Practical tips guiding you from the classroom to corporate leadership.

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Remote Is Not The Only Healthy Career Move

The Challenge We're Solving Today There is something I want to say carefully because I don't want anyone reading this to panic. A lot of you are trying to leave the traditional education space because you're thinking: I need room to breathe....a job that doesn't consume my entire life....fewer a...

Jun 13, 2026

Where the Jobs Are: 2026 Hiring Trends for Transitioning Teachers

This issue is brought to you by: Find $60K+ EdTech Jobs Built for Teachers Edskip helps educators find high-paying roles in EdTech with curated listings — free and premium access. Browse Jobs -> * I may receive a commission if you choose to make a purchase using this link at no extra cost to yo...

Jun 06, 2026

The Summer Job Seeker's Daily Schedule

What's Inside This Issue: No more “what should I be doing today?” Your hour-by-hour job search schedule Click the link. Follow the schedule. Start making progress The Challenge We're Solving Today “I want to make progress in my job search, but I never know what to do each day or if I'm ...

May 30, 2026

This Is A Scam.

If a recruiter messages you about a job and then tells you your resume needs to be “put in the right format,” I want every alarm bell in your body to go off. Especially if the next sentence is something like: “I know someone who can fix this for you.” “I want to make sure you look perfect before...

May 23, 2026

Your Resume Skills Section is Terrible. I Rewrote It For You.

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

May 16, 2026

The 5 Whys: How to Find What You Really Want Next

*]:pointer-events-auto R6Vx5W_threadScrollVars scroll-mb-[calc(var(--scroll-root-safe-area-inset-bottom,0px)+var(--thread-response-height))] scroll-mt-[calc(var(--header-height)+min(200px,max(70px,20svh)))]" dir="auto"> The Challenge We're Solving Today Most transitioning educators start ...

May 09, 2026

A non-linear career isn't a problem. It's normal.

I haven’t had one linear identity. I’ve had chapters. I went from graduate teaching assistant, to Teach For America teacher, to math assessment specialist, to computer science implementation coach, to curriculum editor, to curriculum developer, to learning and development manager, to professiona...

May 02, 2026

Your Resume Is Leaving Out the Good Stuff

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

Apr 25, 2026

This Resume Change Makes Teachers Look More Senior

The Challenge We're Solving Today The biggest resume mistake teachers make during a career change is talking too much about students. I know... that sounds strange at first. You might be thinking, "Wait... are you saying I should not talk about my work and outcomes with students at all?" For the...

Apr 18, 2026

If You Can’t Explain Your Target Job in Two Sentences, Don’t Apply

Read on my website / Read time: 4 minutes A lot of transitioning educators think they know their target job. Then I ask one simple question: What makes you excited to spend your days working as a [target job]? And the person I'm speaking to rambles. Not once.Not occasionally.The last 6 meeti...

Apr 11, 2026

I hit rock bottom.

It wasn't in the middle of a lesson. It wasn’t about the students, and it wasn’t even about teaching itself. It was paperwork. At my school, we had to complete Personalized Education Plans, PEPs, for every student performing below grade level who didn’t already have an IEP. They were handwritten...

Apr 04, 2026

Teachers Who Land $100K Roles Do This Differently

Read on my website / Read time: 4 minutes This issue is brought to you by: Find $60K+ EdTech Jobs Built for Teachers Edskip helps educators find high-paying roles in EdTech with curated listings. Free and premium access. Explore Ed Adjacent Roles Join the $100K+ Club in Your Next RoleL...

Mar 28, 2026

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Practical tips guiding you from the classroom to corporate leadership.

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