Upon Consideration is an audio-first project exploring the fantastical relationships between the Caveman, the Robot and the Optimist.(Other topics include New York City, photography and current news.)
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Edited and published by Wil Anderson. New York City.
Part of The New Communicate, LLC → Book your free GTM review.What’s on this site? | Updated: April 2026
Added: January 2026
What’s on this site...
I get easily distracted and frustrated, especially when I get lost navigating a website. Ultimately, this index table might just be for me: Here’s what’s on this site (and a few related details).
| Section | Description | Last updated |
|---|---|---|
| uc | Home page | 2026-03 |
| index | What’s on this site | 2026-03 |
| listener-response | Provide feedback on podcast episodes! | 2025-12 |
| style | Style guide | 2025-12 |
| ty-support-listener | REMOVED | 2026-03 |
| ty | A redirect for email subscribers | 2025-12 |
| more | A little info about little ol’ me | 2025-12 |
| ethics | How I think about ethics | 2026-01 |
| advisory | How I can help (form) | 2025-12 |
| advisory-ty | Advisory request form redirect | 2025-12 |
| listener-support | REMOVED | 2026-03 |
| brand-partnerships | Brand partnerships | 2026-01 |
| thecaveman-therobot-theoptimist | A discussion on theory and beliefs. | 2026-04 |
Added: April 2026
The Caveman.
The Robot.
The Optimist.
Today is April 30, 2026. I am writing this piece in public, which I expect the first draft to be complete by Sunday, May 3, 2026. The first draft, below, is now complete. I'll still send an update on today/tomorrow in my newsletter. I expect to have another update in mid-May.
What's in this story?
The reckoning.
Here's how I spent my weekend:
I believe I have these angles and themes, however they need to be surfaced and positioned so that I can write about them and defend them in every story I write or record.
I want to start with me as a unique and individual person. What makes me tick? Who am I?
I’m looking for my foundational beliefs that impact everything I do.
I want to rediscover my experiences, all known perceptions and emotions to fully comprehend the foundational beliefs that have guided my life until now.
Here’s a file full of articles I’ve written over the last 20+ years. Kindly review the file and recommend three core beliefs or themes based on on the writings from the attached file.
(I'll stop here. However, this process went on throughout the weekend.)
What was I attempting to do? And was I really asking AI (Google Gemini) to help me find my id, my core beliefs or even my katra.
Yes.
However, that's not the only thing I was using. I listened to podcasts and watched videos. I read philosopher notes and stories. I looked at the 1,300+ articles I've published. I read some emails. I had a deep conversation with my wife.
I just couldn't get there.
(Much like internet searches, AI and human interactions, it's how the question is phrased. I was not asking the question clearly.)
How did I reach Monday with a spud of an idea?
I took everything together and sat (and walked) with it.
My aha! moment was stripping everything back and digging into the things I like to retell in my own words. Which led me to three individuals...
The Caveman.
The Lindy Effect. (1)
The Industrial Revolution. (2)
Laggards. (3)
We, generally, associate Caveman with time. Or age. Or, specifically, the Stone Age. (4)
However, I tend to think about Caveman thinking as:
"It's always worked like that."
"I don't know."
"That's not possible".
In other words, legacy thinking.
I do believe legacy thinking is important in any decision-making process. In these days, "legacy thinking" may include any discussion that does not involve technology, and more specifically, AI.
I've heard that part of (most of?) the decision that goes into backfilling or adding roles to a department includes this question:
How many tokens are you using?
I'll reiterate: I do not believe there's anything wrong with legacy thinking. It all depends on the context. If part of the decision-making process is "how have we approached this previously?" and the conversation drifts towards "here's how we've always done this...", legacy thinking is critical in evaluating all different approaches.
The option we tend to forget during a decision-making session: 'Do nothing'.
Where the Caveman approach falls within my model: The legacy thinking is the end of the conversation.
Because it's the way we've always done xyz. Period. Full stop.
That's caveman thinking.
The Robot.
Knight Industries Two Thousand: "... the first popular texts to visualize and narrativize the potential of [computer] technologies to transform daily life." (1)
K.I.T.T. was probably my first introduction to computers and robots (and, apparently, AI). And I probably still believe maybe that definition could be how I still look at computers and robots (and AI!) today. At least, what their role should be in our daily lives.
More importantly, computers and robots (and AI!) are visions of our future, both from a dystopian perspective and a wonder-supporting perspective. Here's a piece from that same Wikipedia article:
KITT influenced the design of real-world computers interfaces in motor vehicles; a number of studies found that the science-fiction vision of the 1980s, portrayed in the show, was reflected in real life designs in the early 2000s.
Remember these?
The Lindy Effect.
The Industrial Revolution.
Laggards.
The difference between the Caveman and the Robot: These are stopping points for the Caveman, and starting points for the Robot.
Robot thinking think about how these previous approaches fit into today's efficiency + productivity narrative.
How can what we've learned change or impact what we do next?
Can we rethink the foundational approach using technology?
Should we just start over, using a modern approach?
Back to the Hoff and KITT.
While I wasn't of driving age, I was a passenger in my folks' car. And I could make the connection between what KITT could do and our Mercury Bobcat could not do.
If we were to rebuild the Bobcat today, would we start with the back-then car, then modify it to create our own K.I.T.T.?
Robot thinking would start from K.I.T.T. and create a car for the foreseeable future.
Moody, Nickianne (2001). ""A Lone Crusader in the Dangerous World". Heroics of Science and Technology in Knight Rider", via Wikipedia.
The Optimist.
I am an optimist. I do believe there's something good we can learn from any and every interaction. And if that's the case, it can't be all that bad.
I am an optimist to a fault. I know there are bad/unfair things going on in the world. However we can look at those bad/unfair things as the norm or the exception.
For me: Shit happens. What's next?
I also believe we need to sit in the shit for a bit. To better understand what happened. What was my role in the shit-happening event? What could I have done differently? Could this event have been prevented altogether?
The difference is, I think, my sit-in-the-shit-for-a-bit timeframe elapses much quicker than, possibly, others. Shit happens. And shit will happen again. Let's not dwell on the shit too much when there's so much other good stuff going on in the world. (And, likely, right in front of us.)
More.
I remember this story, I'm pretty sure I heard/read it via John Gruber (1). Paraphrasing: However bad things are, look for the helpers.
When I was younger, we lived in Las Vegas (a TERRIFIC city and region to grow up in). We were in Las Vegas when the MGM Grand caught fire. (2)
It was a terrible event for so many people. And as a kid, watching it on TV, I couldn't understand anything good would come from it.
Look for the helpers.
9/11.
Look for the helpers.
The Trump Administration and Congress testing the U.S. Constitution.
Look for the helpers.
The Trump Administration and Congress is actually an interesting test of the Caveman, the Robot and the Optimist model.
If we view Congress as the Caveman, we can see the Trump Administration as the Robot: a force designed to shake the system and test the Constitution in modern terms.
Shaking things up.
Testing the Constitution in today's terms.
Shining the light on stuff we've generally just let politicians manage.
Viewing the Trump Administration as the Robot (modernizing a very old approach to politics and government standards) can be seen as the antidote to legacy thinking. (3)
This approach clearly tests the role of the Optimist:
Do we feel like we're in a better place than we were ## years ago?
Is this the culture we want to live in?
Do we care about America's standing in the world?
I was a computer-then-network administrator in Silicon Valley a bunch of years ago. Part of my responsibilities included ensuring our users (our customers) were happy with the day-to-day use of their computers.
The biggest challenge I had was keeping up with bad actors. Making sure our users were safe and our systems were secure.
There were a few very late-night-turning-to-early-morning days due to new variants being released. (I worked with a global chip manufacturer with a very large, Seattle-ish client who was releasing new game hardware. If we were impacted by bad things, we'd be in big trouble.)
If you asked the optimistic me then, I wouldn't have a problem with those late-nights/early-mornings. Without those bad actors, we'd likely get lazy in how we approach all computer-related things.
(Welcome to Silicon Valley.)
Of course, the super-optimistic me would argue we should live in a world where there are no bad actors, and all efforts should be put towards making our lives the best they can be while we're here.
(Since we live in a capitalist society, the practical-yet-optimistic me chuckles a tiny bit.)
The Robot.
The Caveman.
The Optimist.
This reckoning has been reckoned with.
MGM Grand fire, via Wikipedia.
The challenge/problem with this approach is that Trump and his team are liars. Not that they are incompetent (they are) in their roles, rather they are incompetent in the basic approach to management, communications and transparency.
Added: December 2025
From listeners like you.
One of the best parts of this project happens off-mic.Listeners call or text with questions, disagreements, stories and reflections sparked by individual and specific episodes.A few responses will be read in the next episode, and all feedback will be added here. This page acts as a small, anonymized window into those conversations. An open, true community.
How to participate
If you want to respond to an episode, simply:
Call or text 347-694-5202
Leave a voicemail or send a text message
Kindly include your first name, the city you are calling from, the episode you are referencing and your message
Note: By leaving a message, you’re giving permission for excerpts to be referenced anonymously unless you explicitly say otherwise. Not every message is shared. All messages are read or listened to.
Updated: December 2025
Style.
Calm authority with deliberate restraint.Upon Consideration speaks with confidence, not volume, earned through experience and time. Every word, pause and audio/visual choice exists to create space for thought.Design rule of thumb: If an element doesn’t clarify, it should disappear.Below is a directional style guide.
Typography
Headline: Outfit
Paragraph: Inter
Colors
Deep navy: #0E1A24
Off-white: #E8E5E1
Muted orange: #D2792B
Accent gray: #3A4853
Logo
Minimal stacked monogram
Evokes slow reflection
No iconography, no flourish
Negative space is my friend
Updated: December 2025
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Updated: December 2025
Hi. I'm Wil.
We moved often while growing up, and every new town taught me to quietly pay close attention. To listen first, read the room and align signal from noise.That skill – separating and aligning the real from the rehearsed – became the through line of my career (and my life).I was the first in my family to graduate from college, earning a degree in Business Computer Telecommunications and later an MBA in Marketing. I built a career in technology, leadership and communications – helping organizations bridge people, processes and tools so they could actually get things done.What I learned, though, is that most companies focus on efficiency while neglecting alignment. They talk about innovation but forget about the people who make it possible.That imbalance – between people and the systems and businesses they work inside – continues to fascinate me.So I started documenting what I saw. Writing. Recording. Walking. Reflecting. Trying to understand how work could feel both productive and human.Upon Consideration… is where that reflection lives – a space for slowing down, connecting ideas and finding the confidence to make change.I’m not a guru or an expert – just someone who’s seen a lot of change and learned how to navigate it. My hope is that what you find here helps you rediscover the confidence to make change, too.
Where else you can find me...
Agency: The New Communicate, LLC
Alex: AI Decision Governance
Photos: Wil Anderson Photography
Own your place on the internet: A Box of Corn Dogs
Do something: Don't Do Nothing
Nice things good people say...
Smart, thoughtful and caring colleagues have helped shape who I am as a professional and as a person. I take great pride in the following testimonials.
CEO: “Thank you for everything. You were instrumental in transforming the company’s marketing efforts.”
VP, Enterprise & Wholesale Business: “In addition to Wil’s excellent communications skills, he also demonstrated exceptional business development skills. He was responsible for identifying and pursuing new business opportunities, with his efforts leading to significant revenue opportunities and outside funding for priority projects.”
Director of Strategic Partnerships / Enterprise Networking & Digital Workspace: “One of Wil’s most impressive accomplishments was revolutionizing how the company communicated with its customers, partners and key stakeholders. Wil brought in new vendors and aligned his team to better handle the responsibilities of a modern and powerful communications team. His leadership and change management skills are commendable, navigating a sometimes challenging environment while consistently executing projects.”
Enterprise Retail Manager: “From email campaigns to online and in-person events, Wil used innovative and effective tactics to attract new prospects and nurture them into loyal clients. One of Wil’s most impressive characteristics is his ability to calmly absorb nearly any request and turn it into an actionable, successful project.”
Channel Development Manager: “One of Wil’s most impressive characteristics is his ability to get things done across departments and companies. He has a knack for bringing people together and aligning their efforts toward common goals. He is skilled at identifying the strengths and weaknesses of different teams and individuals, and his ability to leverage these strengths was critical to our success.”
Assistant Director: “Wil and his team continually exceeded my expectations, delivering clear messaging in innovative ways that helped secure long-lasting clients. His combination of deep technical knowledge and ability to turn complex data into CxO-level, creative communications would ensure any business attracts and keeps high-value clients.”
Vice President: “Wil was a key contributor in modernizing our company’s culture and marketing mix in a very short time period. From brand identity to lead generation and marketing operations initiatives, Wil was a great asset to the growth of our company.”
Product Manager: “I worked with Wil for more than two years and in those two years, I saw him transform the marketing and communications functions into a data-driven organization delivering innovative and creative projects.”
Assistant Director: “With Wil’s unique combination of technical know-how, management, and ability to implement new processes, we deployed a communications platform that allowed us to create deeper, long-lasting relationships with key clients.”
Project Engineer: “Wil brings a lot of experience and manages a great team that continuously puts together amazing campaigns that draw attention and has helped make our company successful. One of the kindest, hardworking people I know.”
Media
Upon Consideration... is a website, newsletter and podcast created by Wil Anderson, a communications leader, strategist and two-time kidney transplant recipient.With more than 30 years of experience across business, tech, and operations, and an MBA in marketing and a BSc in Business Computer Telecommunications, Wil brings a grounded, thoughtful approach to leadership and life. His writing and voice help audiences slow down, focusing on what matters while leading with intention.For media inquiries: [email protected].
Updated: December 2025
Ethics.
Upon Consideration... is an independent media project supported by its listeners and sponsors. I strive to maintain the highest standard of professional ethics.
When I make a mistake, I strive to correct the error promptly and disclose the correction.
I maintain the anonymity of any source when asked to do so.
I do not accept payment to write about any company.
I may run ads from sponsors in articles and podcast episodes. Companies I cover are not eligible to advertise, and sponsors have no editorial control what I write about.
Upon Consideration... content is hosted on Carrd.co.
The Upon Consideration... domain is hosted on Cloudflare.
I use Mailchimp for all email automation correspondence.
I use Libsyn to host my podcast files.
I will disclose whenever I use artificial intelligence (AI) for my articles, linking to the specific AI tool and prompt when that tool was used for my articles, pages and podcast.
I welcome comments on how this Ethics statement can be improved.
I used The Platformer Ethics to create this Ethics statement.
Please send comments about this Ethics statement to [email protected].
Added: December 2025
Advisory services: How I can help.
In some cases, listening turns into conversation.
I work with a small number of individuals in an advisory capacity, typically leaders, founders or senior communicators navigating moments of misalignment, transition or complexity.This is not coaching and it’s not therapy. It’s structured thinking enablement, grounded in real constraints. Most advisory relationships begin informally and evolve only if the mutual fit and outcome is clear.
How advisory work functions
Limited availability
No fixed cadence
Async voice or text first
Optional calls when useful
When advisory work is most beneficial
Decisions with reputational or organizational weight
Leadership transitions
Strategic clarity under pressure
Communication breakdowns
Lack of alignment and ownership between Sales, Marketing, Product
Let's talk
If you’re considering advisory work, send a short note outlining:
The context
The decision you’re facing
Why now
I respond to every message. There's no obligation from you. I cannot guarantee availability. I do not share your information with anyone.)
Added: January 2026
Brand partnerships
Upon Consideration is a weekly signal for leaders noticing when decisions quietly start to lose shape.Brand partnerships are limited, editorially independent and designed for organizations that value judgment over volume.
Approach
Upon Consideration partners with a small number of organizations whose work aligns with thoughtful decision-making, operational clarity and long-term judgment.Partnerships support the newsletter and podcast and appear only as brief acknowledgments, not advertising.Editorial independence is non-negotiable.
What partners receive
A short, host-read acknowledgment in the newsletter and podcast
Association with a senior, reflective audience
Consistent presence without performance theater
Acknowledgement examples
Email newsletter
This week’s issue is supported by [Organization], a team focused on helping organizations make better decisions under complexity.Learn more at [Organization.com].
Podcast
This episode is supported by [Organization].They work with teams navigating complex decisions and long-term tradeoffs.Thanks to [Organization] for supporting Upon Consideration. For more information, see this episode's description.
Partner plan
One exclusive partner per calendar quarter
Payment and assets confirmed two weeks prior to start
I have final approval on all messaging and links
Each quarterly partnership includes:
15 newsletter acknowledgments
6 podcast acknowledgments
Sponsor listing on uponconsideration.com
Audience
Upon Consideration is consumed by senior operators, founders and leaders working through growth, complexity and organizational change.Audience size is not built for scale. Building trust is the priority.
Next steps
If this sounds aligned, email [email protected] with a brief note about your organization and why the partnership feels relevant.
Added: December 2025
I've received your message!
Thank you for contacting me.
A quick reminder...
I respond to every message (usually within 48 hours)
There's no obligation from you
I cannot guarantee availability
If you are interested in a dedicated, retainer-based services, learn more about my agency, The New Communicate, LLC.