In 2001, I was an elementary school teacher with what seemed like an impossible dream: work from home 100%.
This was 2001. Remote work barely existed. When I told people I wanted to work from home full-time, they looked at me like I’d said I wanted to live on Mars. The technology was there, technically, but the culture? The acceptance? Not even close.
But I saw something others didn’t. I saw the writing on the wall.
I had already made one major pivot in my life. I’d left law school, actually walked away from Georgetown Law after a year, to get my Master’s in Education from the University of Maryland. Teaching felt like my calling, and I loved it. But even while I was in the classroom, that dream of working from home kept pulling at me.
So I did something that seemed completely random: I signed up for an online web design course through a local community organization.
Even then, I thought I was late to the game. But in reality? The internet was still “new,” and online courses were just emerging. I was actually incredibly early to recognize what was coming.
The Leap That Changed Everything
That web design course wasn’t just about learning HTML and CSS. It was about learning to see possibilities where others saw obstacles.
By 2006, I took the leap and left teaching to start my own design company, Modern Sugar Web Design. I had a dream, I was intentional about it, and I MADE IT HAPPEN. For over a decade, I worked from home, built something from nothing, secured partnerships with major companies like the Home Shopping Network. Possibilities I never imagined suddenly existed.
The feast-or-famine reality of entrepreneurship was real. Some months were incredible, others were terrifying. But I was living my dream: working from my home office, setting my own schedule, choosing my clients.
Coming Full Circle (Sort Of)
By 2017, I was ready for something different. The weight of being a team of one was getting heavy, and I was craving the stability and collaboration that comes with being part of an organization again. So I took a full-time role with the Maine Math and Science Alliance, a nonprofit I’d worked with during my teaching years.
But here’s the thing, even then, I wasn’t willing to give up what I’d learned about the future of work. I was fortunate to find a role that was still partially remote. We were already using Zoom (yes, in 2017!), and I only had to be in the office 2-3 days a week. By the time COVID hit, we were down to just 2 days in office.
Since the pandemic? I’m 100% home, just like I dreamed back in 2001.
I never miss the office. Not once.
The Pattern Recognition
Here’s what I’ve learned from living through this transformation: I’ve been here before.
That moment in 2001 when I saw the potential of the internet and remote work? That feeling of “everyone thinks I’m crazy but I know something’s coming”? That sense of urgency mixed with excitement and terror?
I’m feeling it again.
AI right now is that same moment on steroids. Supercharged. Hypercharged.
The writing is on the wall again, and this time it’s written in neon. The marketers who are learning to truly work WITH AI—not just dabble with ChatGPT, but really understand how to integrate it into their workflows, their thinking, their strategic planning, they’re doing what I did in 2001.
They’re seeing around the corner.
Why This Time Feels Different (And Bigger)
When I learned web design, it opened doors I never knew existed. But AI? AI isn’t just opening doors—it’s rebuilding the entire house.
The overwhelmed marketing managers I work with now are in the exact same position I was in 2001. They’re drowning in tasks, wearing fifteen different hats, trying to create content and campaigns and strategies with resources that never seem adequate.
AI can change that. Not in some distant future—right now.
But here’s what I know from experience: the people who wait until it’s “obvious” will miss the real opportunity. The magic happens in that space between “this seems crazy” and “everyone’s doing it.”
Does the future scare me? Absolutely. It’s terrifying.
Some days I wake up wondering if we’re moving too fast, if we’re breaking things that shouldn’t be broken, if we’re creating problems we can’t yet imagine.
But I’ve learned something important: forward is the way through.
What This Means for You
If you’re a marketer feeling overwhelmed by your workload, if you’re curious about AI but not sure where to start, if you’re wondering whether this is all hype or if there’s something real here, I want you to know something.
You’re not late to the game.
Even if everyone around you seems to be talking about AI, even if you feel like you should have started six months ago, even if the technology feels overwhelming, you’re not late.
I thought I was late in 2001 too. I wasn’t. And neither are you.
The marketers who learn AI now aren’t just picking up another skill. They’re redesigning what’s possible for their careers. Their daily workflows. Their relationship with work itself.
They’re creating the freedom to focus on strategy instead of execution, on creativity instead of repetition, on impact instead of busywork.
Just like I did in 2001 when I signed up for that web design course.
The Question That Matters
So here’s what I’m asking myself, and what I’m asking you:
What impossible dream are you ready to chase?
Because I can tell you from experience, the skills that seem “extra” today become your freedom tomorrow.
This is the first post on my new blog, and it felt important to start with the story of how I got here. If you’re a marketer interested in learning how AI can transform your workflow (without losing the human touch that makes your work meaningful), you’re in the right place. I’ll be sharing practical insights, real examples, and honest conversations about navigating this transformation.
What questions do you have about AI and marketing? What feels overwhelming? What feels exciting? I’d love to hear from you.
