The Pain of Being Overlooked

Some days, it feels like your whole career could just as easily be someone else’s résumé. You give years—decades—to becoming an expert, but you still start to wonder if anyone sees you at all. Nearly half of employees feel undervalued in their roles, and a third worry about growth hitting a ceiling—which tells you this sense of invisibility isn’t just in your head (source).

You aren’t imagining it. Every week, I see smart, talented people—leaders, founders, consultants—buried under a pile of lookalike resumes and generic outreach emails, cycling through applicant systems or LinkedIn DMs that miss the story entirely. It’s the same for business owners pitching services. The words blur, and the spark that makes you worth knowing disappears in the noise.

That’s the friction. All those hours mastering your craft, and you’re left feeding summary bullets into a system built to standardize you, not to highlight what actually sets you apart. You know it’s not just you. The process itself is structured to make everyone seem replaceable. No matter how much you tweak the wording or reach out, real expertise can’t shine through a generic, process-heavy approach.

The shift comes when you productize your career search, treating the act of communicating value not just as a checklist, but as a product challenge that fundamentally redefines your approach. Personal branding, by definition, is deliberately shaping and signaling your value—it’s how people bring together the mesh of expectations and associations they hold about you.

How I Turned My Job Search Into a Product

The turning point came when I stopped seeing my job search as just paperwork. Instead, I decided to treat it as a platform—a way to actually show, not just tell, what I could do.

It would have been easy. Tempting, even, to use AI for custom cover letters and blast them everywhere. But I wanted something different. I wanted people to experience how I think and what I could deliver, not just skim a well-formatted summary. So I built ‘Ask Frankie’—an AI agent that can answer your questions about my background, experience, and how I work before we ever get on a call.

That meant building a knowledge base from scratch. I pulled in over 350 LinkedIn posts I’d written, plus a stack of curated Q&As, stories from past roles, even some technical incident writeups and a couple of Easter eggs for anyone paying close attention. I spent a few late nights iterating, running example questions through the model, pulling out weird or off-kilter answers, then patching the content or prompts. Each tweak would make it a little more specific, a little sharper.

Among other things, framing cuts down back-and-forth, which stabilized how it responded, so I wasn’t constantly revising or clarifying intent. Suddenly, my twenty years didn’t live in a folder—they lived in something you could ask, poke, and follow up on however you liked.

Of course, the fun part was getting Claude Code to stop using deprecated Foundry APIs, and figuring out how to plug gaps when it hallucinated a product that never existed. Sometimes it felt like programming a stubborn parrot, but honestly, those little wins made the process weirdly enjoyable.

Here’s something that caught me off guard. One night during this build-out, I got distracted troubleshooting a bug that turned out to be nothing more than a missing comma. I’d wasted two hours combing through dependencies, convinced it was some deep library issue. When I finally found it—just one tiny typo—I just stared at the screen, then laughed (a little too loudly) in the quiet of my office. It reminded me, again, that there’s always some blind spot, and you only see it in hindsight. Still, fixing it was a small rush.

If you want to help me make it better, share this post or drop an interview question in the comments. I’ll add the good ones to its knowledge base. That’s the beauty of it. My job search isn’t locked down and static. It gets smarter—and more relevant—every time someone tries to break it using an interactive job search strategy.

The Framework to Productize Your Career Search

When I talk about ‘productizing’ here, I don’t mean slapping a logo on your résumé or making a landing page with buzzwords. It’s about turning expertise into solutions by transforming your experience, reputation, and output into something interactive—a tool, a bot, a self-serve portal, or even a guided walkthrough. This is more than branding. It’s building a digital mechanism so others can poke, prod, and genuinely experience your expertise without waiting on you to explain it every time. Think of it like giving your audience a test drive of what you can offer, instead of handing them a brochure.

Here’s how you make it actionable. First, audit your assets. What do you actually have—stories, project writeups, case studies, technical Q&A, anecdotes? Then curate them into answers and narratives that reveal your strengths. Next, pick a platform that’s as simple as you can stand—a Q&A page, a Notion board, a chatbot, or something more ambitious. Finally, map the content to actual needs you see from clients or employers, so you’re solving the questions people really ask instead of just showing off.

The spectrum here is huge, and you don’t need to start with an AI agent. You might build a simple public FAQ that responds to top queries about your consulting work, or set up an interactive portfolio where users filter and compare your case studies by industry or challenge. If you run a marketing agency, you could launch a self-serve audit tool that walks prospects through a brand analysis—letting them try before they buy.

On the technical side, a software engineer might use a chatbot to answer “how would you scale X?” questions, backed by real-world incident reports. At the deep end, you could create a fully automated AI-run demo, like the agent I built for my own search, where visitors ask anything and the system draws live from your curated stories, wins, and failures. If you want to take it further, you can even automate client outreach through these interactive tools. The main point: the complexity is up to you, and the examples span industries, but the logic stays the same.

You might wonder: is it worth the trouble, or do you need to be some kind of developer to pull it off? I get it—these projects sound intimidating at first. Six months ago, I would have assumed automating my own search was way out of reach. But the truth is, most people start with simple steps, then iterate once they see traction. The first version doesn’t need to wow anyone. It just needs to be usable and not break.

If you get stuck, ask for help or look at open examples in your field. And if things feel confusing, remind yourself that the best automation projects usually begin because someone got tired of repeating themselves—not because they mastered new tech overnight. You can chip away at it, just like I did, and the payoff comes from making your real skills tangible and easy to explore.

Squash the Resistance: Productizing Pays Off

I remember the heaviness of sending out applications and feeling indistinguishable from every other applicant—no matter how tailored the note or how long my credentials list got. That ache of blending in never really goes away, does it? These days, though, my phone pings because someone just tested my interactive skills map, or a founder poked around ‘Ask Frankie’ and asked a question I’d never thought to address. There’s less waiting, less wondering if my message got through, because people see what I actually bring—without the friction.

Let’s talk competitive advantage for a second. When you showcase value to employers in an interactive way—letting someone touch it, test it, and get their own “aha!”—you become almost impossible to ignore. Suddenly, the right opportunities aren’t just easier to spot. They start reaching for you, because you’re the only one who bothered to make their decision this easy.

If you’re hiring, know someone who is, or just want to see an AI use case in action—have a chat with ‘me’ about it here: askmyai.chat. Instead of sifting through LinkedIn summaries, you or your team can actually ask about my leadership approach, how I handled complexity at CapTech, or how I’d tackle your thorniest issue. Instant interaction, minimal friction.

If you’re skeptical, I hear you. In fact, my first version of ‘Ask Frankie’ glitched every few minutes and felt awkwardly robotic—so I kept tinkering. Start small. Test with people you trust. When people get hands-on and interact in a new environment, the benefits linger—just look at how a few short VR sessions can reduce anxiety, boost clarity, and improve relational skills for the long haul (source). You’ll pick up ideas and find your blind spots faster than planning could ever give you.

The real shift? When you productize your search, you stop hoping to be found and start controlling how you’re discovered—on your terms, in a way that static outputs never could.

The funny part is, even after all the build-out, I haven’t figured out how to make the agent always deliver the perfect answer. Sometimes it surprises me with an insight. Other times, it misses obvious context or gives a reply that still sounds a little off. Maybe that’s its own signal—I know the tech will never replace the nuance of a real conversation, and I’m fine with that. For now, it’s a work in progress, and honestly, that makes it far more interesting.