Today I helped a career coaching client by walking her through how AI could create a bridge between her resume and the job description of a position she was applying for by analyzing both documents without emotion. My career coaching client Michaela (used with permission) was feeling frustrated and fed up with procrastination and task avoidance related to applying for new jobs that were above her current position’s level but were definitely positions she was qualified for. Elements of her ADHD, such as RSD (rejection sensitivity), overthinking, and squirrel syndrome escapism, were kicking into overdrive. Like so many of my clients with ADHD, Michaela is brilliant and capable in so many areas but tends to sit for way too long in positions that demand excessive grunt work from her while underpaying her for her brilliance.
So I had her open a ChatGPT account while we were still on the call.
The prompt was simple: draft a cover letter connecting the experience in this resume to the requirements in this job description, with particular attention to the new community program initiative she had developed at her current company. From a clinical-coaching perspective, the purpose of this was to override Michaela’s emotional bias to see her accomplishments as not worthy. To prevent task avoidance, I spent a few minutes guiding her through uploading the resume and job description as attachments. Michaela’s read on her own accomplishments was running through a heavily biased emotional filter that discounted them before she typed a single word. A machine has no such filter.
I walked her through uploading both documents right then. Two minutes, maybe. Not because she needed help with attachments, but because When you have ADHD, the optimism around completing a task ‘later’ quickly clouds over once later actually arrives and you’re alone at your desk with twenty other tabs open. This void is exactly where the task avoidance lives, So my first job was nipping it in the bud.
Then we read what it produced.
Her first reaction was that it made better connections than she could have on her own. What it did was pull a clean through-line between her nonprofit background and her program development work —ones she hadn’t seen even after hours pouring over her resume. Nothing was invented. Nothing was inflated. The information was accurate and the experience was hers. It just came back to her without her internal editor marking it up with a fat red Sharpie.
Next, I had her edit it. Keep the newly discovered experience, but write the actual letter, the human parts—her passion for building community-wide programs for disadvantaged populations, the real reason she does this work. Inspired by AI, not written by it. I realize many people have AI write their entire cover letter, I’m not judging. But I’m a professional and the ultimate purpose of this exercise was to to build self-worth through evidence (the CBT term is literally “finding the evidence”). The final letter had to be hers, and not only for integrity reasons. She needed her own fingerprints on the document she was about to read back to herself.
The takeaway here is, when used well, AI can bypass the self-worth barrier that interferes with an objective read of your own skills. That barrier is one of the most consistent things I see holding my ADHD and career coaching clients in back. Not capability or credentials. Certainly not hard work or effort.
This is where I pulled out my ladder metaphor (this won’t be the last time you hear it, sorry-not-sorry). Michaela could see the bottom rung, where she was standing, and she could see the top rung, the job with the fancy title. What she could not see were the rungs in between, so the climb looked impossible, and the reasonable response to an impossible climb is to not start it. We used technology to build the rungs. It provided the concrete connections between where she was and where she was applying—the rungs. And when you have the rungs you can climb the ladder. It’s still an effort, but it’s possible.
Her homework: 1. Apply for the position with the shiny new cover letter. 2. Read the letter to herself three times, out loud, as an affirmation — not the false-manifesty kind (”I have a million dollars,” when you know damn well you don’t have a million dollars. There is definitely a road to manifestation, but trust me, this ain’t it), but as a factual recitation of things she has actually done. 3. Then pull the strongest paragraph into a LinkedIn summary that leads with inner city program development and non-profit leadership.
We spent the rest of the session on positioning. Her LinkedIn had been quietly advertising her as a direct service provider, which is what she has been and what she is ready to stop being. We rewrote it to point toward leadership roles in community programming and the non-profit sector, because her stated goal is financial stability and direct service work was never going to get her there. She has been underpaid for her brilliance for a long time. That isn’t a mindset problem. It’s a positioning problem with a self-worth problem sitting on top of it.
The last thing I did was normalize it. Career advancement is genuinely harder with ADHD — not because of the work, but because of your self-worth running interference and the inconsistency patterns that make you distrust your own track record. If you have ADHD or struggle to be consistent, I want you to know that this is a known pattern. It is not a flaw of your character.
The point here is not the hand holding or the accomplishment of a task that was getting under my client’s skin. The platinum thread here is unearthing the cognitive behavioral pattern of not recognizing a truth — in this case Michaela’s experience that qualified her for the job — then getting stuck in an unproductive behavioral loop (procrastination, task avoidance), because you don’t believe you have the information or substance you need to move forward (belief, the underlying shadow). We accomplished this by using AI to short-circuit both her cognitive behavioral pattern and her underlying shadow belief. In one fell swoop. By letting the robot literally spit the facts in her face.
We went deeper into the shadow to begin the work of integrating it, but I won’t go into all of that here. I just wanted to illustrate how pulling the thread of practical coaching strategy through the fabric of shadows woven deep into a client’s beliefs can spark wins on both a practical and self-worth level.
On that note, Hey—if this was helpful for you, please restack it or share with a friend, and let me know if you’d like to see more of these Platinum Thread moments in future articles or as a series.