303 Days

Or How I Learned to Stop Worrying and Let Claude Write My Resume

It's been 303 days since I last had a job. There are 365 days in a year. But who's counting?

Mom is onto me now. Ever since I told Mom my car was stolen (oh yeah, my car was fucking stolen — long story, maybe I'll write about it someday), her demands have gone from “Your car is a trash heap, buy a Tesla so we don't lose face” to “you know… if you don't like your job, you can just find another one…” to “you know, you can just live with your mother. I can take care of you and cook your meals.”

“Mom, I'm 47; I should be the one taking care of you,” I say as I rush out the door, my fat thumbs looking for the pink buttons that call the Lyft back to the house. I shouldn't even be fucking using carshare.

One crisis at a time, I say to myself.

"No, you're 48. And I'll tell you this until you're old and I'm even older."

I turn around and make a face. She's right; I forgot. I don't even know the face I'm making. Is it sympathy? Guilt? Disgust? Am I just tired?

"By the way," mom calls from the doorway. "It's the black people. They took the car, didn't they?"

Nope, never mind. It's disgust. Definitely disgust.

---

I learned from a contact at Code for America that there is a job opening soon. It's a Federal job—an IT Expert Position in the Technology Transformation Services group. Hurry, she says. They only accept the first 500 applications or next week, whichever comes first.

I've worked government jobs before, although the government you worked with was Miami-Dade County's permitting department, and the modus operandi was “look at all the bureaucracy, then bypass all of that because your neighbor's uncle Chacho knows a guy.”

Reading the role summary: “The strongest candidates will have a background working on cross-functional, multidisciplinary teams that deliver digital products and services in an incremental, user-focused environment.” That is like every job I've ever had, and yet no job I've ever had. Either way, though, they require a Federal resume. I google it. Oh, that's different.

AI to the rescue then, I guess.

---

While I will always have a soft spot for ChatGPT and Vale, the delightful British disembodied voice who tells me bits of trivia about meatballs while cooking, I turn to Claude AI and, in particular, Claude's Projects functionality. A Project creates a little workspace for Claude where I can save certain notes and resumes that I can always pull for reference. Without the project, Claude AI won't be able to remember anything from conversation thread to thread.

Yes, this is the screenshot I used when working with Claude. Yes, I call it “Be Your Own Hypeman.” Do not judge me unless you are a paid subscriber. In which case, judge away.

From there, I included a couple of documents under Project Knowledge: a file containing all my skill sets and my overly detailed master resume, which is way too long to submit on its own.

I also include a “brag document.” This document listed impressive things I've done because I'm so self-deprecating that I often forget them. It includes achievements from Code for America, my last job, and positive feedback and recognition I've received over the years—mostly LinkedIn testimonials and nice notes from coworkers when I got laid off.

Not only does this inflate the ego, but it’s also useful for my workflow.

My workflow for creating resumes usually goes like this: I'll find a job description that seems interesting. I have multiple master resumes because I'm applying for various positions—not just software engineers or web developers but also developer advocates, full-stack web instructors, and AI specialists.

When I find a new job position on LinkedIn or elsewhere, I copy and paste the job description into Claude, start a new thread in that project, and ask Claude if I should apply. Claude usually says something like, “Of course you're qualified, but maybe you should highlight these three things,” and suggests I create a bespoke version of my resume to submit.

One important thing I've learned is to tell Claude not to hallucinate because if you don’t, it will make stuff up to fit the position better. For instance, it might falsely claim that I built 25 full-stack applications while teaching 40 hours a week—mentally plausible but certainly untrue.

Once Claude generates the resume, I'll read it over to ensure it doesn't include anything inaccurate or overly hyped. Then I'll copy it into Obsidian, which is where I keep all of my notes and has a markdown version of my resume for each job I've applied to, nicely formatted. After a quick grammar check, I'll print out a cover letter. Depending on how much I want the job, I'll modify the cover letter through AI prompts or manually to fit my voice better. From there, I will submit my resume and cover letter. Lather, rinse and repeat another eighty times.

---

I spent the next six hours crafting the perfect Federal resume. It's a masterpiece of bureaucratic proportions—every achievement meticulously documented, every academic output and acronym carefully spelled out, and every date precise down to the month. I go to bed feeling accomplished, ready to submit it first thing in the morning.

I woke up to an email that said, “This job announcement has closed. The posting has received the maximum number of applications.”

Somewhere in Miami, I swear I can hear Uncle Chacho laughing. Jajajajaa.

It's been 304 days since I last had a job. There are 365 days in a year. But who's counting?