Practical tips guiding you from the classroom to corporate leadership.

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Why the Edtech Tool You Love... Can't Hire You (Yet)

The Challenge We're Solving Today You’re using an edtech product in your classroom, you love it, and now… They’ve posted a job. At your own district. You’re thinking: "This is perfect. I’m already a superfan!!" But here's the twist... you probably can’t get hired — not because you’re not qualifi...

Feb 21, 2026

9 Job Boards Every Transitioning Teacher Should Bookmark (that aren't LinkedIn or Indeed)

Let me ask you something. Are you only using LinkedIn and Indeed to look for jobs? If you said "yes," this might be slowing you down. I hear this a lot: "I’ve applied to so many jobs.""I check LinkedIn every day.""Why am I not getting interviews?" If that sounds like you, keep reading. Why Th...

Feb 14, 2026

Your Career Change Has a "Drop-Off Point." Here’s How to Find It and Fix It.

The Challenge We’re Solving Today You’ve applied to dozens of roles, tailored your resume (or so you thought), and even landed a few interviews but nothing’s moving. You feel like your job search is stuuuuck. It gets frustrating. Demoralizing. Gutting. You’re doing the work, but the results just...

Feb 07, 2026

When a Recruiter Scans Your Resume for 8 Seconds, Here's What They're Actually Looking For

The Challenge We're Solving Today You’ve heard it before: recruiters spend just a few seconds looking at your résumé. But what’s really happening in those seconds? Nope, they’re not reading your full bullet points. They’re scanning for nouns. Tools. Platforms. Systems. Artifacts. If those aren’t...

Jan 31, 2026

Why Teachers Keep Losing to Less Qualified Candidates (and how to fix it)

Let's get one thing straight before we dive in. Teachers. don’t. lose. out. because. they. lack. skills. They lose because they explain what they did, while other candidates explain what was broken. Hiring managers don’t want "I worked hard, see?!".They need diagnosis and stabilization. Here’s w...

Jan 24, 2026

The Job Market Isn't Broken. You're Just Using Advice from 2022.

*]:pointer-events-auto scroll-mt-[calc(var(--header-height)+min(200px,max(70px,20svh)))]" dir="auto" tabindex="-1"> Read on my website / Read time: 4 minutes This issue is brought to you by: Find $60K+ EdTech Jobs Built for TeachersEdskip helps educators find high-paying roles in EdTech w...

Jan 17, 2026

Ask the Dumb Question. I Mean It.

“I don’t know what I don’t know.”Every week, I hear job seekers ask the same things… but with a little shame in their voice, like they should already know the answers. These questions aren’t actually dumb. They’re a sign of overwhelm or unclear goals or just plain not knowing which way to go. So...

Jan 10, 2026

How to find the "business problem" you actually solve.

Read on my website / Read time: 4 minutes This issue is brought to you by: Find $60K+ EdTech Jobs Built for TeachersEdskip helps educators find high-paying roles in EdTech with curated listings. Free and premium access. Browse Jobs Now * I may receive a commission if you choose to make a purch...

Jan 03, 2026

"Exposure Therapy" Should Be Your New Year's Resolution.

Your resolution: run one solo mock interview every week.Less than 15 minutes. That’s it. You do not need a coach to prepare for interviews. You don't even need an actual interview yet. You need a system you can repeat on your own. Yes, I coach people.And no, you do not need a coach for this part...

Dec 27, 2025

Layoffs are happening. So is hiring. What gives?

The Challenge We’re Solving Today One minute, you see a post about layoffs. The next, someone just got hired. What’s really going on? It feels confusing. You might be asking, “Should I be worried?” or “Am I doing something wrong?” This is my simple take on this. The market is messy right now. B...

Dec 20, 2025

5 Careers for Teachers Who Are Over It

The Challenge We're Solving Today What careers are actually a good fit for teachers... besides the obvious ones? If you’ve spent any time Googling “careers for former teachers,” you already know the top answers: Instructional designCorporate trainingGeneral EdTech These are great paths. But th...

Dec 13, 2025

What's In and What's Out in 2026

The Challenge We’re Solving Today Since you're reading this, your a transitioning educator, and you might still be focusing on things like: “I’m passionate” “I care about students” “I’m a hard worker” Those are all good things. But in 2026, it’s not enough. Now, companies want to know: ...

Dec 06, 2025

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Practical tips guiding you from the classroom to corporate leadership.

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