Stepping Stone Jobs

76 – Stepping Stone Jobs


In this episode, I talk about stepping stone jobs. This is basically any job you go into knowing that it is not going to be your forever career. Instead of thinking of this as being stuck or taking a step backwards, consider it as a strategic way to prepare for future advancement.  

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

Stepping Stone Jobs Transcript

When I was leaving the classroom, I knew I just needed to get out of teaching altogether. At least for that next year. The negative head space that I was in had me really not acting or thinking like myself. After an entire year of extreme stress that was brought on by a really toxic work environment, I just knew that I needed a mental break for my next role.

I remember preparing myself to take basically anything that paid my bills as long as I wouldn’t be miserable. And I’ve heard from so many of you that can relate to this stress and the time constraint that’s given to you with the job search. And you’re starting to kind of fall into the same category.

Are Stepping Stone Jobs a Step Backward?

That’s why in this episode, I’m going to talk all about stepping stone jobs. Now, what are stepping stone jobs? A stepping stone job is basically any job that you go into really knowing that it’s not probably going to be your forever career. Maybe it’s more of a step sideways than upward in your career trajectory.

So maybe it’s a new position that has a similar pay or benefits. It may also feel like a step backwards, depending on how long you’ve been in teaching. It could be potentially a pay decrease, but it might be in the industry that you want to get your foot in the door in. It could even technically be a step up in pay, but just doesn’t really feel like your forever career, because maybe it’s not something that you feel like you want to stick with for forever.

So maybe you’re right now open to in person role when you know eventually you want to move into something that’s completely remote. Maybe it’s a position at a company that you love, but not actually your dream position. Maybe it’s a company that doesn’t spark as much joy as let’s say your top favorite education company.

But you know that this experience can help your resume and help you get your foot in the door at any company outside of the classroom after a couple of years. So instead of thinking of stepping stone careers as being stuck or taking a step backwards, consider this as a strategic way to prepare you for your future advancement.

Is a Stepping Stone Job for You?

Now, before I get too far into this episode, I have to address this. I have definitely seen very upset posts about this exact concept on LinkedIn from teachers saying that no teachers should take anything that is not their dream job, or is a pay cut or is labeled as entry level. And if you are firm on what you want, it is totally okay to skip this episode.

This might not be the right message for you. I never want to convince anyone to stop pursuing their dreams or talk them out of applying for careers that they are certainly qualified for. I don’t want you to take this episode the wrong way or start to talk yourself out of applying for dream roles right now too. Because yes, you are just as qualified as every former teacher I have ever interviewed on this podcast for the same types of roles that you are probably interested in.

You are qualified for all of the roles that I share in my free career quiz, on my website or on the roles that we share on our Instagram at Teacher Career Coach, that teachers are landing directly from the classroom. If you for certain are not open to other suggestions or roles, that’s okay.

I don’t ever want to convince you to do something that you just know isn’t a good fit for you. But this episode is so important for me to write for those of you that know that you’re not going to be going back to teaching no matter what happens.

When Stepping Stone Jobs Might Be Necessary

Teachers have reached out to me who are in physically abusive work environments, where they no longer feel safe or supported, school environments where feel forced to hide who they are due to new rules and new laws being passed, schools where parents are harassing them without any consequences, watching their every move to try and get them fired for teaching SEL or using the word equity in a history lesson.

There are extreme situations where teachers are actually facing sexual harassment from students or other staff members and there are no consequences and they are not feeling supported. Any situation where you just know you need out and you’re open to anything, but you still want to work strategically towards these long term goals.

It can also just be for any teachers who are getting close to the end of the summer, who are starting to be more open to make compromise. Maybe you’ve moved and you don’t want to continue teaching any longer and you have a dream job, but you really haven’t upskilled towards it.

Maybe you’re a younger or a newer teacher, or you just don’t have long term work experience, but you really know that long term, you’re looking for a supervisor or leadership role, but you haven’t really had the opportunity to build leadership in your current positions. And not to add with the ever changing work trends and increasing competitiveness in specific roles or industries due to an influx of teachers leaving.

Having a Plan B

It is okay to have a plan B. It is smart to have a plan B. I’ve always been a really extremely cautious person. I always have a backup plan myself, and I encourage you to have one as well.

So this might be something that you’ve landed on after you’ve been job searching a while. And maybe you’re starting to feel a little bit down if you haven’t been getting any interviews. Or maybe you have and the hiring manager continues to say that you may need a little bit more actual corporate experience for you to land your dream role.

You can begin to do the research to understand what types of careers actually can lead you up to get to that career in a three to five year time. Teaching is a forever career. It takes a lot of schooling to break into, and we’re supposed to be in it for the rest of our lives. It’s also a career that very much feels like your identity. It’s a career that many people want to talk to you about.

Shifting Your Mindset for a New Career

It’s a big sense of community that you get as a teacher. This educator space is amazing, and it feels good to share your job title when you’re a teacher. So the shift in mindset to putting in a lot of work and landing a job that’s not maybe your forever career or not something that you can see yourself as.

So the shift in mindset to putting in a lot of work towards landing a job that isn’t technically going to be your forever career, or is a job title that you feel is as impressive to share can be a challenge. My objective is just to help you open your mind to different possibilities than what may be on your radar at the current moment.

And going back to those LinkedIn threads, I know how insulting it can feel to be told, “Don’t apply for the job you want apply for this other job that you don’t want instead.” After years of feeling disrespected by society, it’s really easy to feel disrespected and to-.

After so many years of feeling disrespected by society, it is so easy to take suggestions like this personally, when you are a qualified candidate who has years of experience and as a professional. But honestly, stepping stone jobs are pretty normal, especially when it comes to people changing careers or industries.

This is all so my chance to stop you from beating yourself up, if something absolutely perfect doesn’t come up, or if you didn’t have enough time or energy. I also just want to stop you from talking down to yourself if something absolutely perfect didn’t come up in the right amount of time.

Or if you just didn’t have enough energy to work towards up skilling, but you know that you need out of the classroom as soon as possible. I also want to address here is what a stepping stone career is not. A stepping stone career is not a career that you cannot live off of. It needs to be something financially stable or your family. It can even be a higher paying salary than your teaching salary.

And it is 100% not something where you know that you’ll be miserable. Something that goes completely against your morals or somewhere or. It’s also not something where you know you’ll be completely miserable, something completely against your morals or at a company that has a really bad track record of work culture.

Stepping Stone Jobs

How Stepping Stone Jobs can Help You Reach Your Career Goals

I always encourage you to continue to check Glassdoor for reviews of companies prior to applying to them. And now let’s take some time to talk about how a stepping stone job can actually be really helpful in your forever career search. If you are in this extreme environment of stress, you probably are not thinking as clearly as you usually would.

I personally suffer from anxiety and I can find myself in really negative thought patterns or acting very impulsively when something is stressing me out and making not so sound decisions. Just being so of stressed out that I can’t even move forward on a big project sometimes. I just procrastinate and look at it. This is pretty normal.

It’s how our body, it’s how our brains react to stress. And I know so many of you are feeling this right now. It is a big challenge to up skill while you’re juggling 1000 teacher tasks and doing this huge change in your life. This is your chance to just have a regular nine to five job that doesn’t drain you so that you can focus on healing and wrap your brain around what you really want long term.

This stepping stone job is that opportunity to take some time to recover. So if you’re one of those people who just finds yourself staring at LinkedIn and refreshing it over and over again, instead of finishing a LinkedIn Learning course that you can put on your resume, I’ve been there too. Also, quick plug here. If you do want to join LinkedIn Learning for free for a month, you can sign up at www.teachercareercoach.com/linkedinlearning.

Gaining Experience with a Stepping Stone Job

But I always want to remind you that you can’t do everything all at once, especially when you are struggling mentally. Another perk is to gain experience that goes on your resume and helps you with that next thing. The ideal situation is that the stepping stone career is in the department of the role that you want or collaborates with that department, or just at a company that you’re the most interested in.

You can do either one or the other. You can’t really bootcamp, up skill, freelance all at the exact same time. And so this is a chance to be really strategic about the role that you take. You can kind of do all of those things all at once. You can learn the company, you can learn the job – you can. You can learn the company. You can learn about other jobs at the company.

You can learn about different skills that you may need for different jobs at the company and gain experience all in these areas while you work. If you want to be in human resources, you might want to start with the recruiter coordinator position, and then you can work yourself up to recruiter and eventually work your way up to a human resources’ manager. Sales roles can lead to so many different directions.

An SDR role could get you to an account executive role or a customer support manager role. Or it can make you a sales enablement trainer and then eventually you can go from sales enablement training to different types of training in the learning and development department.

If you want to work in marketing, if you are writing sales copy for different companies, you can also take a sales role to just truly understand customers and objections while you’re strategically working on your portfolio of copy.

You can also start as a social media marketer or a copywriter or a assessment editor, and then start applying for more marketing specific roles after a few years time. We have a few episodes of former teachers who took stepping stone roles and shared in past podcast episodes.

Former Teachers who have Successfully Used Stepping Stone Jobs

We actually have a few examples of former teachers who took these stepping stone roles and shared about them in past episodes of the podcast. So Episode 64 with Brooke talks about how she took a different position and then ultimately landed her role in corporate training.

And then also Episode 28 with Mallory Mac talks about how she’s worked at three different companies after she left teaching, all of them leveraging herself into new higher paying positions. Mallory was actually someone that I had met in one of my first positions and she helped me get my second position outside of the classroom.

I wanted talk about this a little bit because I’ve met so many amazing colleagues during my time at both of these ed tech companies. Many of them are still at the companies, but probably 20% of them have moved on to even new companies.

I can reach out to them if I ever see interesting openings and want to maybe potentially get my foot in the door at any of these places that they’ve moved onto. As amazing as having a large community presence can be, like if you are connecting with a lot of former teachers on LinkedIn, the best thing as far as networking goes is if you have a large community of people that truly know you, that can truly vouch for you to help you get your foot in the door somewhere.

So working in this position outside of the classroom is going to be a really great way for you to demonstrate how great of an employee you are so that eventually in a couple years time, you can reach out to some of these contacts and see if they can help you in a different capacity.

If you’re not 100% sure if the roles that you’re applying for are great stepping stone careers in the career trajectory you’re trying to go, reach out to someone in that preferred dream role and see if the roles you’re applying for actually can help you. While new former teachers are great to learn from, I do always recommend looking for those with more tenure in their career.

Even if they’re not former teachers, I always say at least three years is a good spot so that you can get advice from people who have more experience in that preferred industry. During the time that you are working in your new role, you’ll be able to network with others at the company.

Learning & Growing on the Job

And once again, they can help you find future jobs down the line. But in addition to this, you’re going to be learning from others at your company, especially when your role works with them. So for example, at one of my companies, I worked as an instructional designer, but I got to collaborate a lot with the marketing department.

So for example, one of the companies that I worked at, I worked as an instructional designer, but I got to collaborate a lot with the marketing department, which was my actual goal for taking that position. I knew that working with the marketing department would help me learn more about video editing and graphic design.

Honestly, I think that the majority of careers outside of teaching can be categorized as stepping stone jobs because there is really a huge likeliness that whatever you take, even if it is your dream position, you’re to have more opportunities for role changes or promotions in the future.

There are just so many paths for growth in new industries outside of the classroom. And this can be foreign coming from this very clear path of either being a teacher or an admin in the education space. But there are just so many more departments and nonlinear career trajectories outside of teaching. One thing that is important to note that even stepping stone careers can be competitive.

Landing a Stepping Stone—or Any Other—Job

You are still going to need to market yourself for these roles by redoing your resume. And hiring managers will 100% be able to see through it if you are miserable in your interview, or just sound desperate for anything. I’ve heard from a hiring manager, that they passed up a great candidate that they knew would be completely capable of doing the job because the candidate said in the interview, “Yeah, I don’t really see myself doing this role. It’s not really my passion, but I am taking this position because one day I want to become a customer success manager.” Now, this is the exact opposite of what any hiring manager wants to hear. It sounds like you’re going to quit this job in six months time. I always recommend that you focus on the positives of the role and the company.

Talk about why you’re truly excited about the position in front of you. Something around the lines of, “I can’t wait to help you with X, Y, and Z. I’d love to grow in my ability and develop skills for X, Y, and Z, as it aligns with this position. And that’s something that I’m really excited about doing. And I can tell that this company would be great to work for because of X, Y, and Z.”

I can confirm that I also had to pass on really great candidates when we were interviewing former teachers for our internal full-time positions here. The candidate that won the role was the person whose interview questions and answers. The candidate that won the role was the person whose interview answers displayed that she would be the happiest in the role where we needed the most help, the role that we were hiring for. And it seemed like she would be a really great fit for the long time.

The candidate that won the role was the person whose interview answers displayed that she would be the happiest in the role where we truly needed the most help. There were other candidates that made it clear that they had other interests. And that’s okay, but the way that you phrase this can raise some red flags with hiring managers that you’re not really interested in actually doing the job that’s in front of you.

And that’s clearly where they need the most help at the time. You can use this opportunity to ask what the room for growth within the company is to see if there’s a clear path upward from your role, especially if you truly just love this company. If you start a role at a specific company, you can plan to stay.

Moving Up with Your Company: Internal Promotions

If you start your stepping stone role within that company, you can plan to stay for a year or two before applying for other work. And many of the times they fill their new positions with internal candidates, meaning people at the company have a better chance of getting some of the open positions because they know the person’s work ethic.

And it’s a lot easier to hire someone from the company than lose employees. But I do want you to anticipate wanting to stay in the role at least a year, so that you have a lot of insight and experience, and so that your resume displays, that you stick with roles and companies for a fair amount of time. There are always going to be caveats to this. And I do not ever want you to be miserable in a role.

So if you feel like you get into something and you have to leave, because it’s just not a good fit for you or due to a work environment issue, leave. There’s always going to be exceptions to any example, nothing is ever set in stone. But staying in roles outside of the classroom, especially as a career pivoter for at least one to two.

How Long to Stay in a Stepping Stone Job

There are always going to be exceptions to any examples I give. Really, truly nothing has ever set in stone. But just a general rule of thumb is that staying in a new position for at least one or two years is going to be something that hiring managers will look at.

Now, if you are applying for rules that are stepping stone positions, and you’re still unsure if you should accept a role in front of you, ask yourself the following questions, what is the worst that can happen if I take this position, what is the best that can happen if I take this position, is the risk now worth the reward, what are my three to five year goals, does this position align with those goals, what could happen if I end it up not liking it, what would be my plan B.

Once again, when you are looking at the role, I want to make sure that the position that you’re applying for is not something that you dread, just knowing that it just doesn’t have to be your ultimate passion either. This doesn’t have to be the quote unquote, “Coolest” or top on your list, especially if you’re working your way towards your top job. But you should still be able to find passion and joy as you learn and grow in this new experience.

And if your bills are paid and when you clock off, you’re done, you can live your life. If you are getting all of those needs met working towards your goals and your mental health is improving, that should be a huge win. There is a vertical career path that everyone really envisions, but with a career pivot, coupled with a time constraint, that’s going to be more challenging.

Feeling Like You’re Moving Backward in Your Career

A vertical trajectory may also take shape of a downward slope. And I know how defeating that may be to hear, but it’s always been my main objective to stay as honest and transparent as possible. Nothing here is black and white. I don’t want to definitively say if you have 11 years in teaching, you’re going to have to take a pay cut because I have shared so many stories that are the exact opposite of that.

But I do want you to know that’s a possibility and it does depend on the roles you’re applying for, the state that you’re in and how competitive those roles are and how much you’ve been able to up skill and work towards those roles.

So even though taking this new position might feel like going on a downward slope for a short period of time, it will still give you time for training and up skilling that’s going to come with the vertical growth in long term compared to your vertical growth opportunities in teaching, which are pretty much stagnant and has a very clear path. And that is something that if you’re listening to this podcast, you’ve decided you really don’t want to pursue.

It’s okay if you didn’t take a bootcamp or up skill or freelance or whatever else other things that teachers are doing to get at their foot in the doors at companies for other positions. You are on your own path. And if you are not able to do everything all at once, it’s okay. Right now, you may be facing a roadblock. And as long as you can recognize and identify that roadblock, you’re on the right path. Every part of our life is a stepping stone.

Dealing with Roadblocks during Your Career Transition

And it’s a lesson for us to think about and learn from. It just depends on how we treat these roadblocks. If we decide to move ahead in the same direction, if we need to pivot, or if we want to give up on the goal altogether, because it’s no longer a goal that serves us in this time in our lives. No one is going to make this decision for you. So it’s something you have to make for yourself.

And after working with thousands of teachers for the last few years, helping them transition outside of the classroom, I’ve heard countless stories of people who have turned down job offers just because it was not in an education company. Even if it was the role that they really wanted their foot in the door in. And they even interviewed at the company and said that the interviewers were really nice and seemed like it would be a great place to work, but they were holding out for their dream position.

Many of those teachers told me how much they regretted turning down these offers because the perfect role really didn’t come up in the next two weeks or four weeks time. And then they returned to the classroom for another year and they had lost that opportunity. There is a likeliness that even. And there is even honestly a likeliness that once you get into a position, it might be what you want.

You may think that you are wanting to take a project management job until you actually take a project management course. Or you might not think you’re going to want to do sales for the long term, but you may actually find out that you are far more driven in sales than you ever imagined yourself.

Getting Your Hands Dirty

I’ve said this a thousand times, but you really aren’t truly going to know what you like until you start to get your hands dirty in those roles, or start to actually take courses and build things in that direction. Maybe you don’t. Maybe the career title isn’t something that you feel super comfortable bragging about, but once you’re inside the actual position, the culture of the company or the product itself just makes you really excited to go to work every day.

You may just have a job where you do somewhat of a mundane or monotonous task, but because you’re not burned out and you love the people you work with, you have this new sense of community. You are better off than you ever were as a teacher, because once you get done with your workload for the day you go home and you get to explore other passions.

I just don’t want you to shut down any opportunities unless you are 100% certain that they are not a good fit for you. It is never really, truly too late for you to take hold of your future and start moving in the right direction. Just knowing that. It’s really never too late to take a hold of your future. No matter how late you are in your career, you can start moving in the right direction.

Just know that moving in the right direction is going to look different for many different people so don’t beat yourself up if you end up wanting to take a stepping stone job to get you in that right direction. Thank you so much for listening to the Teacher Career Coach Podcast. We’ll see you on the very next episode.

Important Links

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