Introduction: Samantha's Journey

In my conversations with hundreds of people about generative AI, I have found an enormous range in experience and perception of what these technologies offer today and what they will mean in our work and lives in the near future. Suspend your preconceptions and imagine the future with me through a professional at the mid-point of her career, suddenly confronted with these AI tools changing her world…

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Samantha had always loved the sound a marker made against a whiteboard. A faint squeak that meant ideas were turning into something alive. On mornings like this, she got to the office before the rest of her team, slid the glass wall aside, and stood in the quiet conference room as if it were a small stage. The room smelled faintly of dry-erase ink and the caramel of yesterday’s abandoned latte. She scanned the horizon line of the city outside, then uncapped a pen and wrote three words across the board in her neat, slanted hand:

“Why us now?”

It was the question she built entire campaigns around. Not “Why us? That was a brand’s ego talking. But instead “Why us now?,” which demanded timing, context, and the little vibrations of culture she felt more than analyzed. It had been her edge for a decade: she could read a mood, hear an unfinished story in the way customers described their day, notice which color made a room straighten up. Executive teams had come to trust that if Samantha said, “The market’s tilting you should listen,” they would listen.

Her phone buzzed: 9:00 with Brandon. The calendar invite had arrived late last night with a neutral subject line, Quarterly Development Conversation, that still made her throat tighten. She capped the marker and wiped the board clean with the sleeve of her blazer, then grimaced and rubbed at the faint blue smudge it left behind.

By the time she reached her desk, Slack was already spitting out AI generated images and “can we try a version that…” threads from her team. A junior strategist, Lily, had posted an overnight brainstorm from the company’s new AI marketing tool. There were twenty headline options, five visual concepts, and a mood board assembled from stock images and UGC that looked… good. Not perfect, but weirdly close. Samantha clicked into one of the visuals: a weekend table, coffee steam, a hand reaching into morning light. A caption mocked in Let weekends breathe with a list of A/B test variants pre-populated. The tool had even attached a predicted lift chart based on past campaigns.

She felt a flick of admiration followed by a dull little drop in her stomach. The image had the kind of surface ease she’d trained herself to produce after years with creative teams, and yet it had been generated at 2:11 a.m. while she slept. Lily had added a note: Tweaked prompts based on last week’s results see v3.4. She hovered over the file name but didn’t click: BrandGPT Lifestyle Headline Kit.

Her reflection wavered in the screen, her brown eyes, her hair in a practical knot, a few faint worry lines that made her look focused rather than tired. Thirty-six, she reminded herself. Old enough to have earned her seat. Young enough to learn.
The learning part, though what did that actually mean?

The last two months had been a blur of “enablement sessions” that tried to show her how to coax, steer, and critique outputs from a system that didn’t get tired, didn’t take anything personally, and improved as fast as it was fed. She understood the basics. She could prompt, revise, ask for alternatives. But the distance between “using a tool” and “building her value around it” felt like a canyon.

Her chat pinged again from Brandon: meet you in my office?

He was already standing when she stepped inside. Samantha respected the easy warmth that Brandon exuded but always felt that it was his performance of what he thought his role should be as opposed to who he really was. His office was the stage supporting this role that he played with a plant, warm lighting, and a single framed photo from the brand’s very first retail store.

“Sam, thanks for coming.” He smiled, gestured to the small round table, and not to the desk, designed to make it feel less like a performance review, more like a conversation. She sat, tucking one foot behind the other to stop her knee from bouncing.
“I’ll cut to it,” he said, leaning forward. “You’ve been a cornerstone of how we tell our story. You already know that. But the way we tell stories is changing fast.”
There it was: a gentle preamble to a hard turn.

“We’re moving to an AI-integrated workflow top to bottom,” he continued. “Creative, media, CRM. This is not a novelty or a trial, this is the new workflow. You’ve seen the pilot numbers. Faster cycles, more iteration, tighter feedback loops.”
“I have,” she said carefully. “The lift on personalization last week was strong.” She could hear her voice behaving itself.

He nodded. “Strong. And we want you to lead the brand-side integration with the data science team. You’d be the point person on model prompts, content evaluation, and QA. Think of it as scaling your taste.” Another smile.

Her mind split into foreground and background. Foreground: Say something smart. Background: the slide deck from last week flashing in her head… Key Roles: Prompt Architect, Model Curator, Data Storyteller. She’d circled those terms, but privately. In pencil. As if they might erase themselves.

“I appreciate the trust,” she said. “Can I ask… how you’re measuring success in this role?”
“Good question.” He tapped his pen. “Speed to concept. Win rate in testing. Quality-of-fit, as judged by creative and brand. And…” He hesitated, then added: “Team adoption. This transition is as cultural as it is technical. People trust your bar. If you’re behind it, they’ll come along.”

“Team adoption,” she repeated, a small echo.

He watched her, reading micro-expressions as if they were numbers on a dashboard. “I know this is an adaptation,” he said softly. “It’s not about replacing the human part. It’s about composing it differently.”

Composing it differently.

She left with a timeline, thirty days to stand up a pilot with two product lines. He had given her a new org chart where dotted lines webbed from her name to people she had never worked with. Back at her desk, she stared at the chart until the overhead light made a glare across it like a bright seam.

“Soooo?” Lily swiveled into the aisle, eyebrows up.

“New hat,” Samantha said, attempting lightness. “I’ll be wearing the ‘integration’ hat.”

“Nice,” Lily chirped. “You’ll be great. Oh, did you see v3.4? The tool finally stopped over-indexing on brunch shots. ‘Let weekends breathe’ is testing amazing with empty-nesters.”
“Of course it is,” Samantha muttered, then smiled brightly. “Let’s review it at eleven.”

By noon the day’s small humiliations had nibbled at her patience. A product manager asked if the AI could “just do the research part” so they could be “more creative.” A copywriter forwarded a dozen variants the system had spit out and asked, deadpan, “Which one is ‘human’ enough?” During the stand-up, Ravi demoed a bulk-generation flow that produced three hundred micro-ads in nine minutes while he narrated in an easy, practiced way, like a cooking show host.

None of them meant anything by it. They were good colleagues trying to work faster inside a new machine. But somewhere between a joke about replacing the coffee with energy drinks “for the models” and a slide titled From Gut to Loop, she felt her rib cage tighten as if someone had cinched it from behind.

By late afternoon, she ducked into an empty phone booth and closed the door. Inside, the world muffled itself. She pressed the heels of her hands into her eyes until bursts of color shimmered there, violet, sour yellow, and let herself feel the two truths she had been trying to keep separate:

There was something breathtaking about this new way of working. Potentially an orchestra’s worth of possibility, if you could conduct it.

Everything that had once made her feel certain. Intuition, consensus-building, the long arc of craft all suddenly felt unmeasured, uncounted, and dangerously “soft.”

She thought about the first time she’d presented to the board. Her hands had shaken in anticipation, not fear; she’d known that the narrative was right. Not because a dashboard told her, but because the narrative made the room exhale. That was what she’d built a career on, pressure-testing stories against human breath.

If a model could produce a hundred acceptable stories in the time it took her to outline one, what was she offering besides… reassurance? Taste? A “bar”?

And if the bar itself could be learned, if the system could with feedback inch closer to her sense of fit, where did that leave her?

Her phone vibrated. Mom. For a moment she considered answering, imagined the gentle script: They’re changing things. I’m fine. It’s just… a lot. Then she let it go to voicemail and watched the call icon pulse, then dim.

On the way home the sky turned the color of old film. Rain threatened, then reconsidered. She walked the three blocks from the train to her apartment without noticing her feet, keyed in, and set her bag down with the careful, pointless precision of someone postponing a thought. The quiet of the place pressed in. She poured water into a glass, drank half, and left it on the counter as a marker of her own presence.

At the kitchen table, she opened her laptop. The cursor blinked on a blank email to Brandon: Happy to lead the integration. Here’s how I propose we structure the first 30 days… The plan formed in outline, the way plans had always formed for her as beats, arcs, contingencies. She could describe stakeholder maps and review cadences and how to keep copywriters from feeling like puppets.

But another window tugged at her. She opened the company’s learning portal and scrolled. Prompt libraries. Evaluation rubrics. Intro to few-shot techniques. Fine-tuning workflows for marketers. The words felt like pebbles in her mouth. Not impossible to swallow but just unfamiliar, edges pressing new shapes into her.

She clicked a course, watched the first minute, and paused it when the instructor said “token.” The instructor’s voice had that vanilla TED cadence, all uplift and glide. She closed the tab.

Her email draft waited, polite.

She thought about her father teaching her to drive: the afternoon light across the hood; the way he’d said, You can’t make the road stop changing. You can only get better at noticing what it’s telling you. It had been good advice for a stick shift on hills. For careers, too, maybe.

She opened a clean document and began writing a different plan, a messy one for herself. At the top she typed: What I’m afraid of. What I can control. What I will try.

What I’m afraid of:

• Becoming a translator of machine output instead of a maker.
• Losing the feeling of knowing a story is true.
• Becoming someone who used to be good at this.

What I can control:

• My willingness to learn in public.
• What it means to set the bar (and how to show it, not just feel it).
• The quality of questions I ask.

What I will try:

• One hour a day hands-on with the tools, no delegating.
• Shadow the data science team once a week; ask the stupid questions.
• Redefine the creative review: not “Do I like it?” but “Which variables moved and why?”

She sat back. The list wasn’t noble, but it was real. It felt like a first rung on a ladder to something she couldn’t yet see.

Her phone buzzed again. Lily: Quick Q if we push the empathy angle harder in v4, too on the nose? Samantha smiled despite herself and typed back: Give me 10. Let’s talk about the empathy we want to land and what the model should show to get there. Not “be more human” specifics. She added a Zoom link.

She reopened the draft to Brandon and finished it with the steadiness of someone who had made a decision not to decide everything today. Yes, she wrote. I’ll lead. Then she added a line that surprised her: I’ll need a dedicated partner in data science for two hours a week and a commitment that creative retains the final call on narrative arc. I’ll show you how we’ll measure both speed and story.

She hit send before she could edit it into something safer.

When Lily joined the call, Samantha asked the question she’d written on the whiteboard that morning.

“Why us now?” she said, and let the words sit in the shared silence. “Let’s build a prompt that understands timing, context, the small human reasons. We’re not asking the tool to be more human. We’re teaching it to listen.”

They began. It was awkward in places, like dancing with a new partner: a little step-heavy, a little anticipatory. But then the work found a rhythm, generate, review, test, refine, and Samantha felt a thin thread of relief unwind in her chest. She could set the bar. She could show it. She could, maybe, compose the human part differently.

Later, when the city had settled into its evening hum, she stood at the window and watched taillights stream like a river, red beads moving in one direction, white in the other. People, all of them, going from one place to the next. She pressed her palm to the glass just to feel that there was something cool and solid on the other side.

Her value wasn’t disappearing. It was rearranging itself in space.

The thought scared her and steadied her at once. She could hold both.

Tomorrow, she’d put a fresh marker on the conference table. And when someone asked what had changed, she’d say the simplest thing she could tell the truth about:
“Everything. And not the part you think.”

Your first exercise

Throughout this journey there will be optional exercises for you to do more hands-on learning which complements this series of articles. Each time you complete an exercise the information you have entered can be saved into your journal (you must create an account) so that you can go back and review later, as you progress. You can also redo any exercise and the new results will also be saved so that you can compare your results over time. The first exercise is intended to just establish a benchmark for where you are on your journey today:

Click here for Exercise 1: Find your starting point

As you start this learning journey, this exercise will help you create a baseline for your current understanding and opinion of AI. If you create an account (free) the results will be saved and you can revisit them as you progress.