Teachers in Transition: Career Change and Real Talk for Burned-Out Teachers

Getting Past the ATS: The Human Job Search Strategy That Works

• Vanessa Jackson

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What do traffic jams, poker strategy, and applicant tracking systems have in common? More than you’d think.

In this episode, Vanessa unpacks decision-making under uncertainty—why the “fastest” route isn’t always the best one, and how both life and job searches can punish us for not being able to predict the future. We talk GPS stress, Annie Duke’s poker-based decision framework, nervous system regulation (Maslow before Bloom, always), and a real-world job search story that proves something important:

Humans still hire humans—even when algorithms try to pretend otherwise.

In This Episode, We Cover

  • Why GPS (and life) makes “best guesses,” not promises 
  • How teachers get stuck outcome-shaming themselves (“If it went badly, I must be wrong…”) 
  • What poker psychology teaches us about uncertainty and decision quality 
  • A Teacher Hack for protecting your nervous system: take the scenic route 
  • The truth about Applicant Tracking Systems (ATS) and why resumes vanish 
  • A behind-the-scenes story of navigating hiring systems by reintroducing human connection 
  • How to spot culture red flags before you accept the job 
  • Why “optimized” doesn’t always mean “healthy” 
     
     

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Keywords 

teacher burnout, leaving teaching, career transition, teacher skills, decision making, nervous system regulation, stress management, applicant tracking system, ATS, job search strategy, networking for introverts, teacher identity, life after teaching, educator mental health, transferable skills

Connect with Vanessa Jackson

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

 

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

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Hi!  Welcome back to Teachers in Transition – the podcast for people who are burned out, stressed out, and wondering what else they can do. I’m Vanessa. I taught for 25 years before leaving teaching to work in the world of staffing. So I know what it feels like on both sides of the hiring table. Now I work for people just like you.  Today we’re going to talk about why making the best decision you can with the information you have is sometimes the only thing any of us can do — even when the GPS, life, and your nervous system are all giving you conflicting data at the same time.  In our Teacher Hack segment, we’re going to talk about taking the scenic route and why the “fastest” path is not always the healthiest one.

And in our career transition and job search segment, we’re going to talk about how I helped my brother strategically navigate around some of the bottlenecks in modern hiring systems by combining ATS strategy with the very human side of networking, relationships, and showing up in person.  

Also the pollens are a little bit and you’ll sometimes hear that in my voice, so I apologize if that’s distracting but beyond that grab your caffeinated beverage of choice, settle in, and let’s talk about it.

When I left my house yesterday morning, I did not think traffic was somehow going to lead us to poker, applicant tracking systems, decision theory, and career transitions… but apparently that was the journey I was on. Honestly, this is probably what happens when your brain spends years teaching. You stop seeing isolated topics and start seeing weird connective tissue everywhere. One minute you are thinking about brake lights on the interstate, and the next minute you are halfway into a philosophical discussion about human behavior and statistical probability while clutching a coffee cup and trying not to miss your exit.

So for those of you who are not from Texas, let me explain.  Distance means something different here. I live between San Antonio and Austin, which are both enormous cities connected by a major corridor that is under eternal construction. Under ideal conditions, I can get where I was headed in maybe fifty  or fifty-five minutes.  It was right at 50 miles. Under less ideal conditions? Well. Let’s just say there are moments where you begin questioning your life choices while moving approximately seventeen miles an hour inside a giant metallic snake made of exhausted commuters and poor urban planning.

Lately I’ve been driving into one of those cities pretty regularly because, as I’ve shared, I’ve been accompanying students at local high schools as a collaborative pianist. And not just “into the city,” either. I mean deep into the city. Past the midpoint. Into the “maybe I should pack trail mix and a support animal” part of the drive. So traffic has become something I think about even more than the weather. Before I leave the house, I check the GPS. I look at alternate routes. I weigh my options. I mentally prepare myself for whether today is going to be a “pleasant scenic drive” day or a “welcome to the Thunderdome” day.  So let me Tell you a Tale of Two Drives. 

I’ve noticed that the GPS is only making decisions based on the information it has in that exact moment. And sometimes that information turns out to be SO wrong. Not maliciously wrong. Not stupid wrong. It’s simply making the best prediction it can with the data available at the time. Last week on my way home, I was NOT about to fight Friday afternoon traffic, so I decided to bail off of the main roads early and take one of my alternate routes through some back roads and smaller areas.  This morning, the GPS showed worsening traffic ahead, but I decided to take the normal route and got there 30 minutes early.  (I wasn’t speeding, I SWEAR!!) 

And honestly? That Friday drive was lovely. It was the Best of Drives.  Trees. Fields. Interesting curves to drive. Beautiful hill country views. The kind of roads where your blood pressure lowers by at least ten points simply because nobody is trying to merge into your soul at eighty miles an hour. I would happily drive a few minutes longer than to deal with what chaos was sure to descend turning my “it’s three minutes faster to take the interstate” suggestion turn into a 30-minute delay. 
 
 Compare that to yesterday morning’s drive: The GPS was all doom and gloom telling me that things were getting heavy and getting worse.  I decided to risk it and stayed on the highway. And I just zoomed right on through. 

The system was wrong.  It gave me the best information it had in the moment, but that wasn’t the information I was going to need in the next 30 minutes.  There was also no guarantee that its predictions would even come to pass.

And I think we need to sit with that idea for a second because humans are doing the exact same thing constantly. We make the best decisions we can with the information available to us at the time. Then later, when we know more, we turn around and beat ourselves up because we didn’t magically predict the future like some kind of an emotionally exhausted wizard with a Garmin watch and unresolved perfectionism.

Teachers especially do this to themselves. I think so many educators have been conditioned to believe that if they prepare enough, sacrifice enough, organize enough, and care enough, then the outcome should logically reward them. If things go badly, they immediately assume they must have made the wrong choice somewhere along the way. And to be fair a lot other people will make you feel that way. But life does not actually work like a multiple-choice worksheet with an answer key in the back. Sometimes good decisions still lead to painful outcomes because new information appears later. Sometimes terrible decisions accidentally work out because luck decided to throw confetti at your nonsense for a few minutes.

This reminds me of Annie Duke and her book How To Decide. Annie Duke is fascinating because she was a professional poker player before becoming a decision strategist and author. And poker is interesting because yes, mathematically speaking, it is a game of probability and statistics. There are odds involved. Percentages. Risk calculations. But professional poker is also deeply psychological. It involves reading people, recognizing patterns, observing emotional behavior, managing uncertainty, and adapting in real time with incomplete information.

And honestly? Teachers do versions of that every single day.  Tell me the truth – how many bluffs HAVE you called today?? Hmmm?

Teachers walk into classrooms constantly reading emotional environments. They notice changes in tone. They monitor group dynamics. They adapt when someone is anxious, overwhelmed, angry, confused, or checked out. Or asleep. They regulate themselves while simultaneously trying to regulate twenty-five (or more!) other nervous systems that are all doing their own weird little jazz improvisation at the same time. That is not simple work. That is sophisticated human observation and adaptation happening at high speed inside environments that are often wildly unpredictable.

One of the things Annie Duke talks about is how people judge decisions entirely based on outcomes. If the outcome was bad, then clearly the decision must have been bad. If the outcome was good, then obviously the decision was brilliant. But reality is messier than that. Sometimes a thoughtful, informed decision still produces a difficult outcome because variables changed later. Sometimes somebody makes an absolutely ridiculous decision and somehow lands on their feet because the universe briefly decided to entertain itself.

I actually find that weirdly comforting.

Because it means we can stop demanding omniscience from ourselves. We are allowed to make thoughtful decisions and still encounter uncertainty. We are allowed to choose carefully and still discover later that conditions changed. Sometimes the storm hits anyway. Sometimes the traffic clears unexpectedly. Sometimes the scenic route turns out to be the better path after all.

And speaking of scenic routes, let’s meander on to our teacher hack.  The teacher hack is something designed to save you in one of the three ways we pay: time, money, or stress.  The idea is to give you back some brain space so you can spend it on yourself and the things YOU want – maybe like finding a way out of the classroom!  Today’s hack is to TAKE THE SCENIC ROUTE.  And that I’m not just talking literally here (although I definitely mean it literally as well).  I think we need to acknowledge that the “fastest” path is not always the healthiest one. The paycheck is not the only math. Stress matters. Recovery matters. Commute time matters. Gas prices matter. Your nervous system matters. My Garmin watch actually records significantly higher stress levels when I’m trapped in aggressive interstate traffic than when I’m driving peaceful back roads through rural areas? I deserve to arrive home with my energy intact and not strewn all over the highway like a 1960s driver’s ed cautionary movie. 

My body knows the difference even when my brain tries to pretend it doesn’t.

Many teachers have spent years overriding the information coming from their own nervous systems. You get so accustomed to functioning while stressed that stress starts feeling normal. You normalize overload. You normalize exhaustion. You normalize “fine.” You sound like Ross from that episode of Friends “I’m FINE!!!”  Meanwhile your nervous system is somewhere in the background waving tiny emergency red flags and filing formal complaints with the management.

At some point, part of healing is learning to listen again so you can practice real self care, which, believe it or not, is sometimes having the space to put yourself first. 
 
 Take the Scenic route.  And as we learned – you might accidentally arrive faster.  You’ll definitely arrive less stressed. 
 
 Moving on to the career transition and job search segment, all of this circles back to a recent experience helping my brother with his job search. I’m going to leave him somewhat anonymous because although he gave me permission to talk about this, he is also establishing himself in a new position and I want to respect his privacy. But my brother recently moved because after our parents passed on, he wanted to be closer to us. We don’t have a whole lot of family left. And with the move came the need to start looking for work in a new city. And his expectation of job hunting was very old-school. And overly optimistic. Fill out an application Monday. Get a call Tuesday. Start work Friday.

Except modern hiring often doesn’t work that way anymore.

So as the self-appointed career transition and job search expert in the family, I worked with him exactly the same way I’d work with any client.  Maybe not exactly the same. Big sisters can be pushy…  anyway, I helped him locate places where he wanted to apply.  I helped him create his resume. I taught him keyboard shortcuts. We talked about tailoring resumes to job descriptions and why applicant tracking systems matter. (and why we love to hate them).  We talked about keywords and filtering and how many applications never even reach human eyes. And after applying online repeatedly and hearing very little back, he started getting discouraged. Which is incredibly common right now, unfortunately.  And to be fair, it had only been a couple of weeks, but like I said, he thought he’d be good to go in week 1.

So, I suggested to him that we network.  Of course he resisted it.  Network just sounds so smarmy, right?  What I meant was that he could take his resume in person to places where he’d applied and his only goal was to shake hands with a manager or hiring person and drop off that resume.  I realize this seems slightly old-school and maybe a little unhinged in the year 2026. I suggested we physically drive to places where he had already applied online. Cue Jason Bateman in Dodgeball saying: “Bold strategy, Cotton. Let’s see if it pays off for them.”

So we spent several hours making a big loop to cover the places he’d applied. Some locations were effectively closed systems. There were literal Gates where we couldn’t get in. A couple of places had everything routed through centralized hiring structures. It didn’t matter if we talked to anyone. Someone at one of those places explained that all hiring went through a third-party system. Another said everything had to happen online. And honestly, that’s important information too because different systems require different strategies.  In fact, the idea of a third party system tells me that they were using a contingent staffing firm to do all of their hiring and all of their onboarding so that if a new hire didn’t work out it’s easier to let them go.  And if they liked the new hire through the third-party staffing firm, then they after six months to a year or whatever the contract says, the would hire that person full-time.  It takes the risk away from the company and moves it to the contingent staffing firm.  I can talk more about that in a future episode if anyone is interested.  That is, in fact, what I did when I worked at the contingent staffing firm. 

Then there was one location -  which shall remain nameless because it wasn’t a store failing – it was an employee issue - where an employee made my brother stand there waiting while they finished whatever they were doing on their phone before barely acknowledging him and dismissively informing him the manager was on break. No offer to take a resume. No attempt at conversation. No “Hey, let me grab your information.” Nothing. And honestly? And as I pointed out to my brother – that tells us something important too.  Big Red flag!!! 

Because organizations leak information about themselves through these interactions.

And, you know, one disengaged employee does not automatically define an entire company culture. We all have bad days. But sometimes the tell is the organization itself. Sometimes how a place treats people who currently have nothing to offer them reveals something important about the environment underneath. Teachers, we understand this instinctively because we spend years reading environments and relationships. We know when a room feels emotionally safe. We know when it doesn’t.

But other places responded completely differently. Managers came out. Conversations happened. Handshakes happened. Human connection entered the chat. At one place, he was asked if he physically felt up to the tasks involved and he offered to do one-armed push ups.  I call that the Jack Palance tactic (if you’re old enough to remember, you know… it was an older actor, who in the middle of his Oscars’ acceptance speech, dropped to the ground and started doing one-armed pushups to prove that he wasn’t too old. I’ll put a link in the show notes (https://www.youtube.com/watch?v=AGxL5AFzzMY) 

One place offered him a same-day interview. Another wanted him back later that evening for an interview. Both of those gave him offers of employment the same day.  And then I got to sit down with him and talk about how to pick the better job because he was worried and he was scared and he was ready to just grab the first offer. I am very happy to report that he is thoroughly enjoying the job that he chose. He started last week It is exactly what he wanted to do, and exactly what he needs right now. 

And perhaps more telling is that even after the same-day interviews and job offers, more request for interviews came rolling in, so I had the opportunity to teach him how to respond to those, and that added to his sense of worth.  I have to admit to a personal sense of professional pride when he commented that he should have trusted me sooner in the process.

And as I reflected on all of that, I realized something really interesting.

The ATS is nothing more than a digital black hole where resumes cannot escape the gravity well to see the light of day.

The applicant tracking system was handling only the statistical side of the equation. Keywords. Filtering. Optimization. Pattern matching. Probability. My brother was operating on the psychological side. He inserted humanity back into an automated process whether it wanted it or not. The system can measure keywords, but it could not measure warmth, professionalism, determination, adaptability, emotional intelligence, conversational ability, relational skill. Or the ability to do one-armed push-ups. 

Humans still hire humans.

And I think teachers underestimate how powerful that is because education has become so metric-driven that many educators unconsciously begin believing the measurable things are the only things that matter. But they are not. The measurable things are simply the easiest things to quantify. Teachers are masters of relationships. They spend years building trust, navigating personalities, resolving conflict, regulating emotions, and creating human connection inside systems that are often increasingly rigid and data-driven. 

Honestly, teachers are incredibly good at functioning creatively inside restrictive frameworks. They are handed pacing guides, standards, testing requirements, Learning Management System limitations, impossible timelines, massive curveballs (CANVAS outages!!) and endless mandates… and somehow they still manage to create moments of humanity and connection inside all of it every minute of every hour of every day. It’s a little like being handed a paint-by-number picture and somehow making it into an artistic masterpiece. That is not a small skill. That is sophisticated systems navigation.

And I think that matters when teachers transition into other careers because not every environment is going to feel healthy simply because it isn’t a school. Some workplaces are deeply relational. Others are highly transactional. Some organizations value emotional intelligence tremendously. Others prioritize throughput and automation above almost everything else.  And occasionally they like to see a one-armed push-up.  I’m just sayin’

That doesn’t necessarily make one universally good or bad. But it does mean fit matters.

Which circles us all the way back to traffic again. The shortest route and the best route are not always the same thing. The most optimized route is not always the healthiest one. And the path everyone else is crowding onto may not actually be the one best suited for you.

Sometimes the scenic route is smarter. 

Sometimes it’s kinder.

And sometimes the bravest thing you can do is trust yourself enough to take a different route.

If today’s episode resonated with you, I hope you’ll take a moment to remind yourself that you do not have to have every answer before you take the next step. Sometimes we are all just making the best decisions we can with the information available at the time, adjusting course as we go, and trying not to let interstate traffic or applicant tracking systems destroy what little sanity we have left.

And if you are a teacher sitting there wondering whether your skills matter outside the classroom, let me say this very clearly: they do. Your ability to read people, build trust, adapt under pressure, solve problems, and create humanity inside rigid systems is valuable. Deeply valuable. Sometimes the challenge is not that you lack the skills. It is simply learning how to position those skills inside a different framework.

If you enjoyed this episode, please consider sharing it with another educator who might need to hear it. Word of mouth is still one of the best ways that independent podcasts grow, and every share, review, and recommendation genuinely helps. You can also support this scrappy little indie podcast through the support links in the show notes for as little as $3 a month, and as always, thank you for spending part of your day with me.

Until next time, take care of yourselves, trust your instincts a little more than you think you should, and remember: sometimes the scenic route turns out to be the better road after all.

 

👋 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!