Welcome to the
Digital Odyssey
This blog explores the collision of imagination, intelligence, and emerging technology. It’s not about chasing trends or hyping tools—it’s about understanding the real shifts beneath the surface. From AI ethics to workflow reinvention, Digital Odyssey documents the journey of those who are bold enough to question defaults, reimagine systems, and shape the future on their own terms.
Rethinking the System Before We Automate It
Why high-velocity organizations start by challenging their assumptions—not just buying better tools. Digital transformation is everywhere. Automation is hot. AI is hotter. Everyone’s racing to move faster, scale smarter, and modernize how work gets done. But too often, companies are doing all of this on top of systems they’ve never truly rethought. Not systems in the technical sense, though legacy platforms are certainly part of the equation. I mean systems in the broader sense: decision-making structures, team dynamics, governance models, and operating assumptions that define how work flows (or doesn’t).
THE ETHICS OF AI: ANOTHER STEP IN HUMANITY'S EVOLUTION
AI didn’t invent knowledge.
We did.
This article traces the real ethical conversation we should be having about AI.
It’s not about fear.
It’s about continuity.
AI learns the same way we always have:
By studying what came before.
Artists do it. Writers do it. Teachers do it.
Machines now do it too.
We’ve been here before:
↳ When writing replaced memory.
↳ When printing replaced scribes.
↳ When digital music replaced vinyl.
↳ When Wikipedia replaced encyclopedias.
Each time, we feared what we were gaining. Each time, we misunderstood the shift.
The Technology Adoption Lifecycle predicts this pattern.
We are early adopters.
We’ve seen this curve before.
Let’s not waste time defending the past.
Let’s shape the future—ethically, boldly, and with full agency.
When the Kids Know the Workflows Better Than You Do
The McKinsey 2025 M&A report wasn’t written for high school students.
But maybe it should’ve been.
Teenagers fluent in generative AI aren’t waiting for permission to innovate. They’re already redesigning workflows, challenging outdated assumptions, and accelerating transformation—often faster than the organizations hiring top consultants.
The future of work doesn’t belong to those with the most experience. It belongs to those with the imagination to question what everyone else has accepted as “just the way things are.”
This post explores why the smartest move an enterprise can make in 2025 might be to pair a fifteen-year-old with a VP and let them loose on the most broken process in your company.
The results will surprise you.
From Blog to Practice: Digital Wayfarer Becomes a Consultancy
Today, I’m officially launching Digital Wayfarer as an independent consultancy. The focus is simple: help organizations navigate complex change with clarity, speed, and systems that actually work.
Let’s Build Something Better. Together.
What if AI isn’t here to replace us, but to connect us?
Imagine students and professionals solving real problems side by side, using AI to break habits, not just automate them.
The future of work isn’t waiting. It’s being built right now—by those bold enough to collaborate across generations.
What Digital Transformation Can Learn from Site Reliability Engineering
Incidents will happen.
This simple but powerful truth drives Site Reliability Engineering (SRE). No system is perfect, no service is infallible, and no transformation happens without disruption. SRE isn’t just about keeping systems online—it’s about building reliability into an organization’s DNA through observability, automation, and continuous learning.
The Next Big AI Opportunity: Developer Experience
For years, the conversation around AI has been dominated by big, sweeping promises—transforming industries, revolutionizing work, and driving exponential efficiency. But as McKinsey’s latest State of AI report highlights, the companies actually seeing bottom-line impact aren’t the ones dabbling in pilot projects. They’re the ones actively rewiring their workflows to embed AI at the core of how they operate. And where is this happening fastest? Developer Experience (DevEx).
The Broken Workflow: Why Your Business Isn't as Efficient as It Could Be
Does this sound familiar? You spend your day jumping between different applications, searching for information scattered across email threads, spreadsheets, and shared drives. You're constantly chasing updates from colleagues, struggling to keep track of project progress, and feeling like you're drowning in a sea of manual tasks. You know there has to be a better way, but you're not sure where to start.
Back in the Saddle: A Deep Dive into Developer Experience, Change Management, and the Power of JSM
It's been a while since I've put pen to paper, or rather, fingers to keyboard, in this way. But after some time away, I'm back and more excited than ever to share my passion for a topic that's near and dear to my heart: Developer Experience. And I'm not just back with a single post; I'm kicking off a long-running series dedicated to exploring the multifaceted world of DevEx, and how it intersects with change management, software development, and operations.
Transforming Onboarding: From Cold Start to Warm Welcome
A new job is like a journey into the unknown. The thrill of fresh opportunities is often tempered by the anxiety of unfamiliar settings, processes, and faces. Now, imagine this scenario:
You're seated at your workspace, heart fluttering with first-day nerves. You power up your laptop and click on your first task. Instead of a mundane checklist, a personalized video message pops up. Your manager appears on the screen, greeting you with a warm smile. They welcome you to the team, outline clear expectations, and assure you that support is just a message away.
The Secret Sauce for Change Management: Everboarding
You might be wondering why I've been talking your ear off about "everboarding." No, it's not a misspelling, and it's not some new extreme sport. It's a concept that's quietly revolutionizing how organizations handle change and how leaders guide their teams through it. Let's dive into why I'm so passionate about it.
The Ever-Boarding Advantage: Fueling Organizational Change
The statistics on employee disengagement paint a stark picture of the modern workplace. The decline in engagement, coupled with the looming threat of turnover, underscores the urgent need for a proactive and continuous approach to employee development and support. The traditional onboarding process, often confined to the initial weeks or months, simply doesn't cut it anymore. The solution lies in ever-boarding, a dynamic process that extends onboarding beyond the initial phase, fostering a culture of continuous learning, growth, and connection.
The Urgency of Leadership: Unraveling the 'Why' Behind the Rush
True leadership isn't about barking orders and expecting blind obedience. It's about transparency, communication, and shared goals. It's about empowering your team, providing them with the context they need to succeed, and recognizing their contributions along the way.
Ever-Boarding: A Strategy for Remote and Hybrid Success
It's the start of my day, and I've just brewed my first cup of coffee. Is it time to dig into deep work? Not yet. In an office, this would be when I'd wander to the break room, catch up with a colleague, and share a casual chat. So that's what I do, virtually. I scan the list of online colleagues on Slack and reach out to one I haven't connected with recently, "Coffee chat?"
The Power of the Pause: Reflections from a Long Weekend
It's easy to get caught up in the whirlwind of busyness. Business, after all, is just one letter away. But there's a crucial difference: the "I". It's about your role in the busyness. Are you actively driving towards your goals, or are you simply reacting to the chaos around you?
In a World That Never Stops, the Power of Slowing Down
The world is a blur. It spins at a relentless pace, demanding more, faster, better. We're constantly bombarded with messages urging us to hustle, grind, and never stop pushing. But in this endless race, it's easy to forget a simple truth: running at full speed only shortens your distance. The financial cost of employee turnover is a staggering $900 billion annually according to the Work Institute’s 2024 report. That's the price organizations pay for neglecting the importance of sustainable employee engagement and retention.
The Great Disconnect: The Alarming Reality of Employee Engagement and the Power of Ever-Boarding
The modern workplace is in a constant state of flux, and the pursuit of employee engagement has become a top priority for organizations. But despite the countless resources poured into engagement initiatives, there's a glaring gap between the perceived importance of engagement and the reality employees face.
Ever-Boarding: The Strategic Investment That Transforms Companies
The cost of employee turnover is a staggering burden on businesses, reaching an estimated $700 billion in the U.S. alone in 2022, according to the Work Institute's 2024 Retention Report. The financial impact is compounded by the rising median wage, making the loss of an employee even more costly. Beyond the direct expenses of recruiting and training replacements, turnover disrupts workflow, dampens morale, and leads to a loss of valuable institutional knowledge.
Scaling Ever-Boarding: How to Keep Your Team Engaged and Aligned
Ever-boarding is about creating a culture of continuous learning and growth, where everyone feels valued, supported, and empowered to reach their full potential. It's about recognizing that the world is constantly changing, and your company needs to adapt and evolve to stay ahead of the curve.