Teachers in Transition – Episode 238: Optimist, Pessimist, and About 40 Jobs You Can Do

In this episode of Teachers in Transition, Vanessa Jackson explores the mindset of optimism and pessimism, how these perspectives shape our decisions, and how they influence career transitions. With a mix of humor, self-reflection, and insightful analysis, she shares personal anecdotes about her own tendencies, from hoarding supplies and skills to embracing lifelong learning.

Vanessa begins by discussing the nature of optimism and pessimism, illustrating how they exist on a continuum rather than as absolute states. She introduces a quadrant system that categorizes different approaches to expectation and preparedness, helping listeners assess their own outlook. Through an amusing yet thought-provoking analogy of twin siblings—one an extreme optimist and the other a staunch pessimist—she highlights the importance of balance in mindset.

Connecting this discussion to the world of education, Vanessa reflects on how teachers naturally develop hoarding tendencies as a survival strategy, ensuring they have the resources necessary to support students. She examines the broader implications of these behaviors, questioning whether they stem from optimism, pessimism, or a mix of both. Additionally, she considers how personal perspectives evolve over time, using the film St. Elmo’s Fire as an example of how shifting experiences reshape perception.

In the career transition segment, Vanessa provides a valuable resource by identifying approximately 40 alternative careers that teachers can pursue without returning to school. She emphasizes that teachers already possess transferable skills that are highly valued in other industries.

Listeners will come away with a deeper understanding of their own outlook on life and work, as well as practical strategies for approaching career change with a balanced perspective. Tune in to gain insights, motivation, and a fresh way of looking at the next step in your professional journey!

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 am your host, Vanessa Jackson – I’m a career transition and job search coach who specializes in helping educators just like you. I taught in a middle school classroom for 25 years, left teaching to work in the corporate America in the world of staffing. Now, I provide tips and suggestions to help with stress and mental health, hacks to help your day, and tips for job-hunting and career transition.  Today on the podcast we explore optimism and pessimism and then in our segment on career transition, we investigate approximately 40 different jobs in big segments of our economy that a teacher can transition into without going back to college!
 
 I am so happy you’re here!
 
 I’ll start with a little confession   - I have hoarding tendencies.  I come by it naturally – both of my parents couldn’t let things go for reasons that were their own.  After cleaning out and selling my childhood home after they’d passed, I have come to sit with and think about what I have and why I have it.  The more we know about ourselves, the better we can make choices – good choices – for ourselves. 

I love to make things – I have all sorts of supplies for all sorts of things.  Does my church want to do something with the My Intent washers and our personal words of the year – I have a set.  Do I need to use a Cricut to make some sort of sticker?  Got one!  And the vinyl to go with it!  Do I want a nifty pocket embroidery design on a polo so I look more professional in the groups I volunteer with? I have an embroidery machine – and I know a guy that digitize the designs for me at a great rate.  We probably shouldn’t talk about the collection of tools I have.  It is vast and continues to grow. 
 
 I saw it written somewhere as a joke and I realized that it was truth – my *real* hobby is to acquire useful skills and the tools that go with them so I can independently do what I went when I feel like it.  
 
 I love to acquire knowledge.  I am voracious reader - I read fiction, non-fiction, news, all the print on any way in my general vicinity.  This works out great for my clients because I am always on the hunt for what is effective in the current job hunt market, and I keep up on current trends in the market to keep my finger on the pulse of what is going on.  Even though it is a technical impossibility, I’d love to learn everything about, well, everything.  I guess all the times I hear “it’s great to learn and knowledge is power!” from the School House Rock intro as a kid really stuck with me.  
 
 A therapist might have their work cut out for them trying to unravel my need for extreme independence.  I’ve read that it’s related to trauma.  If I had to guess, I’d guess that those who had their formative years in the Great Depression 90 years ago (not me) held on to everything because they knew what it was  like to do without.  Some people hang on to everything because they just don’t have the mental space left to deal with it. 
 
 Teachers, by nature, all have some hoarding tendencies.  It’s a survival skill.  You don’t know what you’re going to need from year to year, you don’t know if anyone will budget for you to get things you need, and you like to have supplies for kids for those moments when they don’t have any.  And we all know that those moments always appear.  We know that we are in our classrooms by ourselves and that there likely won’t be help even if we ask for it.  Most of us are told we can ask for help, but when it gets to brass tacks, we are very much discouraged from asking for help.  So we collect, we learn, and become the most amazing problem solvers that exist.  
 
 Does that make us optimists or pessimists?  

 Think about it: Are you an optimist or a pessimist?  I think this is something very important to know about ourselves.  I’ll start with an old joke.

  Once upon a time there were these twins.  They were identical in all ways but one.  One was an extreme optimist and the other was an extreme pessimist.  

The parents were wracking their brains trying to figure out how to bring balance to their children so that their extreme outlooks didn’t set them up disappointments in life.  Nothing works.  The Optimist is always finding the good, the bright side, and the silver lining. The Pessimist always assumes every good thing will go bad and there is no point to really investing energy or emotion into those  things.

The parents finally decide that they will use the twins’ upcoming birthday to settle this once and for all.  There are piles and piles of presents.  The twins come out and sit in front of the presents.  One after the other, the pessimist opens the presents.  The more presents the pessimist opens, the sadder the pessimist becomes.  Finally, there is weeping and wailing.  The parents ask “Why are you crying? Why aren’t you happy?”  The Pessimist replies “because  ALL OF THE toys are going BREAK.  All of the clothes and shoes will one day WEAR OUT!.  It’s all DOOMED!” 
 
 Meanwhile our Optimist is getting wigglier and more excited with each passing gift asking every so often “Is it my turn?”
 
 “Oh, your turn is coming” replies the parents.
 
 

Finally, they lead the Optimist outside to a shed and fling open the doors.  It is full of manure. The Optimist screeches with…. DELIGHT and DIVES right in and starts digging around.
 
 The parents pull the Optimist out by the feet and ask “What are you DOING?  Can’t you see that it is full of manure?  That’s POOP!”
 
 And the Optimist gleefully replies, “With all that poop in that shed, there’s got to be a PONY in there somewhere!!”
 
 I don’t think this is an either/or choice.  Like so many things that start off looking like one thing or the other, there are nuances – like all the shades of gray between black and white and all the in-betweens that happen between day and night.  
 
 So let’s look at this with an X-Y axis.   And let’s see it as more of a continuum. 
 
 Let’s consider the X-Axis to be our expectations.  On a scale from -10  to 10, how would you rate your levels of optimism on how well you hope for or expect things to go?  How much do you expect that everything will go wrong? Or right?  

And let’s consider the Y-Axis to be our levels of preparedness for our expectations. Again, considering from a scale of -10 to 10, where number would you assign yourself based on how you prepared for what you expect?  

An Optimistic Optimist both expects for things to go well and prepares for them to go well.  

A Pessimistic Pessimist expects things to go 8 different types of wrong and therefore doesn’t put a lot of work into preparations – they’d just go wrong anyway.   And the Pessimist knew it would happen that way. 
 
 But we have two other pieces to the quadrant we’ve created. 

For someone who hopes for the best but worries about the worst with out a lot of planning, we have an Optimistic Pessimist.  This is a more balanced perspective but without preparation in one direction or another, they tend to rely on their optimism to take on challenges and believe in their ability to overcome whatever may come their way.
 
 And finally, we have the Pessimistic Optimist.  This person is fundamentally hopeful, but can’t stop thinking about (and thus preparing for) all the ways something can go wrong.   Think of it as hope with a side of hesitation.  These folks get called out for anxiety because thinking about all the ways something can go sideways naturally brings out the anxiety.  They Expect the best, but they’re prepared for the worst.
 
 Everyone likes to use the glass test to determine whether you’re an optimist or a pessimist.  Is the glass half-full?  Optimist!  Is the glass half-empty?  Pessimist!  And once again, the nuance gets lost.  Memes galore make fun is this.  I have posted a link to one in the show notes.   A physicist might see it as completely full – half full of liquid and half full of gas.   A relativist sees both half-empty and half-full at the same time.  A realist takes the glass and enjoys the drink while the optimist and the pessimist are arguing and the skepticist (skeptic, I know the real word, but I was drawing a parallel here!) points out that the liquid may not be lemonade in the glass.
 
 Perspective can matter a great deal with whether you want to lean one way or the other.  As a teen in the 80s, I watched a lot of movies.  There wasn’t much else to do back then.  As an 8th grader in junior high, I watched St Elmo’s Fire.  Given when it was released, I bet my friend and I went on my birthday weekend.  These seven characters seemed SO grown up and glamorous – navigating their grown-up problems and making their own choices.  It was, dare I day, aspirational to a 13- (probably a 14-) year old me.
 
 I saw it again on VHS or regular television view once again when I was myself in college.  I understood their issues a little better.  Who I liked and who I didn’t like in that movie shifted a little.  Their idealism was still inspirational, but that wasn’t what I was aspiring to anymore.
 
 I watched it once again as an adult with kids of my own.  Now those characters seemed somewhat whiny to me.  They were clearly the architects of their own downfalls, and only one (maybe two) of them moved forward in any real character arc.  And by our 2025 standards, there were things that were clearly written to be flattering 40 years ago, but it’s really disturbing behavior now.  ScreenRant has a whole article on it that I’ve linked in the show notes. I do not recommend having teens watch that without some prep first!
 
My perspective on what happened in that movie changed a great deal given my life experiences and place in my own timeline.  Our perspective is based on the lens on which we see something and the phrase “too close to the situation to see it clearly” is a very true statement.  We know that in our profession, we do a lot of mediation between two individuals and they can see the same event very differently. 
 
From the inside looking out, we are routinely gob-smacked that people can’t see what is going on – we live it everyday.  They don’t. 
 
Now that I have been out of education for a few years, I look back at a younger Vanessa and really wonder what she was thinking hauling young kids back to school after evening meal to finish up things that had to be done in the classroom.  Why spend SO much time on things?
I had a lot to prove back then, and I always felt like I was running to catch up.  I had big goals and I felt that if I just worked hard enough, I could make anything happen. 
 
You have to ask yourself what it means to achieve success as a teacher. Policy would tell you that test scores determine your level of success, I think a better measure is one that can’t be quantified in the moment – in fact, we may never  actually know. 

I attended a wedding of a former student this past week.  The whole family had big hugs for me that I didn’t see coming.  My former student mentioned me in his wedding toast.  I had no idea I’d affected his life to be more than a mention. It made me miss my classroom and what I used to do even though I can look at the matter with a wider perspective and realize it isn’t a healthy place to be. 
 
 But I like to remind you that YOU MATTERED to a kid whether you’ll ever know it or not.  And what you did took root.  I am taking a Data & Decisions class which has a LOT of statistics in it.  Y’all, I was a music major – this has not come up for me in the past in any college degree.  It is a STRETCH.  I know it’s great for my brain but I am working harder than I have in a while.
 
 And in the first lesson it goes over the fundamentals.  And I could hear my 7th grade teacher (who was also the cheerleader sponsor and drove demolition derby on the weekends)  talking about mean, median, mode, range.  And I was reminded of the meme that says about nothing in particular “yes, we covered that in school, you probably weren’t listening”
 
 

But I took a moment to marvel at how those lessons from slightly before St Elmo’s Fire was ever released were still rattling around in my brain looking for an opportunity to be useful as I worked on new things.  Somewhere out there, you have former students who randomly remember things you taught them at the very times they need that information.  Even if they never turned the work in. 
 
 And moving on to our career transition and job search section, I want to highlight jobs that may not be in your field of vision or perspective when considering a career change.  Many teachers wonder what they can do.  The economy is changing rapidly, so we want to consider jobs in fields.  IN order, the top ten segments of our Gross Domestic Product in the US are: 

1.      Real Estate

2.      Government Spending (although this is changing as I speak)

3.      Healthcare 

4.      Business

5.      Finance and Insurance 

6.      Manufacturing

7.      Retail 

8.      Wholesale

9.      Information Technology

10.  Construction 

With honorable mentions to: transportation and warehousing, education services, and the Arts, Entertainment, and Recreation areas. 

Obviously in the field of real estate, we think of real estate agents and houses, but there is so much more!   Property Management is an area of real estate - and sometimes that might even come with benefits like reduced rent if you are working in apartments. Real estate covers residential, commercial and industrial! Some jobs include: 

Facilities Manager

Project Manager

Real Estate Analyst

Real Estate Marketing Specialist

Title Abstractor (lots of research)

Leasing Agent

Urban Planner

Transaction Coordinator (great way to dip your toe in the real estate waters)

Relocation Specialist

Vacation Rental Manager

Auction Coordinator

Estate Sales Manager/Coordinator

Healthcare is 1/6 of our economy.  There are a lot of jobs in healthcare many of which aren’t directly medical.  You have:  

Medical Administrative Assistant

Patient Advocate

Health Educator

Medical Scribe

Pharmacy Technician

Medical Billing/Coding Specialist

Community Health Worker

Medical Receptionist

Medical Transcriptionist

Health Coach

Telehealth Coordinator

Medical Interpreter (if you are bilingual)

Wellness Coordinator

Clinical Research Coordinator

Health Information Technician

And Finance and Insurance: 
Mortgage Loan officer (could also be relate that to real estate) 
Underwriter 
General Appraiser
Financial Advisor/Planner
Credit Counselor
Claims Adjuster
Compliance Officer 
Finance Coach 
Financial Writer/Content Creator 
Insurance Sales 
Customer Service Representative in insurance
 
And don’t forget there is a whole realm of things you can do as an entrepreneur – we live in a world where everyone wants personalized  services and assistance, so tutoring and coaching in an education-adjacent capacity on things like life skills, finance, health, fitness or hobby based – think music, art, sewing, yarn, woodworking, … the list is only limited by your creativity.
 
That’s a lot of jobs!  I’ve talked about about  40 of them today! I encourage you to check out the transcript of this podcast over on our Buzzsprout homepage and examine this list a little more closely.  You can run job titles through ONetonline.org and get an idea of what is required in the job, what training is required, and what you might be expected to do on a day-to-day basis.   

In today’s job market, it’s crucial to pay attention to what industries are growing and evolving. Healthcare and insurance are two sectors that aren’t going away anytime soon and are relatively safe bets for career transitions. 

If you are thinking of leaving the classroom, or if you just KNOW it’s time to go, I’d like to encourage you to reach out and sign up for a free discovery session with me.  I can help you sift through all the noise and find a career path that resonates with you and I can teach you the skills you need to be competitive in today’s ridiculous market. 

It can take quite a while to find a job especially right now, so it very smart to get started on a career transition plan and an exit strategy several months before you actually plan to go. Now is the best time for that!  Reach out today to learn how I can help or if you just want to make sure that you aren’t imagining things when you wonder if you are taking things too personally in your classroom. 
 
 You aren’t.  You are amazing, and don’t you forget that!  Let’s look optimistically at the future and prepare for all of its possibilities!

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!