Teach17

From violinist and music teacher to arts education leader and career coach, Jason Leshowitz has spent more than 30 years helping people recognise their potential. Through RejectionProofCareer and his book The Rejection Proof Educator, he helps teachers recognise their transferable skills and explore new career opportunities. In this interview, Jason shares his thoughts on career changes, leadership, burnout, job rejection and why teachers should never underestimate their experience.

1. What first inspired you to become a teacher?

Music was the doorway for me. I was a violinist, and teaching gave me the chance to take something I loved and use it to help young people discover something about themselves.

There’s a moment when a student who was convinced they couldn’t do something suddenly can. I’ve been chasing that moment for more than 30 years.

2. How has your career evolved over the past 30 years?

I started as a music teacher and orchestra director. Today, I supervise close to seventy K–12 visual and performing arts teachers across an entire school district.

So, somewhere along the way, tuning violins turned into supervising people, building programmes, hiring staff, managing budgets, developing curriculum, advocating for the arts, speaking, writing and now running a career coaching business alongside my district work.

I definitely didn’t have that career map at 22.

And I think that’s part of the point. Careers make a lot more sense looking backwards than they do while you’re living them.

3. What inspired you to establish RejectionProofCareer?

This is slightly less glamorous than people probably expect.

I once opened a document and titled it “Side Hustle Ideas for Vacation Money”.

That was the beginning.

What I eventually discovered was a problem I couldn’t stop noticing: incredibly capable people were being rejected because they couldn’t explain what they were capable of.

Their experience was strong. Their translation was terrible.

RejectionProofCareer grew out of helping people close that gap.

4. Why do talented teachers sometimes struggle to progress?

Because being good at your job and being good at getting the next job are completely different skills.

Education can train people to become phenomenal professionals while giving them almost no training in how to communicate their value.

So somebody spends 18 years leading people, managing conflict, developing programmes, analysing data, communicating with difficult stakeholders and solving problems all day.

Then the résumé says:

“Planned and delivered engaging lessons.”

That’s the problem.

5. What transferable skills do teachers often overlook?

Usually, the skills they use so often that they’ve stopped recognising them as skills.

Teachers facilitate groups. They train people. They analyse information. They manage competing priorities. They present constantly. They solve problems with incomplete information. They communicate with wildly different audiences. They make hundreds of judgement calls every day.

And because they call it “teaching”, they sometimes assume none of it counts anywhere else.

It does.

6. Where should teachers begin when considering a career change?

Please don’t begin by typing “jobs for former teachers” into Google.

That search alone puts you in a box.

Start with the problems you’re good at solving, the work you actually enjoy, what you want your life to look like and which parts of teaching you’d happily never do again.

Then investigate where those abilities have value.

You’re looking for a match between your capabilities and somebody else’s problems, not a list of approved escape routes for teachers.

7. What are the biggest CV mistakes teachers make?

They write résumés for other educators instead of for the person they’re trying to get hired by.

Too much jargon. Too many duties. Almost no evidence. Very little scale. And bullet point after bullet point that could belong to any teacher in the building.

If I removed your name from your résumé, could somebody who knows you identify it as yours?

If the answer is no, we’ve got work to do.

8. What makes a great job interview?

I tell people that the interview changes when you stop trying to give impressive answers and start giving believable ones.

Specific stories win.

Tell me what was happening. Tell me what you noticed. Tell me what decision you made. Tell me why. Tell me what happened next.

Anybody can call themselves strategic, collaborative, resilient or passionate.

Show me the receipt.

9. How can teachers demonstrate leadership without a formal title?

Pay attention to what happens when nobody knows what to do.

Who do people look at?

Who organises the response? Who mentors the new person? Who fixes the broken process? Who gets the event off the ground? Who sees the problem before everyone else does?

That’s leadership.

A title is useful because organisations like labels. But plenty of people are doing leadership work years before somebody gives them permission to put “leader” in their title.

10. How should teachers deal with repeated job rejections?

Don’t let rejection write a biography about you.

A rejection tells you one thing with certainty: you didn’t get that particular opportunity.

That’s it.

It doesn’t tell you that you’re untalented. It doesn’t tell you that you waited too long. It doesn’t tell you that nobody outside education will want you.

Look for patterns. Adjust what needs adjusting. Get better at the parts you control.

That’s what I mean by becoming rejection-proof. Rejection still happens. It just loses its authority over what you do next.

11. What advice would you give to teachers feeling stuck in their careers?

Interrogate the word “stuck”.

Are you exhausted? Bored? Underpaid? Underused? Angry? Passed over? Done with your school? Done with education?

People can spend years trying to solve the wrong problem because all of those feelings get bundled together as “I need a career change”.

Figure out what you’re actually trying to change.

Then make one move that gives you new information.

You don’t need the entire staircase. You need the next useful step.

12. How can teachers make better use of LinkedIn?

First, stop letting your LinkedIn profile read like the identification badge hanging around your neck.

“English Teacher at X School District” tells me where you work. It doesn’t tell me much about you.

Use the profile to establish what you know, what you’ve built, what problems you solve and where your expertise might travel.

And then talk to people.

LinkedIn works considerably better when you remember the “social” part of professional networking.

13. How can teachers become more confident about promoting themselves?

I think teachers have been trained to confuse visibility with vanity.

They’ll spend all day advocating for a student, a colleague, a programme or a school and then become unbelievably uncomfortable when asked to explain what they themselves are good at.

So take ego out of it.

What did you build?

What grew?

What improved?

What problem disappeared because you handled it?

That isn’t bragging. That’s evidence.

Your work deserves a witness, even when the witness has to be you.

14. What can school leaders do to support teachers experiencing burnout?

Before booking the mindfulness speaker, look at the meeting calendar.

Burnout isn’t always a wellness problem. Sometimes it’s an organisational problem.

Too many initiatives. Too little planning time. Constant interruptions. Unclear priorities. Work that gets added but somehow never gets removed.

One of the smartest questions a leader can ask staff is:

“What are we doing that we could stop doing?”

Sometimes supporting people starts with subtraction.

15. What inspired you to write The Rejection Proof Educator?

I kept meeting people who had spent 10, 15 or 20 years becoming extraordinarily good at things, then decided that none of it counted because they wanted to do something different.

That made no sense to me.

Changing buildings doesn’t erase your experience. Changing industries doesn’t send you back to professional kindergarten.

The idea at the centre of the book is one I come back to constantly:

Your experience belongs to you, and it travels.

The challenge is learning how to translate it so the next person can recognise its value.

16. How might AI change career opportunities for teachers?

AI is going to remove some tasks, change others and create work we haven’t named yet.

That doesn’t make me pessimistic about teachers. Quite the opposite.

Teachers have spent their careers doing things AI still struggles with: reading a room, earning trust, adjusting in real time, managing ambiguity, motivating people, facilitating difficult conversations and making judgement calls when the neat answer doesn’t exist.

Learn the technology.

Use it.

Get very good at it.

But don’t hand it the parts of you that are actually valuable.

I use AI quite a bit. I still want the thinking to be mine.

17. What one piece of career advice would you give every teacher?

Stop letting your current job title negotiate the size of your future.

You’re not starting over.

You’re starting from experience.

Learn how to name it, prove it, translate it and carry it with you.

Because your experience belongs to you.

And it travels.

Connect with Jason Leshowitz and follow his work on LinkedIn .