🧠 Job Searching Like a Systems Thinker: What Broke, What Worked, and What I’ll Never Do Again

📌TL;DR: I’m a hybrid job seeker—part old-school connector, part digital detective.

Here's what I know: I hate to break it to you, but your next opportunity is probably a few human connections away, not just a few clicks.

But since we are the internet generation, we all must use digital tools to our collective advantage—learning the hard way what works, what doesn’t, and where the jewels of wisdom are buried. ⛏️💎

Because in this market, time (and clarity) is everything. ⏳

Sidebar: This article has been recently updated with a workaround for failed Boolean searches. Now, there are a couple of ways presented here to find newly posted opportunities in your designated locations. 🎉

🎯 The Experiment: Boolean Strings & Global Listings

Earlier this week, I attempted to enhance my job search using custom Boolean strings.

It felt strategic. It also turned out to be painfully tactical. 😭

I was taking a 30,000-foot view while simultaneously buried in weeds. 🤪

Soon, I found myself reviewing expired job listings in London, Munich, and Singapore—while sipping coffee in my kitchen in California, thinking: "Geez, that would be one looooooong commute!" ✈️☕

I can be in-office, but here, not internationally. I can work internationally, but I am physically based here, and remote as opposed to in an office located in an international location. It’s as simple as that! Sheesh! 🥴

Somehow, with Boolean strings, the math wasn’t mathing for my multi-faceted, multi-dimensional job search.

However, this wasn’t a glitch because, on some level, Boolean strings do work. It was a system issue that prevented them from working for me.

And it needed a systems thinking approach to fix it.

🧩 What Is Systems Thinking (and Why It Helped)

Systems thinking means seeing the whole, not just the broken pieces.

It’s not about blaming the tool—it’s about understanding the structure that led to the result.

In job search terms, that means:

• 🔍 Spotting patterns, not just frustrations
• 🧱 Identifying root causes, not surface-level pain
• ⚙️ Designing sustainable workflows instead of repeating what doesn’t work

It’s the same mindset I’ve used to lead enterprise transformation—and this time, I applied it to something deeply personal: my job search.

🔍 The Test: From Failure to Fabulous: How I Accidentally Unlocked the Google Jobs Tab

I mapped my target companies, preferred roles, and crafted precise Boolean strings to hunt for U.S.-based remote and hybrid roles. But soon, my plan encountered two major issues:

🔐 CAPTCHA kept asking me if I was a robot. Repeatedly. 🤖🤖🤖🤖🤖🤖🤖 

As I scrolled through my search results for all the different roles of interest, I had to click a checkbox several times to prove that—yes, I was, indeed, and continue to be a human being. 😆

I couldn't help but laugh—turns out if you search like a machine, the internet starts to question your existence. But even when I passed the tests, my results were…

 🌍 Mismatched Results:

• 🤔 International listings with vague or misleading location labels
• 🥸 “Remote” jobs with unclear definitions (global? U.S.-based? hybrid-but-remote-ish?)
• 👻 Expired postings, even with date filters applied

The takeaway: basic Boolean logic is useful, but search engines aren’t built with job seekers in mind—especially when geography and flexibility matter.

🚨Nerd alert! This Boolean failure became the thought that woke me up in the middle of the night. "What if basic Boolean isn't the way? What if...there is a different way." And thankfully, there is...so I've updated this section with the result, which now has a much happier ending. 😅

🔥How I Optimized My Boolean Strings to Unlock the Google Jobs Tab

At first, I assumed the best way to find targeted job listings was to paste long Boolean strings directly into Google. It felt logical and efficient—just use the right keywords, add a few filters, and let Google do the rest. The problem? The results were all over the place: expired jobs, irrelevant links, and random blog posts.

So I took those Boolean strings and put them into Chat GPT and asked:

Can you clean up and consolidate all of these Boolean job search strings into one optimized version that works effectively in Google Search? Please ensure it's structured to trigger the Google Jobs module, uses correct syntax (e.g. OR, quoted titles, targeted sites), and includes filters for U.S.-based remote and hybrid roles.        

But once I optimized those strings specifically for how Google Search interacts with structured job data, something shifted. Instead of returning a list of links, Google began surfacing roles inside the Google Jobs module—that blue box with built-in filters for title, company, location, and date posted. Same search bar, completely different interface. Here’s what changed:

❌ Basic Boolean (Not Optimized) This type of string tends to return generic web results, not job listings inside the structured Google Jobs tab:

change manager OR transformation manager site:jobs.com | site:greenhouse | site:lever        

• No quotes around job titles
• Uses “|” instead of “OR” (Google doesn’t interpret this consistently)
• Targets vague or low-signal sites like jobs.com
• Lacks U.S.-specific location terms
• Rarely triggers the blue “Jobs” interface

✅ Optimized Boolean (Triggers Google Jobs Module) Once I restructured the same query using exact-match syntax and better site targeting, Google began returning curated job listings:

("Change Manager" OR "Transformation Manager") ("Remote United States" OR "California" OR "San Francisco Bay Area") site:greenhouse.io OR site:lever.co OR site:myworkdayjobs.com        

• Quoted job titles = precise matching
• Proper “OR” usage for Boolean logic
• Includes common U.S. location phrases that match structured job metadata
• Limits search to known ATS platforms like Greenhouse, Lever, and Workday
• Triggers the Google for Jobs blue box, enabling filters like “Date Posted” and “Type”

Turns out, optimizing for Google Search isn’t just about Boolean logic—it’s about formatting it in a way that aligns with how Google reads and categorizes job data. Same keywords. Smarter results.

🤖 A Word on Aggregators

I also tested several modern job aggregator platforms—those with sleek interfaces and filters aimed at tech-savvy professionals.

What I found:

• 💌 Spammy follow-ups
• 🛑 Vulnerability in sharing personal info
• ⏳ Delay between job posting and job listing
• 🌐 Vague hybrid/remote labeling

There are a few that I like a lot, though. However, for the most part, these platforms are helpful for exploration and trend spotting; yet, if you’re in active application mode, they can slow you down.

✅ The Fix: Rebuilding My Search on LinkedIn

I shifted my focus to what I could control: LinkedIn’s job search tools.

Here’s what worked:

• 🎯 Filtering for “Past 24–72 hours”
• 📍 Specifying “Remote – U.S.” or “Hybrid – SF Bay Area”
• 📘 Using actual job titles from real-world postings
• 🏢 Prioritizing roles posted directly by companies

The results?

• 🚫 No more expired listings
• 🌐 Fewer international+onsite mismatches
• ✅ Stronger alignment with my skills
• ⏱️ Time well spent

This wasn’t luck. It was structure.

And that’s what systems thinking delivers—clarity, efficiency, and results.

Sidebar: While I won’t go into the specifics of what I did to customize my specific search, you can check out these super helpful posts from Emily Wordon with tips on how to use LinkedIn to: 

• Be One of the First to Apply 
• Find People Hiring 

These are game-changers when it comes to maximizing your search.

🔁 The Bigger Pattern: Stop Hustling Through Broken Loops

Job searching today is full of friction:

• ❌ Outdated listings
• ❌ Unclear labels for remote/hybrid
• ❌ Platforms not designed for job seekers’ real needs

But when you zoom out, you stop reacting to the chaos and start spotting the system beneath it. Ask yourself:

• 🔎 Where are you spending time that’s not producing results?
• 🧠 What inputs are consistently leading to dead ends?
• ⚙️ What small shift could unlock a new outcome?

Smart systems aren’t perfect—they’re responsive.

And smart candidates don’t just hustle harder—they design better processes.

💬 Let’s Crowdsource Smarter Job Search Systems

If you’ve built your own job search engine—Boolean logic, custom alerts, job tracking, tools you trust—I want to hear what’s working for you.

We’re not just job hunting.

We’re building smarter systems that respect our time, energy, and value.

Let’s keep improving—together. 🤝

🙏 Big thanks to Kristen Jacobsen for inspiring me to think beyond my current routines and push into new territory.

#jobsearch #systemsthinking #careerstrategy #booleansearch #transformation #changemanagement #resilience #linkedinwisdom #humannetworks