Teachers in Transition – Episode 257: What They Called Weak Was Just a Different Kind of Brave

Episode Overview

In this episode, Vanessa explores How to Train Your Dragon through a powerful lens: not just as a fantasy adventure, but as a roadmap for reclaiming agency, curiosity, and purpose in career transitions. The conversation covers how Hiccup from a collection of children’s books to a live-action movie, themes of belongings, the Huge different between ‘couldn’t’ and ‘wouldn’t’, and finally some career transition tips that are fireproof – even on the inside!

See for Yourself

Animated How to Train Your Dragon (2010) is streaming now on:

• Max  (max.com)
• Rent or buy via Amazon Video, Apple TV, Google Play, Microsoft Store 

💡 Vanessa tip: I encourage checking out the live-action remake in the theaters.  It’s an excellent live-action update. 

Links

• Read up on Cressida Cowell’s original book series at Wikipedia
• Watch Cressida talk about her newest books 
• Music by John Powell – soundtracks on Spotify/Apple Music
• DIY Career Courses Coming Soon – email Vanessa directly for early access to DECIDE, CLARITY, and BUILD at a special reduced rate for the first few enrollees

🗝️ Key Takeaways for Teachers in Transition

• Belong while true to yourself — your unique perspective is your superpower.
• Choice = Power — shifting from “couldn’t” to “wouldn’t” restores control and motivation.
• Lead with empathy — the kindest solutions often bring the strongest outcomes.
• Music moves us—don’t underestimate the power of emotional connection, even in career work.

Connect with Vanessa

Vanessa@TeachersinTransition.com

Leave a voicemail or text at 512-640-9099

Connect with Vanessa on LinkedIn!

Schedule a free Discovery Session with Vanessa here

Follow Vanessa on Bluesky @beyondteaching.bsky.social

Visit the homepage at TeachersinTransition.com to learn more!

Help Grow the Podcast!

Please share this podcast with someone that you think might like what it has to say – many teachers are aching to find a way to a new career.  You can help them. People find new podcasts mostly because they’ve been recommended by someone they know.   

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

Transcript

Are you a teacher who is feeling stressed out and overwhelmed? Do you worry that you're feeling symptoms of burnout - or are you sure you've already gotten there? Have you started to dream of doing something different or a new job or perhaps pursuing an entirely different career - but you don't know what else you're qualified to do? You don't know how to start a job search, and you just feel stuck. If that sounds like you, I promise you are not alone. My name is Vanessa Jackson; and I am a career transition and job search coach, and I specialize in helping burnt out teachers just like you deal with the overwhelmingly stressful nature of your day-to-day job and to consider what other careers might be out there waiting for you. You might ask yourself, what tools do I need to find a new career?  Are my skills valuable outside the classroom?  How and where do I even get started?  These are all questions you deserve answers to, and I can help you find them.  I’m Vanessa Jackson. Come and join me for Teachers in Transition. 
 
 Hi, and welcome back to another episode of Teachers in Transition! I'm Vanessa Jackson I spent 25 years in the classroom teaching in Texas and Alaska, left teaching to go work in the staffing industry for a Fortune 500 company, and now I work for teachers helping them leave toxic situations in pursuit of the life they deserve. I’m spending the summer framing my message surrounding wellness and career transition through the lens of some of my favorite things:  movies.  This week, I am talking about Dreamworks’  animated classic, How to Train Your Dragon.

Fun fact—this film is actually getting the live-action treatment, which at first made me say, “Wait, how do you do live-action dragons?” But honestly, it’s been beautifully done. It expands on things that didn’t get much airtime in the original and gives the story some extra heart.  I am sure that the reason the live-action is faithful and a deeper treatment of the original animated version is because the same director was at the helm. 

Let’s rewind to 2003. That’s when How to Train Your Dragon first appeared - not on a screen, but in a children’s book by British author, Cressida Cowell. This kicked off a 12‑book saga about Hiccup Horrendous Haddock III, the skinny, curious kid who fails at being a typical Viking and ultimately becomes the hero he was always meant to be. DreamWorks later adapted it into the 2010 animated film, aging Hiccup slightly and giving him Astrid as a love interest - a strong, confident counterpart. It’s a nice nod to strong women even if the movie doesn’t pass the Bechtdel test (as a reminder, to pass the Bechtdel test, it has to meet three small requirements: (1) Are there two or more named female characters? (2) Do they talk to each other – even just one line? And (3) Is that conversation about anything other than a man? 

And now with the 2025 live‑action version, they've aged Hiccup into a full‑on teenager, deepening that romantic heartbeat and making it fit better.

But today, I want to stick with the animated version. The classic. We were renting a home while stationed in Texas as a military family, and our landlord was an animator on the film. They sent us a copy as a Christmas gift because they were proud of their work—and rightfully so. It’s stunning. The animation is gorgeous. The story is rich. The music is (chef’s kiss!) AMAZING! And it holds more life lessons than a professional development day ever did.

At its core, this is a story about Hiccup, the little Viking boy who doesn’t fit in. He’s not the dragon-slaying, chest-thumping kind of kid his tribe reveres. He has no bravado. Everyone else is built for battle; Hiccup is built for curiosity. He tinkers, he invents, questions—and in a village where survival is tied to a single purpose, that makes him a problem.

But here’s where the magic kicks in even in a world screaming at him to become someone else, Hiccup leans into who he actually is. It might be more accurate to say that he can’t stray away from who he really is because of who he is. He is full of compassion and curiosity.  And that curiosity? That refusal to kill a downed Night Fury when he had the chance? That is our inciting event.

There’s a point in the movie that always makes me choke up. It’s later on. Hiccup is just sitting on a grassy cliff staring out at the boats leaving.  He is devastated. His dad has taken his dragon, Toothless, to find the dragons’ nest, and Hiccup feels like he’s lost everything. And what makes it hurt so much is because Toothless gave up everything to save – all of Hiccup. And Astrid, the love interest - sharp, brave, brilliant - sits with him. She doesn’t cheer him up. She doesn’t tell him what to do. She just displays a very Hiccup-like curiosity and asks questions.  She tries it his way.  It doesn’t take long to get to this point: 

Hiccup says, “I wouldn't do it. I just, I wouldn't do it." 

And Astrid asks, "Wait, that time you said wouldn't. Is it couldn't or wouldn't? 
 
 Hiccup responds with “What does it matter? I’m the first Viking in history who wouldn’t kill a dragon.”

That line wrecks me.

Because those two words? They’re worlds apart.

“Couldn’t” means you lacked the power. “Wouldn’t” means you chose not to use it that way.

And I think about that in terms of leaving teaching. When I left, it felt like I was being run off. I wasn’t fired, but they were absolutely making an environment designed to make me miserable - I left because I wouldn’t keep sacrificing myself in a system that refused to be curious about what teachers actually need. I left because I wouldn’t keep pretending I was okay when I wasn’t. To be completely truthful, I was failing at that. When asked what I was going to do when I left teaching, I answered (somewhat indignantly, might I add) with a somewhat stronger version of:  “Anything I darn well please!”

There’s a big difference between “I couldn’t take it anymore” and “I wouldn’t take it anymore.”

If you’re listening to this and stuck in that murky middle, maybe it’s time to ask yourself: Is it that you can’t stay in the classroom... or that you won’t continue being treated like this?

There’s power in that distinction. Power in reclaiming your agency.

The conflict doesn’t end in How to Train Your Dragon because Hiccup becomes the biggest, baddest dragon killer. The conflict ends because he chooses to understand what everyone else feared and he connects everything he has learned about the dragons with everything he knows about his fellow trainees. He listens. He learns. And he changes his world - not with might, but with insight.

And in the third act – the final battle sequence – Hiccup has to go in and clean up a mess that he knew he wouldn’t have made, and that he had specifically warned his Father against.  And he just tells his dad “Hey, we’re Vikings!  It’s an occupational hazard.”  And his Dad apologizes and admits that he didn’t know.  He just didn’t know.
 
 That scene also strikes me as one teachers are all too familiar with in professional life.  How many times have your ranted in your car “I told them that was gonna happen!!!”  Hiccup shows us how to show a little grace when cleaning up the mess.  How often have we yearned to hear someone apologize to us for making the mess and acknowledging that they didn’t know what we knew?
 
 At the heart of How to Train Your Dragon is a yearning for belonging - or more accurately, wanting to belong without abandoning who you are. Hiccup isn’t a dragon‑slayer. He’s a thinker. He invents. He wonders. But in a village built on toughness, grit, and might, his identity becomes the problem.
 
He wanted to be valued for who he was on the INSIDE. People would sum up their  complaints about Hiccup with about "all of this" and he would respond "You just gestured to all of me" The message he got was that everything about him was wrong. 
Teachers get that too, ya know? No matter how much or what, someone is unhappy with things.  It’s hard to feel proud about what you’re doing and to relax into a rhythm of work when you always have to be defending what you do from people who don’t really understand.

There’s nothing wrong with us no matter what impression we’ve been given.
 
 Remember, Hiccup got their attention when he (and Toothless) were willing to sacrifice themselves with the Dragon of Red Death. He was able to change their worldview/paradigm by sticking to his principles of curiosity and compassion. He turned the dragon war into peace by bridging worlds. That’s leadership rooted not in dominance, but in values.  Think about the leadership that you’ve loved and appreciated over the years – chances are it was because it was also rooted in values and not expressed in dominance or micromanagement.

And all of that started because he approached Toothless with curiosity, and he LEARNED about what Toothless liked and didn’t like
 Teachers do that all the time – you watch, and you apply what you’ve learned to other people and other situations.
 
 Spoiler alert: that works outside the classroom even more beautifully that it works inside it. 

 Gotta pause for a minute and talk about that music.  I highly recommend that you add this soundtrack to your playlist. The Test Flight theme, the Romantic Flight - it gives me goosebumps every single time.  I bought the sheet music, and I’ve started working on learning how to play it.  It is a lot of notes!  That music isn’t just background - it is the emotional arc. When that music plays, it enhances every aspect of the movie.  And I am SO glad they did not mess that up when they made the live-action. 

 The new live‑action version brings the story back into our moment. Hiccup appears older, love is more complicated, the stakes feel higher. But the themes are the same, reminding us: Your voice is your strength. Empathy is brave.  You don’t have to be someone you’re not just to impress someone else.  That never works.  You make an impression by being you. Remember that when you are out and about networking.
 
And I hate to mix my movie metaphors, but this just seems too good an opportunity to NOT slip in a quote from Avengers: Endgame by Frigga when she realizes that the Thor in front of her is from her future, and she gives him some motherly advice. 
“Everyone fails at who they're supposed to be. The measure of a person, of a hero, is how well they succeed at being who they are,"
 
Hiccup found a way to be who he was and it was VASTLY better than who everyone else thought he was supposed to be.  Remember that.
 
My wish for you is that you can find that place of authenticity and self-acceptance without allowing anyone to gesture at “all of this” and try to make you believe that you are anything less than amazing. 

Let’s tie this to career transition!

As you move toward something new, Hiccup offers us a few blueprints:

1. Belonging ≠ becoming someone else. Your difference is your strength. Your unique value-add, one might say.
2. Agency comes from “wouldn’t,” not “couldn’t.” Clarify your boundary: won't stay burned out? won’t stay unheard? That is your launchpad.
3. Empathy builds bridges. You can lead, motivate, change lives without losing yourself.

 Think of it as if you are standing in the training arena. It feels like facing down a fire-breathing beast.  A fire-breathing ANGRY beast that we don’t yet understand.

The résumé? Feels like a manual in a language you don’t understand.
 LinkedIn? A village square where everyone else looks like a Viking.
 Interviewing? Like being sent into a ring to slay something... except you’re the one being sized up.

But here’s the How to Train Your Dragon take: Maybe we’re not supposed to slay this particular dragon. 

Here’s how to start:

Name Your Dragon
I don’t mean like “Bob”.  What’s the scariest part of your job search? Is it imposter syndrome? Fear of rejection? Is it fear of failure?  Or success? Not knowing what jobs to apply to? Name it. You can’t train what you won’t face.

Next?

Learn the Patterns
Just like Hiccup studied Toothless, study the terrain. What skills are in demand? What’s missing from your current résumé? Where are the gaps, and how can you fill them with storytelling, not just bullet points?

Next:

Use Curiosity, Not Combat
Your superpower as a former teacher is your ability to learn, adapt, and connect. Bring that to the table. Don’t approach your transition like a battlefield—approach it like a discovery mission.

And…

Find the Right Flight Partner
Toothless had Hiccup. Hiccup had Toothless.  That is THE most synergistic duo I’ve ever seen. Their 1+1 = WAY more than just 2. You don’t have to do this alone. Whether it’s a mentor, a career coach, or a supportive friend who reads your cover letters - find your team. This journey is wild, and it’s better with company which should include someone to watch your back!

Some Final Thoughts…
Teaching isn’t the end of your story if you want something different.  These are your first forays into real flight. And yes, your wings might feel shaky. That’s normal. But like Hiccup, you’ve got heart, and the brain, and the bravery to fly. 

That’s what happens when you stop fighting your nature and start following your values.

That’s how you train your dragons - and yourself.
 
 
 

If this epsiode resonated - if you’re feeling the pull to do something with all this fire - you don’t have to wait for the stars to align.

Teachers in Transition is launching a series of DIY courses that mirror what I believe is the 5-step  path out of the classroom: Decide, Clarify, Build, Refine, Attract.  The first three will be launching any day, so keep an eye out on that. These courses are built especially for teachers like you who are ready to make a move, but need a little guidance (and a lot of heart). I’ve poured everything into these, and you’ve got a front-row seat to their debut

Here’s what’s coming in the first three:

• DECIDE is for the teacher asking, “Should I leave?” This course helps you get honest about what’s sustainable, what’s not, and what comes next.  It can help you decide if you want to stay where you are, shift into a different flavor of teaching, or start strategizing that exit. 
• CLARITY – I think this is the most important part. It’s to go soul-searching but to really dig deep to consider all the possibilities of what could be next.  We’ll map your skills, explore your values, and outline your best-fit roles.  It can be hard to know who are when you aren’t a teacher. 
• BUILD – Learn how to write a resume, get the most out of your LinkedIn Page, grow your network, and how to assess and fill in the gaps between where you are and where you want to go. 

Launch Bonus!
and because these are sort of in beta mode, and for a very limited time, the first few who enroll in each course will get them at a reduced rate - because I believe in rewarding early action and fierce courage. 

  Keep an eye on your inbox, my social channels, or the website.  You can find links in the show notes to all of these. These courses are rolling out very soon - and I want you to be ready to soar.

You’ve trained students, led classrooms, and survived more than most.
 Now it’s time to train your for your future and build something that gives back.

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!