Why Teachers Get Called “Difficult” — And Why That Might Be a Good Thing

What if being labeled “difficult” wasn’t a flaw — but a sign that you refused to walk away from your integrity?

In this episode of Teachers in Transition, Vanessa continues her anti-shame crusade with a powerful conversation about boundaries, conviction, and why educators who speak up are often misunderstood.

Inspired by Toby Ziegler from The West Wing, this episode explores how integrity can look uncomfortable — and why real change doesn’t always come from being warm and fuzzy.

You’ll also get a practical AI productivity hack to help reclaim your brain space, plus a deep dive into the myth of the perfect resume and how to navigate the modern job search like a journey across different terrains — from jungle-like application systems to endurance-based government hiring processes.

If you’ve been feeling unsettled, protective, or quietly questioning systems that once felt safe… you are not alone.

Ready for More?

If this episode resonated and you’re realizing you might need a guide as you move through unfamiliar professional terrain:

Book a Discovery Session:
 https://teachersintransition.com/calendar

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Keywords (SEO Tags)

teacher career transition, leaving teaching, teacher burnout recovery, job search strategy, ATS systems explained, USAJobs resume tips, AI productivity for teachers, career coaching for educators, Toby Ziegler West Wing leadership, anti-shame coaching, boundaries for teachers, resume myth, corporate transition for teachers

If This Episode Helped You…

Follow, rate, and share with another educator who needs to hear:

You’re not difficult.
 You’re dedicated.

CONNECT WITH VANESSA

• 💌 Email: Vanessa@teachersintransition.com
• 📱 Call or Text: 512-640-9099
• 📅 Book a Free Discovery Call: teachersintransition.com/calendar
• 🔗 Bluesky: @beyondteaching.bsky.social
• 📸 Instagram & Threads: @teachers.in.transition
• 👍 Facebook: Teachers in Transition

 The transcript to this podcast is found on the episode’s homepage at Buzzsprout

Transcript

Hi! Welcome back to Teachers in Transition!   I’m Vanessa.  I worked as a teacher for 25 years before leaving education for corporate America where I worked for a Fortune 500 company that specialized in helping people get jobs. So, I know what it’s like on BOTH sides of the hiring table!  I am really happy you’re here today!  Today I am continuing on my anti-shame crusade, and we are going to talk about why sometimes being labeled “difficult” is just another way of saying you refused to walk away from your integrity. I’ve got a quick hack on using AI as a personal assistant, and then we’ll head into the career transition segment to ditch the myth of the perfect resume and talk about how to navigate the uncertain terrain of the job application process.

I am still on what I’ve been calling my anti-shame crusade — not to stir up chaos or drag anyone into political arguments, but to talk about things many of us were taught not to name out loud because it was never our shame to carry. 

For some of us, it brings up questions we didn’t even know we were carrying. About the messages we grew up with. About what was normalized. About how often shame was placed on the wrong shoulders. As an example, so many teachers carry shame because they can’t keep up with the workload when instead the shame needs to be placed on those who think that that was an appropriate workload in the first place.  

And  I’ve been hearing from a lot of teachers who feel unsettled. Not just tired — unsettled. Like something in the world shifted and now we’re looking back at parts of our own lives, our own classrooms, and even our own childhoods with a different set of eyes.

 I’m not here to assign guilt, speculate, or turn this into a political sideshow. That’s not what Teachers in Transition is for. But I do think we need to acknowledge that when stories surface about young people being harmed — when headlines remind us that victims were young — it can shake something deep inside those of us who have spent our lives protecting kids.

If you’ve felt yourself reexamining things lately — you are not alone.

I grew up in a generation where a lot of signals were confusing at best and harmful at worst.  We were literally told things like you can’t be too rich or too thin.  We were told that our youthful beauty was all that we had – don’t lose it at any cost.    And now many of us are sitting here decades later realizing just how strange some of that messaging was.  I saw one post point out that one of the most popular perfume scents for teens in the 80s was designed to evoke the idea that we were much younger than we really were – and we were still JUST teenagers. 

And when you stand in a classroom today, when you look at the students in front of you - that realization hits differently. Because suddenly you’re not just processing your own past. You’re feeling protective. Deeply protective.  And there’s that unsettled feeling that we can’t really protect them because so much is coming from so many different directions.

That’s where I find myself lately - feeling very protective and wanting to put my umbrella out and to hold space for teachers who are younger than me, teachers who my age who are quietly rethinking things, and teachers older than me who carry wisdom we’re only now learning to name.

I’m here to say that if you’ve felt unsettled, protective, or quietly questioning the systems we trusted to keep kids safe, you are not imagining things, and you are not alone in that feeling. I’m having a hard time looking at my Lifetouch yearbooks the same way anymore even if it turns out it was innocent the whole time. 

And maybe that’s why a certain character kept coming back into my mind as I was thinking about all of this — Toby Ziegler from The West Wing. The West Wing ran from 1999-2007 and it was about the staffers in a White House. 
 
 

Toby is the communications director – a  guy whose job is literally words. Messaging. Optics. He makes sure that the words are perfect to their purpose.  He’s also a serious idealist, so he’s also looking to make the world a better place.  

And what I love—and also what makes him hard to watch sometimes—is that Toby is not built for calm.  For better or worse, Toby always does what he has carefully considered to be the right thing. Even when that thing can get him in a lot of trouble. 

He’s not a “let’s all just get along” kind of character.

He’s the person in the room who hears something being softened, glossed over, sanded down… and he can’t let it go.

He pushes. He interrupts. He’s blunt. He’s not always polite about it. In fact, there is a piece of trivia that Toby smiles only 8 times in the series.  I’ve tried to count them – I don’t know if that is true because I haven’t had a good system to track my counting, but there are very few genuine smiles from Toby. 

And if you’re the kind of person who was trained to manage everyone’s comfort - if you were trained to be the peacekeeper  - you watch Toby and part of you wants to say, “Sir. Sir. Could you… not?”

But another part of you recognizes something else because Toby isn’t difficult for sport. He’s not difficult for the sake of being difficult.  He’s difficult because he believes words matter. Because he believes integrity matters.

Because he believes that if you let the room slide into convenient lies, people get hurt downstream.

And here’s where the actor, Richard Schiff’s performance is just… masterclass.

Toby isn’t played as a lovable grump. He’s not a sitcom “sass machine.” Schiff plays him like someone carrying weight, like the price of caring is high, and Toby has been paying it for years.

It’s not just anger, although that’s there. It’s conviction that has been in the same room as disappointment for a long time… And that’s something that hits teachers right in the chest.

Because teachers know what it’s like to be the person who keeps saying, “Hey—this isn’t okay,” while everyone else is trying to make it go away with a smile and a slogan.  You know how frustrating it is to be the person asking for an accounting of time or money when someone throws an unfunded mandate at you.  

And then you become… difficult. Not because you’re unkind.

Because you’re unwilling to pretend, and you’re the person asking the questions others are afraid to ask – because you stopped being afraid.

So let me say this plainly, because I think some of you need to hear it: We don’t create change by being warm and fuzzy all the time.

Sometimes the most loving thing you can do is be inconvenient. Sometimes the most ethical thing you can do is make the room uncomfortable. Sometimes “being nice” is just another word for “being quiet.”

And there is no shame in being difficult when it is necessary.

There’s a difference between being difficult because you want to win… and being difficult because you refuse to abandon what’s right. There’s a difference between being difficult for the sake of being difficult and being difficult because you are drawing an important boundary.

Toby refuses to abandon what is right, and he isn’t afraid to point out the boundaries we need to keep as well as the ones we need to push past.

And if you’ve been carrying that same weight—if you’ve felt unsettled, protective, awake, and quietly furious at the way systems can minimize harm and keep moving—then I want you to know something.

You’re not alone.  And you’re not broken. And you aren’t difficult – you’re dedicated, principled, bold, and compassionate.  And sometimes that looks like “difficult” to those who have trouble seeing the whole chessboard. 

 And moving onto our hack: I like to share hacks to help you regain time, money or brain space so you that can spend it on the things you really want to.  And today I have another little AI hack – this time to function as a personal assistant. If you have AI that you regularly, designate specific chats for specific things.  These can help you remember. 
 
 Example: I have one called “Memory Container”
 In my memory container, I can put into a reminder:  I put the Valentine’s cards in the lavender file by my desk.  Please remind me on Friday at 3:00 to get those ready.”  Then I get a reminder to do the thing.  And if I forgot where they were, I can ask “hey, where are those Valentine’s cards” and I get a specific location.  *Side Note – a system is only good if you follow through. My guys still didn’t get their Valentine’s cards until Tuesday night.     
 
 Another Chat is named:  Daily Standup
 I can dump everything I am thinking of into that chat the night before, the week before, whenever things come up.  The next morning when I ask it for the daily task list.  I can add things to it as needed.  I’d REALLY recommend something like this to be spoken into your AI before you leave school for a couple of reasons.  (1) many of us deal with trauma and trauma can negatively impact your memory and (2) science has figured out that we tie short term memory to location.  This is why you put your things in your bag and say you’ll do them at home, get home and think “hey, I don’t have anything to do for work,” only to get back into your classroom and be hit with all the memories you forgot.  Same things happens when you go to the kitchen to get the thing, but you don’t remember what the thing was until you sit back down in the other room.  #Science! AI can keep these things for you. 
 
 In post-op, I created a chat to put guardrails on my day to make sure I didn’t do too much.  It was MUCH more conservative than I would have been.  I’ll argue I am healing better because the AI was programmed to argue with me about capacity. 
 
 Other potential chats that might would be useful – here’s a running list:

·         Gift Ideas

·         Brilliant Ideas

·         Open Loops- for emails that needs to be sent, follow-ups, paperwork reminder

·         Parking Lot – like the memory container but feel more immediate

·         Meal planning ideas - collect enough of meals and menus in one chat and eventually you’ll be able to ask it to create a menu plan and shopping list

·         Someday Dreams – you can park them here and ask the AI to help you dream the dream.  AI has the ability to research MUCH faster than you can. 

If you want to use these designated chats towards career transition, you can try having a few titled:  

·         Clarity Corner – put all your ideas here about what you can do.  

·         Translated Skills – used your resume bullet points and ask it to translate that same skill to be more understandable for a completely different job.  Eventually, you have enough in there that you search the skill or the job and they’ll all pop up. 

·         Boundary Build – give it the guidelines at the beginning in best practices and you can draft responses, reframe guilt-heavy transitions, and practice saying ‘no’.  Example:  “rewrite this email so I sound firm but not apologetic”  Or, “rewrite this email and take my gut-reactions out of it, but get the idea across as a professional.”
 
 

The AI can hold all this to free your brain to focus on creativity.

Career Transition and Job Search

Alright — let’s shift gears for the career transition segment, because I want to talk about something I see over and over again with job seekers, especially teachers stepping into new professional landscapes.

The myth of the perfect resume.

I see people spending hours — sometimes entire weekends — tweaking fonts, colors, spacing, templates… adjusting margins by half a centimeter like it’s going to unlock a secret door somewhere. And I understand why. Teachers are wired to chase the A+. We want the rubric. We want to know where the points are. We want to believe there’s a version that earns full credit if we just refine it enough.

And honestly? That instinct has served us well for a long time. But there’s another layer here that I think is quietly shaping how teachers approach job searching, and that’s the way education has slowly shifted into edutainment.

We’re trained now to make things engaging. Visually inviting. Easy to digest. We build slides that sparkle. We create materials that feel warm and welcoming. We learn, over time, how to make information not just correct… but palatable. In my last year of teaching, I described my teaching styles as Bob Ross meets Robin Williams. 

So when teachers sit down to build a resume, a lot of that instinct shows up immediately.

“Is it attractive enough?”
 “Does it look modern?”
 “Should I add color here?”
 “Maybe a different template will finally make it land…”

It makes sense because creativity is part of what makes teachers incredible communicators. And past wisdom has beaten it into our heads about making the resume perfect – formatting, spacing, spelling. And to some extent, that is still true.  Spell things properly, get the grammar correct, and make it easy to read.  But beyond that, creativity isn’t adding any bonus points in most job applications. Unfortunately, the hiring process doesn’t always reward pretty.

It rewards navigable.

And that’s where I want to introduce a different way of thinking about this whole journey. Because the modern job search isn’t one road.  It’s a little like a map.

And most of us were handed a map that only shows one kind of terrain: the classroom. The urban environment.

But the moment you step outside of that familiar landscape, you start crossing environments that behave very differently.

Some feel like a jungle: Dense. Rules-heavy. Low visibility. You send out applications and it feels like your path disappears behind you. You might be moving forward… but you can’t always see the trail you’re leaving.

If you were actually traveling through a jungle, you wouldn’t pack decorative gear. You’d pack tools that help you move forward — simple, functional, durable (and waterproof!). You’d focus on form over appearance

And in resume terms, that might look like simplifying headings, keeping formatting straightforward, and letting the structure do the work instead of the design.

Not because design is bad — but because visibility matters more than beauty when you’re under a canopy.

Then there are environments that feel more like a swamp.

And if you’ve ever felt like you’re doing everything right but nothing is moving, you know exactly what I mean.

The ground feels uncertain. Processes happen beneath the surface. You take a step and you’re not always sure if it’s solid or if you’re going to sink a little before you move forward again.

In a real swamp, you wouldn’t sprint. You’d slow down. You’d distribute your weight carefully. You’d test each step before committing to it. You would NOT go wading into what you can’t see (gators, you know?)

In the job search, that might mean filling out every application field even when it feels stupidly redundant. Matching language closely to the posting. Accepting that sometimes progress happens quietly, behind systems we don’t see.

And I know — for teachers used to immediate feedback, that kind of silence can feel disorienting.

Some environments feel more like open water.

There’s movement. There’s current. Sometimes you notice that when you step outside of LinkedIn and follow an application link directly to a company’s website, the experience shifts — like you’ve left the dock and entered the river itself.

And while we’re floating here together for a moment, a gentle reminder: try not to let “Easy Apply” be your only route. It’s convenient — absolutely — but sometimes it keeps you standing at the edge instead of letting you drift into the stronger currents.  LinkedIn loves to promote it, but it contributes to noise. Application noise. Do you know anyone who has clicked apply and gotten a job from it? Me neither.  

Open water requires a different mindset.

You pay attention to timing. To momentum. To where the flow is already moving — instead of trying to paddle against it.

Then there are coastal environments.

Places where the system still exists, but the human shoreline is visible. Conversations matter. Referrals matter. You start to recognize familiar landmarks — a person you’ve spoken with, a connection who introduces you to someone else.

Navigation there feels different. Less like hacking through vines… more like steering.

And then we have the desert. Government systems. Spaces like USAJobs.

These are endurance journeys and if you are not prepared, you will not make it across.

If you were crossing a desert, you wouldn’t carry extra decoration. You’d carry documentation. Water. Clear instructions. You’d expect the pace to be slower — and you wouldn’t judge yourself for that.

In those environments, success isn’t about flair. It’s about detail. Precision. Respecting the structure of the path that’s already laid out.

And here’s the part I really want you to hear.

If you’re trying to create one perfect resume that works everywhere, it’s going to feel like you’re lost — because you’re using one map for a journey that crosses multiple terrains.

And when teachers feel lost, we often assume we did something wrong.  We always assume it was us.  

We rewrite. We redesign. We try to make it more appealing.

But sometimes the issue isn’t the resume.

Sometimes it’s that you’re walking through a jungle with desert gear… or trying to cross a desert at ocean speeds.

Your job isn’t to design the perfect document. Your job is to learn how to read the landscape.

To notice where you are.                                                 

To adjust your pace.

To choose tools that match the environment instead of tools that look impressive in isolation.

Because once you start seeing the journey this way, something really powerful happens.

The pressure to be perfect softens.

The silence stops feeling personal.

And the path forward starts to feel a little less mysterious.

In Alaska, we have a saying “we don’t change our plans, we change our gear.”  
 So if you’ve been staring at your resume wondering why it’s not working… take a breath.

You may not be off course.

You may just be traveling through a different part of the map than you expected and you need different gear.
 
 If today’s podcast resonated, and you’re realizing you might need a guide as you move through unfamiliar terrain, this is what I do. Outside of the podcast, Teachers in Transition has programs offering a variety of services designed to help teachers find their way out of the classroom from simple resources, to courses, to 1:1 coaching.  I encourage you to sign up for a discovery session with me. These simply a chance for us to look at where you are, where you want to go, and what the landscape in front of you actually looks like — no pressure, no performance, just clarity. 

There's a link in the show notes or you can head over to the homepage at teachersintransition.com and find a time that works for you. Just know you don’t have to navigate this journey alone. It's easier with a guide whose been there before and knows the way out.

👋 CONNECT WITH VANESSA

• 💌 Email: Vanessa@teachersintransition.com
• 📱 Call or Text: 512-640-9099
• 📅 Book a Free Discovery Call: teachersintransition.com/calendar
• 🔗 Bluesky: @beyondteaching.bsky.social
• 📸 Instagram & Threads: @teachers.in.transition
• 👍 Facebook: Teachers in Transition
• 🐦 X (Twitter): @EduExitStrategy

That’s the podcast for today! If you liked this podcast, tell a friend, and don’t forget to rate and review wherever you listen to your podcasts. Tune in weekly to Teachers in Transition where we discuss Job Search strategies as well as stress management techniques.  And I want to hear from you!  Please reach out and leave me a message at Vanessa@Teachersintransition.com  You can also leave a voicemail or text at 512-640-9099. 

I’ll see you here again next week and remember – YOU are amazing!