How to Quit Teaching in 2022 (Part 2)

Part 2: Searching Smarter, Not Harder

Is your 2022 new year’s resolution to quit teaching? Congratulations on making this big decision. I know personally that it’s not an easy one. Seven months into my job search, I have been hired for several contract roles as a curriculum designer and adult learning facilitator. But I’m still looking for my next full-time job. I’m doing my best to share some of the lessons I’ve learned from my search so far. In Part 1 I wrote about preparing for your job search. In Part 2 I will walk you through how to be strategic in your job search.

For some people, my advice may be obvious. However, for me, some of these steps were not intuitive. Finding a new job can involve some self-promotion and reach out to strangers for help. It took some time and effort to get over my discomfort with these skills. Overall, social factors like race, class, and gender impact so much of the job searching process. Ideally, all job searchers deserve the same opportunities. Unfortunately, not all of us have equal access to the "tricks" of the job search. Hopefully, this post will reveal some strategies you did not already have.

Step 3: Start Your Search

One of the most important pieces of advice I got (but repeatedly forgot) was to focus on companies and organizations that excite you, not specific jobs. Each job posting is getting hundreds of applicants. You need to find a way to break through the crowd. One way to do this is by ensuring you’re applying for jobs with companies and organizations that you know well. The ability to speak clearly and passionately about why you’re excited to work for a company/organization will go a long way. This is especially valuable if you’re looking for a job in edtech where companies value candidates with knowledge of and experience with their products.

A lot of the companies/organizations you’re interested in might not be hiring for the job you want…yet. That’s where networking comes into play. Following advice from others, I created a list of the organizations I knew I would be excited to join. This list has been helpful in two ways. Firstly, when looking for fresh job openings I go straight to these organizations’ jobs’ page. Usually, companies will post jobs here before they show up on LinkedIn, Idealist, or Indeed. So going directly to the source gives you a slight advantage.

Step 4: Network, Network, Network

The other reason for developing a “Wish List” of companies is to focus your networking efforts. Whether or not the company you want to join is hiring, you should reach out for an informational interview. This will give you a chance to learn more about the organizational culture, the work you want to do, and the hiring process. It will also give you a chance to introduce yourself and make a positive impression. When this company is hiring, you’ll have someone there who can help you get past the initial screening process.

Some folks you want to reach out to at an organization you like include people you know (!), people with the job title you want, people supervising the job title you want, or people on the HR/talent acquisition team.

It’s helpful if you have connections to a company. For example, using LinkedIn you can find out if a former co-worker or college classmate knows someone at the company. But if not, you can send a “cold” message through LinkedIn or e-mail. Whether a contact forwards this message for you, or you send it yourself, your request for an informational interview should be some version of:

Hi X,

I’m an educator interested in exploring opportunities in _____ (curriculum design/product management/etc). 

I’m reaching out because I’m interested in learning more about the work you’re doing at ___. Are you free for a short phone or video call in the next couple of weeks? I’m free at ___ and ___ on _____.

Looking forward to connecting!

I have had many people accept my LinkedIn connect requests, but ignore my requests for an informational interview. That’s okay, I’ve still had many valuable informational interviews as a result of my outreach efforts. So don’t get discouraged! Be patient, polite, and persistent.

Step 5: Always Follow Up

Did you send a request for an informational interview, but didn’t get a response? Send a polite follow-up. We’re all overwhelmed with e-mails/messages these days. A concise and friendly reminder might land you the conversation you’re hoping for.

Did you have a great conversation with someone about their work at Company X? Send a thank you.

Following up is not just good manners, but it can help you make a positive, lasting impression.

After a job interview, I like to send a thank you that also includes a very brief summary of our conversation, i.e. “I loved hearing about the work you’re doing to support math teachers in X Public Schools. I can tell you’re really proud of your impact there. I hope you got a clear sense of my expertise with facilitating PD and coaching teachers, and why I am a good fit for Company X.” 

I also have made it a habit to follow up on rejection e-mails as well. As always, don’t be surprised if you get no response or if you get a generic one. However, you may get specific and concrete feedback on your application that will help you with your future efforts. And signaling that you’re receptive to feedback is always a good look, regardless of the job title or organization you’re targeting.

You’ll notice I didn’t write about cover letters or the application process itself. I chose not to focus on these aspects, although they’re central to the job search. That’s because in my own search, I initially focused too much on finding jobs and applying, without doing the preparation and networking. I got the majority of my interviews by first connecting with someone at the company right before or after applying. Out of 40 - 50 applications, I only got one interview without doing additional networking. If want help with cover letters, interviews, or any other stage of quitting teaching I’m here to help! You can find me on LinkedIn or Twitter! 

Many thanks to Mark Danforth, Jacquelyn Gause, Gabe Brosbe, and others who have helped me throughout this job search process.