. I can maintain them now without thinking about them.

Why was it that I had failed a couple of years back when I tried to develop a journaling habit?

I’ve read countless articles that advise aspiring writers to write every day no matter what – even at the same time and at the same place if possible. While this made perfect intuitive sense to me, the application of that axiom was difficult.

I thought about completely unleashing my obsessive nature and all of the angst that can sometimes accompany it to force myself to write every day, but I didn’t like the juxtaposition of the two and how it would invariably affect my writing in the end.

First Epiphany
Then an epiphany came to me one morning on my walk. – take the experience and the hard earned and learned lessons from my raw veganism and daily walking from the past four years and simply apply it to my writing. So I downloaded the Day One app and started journaling on July 31st.

I haven’t missed a day since.

The same way that I know that I am going to walk every morning, rain or shine and I know that I’m not going to have bacon and eggs for breakfast when I get back, I KNOW now that I will write every single day. I no longer wait to be compelled by my muses. I simply sit down and write about whatever I want, no pressure.

I must say that my writing has markedly improved. My thought processes are much better, clearer and often more concise, although I still have a tendency to be wordy as evidenced by this very sentence and the article in which it sits.

I’m working on it!

The muses still show up from time to time. They are still very helpful and I welcome them when they come, but I no longer need them in order to write. And, I no longer allow them to hold me against my will.

I’m preparing to write a novel for NaNoWriMo in November. I’ve already come up with a story line and plot, developed the main characters and am currently working on outlines for scenes. Come November 1st I will fire up Scrivener and meet my writing goal for 30 days. I’m not sure if the end product will be a literary masterpiece or something that I will even want to read myself, but I do know that I will finish.

How do I know this – the same way that I know that if I wake up tomorrow that I will go out for my morning walk and I won’t have a steak for dinner.

Second Epiphany
Not too long ago, I had another epiphany on my morning walk. It was the straw that broke the camel’s back in my transition to wanting to be a writer to absolutely knowing that I am one. I was reminded of an incident that took place 17 years ago when my son was 8 years old.

Advice to My 8 Year-Old Son

My son’s name is Wynton Kelly Stone Guess. He is name after the late great pianist Wynton Kelly and for my friend and former colleague, Grammy and Pulitzer Prize winning trumpeter and composer Wynton Marsalis.  Marsalis has known my son since he was 6 months old. He is like a godfather to him.

My son has always loved music. He started playing violin at age 6 and started piano shortly before we moved to NYC for my job at Jazz at Lincoln Center.  I used to take him on the road with me when I traveled with Marsalis and the Jazz at Lincoln Center Orchestra (JLCO).

One day when my son was 8, we were backstage after a JLCO concert. He was playing the piano.  A gentleman who had attended the concert gravitated to the piano when he heard him playing Scott Joplin’s Maple Leaf Rag. When young Wynton finished playing, the man stooped down to his level at the piano bench and said, “Young man, do you want to be a musician when you grow up.”

10 year-old Wynton Guess paying the piano backstage at a JLCO concert in Connecticut. Proud papa, far left. Photo Credit: Frank Stewart ©

A perplexed look suddenly appeared on his face. He scrunched up his nose, cocked his head ever so slightly to the left and said, “What do you mean, I am a musician.”

Out of the mouth of a babe, came a startling revelation.

Wynton went on to graduate from The Boston Conservatory with a bachelors in Music Composition and from the Royal College of Music in London with a Masters in Music Composition. He currently lives in London as the musician that he has always known himself to be.

Not too long after that backstage exchange I told him that he was truly blessed. “Son,” I began, “Most people spend their entire lives trying to figure out what they want to be when they grow up. You’ve always known what you are – a musician. You just have to figure out how to make your way through life being who you are.”

I finally followed my own advice.

I actually became a writer over 25 years ago. I just never gave myself the license and the liberty to self-identify as one and really believe it.

It was as if I was trying to a writer when I grew up – as if I was waiting for someone to validate me as such.  Because I wasn’t making a living as a writer, then somehow in my mind I didn’t qualify.

What my son intuitively knew about himself for his entire life took me nearly 25 years to come to grips with.

I am many things, but now instead of trying my best to become a writer I now know with certainty that I am indeed one and have been for quite some time.

Now I just have to keep navigating my way through life utilizing the lessons that I continue to learn from self-discovery to try to be the best writer I can be.

About the author

Andre Kimo Stone Guess
Andre Kimo Stone Guess

Andre Kimo Stone Guess is a writer and cultural critic from the Smoketown neighborhood in Louisville, Kentucky. He was VP and Producer for Jazz at Lincoln Center in New York and CEO of the August Wilson Center for African American Culture in Pittsburgh. He now runs GuessWorks, Inc. with his wife Cheryl.

Educated Guesses A Blog Full of Guesses