Two Roads Diverged In A Digital Wood

And I am trying to decide which road to take. In the spirit of Robert Frosts poetic words, in celebration of the fact that I'm lucky enough to have choice and options, I would like to take the one less travelled. (Full poem linked below, because I think it's always an inspirational read). My intent is that this introductory blog post starts me down the less travelled path towards a more fulfilling career that deviates from the path I've been on for the past 20 years. I've sometimes leaned towards chasing higher compensation and looking for startup options with big payouts. And while I've been successful in chasing, after more than 20 years I'm finding it less than fulfilling and harder to keep motivated. The teams are great, the products are innovative and the markets are challenging so I have no reason to complain - and I'm not. But as I mature in my career I'm thinking more and more about how I could be putting my experiences and skills to better use than tweaking features on niche software used by billion dollar corporations.

The Road Not Taken
By Robert Frost

Two roads diverged in a yellow wood,
And sorry I could not travel both
And be one traveler, long I stood
And looked down one as far as I could
To where it bent in the undergrowth;

Then took the other, as just as fair,
And having perhaps the better claim,
Because it was grassy and wanted wear;
Though as for that the passing there
Had worn them really about the same,

And both that morning equally lay
In leaves no step had trodden black.
Oh, I kept the first for another day!
Yet knowing how way leads on to way,
I doubted if I should ever come back.

I shall be telling this with a sigh
Somewhere ages and ages hence:
Two roads diverged in a wood, and I—
I took the one less traveled by,
And that has made all the difference.

As I considered my career to date, I reflected on what I've learned and what things I have experience with that are valuable enough to share with others. Not just share, but ideally provide others with a means to become more successful in their own endeavours. I'm a fairly humble person, but my personal assessment is that I'm particularly good at solving problems. Over the past 25 years, I've specifically focused on solving business problems by building solutions using technology. What I think is also somewhat unique to my experience, is the breadth of technological change and innovation that has occurred in my lifetime to date. My academic and professional career have brought me on a journey that went from Pong and Early PCs through the Internet, Email, the first Smartphones, the first social media companies, dot com bubbles and great financial crises, self driving automobiles, virtual and augmented reality, gene editing, artificial intelligence and now the rise of drones, AI and cyber warfare.

My early interests led me on an academic path in math and computer science, and a career path in startup and small tech companies across a variety of industries and markets. I was particularly drawn to money markets - not in the short term lending sense, but any transactional market where money changed hands. I built mobile wagering engines for poker, sports betting and mobile & contactless payment applications, currency exchanges and trading platforms, day-trading algorithms, and even the demand and supply side of ad networks building programmatic media buying tools and ad optimization engines. I've worked with investment managers who traded hundreds of millions daily, algorithmic day traders who traded millions in microseconds, economists who spent decades analysing economic patterns and geopolitical influence and media buyers who spent millions on algorithmically optimized social campaigns. While I can't claim to be good at betting, investing, trading or media buying I can confidently claim that I spent years understanding the intricacies of these markets in great detail, learned from some of the people who were best at what they did in their respective areas of expertise, and I've learned a great deal in my journey.

I spent the first half of my career coding and designing software as an individual developer and architect to leading small teams as a co-founder or CTO. The latter half of my career was still spent building things, but more as a product designer and business architect as I worked as Product Manager, Director, Chief Product Officer and Co-Founder across a number of markets and products with a problem solving focus more on user personas, jobs to be done, optimal workflows and easy adoption of business solutions.

So where does that leave me? I want to put my skills towards something that has a positive impact on our community. And it has to be something I'm passionate about to ensure I'm committed to following through. I've always loved the idea of Ikagi: (生き甲斐, pronounced "ee-kee-guy") is a Japanese concept that means "a reason for being" or "a reason to live"34. It combines two Japanese words: "iki" (生き) meaning "life" and "kai" (甲斐) meaning "worth" or "value

If I consider what the world needs, and to be realistic I narrow my 'world' to the locations or communities that I think I'm able to reach and impact. In terms of what the world needs, I think alot of the next generation may struggle to find employment or lack direction on how to navigate these potentially turbulent times economically as compared to how life has been (in North America). In terms of what I'm good at, I think I have a good perspective on where technology is going, how it might change economic and job markets, here the future demand for work might be and how you can prepare for that future. What I love could be many things, but I enjoy building things with technology and I love helping people learn new things. By no coincidence, I've also spent a career geting paid for building things with technology or consulting in product and technology. I've had the pleasure of teaching computer science university labs, teaching kids math, speaking at conferences and events and leading teams of both product and technology experts in complex systems.

So the decision I'm dancing around is to diverge from the path in front of me that is more well worn, and take the one that is grassy and wanting wear. Instead of continuing to lead Product and Technology teams at startups or big tech companies, I would rather spend my time trying to teach others in my network or community to position themselves for future success in our ever changing digital world where machines and software will rapidly start overtaking simple and low risk jobs that humans perform today. In an ideal situation, money wouldn't be an issue and I could make it as free and open as possible. I'd also like to focus my efforts on communities or areas that historically struggle to get access to the latest technology that can deliver a better education experience.

Where does it start? It starts with this post. My goal is to start by writing - by sharing my experiences across a mix of mediums to get a better sense of what people most need help with and what formats are most effective for them. Of course, my area of expertise will be limited to what I know - But I will...

My goal is to share what I've learned, (and continue to learn through shared research and application) with others who want help learning how to design, build or launch a new product or services business around their personal domain of expertise.

Practically speaking, I plan to share my product development research, analysis and experiences with entrepreneurial minded people who are looking for help taking a product or business idea from conception to operation. The innovations available since the launch of chatGPT and Generative AI technologies have made it easier for an individual or small team of people to build digital products or remote services alot easier by using AI to automate or supplement some of the recurring tedious tasks or even specialized expertise that is critical when launching or running a small business.

What's In It For You?

It starts by me creating material that I hope is valuable to every level of builder out there. Content will be very focused on areas I feel experienced in (product management, computer science, software systems & financial systems) as well as areas that I'm still exploring, researching and learning about (generative artificial intelligence). Part of my journey will be sharing my exploration of switching to an AI mindset when it comes to building a career or business around technology products or services. The goal I have in mind may not be entirely possible at the start of my journey, but I expect it to rapidly evolve and the only way to stay ahead of the curve is to study it and put it into practice so you can learn where to improve and excel. The format I have in mind for sharing this includes a mix of:

• Personal research, analysis and opinions on building a personal service or business by using AI to manage all the tedious tasks and allow you to focus on what you are good at. (To achieve your own Ikagi). This will mostly be in article or blog format, with conversions into podcast format.
• Tutorials, Demos and How-To's when I come across some compelling tools, technologies or novel ideas for tackling common problems or automating regular tasks. This may be a video tutorial, article, presentation, hands-on exercises and accompanying source code or open source artifacts that let you try it for yourself at minimal to zero cost.
• In Person Events, Training and Consulting is something I may need to do in order to pay the bills. If money becomes a non-issue I would love to expand my reach and travel to areas or communities that are most in need, and do it at no cost. But until that happens, I will try to achieve a balance of in-kind in-person services vs. paid work.
• Paid Jobs or income generating opportunities for people who achieve the skills that are required for next generation of technology product development. If I'm truly good at what I do, then I will hopefully be good at finding business opportunities as the world transitions to new AI tech, and pairing those opportunities with people in the community of builders and learners I hope to foster.
• Open Source Products supported by Commercial Services. Similar to my statement above, if I'm truly good at what I do, then I may be able to quickly build or compose novel products and make them available to anyone who finds it valuable. These might be prototypes I build as Tutorials or based on research, but if I've been able to build something people want then I will happily make it open and try to maintain it for others to try. If there is demand, and supports a commercialization effort I would love to have community members participate or operate if interested. (Think ghost or strapi like model to offer SaaS hosting of open projects).

To put a finer point on it, a focus of my research and prototyping is to try and build a suite of software applications and tools that essentially provide me a team of AI agents that are focused on specific areas of product development (UI design, system design, development, testing, deploying) and eventually business development (as in taking your product or expertise as a service and developing it into a full time business). I envision a one to five person business operation among family or friends that can operate at millions of dollar annual revenue at a very efficient rate (high profit margins). I anticipate some of my potential audience will already have a unique skill or expertise and just need help creating a product or service around it and automating aspects of a small business operation focused on themselves. Another audience will probably just be seeking the core skills to be competitive in an ever changing job market, and I hope some of the basic builder content and references will help people in the earlier stages of their career.