Teachers in Transition

Teachers in Transition Episode 234: To Boldly Go Beyond Your Comfort Zone in your Job Search

• Vanessa Jackson

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In this podcast episode, Vanessa mixes of storytelling, sci-fi references, and actionable advice to emphasize the transformative power of discomfort in personal and professional development. Inspired by Michael Easter’s quote, “Do not go too comfortably into 2025,” She shares actionable strategies and personal stories that demonstrate how stepping outside our comfort zones leads to meaningful growth.

Vanessa underscores the rewards of embracing fear and pushing through discomfort. Drawing parallels to the Star Trek: Voyager episode “Good Shepherd,” Vanessa explores how finding the right environment and overcoming challenges can lead to personal success.

The episode provides practical advice for job seekers, encouraging them to stretch and grow. Vanessa also offers insights into identifying work environments that align with personal strengths and values, along with tips for introverts to ease into networking.

Listeners are encouraged to set weekly “uncomfortable” goals to build resilience and confidence in their job search. 

Resources and Recommendations

 

Connect with Vanessa:

  • Email: teacherintransitioncoaching@gmail.com
  • Voicemail/Text: 512-640-9099

·         Follow Teachers in Transition on Facebook!

·         Connect with me on Blue Sky: @beyondteaching.bsky.social

·         Connect on LinkedIn

 

Share Your Story!
Have you recently stepped out of your comfort zone? Share your experience with me! Your story could inspire others! Would you like to hear a specific topic on the pod?  Send those questions to me and I’ll answer them. 

 

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The transcript of this podcast can be found on the podcasts’ homepage at Buzzsprout.

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 who are stressed, burned out and overwhelmed - just like you.  If you are frustrated with your current teaching position and you are thinking about what it would take to do something different – you’re in the right place!  Welcome! Today on the podcast, I talk about getting comfortable with discomfort – how it applies in life and how you can use it in your job hunt.  I also have a recommendation about planners.  Let’s dive in!

I just read an interesting quote from Michael Easter, an author who combines modern science and old-school wisdom to share ideas for improved health and meaning, and performance. He says, “Do not go too comfortably into 2025,” and my brain just started drawing all kinds of connections. Success happens outside of the comfort zone. So my challenge to you is this: do something uncomfortable.

In order to do something uncomfortable, you need to spend time identifying what is comfortable and what is not. You can make a list on your phone or carry around a little paper T-chart. One side lists things that feel comfortable and good, while the other side lists things that frighten you a little or feel uncomfortable.

Here’s a story that illustrates this: As we were driving south from Alaska to Texas, we decided to take the California route to do some sightseeing and turn it into a mini vacation. While coming through British Columbia, we entered the Sea to Sky Highway. I was very interested in it specifically because of the Sea to Sky Highway because I had participated in a Yes.Fit challenge based on that route. If you’re unfamiliar with Yes.Fit, it’s a fantastic way to get moving and stay active. There are no strict rules—you set your own. At the time, I was using active running and bicycling as my goals, but on tougher days, I counted all movement towards my milestones. As you log your progress, you accumulate mileage, and once completed, they send you a beautiful, sturdy medal.

Having completed the Sea to Sky Highway challenge, I wanted to see it with my own eyes. The medal that I earned was shaped like the gondola from an attraction in British Columbia. Here’s where things get uncomfortable: I’m afraid of heights. More specifically, I’m afraid of the splat at the end after falling. As we ascended in the gondola, my mind spiraled with irrational thoughts: “What if the cables snap? What if we plummet to our deaths? My dogs are in the car; it’s not hot now, but they can’t stay there forever.” My thoughts were out of control.

However, I managed to harness the small, rational part of my brain and ask, “How many of these gondolas have gone up and down without incident? What are the actual odds that this is the one that will fail and this is the day that it will fail?” The answer, of course, was exceedingly slim. I muscled through my fear, and I’m so glad I did. The views from the top were absolutely breathtaking, and there was ice cream (always a win), souvenir shops, and the feeling of being literally on top of the world.

After conquering the gondola, I decided to tackle the suspension bridge. It swayed in the breeze, and standing on it, I could feel the movement beneath me. The drop below was significant, but I did it. I stepped onto that scary ledge, embraced the fear, and had an amazing experience. I didn’t die, and the views were worth every moment of discomfort.

This brings me to my point: Never underestimate what you can achieve if you’re willing to step outside your comfort zone. Sometimes, though, the discomfort isn’t about physical challenges. Sometimes, it’s about leaving behind shared pain, frustration, misery – complacency?  Often, the most uncomfortable step is moving toward a place where you might feel better. That’s worth sitting with and thinking about.

Misfits from Star Trek: Voyager

If you’ve been listening for any length of time, you know I’m a fan of good science fiction. One show I’ve been rewatching for comfort is Voyager, a Star Trek entry. It’s about a small ship, not a grand Enterprise-class vessel, that gets flung to the far side of the galaxy. At maximum warp, it will take 70 years to get home, so the show chronicles their adventures in uncharted space.

Season Six, Episode 20, titled “Good Shepherd,” focuses on three misfits aboard the ship. One constantly needs her work checked because she’s always making mistakes. Another hides in his little corner and does the bare minimum. The third is a raging hypochondriac, convinced he’s always ill. Captain Janeway blames herself, believing she’s failed them. Her first officer, Chakotay, reassures her that every starship crew has members who struggle, but in their unique situation—stranded far from home—there’s no option for them to transfer out.

Janeway decides she doesn’t want them to fall through the cracks, and she is going  to take them on an away mission, giving them one-on-one attention. Predictably, their worst fears come true. The mistake-prone crewmember makes an error, but as Janeway later points out, “I looked at the same data and reached the same conclusion. Sometimes mistakes just happen.” The hypochondriac has an uncomfortably close encounter with an alien. The bare-minimum guy who always thinks he’s right makes a wrong decision and attempts to redeem himself with an act of self-sacrifice, which doesn’t go as planned. Despite these challenges, they all grow, face their fears, and emerge as better crewmates.

The episode raises an important question: Would we blossom, too, if placed in the right environment? Not every setting is conducive to success for every person. Consider your own work or life experiences. If you’ve taught at various grade levels, you likely know which ones suit you best. For me, middle school was my sweet spot. I enjoyed high school and elementary students, but middle schoolers—with their sarcasm and energy— that’s  where I thrived.

And many of you out there just heard that and thought to yourselves “never in a million years would I want to teach middle school.”  but you thrive in elementary school of high school.  We all have our place. 

The same applies to work environments. What kind of people do you enjoy working with? What type of leadership helps you excel? Knowing yourself is key to finding the right fit and advocating for what you need. Take time to reflect on this, because understanding your environment—and what’s uncomfortable—can lead to personal and professional growth.

And in today’s recommendation – I have a simple one: use a physical planner.  I know digital planners are all the rage, and I’ve always felt bad that I can’t make a better go at one.  I talked a lot of planners in episode 183.  (I’ll have a link I the show notes). Sometimes I feel like it is a failure or a sign of my age that I’ve never been able to make a go of a digital planner. Then again, I know what works for me, so that’s a win. 

I finally figured it out thought  -  because with a digital planner, I feel like I am only looking at one tree, whereas with the paper planner, I can see the entire forest and there’s even a spot for all the chores and tasks I need to accomplish.  It allows me to better spot patterns and coordinate with my family. 
 
 Teachers often like to have planners that start in July or August and there is a whole market that caters specifically to that. 
 
 But if you’ve been frustrated that a digital planner doesn’t work for you, or you feel like a lot of things are falling through the cracks – try a physical one – and use the flair pens to color code it! It’s not a personal failing. 

# Uncomfortable Things you’ll encounter in Job Hunting

Let’s take this idea of stepping out of your comfort zone and apply it to job hunting. How often do you look at a job description, see a requirement you don’t think that you meet, and immediately decide, “That’s not for me”? That’s your comfort zone talking. But growth happens when you stretch. Challenge yourself to apply for roles that feel just out of reach. Maybe it’s a role in an industry outside of education or a position that requires a skill you don’t think you’ve mastered yet. If you wait until you’re perfectly qualified, you’ll miss opportunities. Trust me, you’re have a lot more skills than you think you do. 

One way to start is by creating a job search version of the T-chart. On one side, list roles, industries, or tasks you feel comfortable with. On the other, write down the ones that intimidate you or seem like a stretch. Then, set a goal to see what you can move from the “stretch” side to the “comfort” side  with perhaps some learning or effort. Then, at regular intervals – whether that’s weekly, monthly, or quarterly see if you can move things from the discomfort to the comfort side.. This might mean taking an online course, seeking advice from someone in the field, or simply applying for the job and seeing what happens.  It’s your own atmosphere of growth. And it’s hard as we start to move into a time of year where things get busier and busier and things feel more out of control. 

We all have environments where we thrive and others where we don’t. Part of the job search is figuring out where we belong. Start by reflecting on past roles. What kinds of teams have you enjoyed working with? What leadership styles brought out your best work? 

When you’re evaluating potential jobs, think beyond the job description. Consider the company culture, the team dynamics, and the leadership style. Do some research. Look at reviews on sites like Glassdoor, or connect with current or former employees on LinkedIn, and ask questions in interviews. It’s better to spend the extra time upfront than to end up in an environment that isn’t going to work for you

Rejection as a Growth Opportunity

One of the most uncomfortable parts of job hunting is rejection. No one likes hearing “no,” but each rejection is a chance to learn and grow. Remember, failure just teaches us what didn’t work.  If you don’t get a job, ask for feedback. Not all companies will provide it, but when they do, use it to improve. Maybe your resume needs tweaking, or perhaps you are lacking a course or certification that the job requires.  Every piece of feedback gets you closer to a “yes.”

There’s a big lesson that can be learned from actors here.  In general, they expect 50 No-s before every getting to a Yes.  And some of the roles they land in those ‘yes’ opportunities are just enough to get them to the next gig.  In today’s job market, that is even more true job hunters. There has been a very frustrating statistic that the job-listing to hire ratio is under 50% right now. That’s one of the reasons it is so important to have a strategy when you go in. A targeted strategy will save effort and prevent job hunting burnout. 

Networking Outside Your Comfort Zone

Sooo… networking. Networking can feel awkward, and is definitely outside most people’s comfort zones - especially if you’re an introvert or not used to putting yourself out there. But it’s an essential part of the job search. It is, in fact, the MOST important part of the job search. Start small. Reach out to people in your network for informational interviews. Informational interviews are opportunities to learn about aspects of their career. You can ask them about their roles, their companies, and their career paths. Your network is vast and broad and you don’t even know it yet!  Your network is everyone you know and everyone they know.  (and so on and so on…in fact, if you network enough, you’d eventually probably connect to Kevin Bacon, lol I believe it!) Another way to network is to attend industry events, even if it feels intimidating. You don’t have to walk in and be the life of the party; just aim to make one meaningful connection.  Maybe two. Think of it like making a friend. 

If the idea of networking still feels overwhelming, think of it like an old elephant joke:
 How do we eat an elephant? 
 One bite at a time!
 
 Take it one step at a time. Each step might feel shaky, and often you’ll wonder if you’re making any headway, but you are.  

Setting Uncomfortable Goals

As you navigate your job search, set one “uncomfortable” goal each week. Maybe it’s applying for a role that feels like a stretch. Maybe it’s reaching out to someone you admire on LinkedIn or writing a cover letter for a challenging position. Each goal, no matter how small, is a step outside your comfort zone and towards growth.

The job search isn’t easy, and it’s often filled with moments of self-doubt and discomfort. But remember, those moments are where the growth happens. Like the misfits in Voyager, you’re capable of more than you realize. Step out onto the suspension bridge, take the leap, and trust that the view on the other side will be worth it.

If you are stuck in your job search, and you want to get away from the overwhelm and frustration of your current position and move across the proverbial suspension bridge to cross over to a career that allows you space to breathe and weekends without work, then reach out to schedule a complimentary discovery session with me to see how I can help you pivot careers and make that transition. It’s time to thrive in ’25!


 Remember the best time to start your career transition is MONTHS before you are willing to go.  This is a GREAT time to get started, and *I* can help you!

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 Teacher in transition coaching at gmail dot 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!