Common Roadblocks you may face in your job search - Teacher Career Coach Podcast

97 – Common Roadblocks You May Face

Abbey Vogt

It’s likely that you’re going to hit a few roadblocks along the way that make you question if this dream of finding the perfect role outside of the classroom is actually possible for you. In this episode, we’re addressing the most common roadblocks you may face during your transition out of the classroom.

Listen to the episode in the podcast player below, or find it on Apple Podcast or Spotify.

Common Roadblocks You May Face in Your Career Transition

I wanted to share about a brand new podcast with you that I was actually able to be a part of and I’m really excited about. It’s called Those Who Can’t Teach Anymore. In this new podcast, they give interviews with former teachers about why they quit teaching, they explore how the history of education and pop culture depictions of education actually contribute to this crisis in education, and they share stories about what teachers do when they quit teaching and efforts being made to actually keep teachers in the classroom as well. So, if you want to hear other teachers share why they’re leaving and learn a little bit about what could be done to potentially stop the exodus, you can subscribe to Those Who Can’t Teach Anymore.

Getting into this episode today, I just want to start by saying, I wish I could promise you that the stars would align for you and that everything would work out perfectly and go according to your plans. I wish that you would figure out the exact role that you want from the start, create this really amazing resume that’s perfectly aligned with that position. Hiring managers see it, they want to interview you, and you’re able to actually choose your perfect company within the timeline that you really need to get this job. And all of these things just happen one after the other, but it is very likely that that is not going to happen. It’s really likely that you’re probably going to hit a few road blocks along the way that really make you question if this dream of finding the perfect role outside of the classroom, it’s actually possible for you and make you want to probably give up altogether while you’re working on this goal.

I also want to say right now that it is absolutely okay if going through this entire process, working on your career goals, interviewing for other jobs actually gives you the clarity to realize that this is no longer a goal that you want to pursue, that you no longer want to leave the classroom. And while it’s really frustrating to feel like you put through all of these steps or potentially wasted hours on a goal that’s no longer your priority, what you did do is you gained clarity that the profession that you’re in right now is the one where you plan to stay at least for now. And that means that you can work towards identifying what you can do in this situation to try and become happy again. But I know that many of you who are listening to me say anything about staying in the classroom are probably squirming that you are not feeling comfortable with that idea and you don’t plan on staying in the profession long term because you know in your heart that is not what you want anymore.

So, what I do not want for you to do, if that sounds like you, is to allow your struggles that may be truly figureoutable to prevent you from achieving these long-term goals. I don’t want you to know in your heart that you are settling for a career that you’re unhappy in just because you felt frustrated, or you got caught off guard by a roadblock that was put in your way. And that is why in today’s episode I’m going to do a deep dive into the five types of roadblocks that you may face during this career transition. Starting off by letting you know there are actually two different categories of roadblocks that you’re going to face during a career change. There are external and internal roadblocks.

And external roadblocks are all of those factors outside of your control. The ones that I actually talked more about back in Episode 94 about things that are outside of your control, that would be what other people say or think about you, how other people act, how other people react to your boundaries or the economy or a pending recession, that timeline that you ultimately get your one yes, what hiring managers think about you and you know what people actually think about those in a career transition, especially from teaching. Those are all things that are completely outside of your control or external roadblocks that are potentially going to impact your job hunt. And if you haven’t listened to episode 94, I would recommend doing that after you finish this one. But other things that may happen is you may end up investing time and energy, learning a specific career path to realize that it’s not a good fit for you for one reason or the other, and feel like you have to start all over again or you might actually land your very first role outside the classroom and be really happy and then be one of the few that unfortunately get laid off. These can be huge and devastating blows that convince you that you may want to give up on your long-term goal altogether and go back into the classroom.

But even with all of these curve balls or all of the different rejections that teachers in transition end up facing, we still see success happen time and time again with other former teachers who are going through the exact same process and heading off some of these exact same roadblocks. So, what are they doing that is different than what you are potentially doing right now? What can you do in order to feel like you are headed in the right direction and going to be more successful with this really big and daunting task? A very large percentage of this is going to be strategy, that’s the actual approach that former teachers are taking.

That is how they are writing their resumes. That is what types of jobs that they’re applying for, it’s how they’re actually preparing themselves to interview for these positions. And I talk all about all of those different strategies on different episodes of the Teacher Career Coach Podcast and also inside the course The Teacher Career Coach Course. But even with the most perfect of career strategy, you are still going to hit roadblocks and there are going to be times that you are going to feel like giving up. You are probably going to face situations that make you question whether or not you can continue to do it, and it’s still going to take a lot of determination and grit to continue to move past these obstacles that are going to get in your way.

So, in order to work past some of the external roadblocks, those ones that we just cannot control, it is so important to focus on how we navigate our own internal roadblocks, because these internal roadblocks are the things that actually get in the way of our own successes and the very first step to beating them is to identify them and start to understand them a little bit better. Now, the first roadblock that I’m going to address here is guilt. And I know that I’ve talked about this on episodes in the past, but it’s such an important thing to address because I have seen teacher guilt time and time again hold back teachers who are truly unhappy and suffering from ever even taking the first step.

I have heard countless stories of teachers who are so overcome with guilt that they don’t want anyone to ever know that they’re even thinking about applying, they don’t want to ever apply to any positions outside of teaching. And that physical act of actually pressing an application send button makes them feel too guilty because they can’t stop thinking about how that act will impact other people that they love and their lives like their students or their colleagues. I know that for some of you this might sound extreme, that you are probably like clawing for your way out of this profession and you don’t care who knows about it, but for some teachers who struggle with this, it’s really important for me to address it all the time because this is something that you have to overcome and it makes sense.

Our entire careers in teaching you are conditioned to put everyone before yourself. To put your students before your own needs, whether that is your physical need of needing to go to the restroom or whether it’s your family life and what you are asked to do after your regular working hours. But basically you are conditioned to feel like you are abandoning anything that is good and you are a terrible person anytime you put yourself first. Anytime you ask for a single day off to have a mental health day or you are actually physically sick. Anytime you’re trying to set a very clear boundary of work expectations, you are kind of conditioned to think that you are selfish and a bad person because of it.

And that’s not who we are in nature and so it’s really, really challenging for us to kind of snap out of that and start to put ourselves first. Just think of all the times doing it for the kids has been weaponized against you to push you past a sustainable workload. And even think about all the times that you’ve been told you can’t even think of changing careers, like you should not even imagine that because you’re a “good teacher” and what happens to the kids if you leave the classroom. Guilt-tripping and once you start this profession, you’re not allowed to leave mentality does not happen in any other industry. Guilt-tripping doesn’t happen to the sales guy in the other department when he decides that he wants to go into product management, he is able to make that choice and people just are happy for him for choosing a path that makes him satisfied.

There is this very long list of things that you may be feeling guilty about. It’s probably leaving the kids, leaving your colleagues with more work, position that the school will have a hard time filling, leaving what was supposed to be your forever career or even just like the guilt of giving up on job that you spent time and money to pursue, especially if you’re still paying off student loans. And if this feeling of guilt is something that you’re struggling with, I’m just going to share a little bit more advice from Episode 7 on battling teacher guilt and that is you do not have to sacrifice your entire life for a career. Moving on for whatever reason is absolutely okay. You were a good person when you decided to be become a teacher and you’re still going to be a very good person if you decide to pursue a new career.

One of the things that I tell teachers who are overcoming this really big feeling of guilt is take a moment to reflect and think about if it was your best friend having the same feelings that you’re feeling, what advice would you give them in this exact same situation? Would you tell them that it’s okay for them to choose themselves? Would you tell them that it’s okay for them to choose their family? Would you tell them that it’s okay for them to pursue their dreams and that even if they changed careers, it wasn’t completely starting over, that they’d still learned so much and accomplished so much in that career that they’ll take it on to their very next career and that this is just a stepping stone for who they’re going to be in the future.

Common Roadblocks you may face in your job search - Teacher Career Coach Podcast

It’s so much easier for us to have that compassion for another person that we care about and forget that these are things we should be telling ourselves. We should have compassion for ourselves in these exact same situations. I even want to go further into this feeling of guilt, because even after you have 100% decided to leave, many still feel way too guilty to leave their teaching contract midyear and I completely understand that feeling because that’s where I thought I was at the end of my last year as well. If someone would’ve offered me a job, it would’ve been another story, but I thought I was going to at least finish out the school year. But there are people who reach out to our team all of the time, who talk to us about their doctors or their therapists, urging them to get out, their loved ones who say they need to get out immediately.

People who say things as devastating us thinking about being in a car accident would be better than going into school for the day. People who feel totally unsafe in their workplace for one reason or the other, maybe it’s their students in the classroom management is starting to get more dangerous or maybe they just feel unsafe because of bullying or discrimination going on and it’s impacting their mental health or those who just want to get out for their mental health, to have some space and they are fortunate enough to have significant others that can potentially help them with the finances and then they’re not in a need of having a job immediately.

Leaving teaching midyear is a very personal decision and this one has potential serious repercussions such as losing your teaching license, maybe potentially getting fined but that does not mean that it is not an option. This is not something that I ever want to downplay. These are serious decisions, they have serious consequences, but sometimes the pros outweigh the cons. There are people who have decided that they are actually going to leave teaching midyear, they decided that they’re ultimately ready to do what’s best for them and their timeline is just something that needs to move forward now and they’re not willing to wait until the very end of the year and knowing that they have made this decision, go through the hiring process and still get too scared and overcome with guilt to actually say yes to a job that is even actually given to them at the end of that interview process.

And because I speak with and work with hiring managers, this is something that actually does come up that they have interviewed transitioning teachers that posted a role, specifically one conversation I had pretty recently that there was a role that was open in January and they started to go through the interview process with a couple of different candidates and they ultimately decided to make an offer for a teacher. And at the very end of the process, the teacher was kind of leaning on the hiring manager for more emotional support and help weighing the pros and cons of leaving teaching.

And as empathetic as the hiring manager felt, because it’s such a tricky and unusual situation, it also actually raised more concerns that this teacher wasn’t fully in love with the position or ultimately even prepared to transition into a corporate environment just because they hadn’t kind of figured this out on their own and they were asking their new employer to help them out with this decision that’s really outside of the scope of what you should be talking to a hiring manager about in the interview process.

But you and I know that this teacher would not have gone through weeks worth of interviews, rewritten their resume, applied for the position, all the steps that went into this if they did not know that they wanted out of the classroom. But once they got to the point of actually getting the job offer, the guilt was really challenging for them to navigate and it impacted their decision-making. I’ve heard from other former teachers who found themselves saying no to positions as well and just didn’t want to take the next step based off of guilt because they were worried about what the former colleagues were going to say and think about her even though in her own words, she felt completely inauthentic doing it. She knew that it was something that she wanted.

I’m not going to tell you that listening to this podcast is going to cure you from feeling these big feelings. You are a big hearted person. You would’ve not gone into this profession if you were not a good person. And you at the core of your being want what is best for other people, you are used to lifting other people up. You are used to putting other people first. This is one of those tricky situations that does impact other people and it’s not in our nature to put ourselves first in this type of way. The best thing that I can do to help you move past these feelings is urge you to get mental health support, work with a therapist if you can, but ultimately just really come to terms and realize that it is okay to make a decision that is the best one for you and your family.

You have given all you have to give for this specific career. You went into this because you believed in the cause and the career itself, we know all it asks is for you to give, give, give. But right now you are in a season of your life where you no longer have anymore to give and that is okay. You are not letting anyone else down, the reality is the education system let you down. There is nothing to feel guilty about because you are not the cause of this crisis. And one more miserable teacher staying in the classroom, that is not going to solve the crisis either. So, I hope that that helps you. But if you have not gone back and listened to episode seven on teacher guilt, I really encourage you to go there.

But moving on to the very next roadblock that I see holding teachers back is the urge that you may have to follow the crowd. The sense of community that comes with teachers in transition is huge. I do not want to downplay this at all. We have a private community within the teacher career coach course where all the former teachers and teachers are working together towards certain goals. They’re able to bounce ideas off of one another towards these specific careers. They share resources with one another. They talk about their own experiences and what happened in their interviews. That is so huge and helpful, especially if you are feeling very isolated and alone in this journey.

Having a community is such a great way to stay motivated and to push towards the goals that you have. But one of the roadblocks that you may start to face is your urge to follow what a crowd is doing, because I have seen teachers who are early and in their phase of figuring out what they want in a career, being pulled in specific directions or actually told not to pursue certain positions based on whether or not another former teacher thought it was a good fit for them. For example, just because another former teacher doesn’t feel comfortable in sales positions doesn’t mean that that’s not an area where you would actually thrive.

So, check in and notice when you are looking for someone else’s opinion besides your own. Check in with yourself and see if you’re forgetting to trust your own gut and your own judgment when it comes to what you need in your next career and what you like and dislike. I’ve seen these big waves of teachers who at first were interested in instructional design and then everyone was interested in project management and then everyone was interested in customer success manager roles. And these are all really great positions for former teachers. You are a unique person and you’re going to come to this with your own unique strengths, your own unique needs, and your own unique dislikes.

Think about it from your teaching perspective. As a teacher, you probably did not have the exact same teaching style as every other teacher, and if you met other teachers teaching the exact same grade in every other district, you probably would have disagreed with some of the ways that other people taught the same subjects that you taught and their reasoning behind why they would teach those specific subjects in that specific way. You may not like the same tech tools that they like. You may not like the same literature that they read to their students and you may have really strong opinions and you may realize that you are a very different person than other people in the same grade level with the same position as you.

So use that same logic when it comes to teachers in transition, that same reasoning that when you are seeing other teachers give their opinions or advice about something know in your gut that you may be a completely different person than they are, you’re unique. You’re going to have all of these different unique things about you and your own journey. So if you hear someone say something that they didn’t really like, I would just really reflect on it and make sure that you know whether or not it’s similar to your own needs, your own skills, your own interests before you start to disqualify it as a path that you potentially would be interested in.

And also, I always have to say this, just don’t only look for teachers in transitions opinions especially on like LinkedIn, you are leaving teaching, you’re always going to have this experience and you’re always going to have this as your past, but this is not going to be the only community that you will communicate with in the future. You’re moving on into a new field. So, branch out and start to learn from other people with three years experience or more in the industry that you are looking to move into to get their experience, to hear their opinions, to start to reflect on whether or not they may be more aligned with your personality and be able to give you more accurate advice about the careers that you are interested in pursuing.

And lastly, in this same kind of area, there’s also something that’s happening, which is the comparison game. That is whether or not you should apply for only jobs that are going to be impressive to other people, whether or not you should feel ashamed if you actually took a salary cut when you left teaching, whether or not you should only be applying to remote only positions or if you’re open to working in an office just based on what seems to be the most impressive thing that people are the most excited to celebrate for other teachers in transition. Applying for smaller companies that are in person roles, taking a potential stepping stone position, doing all these types of things can be really effective strategies to help you get out of the classroom sooner.

And if you are miserable and you know that you need out and you don’t want to be up against a lot of competition at some of the bigger name tech companies, you can do these things that you know are right for you. There is no shame in making that decision for yourself. But I have seen threats on LinkedIn shaming former teachers for sharing or even thinking of applying to different types of positions, saying that it’s insulting to your qualifications. Even entry level positions still may potentially be a salary increase for teachers. I cannot shout this from the mountain tops any louder. There are a couple different things that I teach back in our episode all about salary, so I urge you to go back and check that out about how to actually research salary.
But the biggest damage that these types of threads probably are doing are shaming people from applying for jobs that may make them happier and may ultimately be a better fit for them. And that damage does not sit right with me. Do not shame other people for doing things that are right for them and do not make your own decisions based off of what other people are telling you that you should do. You know in your heart whether or not is the right thing for you, but the very next roadblock that you may hit can also help you with identifying what is or is not a good fit based on your needs, and that is getting clarity.

What are you really hoping to achieve with your next role? Why are you planning on leaving the classroom? What is your main reason? Are you looking to have more time with your family? Do you want to focus on getting your mental health back? Do you want to find a dream position that lights you up day after day after day? Are you looking just for a huge salary increase? All these things are not mutually exclusive, but until we really understand what our most important goals are and why we are working towards these goals, it is going to be very difficult to differentiate what is a good fit and what is a bad fit because ultimately you may have to make some sacrifices in order to get your first job outside of the classroom.

I talk to teachers all the time that just haven’t taken the time to sit down and really think out what their non-negotiables are. For example, many will tell me that they are only really looking for a remote position and that there is no chance that they would take a class or an in-person job. There’s no shame in that. If you are a remote only person and you know it, be proud in it, that is your firm non-negotiable. But when I’m having these conversations I start to say, “Okay. Well, that is just to let you know.” It means that you’re going to compete against a lot more people and so it is going to be more competitive and might take a little bit more time if you’re not open to hybrid roles or in-person jobs as well.

And as I start to talk about them and ask more clarifying questions, they will start to change their opinion and say, “Well, actually after all, I might be open to this or that under these specific guidelines.” We put so much unnecessary pressure on ourselves to find this dream position that we may not even be open to other positions where we could be truly happy because we really don’t have the clarity on what is a non-negotiable, and this is going to be really different depending on what level of burnout you have and what timeline you’re comfortable taking leaving the classroom.

So let’s just say you are set on being a very specific type of corporate trainer. You only want to focus on one type of topic and that is a really wonderful goal to have and it gives you a lot of clarity, but you have to decide if that’s your long term goal or your firm non-negotiable straight from the classroom goal. And if that is the only thing that you would want for a career outside of the classroom, then that is going to limit the amount of opportunities that you are going to be able to be applying for. For me personally, I was so unhappy when I was in my teaching career, I was probably at a level two or a three out of a 10 as far as my happiness goes and leaving teaching for any job that paid my bills and brought my mental health back to like a five would’ve been a huge win for me.

What I ended up finding was a job that not only paid my bills but that my mental health was like a 9 or a 10 within the first few months of leaving the classroom and that was something I could have never anticipated. So, you are going to have to kind of weigh whether or not your decision is just to get your mental health back, whether your decision is going to be for a very specific dream job and start to really focus and reflect on that to help you with shaping what your non-negotiables are so that you have a realistic understanding of how long it may potentially take due to these non-negotiables. And if money is your key indicator and you’re only open to specific jobs that have a very high salary range, let’s say closer to six figures, that’s also going to limit and restrict the amount of opportunities that are going to be good fits for you straight from the classroom.

It doesn’t mean that this is impossible, but it’s just important for you to get the clarity of what you need as far as that goes or if you are open for a stepping stone position that would potentially allow you to work towards that goal within a two to three year timeframe. And when things get hard or if you have to potentially make a pivot of what your approach is, what types of jobs you’re pursuing, go back to that main question that I ask, why are you leaving the classroom? What are you hoping to achieve with this first role outside of the classroom? Because it’s not potentially going to be your forever career. It is the stepping stone of where you’re kind of laying your foundation and where you’re taking your next steps, but it does not have to be a forever career.

So, starting to reflect on, I just am doing what I need to do right now in order to get this specific salary or in order to get towards a training and development job or in order to get closer to an instructional design position or in order to just get my foot in the door at this really cool company and hopefully I can work for them for the next 10 years and work my way up the ladder there. Those types of questions can help you really move in the right direction when you start to feel stuck or overwhelmed or are unsure if what you are doing is the right thing. The next roadblock that you are potentially going to face in your career hunt is imposter syndrome.

Now, if you’re not familiar with the term, it’s essentially the self belief that you don’t have the skills or accomplishments to belong or that you’re just some kind of fraud when you’re starting to try something new. And let me be the first to tell you that there are a lot of people who suffer from the syndrome, including myself and you can definitely overcome it. It presents itself in a variety of different ways. It can be perfectionism and not wanting to put anything out there like even a resume until it’s absolutely perfect. Maybe it’s not wanting to put a portfolio out until it’s absolutely perfect. It could also present itself like feeling like you’re always behind other people, that they’re always one step ahead of you or better than you in one way or the other.

It can be fear of ever stepping outside of your comfort zone. Maybe you’ve been a teacher for a really long time and you’ve always been feeling pretty good about your ability to be a teacher and so you don’t want to do anything that makes you feel lesser than. It might be difficulty accepting any sort of help or support or investing in a program that can actually help you get to the next step. It just can be difficulty even telling people that you need support or help or that you’re struggling in one area or it can be giving up easily. Imposter syndrome can surface during any stage of the career change and it could persist even after you land a new role.

You can potentially feel like everyone’s going to figure out that you are faking it until you make it and that you might be losing your job at any moment just because you’re not as experienced in this new position. It is a big roadblock on the way to a career change and one thing that you can really do is just start to really believe in yourself and realize that you are more than “just a teacher”, recognize all of your skills, experience your accomplishments, really start to practice identifying when it sneaks up. When you feel yourself getting in those patterns of negativity, learning to shift your mindset can help get you back on track and determine that you are worthy of success in this entire process.

If you find yourself struggling with perfectionism, set small achievable goals. Practice what’s called shipping it, so just send it before it’s absolutely perfect and start to get over those small fears of putting something out there before it’s 100% ready. Focus on your progress and what you can control and celebrate any sort of achievements you have. The bigs and the small ones. Everyone really struggles with feeling outside of their comfort zone in this process so, just remember that you are capable of anything, you are determined, you are intelligent, and you will absolutely get through this and feel more comfortable after you’ve been in the role for quite some time.

Now, the last one that I want to touch on is losing your optimism. Hope is really what is going to enable you to push past the hardest parts of this journey. And if you are not optimistic and if you do not believe that this will happen for you, you will potentially end up giving up far sooner. There are so many teachers that I’ve talked to that are on the verge of giving up just based on their fear that it’s absolutely impossible, but what I want you to really look around at this community and realize is that every former teacher is coming from a different situation and there are so many of them in situations that are exactly what you are going through right now.

And if they got through it, you can get through it too. If one former teacher, if one single former teacher got the job that you are looking to achieve, that means that there is a path, there is a way that you can do that exact same thing. We have helped former teachers in a variety of states, in a variety of experience levels get jobs like project manager, instructional designer, even software engineer. And yes, some of them are easier to get than others, some of them take less upskilling, but whatever you are telling yourself right now is impossible, look and see if there’s another person in this community that is an example of it being actually possible and then start to drown out that negative voice with positive optimism

It is possible. It can be realistic optimism. It can say this is going to be challenging, but you still need to remain hopeful that this is going to happen for you, for you to continue to push past all of the hard parts. Now, to recap this episode, the different roadblocks that you are going to face are teacher guilt, the urge to follow the rest of the crowd, lack of clarity, imposter syndrome, and losing your optimism. I hope that you can recognize these if they start to happen to you in your career journey, and I hope that you can identify them and help get yourself back on the path that you need to be on, in order to ultimately get that one yes that you are waiting for.

Mentioned in the episode:

Step out of the classroom and into a new career, The Teacher Career Coach Course