Leaving Teaching: Now With More Imposter Syndrome

Person in pajamas looking at job boards on a laptop, surrounded by everyday clutter and a coffee mug.

Teachers are the most adaptable, organized, and quietly brilliant professionals in the job market.

We manage impossible workloads, coach kids through emotional regulation while logging attendance, tracking behavior data, and meeting with parents, sometimes all before the second period.

So why did leaving teaching amplify the feeling that I wasn’t qualified for anything else?

Despite completing multiple certifications, building an entire instructional design portfolio from scratch, and spending hours tailoring every job application to speak to what recruiters say they want.

Bare Minimum? Still Heroic. Still Not Appreciated


It wasn’t new. Even in the classroom, I carried a constant sense of falling short. There’s a culture of martyrdom in education where the “best” teachers seem to have endless passion, energy, and time. They volunteer for everything, stay late to tutor, and somehow grade a stack of essays with personalized feedback in a single weekend.

Meanwhile, I was doing the bare minimum—because even the bare minimum in teaching is already above and beyond the job description. Still, it never felt like enough.

When I told my instructional coach I was planning to leave teaching and was considering project management, she tilted her head with that tight smile she always wore when pretending to be curious, and asked, “Do you think you’re qualified for that?”

“Do you think you’re qualified for that?”

This was the same coach who once handed me a stack of unrequested “growth data” printouts during a ten-minute check-in, so I shouldn’t have been surprised. But still, after three years of working together, I expected at least a little support. Or basic tact.

It was a moment that stuck, especially when it confirmed what I feared.

Where Dreams Go to Die (a.k.a. LinkedIn)


I’ve had postings close before I even finished applying. Once, I applied and got the rejection email less than 12 hours later—basically before they could’ve opened my portfolio. Another time, I landed an interview only to find out they’d already chosen someone internally and were just “fulfilling the external candidate requirement.”

Job Hunt Highlights

  • Rejected less than 12 hours after applying
  • Listing closed mid-application
  • Interviewed just to check the “external candidate” box
  • Got ghosted after two rounds of interviews

It almost forces you into nihilism.

You can’t take the rejections personally because the system feels like a lottery. The person who gets the interview probably isn’t a unicorn. They’re just a lucky star—barely more qualified than me, if at all. And it’s not always about qualifications, anyway. It could be timing, a personal connection, or simply the fact that you’re employed, which somehow makes you more desirable.

Every job-seeking cliché you’ve ever heard?

True. Every single one of them.

Burnout, Hyperfocus, Repeat


I’ve recognized a pattern in myself.

Some days, I feel unstoppable—riding a high of self-confidence where I tackle portfolio projects like a madman, hyper-focused and productive to the point of obsession. Other days, I hit a wall. I want to escape into a world where no one’s job hunting or formatting resumes.

The middle ground is where I function best. It’s not glamorous, but it’s consistent: a mix of job search tasks, gig work, and house projects. The structure helps me feel like I’m making progress, and the variety keeps burnout from creeping in. It’s the space where I can contribute something without spiraling into hopelessness or delusions of grandeur.

I’m figuring things out as I go—applying, building, learning.

Lately, I’ve been forcing myself to name the actual skills I built as a teacher, not the vague “multitasker” fluff, but the real stuff. Like planning units with clear outcomes. Managing time down to the minute. Reading the room. Tracking progress, adjusting plans, presenting ideas clearly to any audience. That’s instructional design. That’s project management. I just don’t have those labels.

Skills I Gained as a Teacher (That Nobody Lists on LinkedIn)

  • Managed a classroom, a Google Sheet, and a student meltdown—all before 9:00 a.m.
  • Presented a lesson on conflict resolution while two students threw pencils at each other
  • Met deadlines even after covering for a coworker who ghosted mid-week
  • Delivered data reports to admin while pretending not to cry in the bathroom between classes

Planting Seeds. Watering. Waiting.


I’ve learned a few things that help me stay on track—setting small, measurable goals each day, treating gig work like stepping stones instead of detours, and reminding myself that learning a new tool or finishing a course is progress, even if no one sees it.

Even if landing the right job takes longer than I hoped, the skills I’m building now will still matter when I get there. The habits, the self-discipline, the ability to pivot and keep going—those are career skills, not just coping mechanisms.

And in the meantime, I’m choosing to believe that leaving teaching wasn’t the end of something. It was the start of finally learning to bet on myself.

Are you a fellow teacher in transition?
I’d love to hear how you’re navigating your pivot—drop a comment below!