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.

Building a Team of Chaos Warriors
people Caroline Adams people Caroline Adams

Building a Team of Chaos Warriors

Ben Horowitz's "The Hard Thing About Hard Things" perfectly captures the essence of building a team that can thrive in the ever-changing business landscape. In a world of constant disruption and unforeseen challenges, you need a team of chaos warriors – individuals who are adaptable, resourceful, and quick on their feet.

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No Pain, No Gain
people, process Caroline Adams people, process Caroline Adams

No Pain, No Gain

Think building a successful business is all sunshine and rainbows? Think again. Ben Horowitz's "The Hard Thing About Hard Things" throws that fairy tale out the window and reveals a stark truth: growth is born from struggle.

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Why Embracing Chaos is Key to Business Success
people, process Caroline Adams people, process Caroline Adams

Why Embracing Chaos is Key to Business Success

In the first installment of my series on "The Hard Thing About Hard Things," I laid bare Ben Horowitz's central message: business isn't for the faint of heart. It's a messy, chaotic journey with no easy answers. Now, let's dig deeper into one of his most potent insights: the power of embracing chaos.

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CrowdStrike's Global Meltdown: A Lesson in "Speed Kills"
process, technology Caroline Adams process, technology Caroline Adams

CrowdStrike's Global Meltdown: A Lesson in "Speed Kills"

Yesterday, the world held its breath as CrowdStrike, a leading cybersecurity firm, accidentally unleashed a software update that triggered a cascade of system failures across the globe. Flights were grounded, hospitals scrambled, and even 911 services were disrupted in some areas. The culprit? A seemingly routine update that contained a critical flaw.

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Turbulence
people Caroline Adams people Caroline Adams

Turbulence

You're 30,000 feet in the air, halfway through a transatlantic flight, when the captain's voice crackles over the intercom. "Folks, we're hitting some unexpected turbulence. Please fasten your seatbelts and remain seated."

That sudden jolt, the uncertainty of what's coming next...it's a microcosm of life itself, isn't it? Just like those air pockets in the sky, unexpected changes can hit us out of nowhere, throwing our carefully laid plans into chaos. For me, this hit home HARD over the past 48 hours trying to get home from Lisbon. Delays, missed connections, and eventually, a canceled flight due to extreme weather.

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When Change Hits Home: Navigating Chaos in Dysfunctional Organizations (And Lessons from My Own Journey)
people, process Caroline Adams people, process Caroline Adams

When Change Hits Home: Navigating Chaos in Dysfunctional Organizations (And Lessons from My Own Journey)

Change is hard. But change in a dysfunctional organization? It's like navigating a hurricane while building a sandcastle. đŸŒĒī¸đŸ°

In honor of Pride Month, I'm reflecting on my own journey of change and sharing lessons learned from navigating chaos, both personally and professionally. đŸŗī¸â€đŸŒˆ

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Chestnut Books: Where My Love of Reading (and Writing!) Took Root
people Caroline Adams people Caroline Adams

Chestnut Books: Where My Love of Reading (and Writing!) Took Root

Do you remember that feeling as a kid of discovering a book that absolutely captivated you? The kind of book that transported you to another world, made you laugh out loud, or taught you something unexpected? I was lucky enough to have a childhood filled with those moments, thanks in large part to my grandmother and her bookstore, Chestnut Books.

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Ctrl+Alt+Oops! When User Experience Meets Sewing Machine Logic
people, technology Caroline Adams people, technology Caroline Adams

Ctrl+Alt+Oops! When User Experience Meets Sewing Machine Logic

Ever had a tech support call that left you in stitches? In the early days of dial-up internet, I fielded a call from a sweet southern lady whose "foot pedal" had stopped working. Turns out, she was using her computer mouse like a sewing machine pedal! 😂 This hilarious experience taught me some valuable lessons about user experience, the importance of humility in learning, and why we should never assume anything when it comes to technology.

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The Unexpected Smile of Technology: AI's Potential to Surprise and Delight
people, technology Caroline Adams people, technology Caroline Adams

The Unexpected Smile of Technology: AI's Potential to Surprise and Delight

The other night at IHOP, while pancakes steamed on the griddle, I watched my mother-in-law unlock her phone with a broad smile. Chuckling, I asked, "Having fun with FaceID?" Her laughter filled the booth, "I thought I had to smile for it to work!" We both dissolved into giggles, a reminder that technology often surprises us, sometimes in the most delightful ways.

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The Infinite Learner's Advantage: Unlearn, Learn, Relearn Your Way to Career Success
people Caroline Adams people Caroline Adams

The Infinite Learner's Advantage: Unlearn, Learn, Relearn Your Way to Career Success

Picture this: It's your first day at a new job. You're handed a stack of manuals and told "Here's what you need to know. Learn this, and you're set." A one-and-done learning experience to master your role.

Sound familiar? Probably not, because that's not how careers work anymore.

As Helen Tupper and Sarah Ellis, authors of The Squiggly Career, put it: "Where we once went to work to learn to do a job, learning now is the job." Mind. Blown. đŸ¤¯

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Winning Friends and Influencing Operations: Dale Carnegie's Timeless Wisdom for Modernizing Digital Operations
people, process, technology Caroline Adams people, process, technology Caroline Adams

Winning Friends and Influencing Operations: Dale Carnegie's Timeless Wisdom for Modernizing Digital Operations

In today's rapidly evolving digital landscape, modernizing operations is no longer a luxury, but a necessity. It's about more than just implementing shiny new technology – it's about empowering your people, fostering collaboration, and creating a thriving digital workplace. In this post, we'll delve into the timeless wisdom of Dale Carnegie, exploring how his principles of human connection and influence can be your secret weapon for navigating the complexities of digital transformation. Meet Sarah, an IT consultant who masterfully blends technical expertise with emotional intelligence, showcasing how Carnegie's teachings can revolutionize your approach to modernizing digital operations.

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Drowning in Meetings? Andy Grove's Advice + Atlassian Hacks for Managing Smarter (Not Harder)
technology Caroline Adams technology Caroline Adams

Drowning in Meetings? Andy Grove's Advice + Atlassian Hacks for Managing Smarter (Not Harder)

Let's be real, being a manager often feels like a never-ending circus act of juggling emails, meetings, and the occasional existential crisis. But legendary Intel CEO Andy Grove dropped some serious wisdom in his book, "High Output Management," and it's got me rethinking how we approach leadership.

Grove's big idea? Your success as a manager isn't about how much YOU do, it's about how much your TEAM does. That means your wins are directly tied to their wins, and your biggest impact comes from helping them shine. But with the daily grind of endless meetings, emails, and fire-fighting, how can we possibly make time for that kind of high-impact leadership? The answer lies in leverage and the smart use of technology.

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Grove's Timeless Principles Meet the Modern Workplace
people, technology, process Caroline Adams people, technology, process Caroline Adams

Grove's Timeless Principles Meet the Modern Workplace

The modern workplace is undergoing a seismic shift. We're moving away from the traditional 9-to-5, office-bound model toward a more flexible, human-centric approach. But how can we navigate this changing landscape while ensuring our teams thrive?

The wisdom of legendary Intel CEO Andy Grove, as outlined in his book "High Output Management," and the forward-thinking insights of Atlassian's Dom Price offer a powerful framework for building a sustainable future of work that goes beyond mere productivity.

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The Power of People at TEAM 24
people, technology Caroline Adams people, technology Caroline Adams

The Power of People at TEAM 24

The buzz of TEAM 24 wasn't just about new features or AI demos (though those were thrilling!). What truly stood out was the energy of connection – the Atlassian community, partners, and customers coming together in person after so long. It was a powerful reminder that even in a tech-driven world, change is ultimately a human endeavor. The most brilliant tools can't replace the relationships and collaboration that drive true transformation.

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TEAM 24 Buzz: Rovo, AI, and the Future of Enterprise Search
people, technology Caroline Adams people, technology Caroline Adams

TEAM 24 Buzz: Rovo, AI, and the Future of Enterprise Search

Atlassian's TEAM 24 conference was packed with exciting announcements, but one that has the potential to be a game-changer is the unveiling of Rovo. While still in its early stages, Rovo promises a unified search experience across the entire enterprise, powered by cutting-edge AI capabilities. This goes beyond simply finding that elusive document faster. Rovo has the potential to revolutionize how we address one of the biggest challenges of remote work: knowledge accessibility and breaking down information silos that can stall progress and hinder collaboration.

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The Water's Path: Persistence, Power, and Change
people Caroline Adams people Caroline Adams

The Water's Path: Persistence, Power, and Change

Nature provides some of the most powerful metaphors for understanding the complexities of change. Much like water, change can be a slow, persistent force, gradually carving its path through the most resistant landscapes. Yet, it also possesses the potential for rapid, transformative power, capable of reshaping its surroundings in unexpected ways.

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