That's All Folks: Goodbye To Leaving Teaching

It’s time to say goodbye to Leaving Teaching.

I started this newsletter in August of 2024, weeks after I resigned from teaching. Quitting was a total leap of faith—I had no other job lined up and no idea how it would work out. All I knew was that I wanted to write and edit, and that I couldn’t go back to the classroom.

Terrified of failing and letting my loved ones down—and of the uncomfortable feelings that rose up the moment I sat still—I launched into action. I chased leads and submitted proposals for freelance projects, started waking up at 5:30am to work on my novel, and launched this newsletter.

I wasn’t sure what, if anything, would stick. At first, I thought of this newsletter as a portfolio piece, a place to demonstrate everything from my SEO writing to my content strategy and marketing skills.

It worked. Six months after resigning, I started my current position as the fractional managing editor of Motley Bloom, a start-up publication dedicated to neurodivergent-first living. The work is fun, engaging, challenging, and expansive. I’m learning and growing in new ways and doing what I’ve always wanted to do. The fact that I also get to do work so aligned with my own values is just icing on the cake.

My novel is gaining momentum as well. In November, I had the dream-come-true opportunity to attend Tin House’s Autumn Workshop as the inaugural Break Scholar (as in, full scholarship!). Last month, I earned another, bigger dream-come-true—dare we say life-changing—opportunity. I’m not yet ready to share that publically, but trust me—it’s good.

That leaves this newsletter. In its nine-month run, I’ve published 21 interviews with former teachers, 14 researched and reported resource posts, and 12 first-person or opinion posts. To make that happen, I’ve spent uncountable hours on teacher forums and groups researching relevant topics, promoting the page to grow the audience, networking with experts in the teacher transition space—and of course, writing. I’ve also invested a pretty penny of my own money in the operating costs.

These last nine months, people have been asking me: “How you are doing it all!?”

And the answer is: “I never rest!” (Really, I wrote a whole post about it.)

As both my paid and creative work have taken off, I’ve tried to keep this newsletter going. I’ve experimented with various ways to balance the demands—reducing publication to once per week, hiring other teachers to transcribe interviews, and offering perks and giveaways to make membership more enticing. These efforts aren’t not working, but they aren’t generating as much forward momentum as my other projects. And they aren’t enough to make this newsletter sustainable.

The lack of rest has also become unsustainable. The longer I spend out of the classroom, the more I’ve come to appreciate the importance of pacing and rest. On top of that, a health condition has flared up, and I’m literally under doctor’s orders to slow. the. fuck. down.

And the only thing I can cut out of my life—other than caffeine (God help me)—is this newsletter.

I’ve held on for a few months longer than I probably needed to, because I love writing this newsletter. It’s fun. I love the emails you all send me, and more than anything, I love teachers. Writing this has been a way to stay connected to teachers and to that part of myself, which I miss dearly. (Though I will soon have the opportunity to return to a different kind of classroom in a different capacity—more on that another day.)

I’ve also had a few lingering interviews to turn into posts. But I just can’t seem to get myself to do it. The moments I do get some downtime, I want to relax, read a book, hang out with my kids, or just sit outside and stare at the sky.

So instead of those final posts, I’ll give you just a quick recap:

• Pay It Forward Coaching: Free career coaching might sound too good to be true but it is real and it is here, at Pay It Forward Coaching. The 501c3 nonprofit is the brainchild of Mike Connolly, who created PITC as a place for people to give and receive career guidance free of charge. A trained team of volunteers donates their time to help job seekers with everything from resume review to interview prep. There’s also a Slack channel for quick questions. Like this newsletter, PITC is a labor of love and primarily self-funded, so if you do book a session, for the love of God, donate what you can to help cover operating expenses.

• I chatted with Tyrina Lassiter about her expanding empire and the importance of getting clear on why you’re leaving teaching before you begin your transition. Basically, your personal reasons will serve as a roadmap for the kind of career you should target, where you’ll actually thrive. Tyrina is such a force and a wonderful cheerleader of folks in the teacher transition space—including yours truly—that she’s become one of the few coaches I recommend. Her services aren’t cheap—or free, like PITC—but she’s a pro. All her services also come with ongoing support, so no one-and-done’s with her!

• I also chatted with Kim Brooks, a former teacher turned wellness coach. Though she works with a variety of clients, her specialty is working with burnt-out teachers. Whether you’re still in the classroom or are long gone but still carrying the stress (not me at all), her private sessions could be beneficial. She’s also got a great story about working overseas at various international schools and facing her own burnout upon returning back to the States.

Now that all the official stuff is out of the way, I want to say thank you. It has meant the world to have you on this journey with me, from leap-of-faith to fully transitioned. There is so much sadness that comes with walking away from the classroom and from the career I worked so hard for, and it’s been an incredible gift to have you all accompany me through these early months.

If you’ve shared a post or sent a message of support, thank you—it’s what’s kept me going on the hard days, when I’ve felt like I was just screaming into the void.

If you’re one of the people I interviewed, thank you for generously donating your time and sharing your story. I’ve enjoyed connecting with each and every one of you.

If you’re one of the people who donated to support this publication, thank you most of all. You’re literally what kept this going—because while I want the information here to be free, the maintenance of this newsletter is not. I’ve primarily paid out-of-pocket for the hosting fees, promotions, giveaways, etc.

I hope the interviews and information here have served you in some way. If you want to give a final thank you, you can toss some change into the virtual tip jar. This will go towards the hosting fees to keep this information alive on the internet for all to see. I’ll keep it up as long as I have funds.

It’s a terrifying time in this country for teachers and public education as a whole. I’m rooting for you all and will be beside you as we fight for the schools our kids need—and the respect our teachers deserve.