Career Transition Timeline for Teachers


If you’re a teacher who has decided to leave the classroom, this post will help you plan out your career transition timeline. We’ll cover the pieces to your career transition that take an extended period of time and what you can get started on right away to begin your job search.

If you need help leaving the classroom, check out the Teacher Career Coach Course. This step-by-step guide has helped thousands with a transition from teaching. Save time and get support with every step of picking a new path, rewriting your resume, and answering tricky interview questions.

Creating a Career Transition Timeline

First, allow me to start with a disclaimer. Everyone’s timeline will look different and there are no guarantees. How long your job search takes is dependent on a variety of outside factors. For example, if you are starting out with great contacts who know of an open position that feels like the right fit, your career transition can happen very quickly! However, many teachers find that it can take months, a year, or even longer to find the exact right position.

Please don’t feel discouraged if your job search is taking longer than anticipated. Most former teachers I’ve worked with have said they felt like giving up just days or weeks before they received their new offer. They were just one ‘yes’ away from completely changing their lives, but at times it can feel SO far away or impossible.

Taking the First Step

If you’re just beginning to think about leaving teaching, brainstorming other options is a great place to start. But if you’re like many others, teaching was your only plan – there never was a Plan B. You might feel at a loss when it comes to figuring out what alternative careers are out there and creating any sort of transition timeline. Getting clear on what you want is the first step. One resource that may help you gain some clarity is our Free Career Quiz.

What career outside the classroom is right for YOU? Free Quiz

Finding a Direction

For all of the teachers who are looking for a new career direction, here is my best piece of advice:⁠

Don’t back yourself into a career path corner based on what others are pursuing or the most obvious choice. Focus on what excites you in your teaching career.

  • Do you like building and execution? Check out UX design, curriculum design, software engineer, instructional design, project management
  • Words? Learning and development, curriculum writing, marketing roles
  • Are you passionate about numbers? Data analyst, sales
  • Does the intrinsic motivation of knowing you are serving others light you up? HR, customer success manager

Start exploring those big ideas and then examine the careers you are pursuing to see if they align with you.

If you’re looking for a variety of directions, I’ve interviewed former teachers on The Teacher Career Coach Podcast. They’ve gone on to become learning designers, instructional designers, UX designers, copywriters, software engineers, real estate agents, corporate trainers, government account managers, customer engagement specialists, training consultants, project coordinators, and work in EdTech sales. Listen to these episodes as informational interviews to see which stories resonate most with you.

Related post: Best Jobs for Former Teachers

Focusing in on a Specific Path

As you’re investigating different paths, you’ll hopefully start to see how your skills translate into various positions. But it is important to have a clear focus. The more you are trying to market yourself for every position, the less you are truly marketing yourself for any specific position.

Teachers transitioning that have identified one or two clear directions do a much better job of standing out in the crowd without a clearly defined path.

Planning Your Career Transition Timeline

“If my teaching contract expires in June, exactly when should I start applying? What if I interview in May and they arent able to hold the new position until my contract expires, should I leave mid-year?”

You’ve gotten to the point where you have explored new career opportunities and have an idea about what you’d like to do, it’s time to take the next steps. But when? And how long will it take?

I would love to tell you that the timing will work out perfectly, but often in life it does not. This is particularly difficult for teachers who are locked into a teaching contract from August to June. Breaking your contract mid-year may come with repercussions and penalties. However, many teachers I work with want out ASAP, no matter the consequences.

Deciding When to Leave Your Teaching Job

Making the decision to leave teaching is not one that any of us take lightly. But I am an advocate that anyone can leave any job for any reason – even teachers. No judgement here.

When you leave the classroom is entirely up to you. The vast majority of teachers will want secure a new, full-time position before telling administration that they plan to leave. But many decide to take part-time or freelance work as a short-term solution while they job hunt. Others qualify for extended medical or other types of leave and use that time to search. And some, but very few, leave without a safety net.

Getting the Timing Right – For You

If you are considering leaving teaching ASAP, which also might mean breaking your contract mid-year, I’ve created a special episode of The Teacher Career Coach Podcast to help you understand the process: EP 52 Breaking Your Teaching Contract. You can work on the following career transition timeline at your own pace, during the school year or on breaks. Use the timeline described to give you an idea of what to expect.

On the other hand, if you are dedicated to staying until the end of your contract, the following times can give you an idea of what you should be doing in the latter half of the school year. Do keep in mind, however, that there are many outside factors at play. The timing will not always be perfect. You may find yourself with a job offer very quickly & have to weigh the pros and cons of leaving in April or May. Or your job search may go through the summer. At that point, you will need to decide whether or not signing on for another year is best for you.

Working on Your Resume

Working on your resume is something that you can start anytime during the school year. You will need to tweak your resume for specific positions you are applying for. If you are applying for a variety of different roles, you may even want to have a few versions on hand.

For help with your resume, one podcast you might want to check out: Episode 29: Writing a Transferrable Skills Resume. Alli Arney, our resident HR expert and professional resume writer, gives some excellent tips for getting started building your resume for roles outside the classroom.

Your transition timeline for your resume will begin when exploring new careers and noting any applicable experience and transferrable skills you have. It may continue right up to when you are applying for jobs as you make adjustments for individual positions.

Career Transition Networking Timeline

Networking is always a great thing to start right away. Don’t worry, it isn’t as hard as it sounds! You can begin networking just by telling your friends and family that you are looking for a new job. This can lead to warm introductions and new professional connections.

I recommend beginning cold networking within 3-6 months of your planned transition. You’ll then want to follow up on those networking connections very thoroughly 2-3 months out. Having connections will often help you work things out for your start date to be at the right time. 

Networking can feel incredibly intimidating if you haven’t done it before. If you have no idea where to start when it comes to warm and cold networking, I’d recommend reading this blog post: Teacher Networking: 5 Tips for Your Career Transition

Applying for Jobs

Applying is a different story. The average job takes at least 6-8 weeks from first interview to start date. I recommend you start applying aggressively two months out from the end of your contract. That being said, have your game plan ready so that you can hit it hard. Know the companies and position types you want to target, have alerts set up, resume ready, etc.

Additionally, you may want to investigate peak hiring season for the positions and companies you plan to apply for. Many companies, especially in the education sector, do the majority of their hiring during specific periods in the year. This gives the company time to interview candidates, hire, and onboard before their busy season.

The Interview Process

The interviewing process typically takes a couple of weeks. Most businesses will wait 2-3 weeks for you to start. A professional notice is generally 2 weeks. VERY rarely will they wait longer than 3 weeks, however. It’s important that you come across as a solution seeker, though. So when discussing availability or start date, you need to have a plan.

“Ideally, my start date would be June 13 so that I can finish the school year, but if that’s going to hinder my candidacy for this position, I am happy to work something out.”

I want to also note that interviewing during the school year can be challenging. You may have to take a half-day or full-day of your PTO in order to make it to an interview. At times, a company may need to reschedule an interview when you’ve already planned to take the day off. This can be incredibly frustrating, but I urge you to remain professional and not give up. If your goal is to get a new position, it’s important to be flexible and understanding, especially when it comes to interviews.

Making Negotiations Near the End of the Year

If the timing isn’t right for your start date, it may be possible to make some negotiations with the company and your school. You could possibly negotiate to teach half days for the last week or two and train in your new position half days. Split the week and teach a couple of days and train a couple of days. Or use your accumulated PTO so that you’re technically finishing out your contract while you begin your new job. That way you can start your new position and still finish your contract.

There are always extenuating circumstances that exist for certain companies, so this may not be a solution for every company. Most employers should understand and be willing to work with you. Honestly, they will admire your commitment, desire to fulfill your obligations, and leave on good terms.

Of course, this is also dependent on how your school administration responds to the news that you’re leaving. If you have a supportive admin who is willing to work with you during this transition time, that can make a big difference.

Staying Organized and Accountable

No matter where you are in your career change, one of the most difficult challenges is staying organized and accountable throughout this process. It’s important to continuously focus on what is moving the needle forward – and what is making the biggest impact. Balancing a job hunt with your current teaching job and life in general can be a struggle. You may be job hunting for months or even up to a year before you land your next role. Total transparency, it takes a lot of time and dedication to change careers.

To help you get (and stay) organized and accountable throughout this process, I’ve developed the Career Pivot Planner.

Career Pivot Planner - Teacher Career Coach

I knew I wanted to create a planner because changing careers is not a small task, and teachers already have a lot on their plates. I saw the need for a tool that can help you both get organized and stay accountable as you take steps toward changing careers. And I wanted to create something unique to teachers transitioning so you can focus on your career goals and track the progress you make throughout this process.

The Career Pivot Planner was created to help you organize your career change. This planner has the space to write out your goals, schedule in your career change plan, and hold yourself accountable on important action items.

You can use this planner entirely on its own – or simultaneously with the Teacher Career Coach Course, where we break down your action items into baby steps and guide you through the entire process.

Find out more and take a peek inside this planner here: Career Pivot Planner by Teacher Career Coach

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