Job searching, the systems way

Treat it like a pipeline, not a lottery

Most job-search advice boils down to “apply more.” For neurodivergent brains especially, that's a recipe for burnout: every application costs executive function, and spending it on roles you don't really even want to take will make your rejection sensitivity very upset, very quickly.

Because of this, I run my search like a pipeline with four stages: intake, filter, apply, rest. Each stage is separated by days and has its own rules. I collect leads throughout the week, and on Sunday night the evaluation runs, so when I sit down at my desk on Monday morning, I have a list of prospects and a breakdown of the role and the evaluation.

If there's a job I'm really excited about, I apply right away, and that usually gets me a few more applications in before I'm done for the day. I'll go back a second day that week and submit a few more applications; I usually finish the stack by the end of day 2. Sometimes I apply to a few more roles on day 3, but that's rare.

On weeks where I have a lot of interviews or a busy schedule, I might skip the week altogether, but I always have the list available to go back to and apply again when I'm ready. If a job is marked ‘Strong yes’ and I don't apply to it, the system automatically pushes it forward to the next week.

The rest stage is not a reward. It's load-bearing.

Intake: collect leads without doomscrolling

The intake rule is that browsing and deciding never happens at the same time. While I'm collecting, anything vaguely plausible goes into the pile. There's no evaluating, no assessing, and definitely no research happening at that point.

Leads come from three places:

• A list of saved boolean searches (below) that runs automatically for me. You can run yours once or twice a week.
• Email alerts, with an automatic rule in Gmail forwarding the ones with job listings into one folder that Claude processes for me. Someone running this on their own can either process all of them in a single sitting or keep a tab open and paste the URLs into their tool or list whenever they check their email.
• Companies I come across. I'm on a computer all day, so I run into a lot of tools and sites. When a product impresses me, I check its careers page to see if they're hiring in my field, and anything I add by hand gets a slightly higher priority.

Boolean searches that actually work

Job boards reward whoever writes the better query. A few operators do most of the work: quotes pin an exact phrase, OR (capitalized) broadens, the minus sign excludes, and site: searches inside one specific website. Some of my workhorses:

site:ashbyhq.com ("Senior Product Designer" OR "Lead Product Designer") ("New York City" OR "Remote")

site:jobs.a16z.com "Product Designer"

"Lead Product Designer" filetype:pdf

The site: part limits your results to one website, like the systems companies use to post their jobs, or a venture capital firm's job board. That's how you find roles that never make it to the big job sites.

You can run the same search for several different levels or titles, depending on your experience. A ‘Senior’ role at one company can be a ‘Lead’ role at another, so it's worth searching a level up and a level down.

My full list of search strings is at the bottom of this page, ready to download, along with a Claude skill that writes new ones for you.

The ethical and practical filter

Before I evaluate a single posting, I write down my no-go categories — the industries and employers I won't work for regardless of the compensation. Deciding this in advance matters, since turning down a shiny offer is hard to do, even when your values aren't aligned. I am of the opinion that you'll pay for it eventually, though.

Part of the reason I'm writing this is an attempt to extend the amount of time I can stay in tech doing something I really love without feeling the intense burnout I've experienced at previous jobs. The burnout was always amplified by the lack of autonomy and mission, when there was one.

My list includes categories like crypto and defense contractors; yours will likely look different, and that's exactly the point. We all want to be able to choose where our energy is going while still being able to afford to live. In addition to the ethical lines go the practical ones: a compensation floor, location and remote requirements, and the team types and structures you already know you work well in.

Every URL is evaluated against that written list, and given a verdict: ‘strong yes,’ ‘yes,’ ‘maybe,’ ‘no,’ and ‘strong no.’ There's always reasoning behind the decision in the notes. A ‘maybe’ gets one week to resolve or it becomes a ‘no,’ which stops you from reevaluating the same posting four times.

The Claude + Notion workflow

I run the entire process using three tools: Claude, Notion, and Gmail. Because I pay for Claude, I run the entire process through that app, using the Cowork feature.

The pipeline lives in a Notion database: one row per lead, with source, status, verdict, and dates. Claude does the reading-heavy middle: it checks each role against my written criteria and drafts the verdict with its reasons, so it's ready for me to review on Monday morning.

The division of labor is deliberate. Claude is tireless about reading the two-thousandth job description, and nothing gets sent to anyone without my eyes on it.

How this became Good Prospect

Eventually I did what designers do to any process they've run more than twice: I turned it into a product. Not everyone has access to a paid Claude plan (especially while they're unemployed!), so I built a tool where you can pretty much replicate the process.

Good Prospect is this whole system as an app: paste in your leads, run them through your own ethical and practical filter, and get bucketed verdicts with the reasons attached. The only difference is that you have to manually paste in the links, instead of the automated process I have running for me.

It's live, and free to use. This isn't an ad for the tool, but if you're so inclined, you can check it out at goodprospect.app.

If you do have Claude, you can also run the same steps right there. I packaged the triage and the boolean searches as two free Claude skills: one runs a job posting through the same filter and gives you a verdict with its reasons, and the other turns a plain-English description of the roles you want into search strings. They're at the bottom of this page, with instructions for adding them to Claude.

The cadence that doesn't burn you out

A job search is a marathon that keeps insisting it's a sprint. The system above exists so that no single day requires you to be brave, organized, and resilient all at once. Each day borrows only one of those.

And here's the reframing that keeps my perspective: every ‘no’ is the pipeline working. Every verdict, including any rejections I receive, gives me more data and narrows it all down toward the role I'm actually going to take. You only need one yes, and you can't run out of nos before you get there (🥲).