The Messy Middle- Transitioning Out of the Classroom

From classroom teacher to…

Sorry, this isn’t one of those polished success stories.

I want to share the part many don’t like to talk about: the slow, uncertain stretch in between. For many transitioning teachers, I call that the messy middle.

After leaving the classroom this school year, I was trying to figure out what I wanted to do. I had done my research, but I still wasn't certain about the next steps.

Did I want to work for a company? Perhaps, working in edtech?

That seemed like the logical next step. I have the training and presenting skills, but I learned it wasn’t going to be easy, especially given the residency requirements of where I live. Remote-anywhere jobs seemed to be the answer, but they aren’t exactly plentiful, and when they do pop up, it's incredibly competitive due to the sheer volume of applicants from all over the world.

At the same time, I needed to bring in some income, so I networked and began freelancing for two companies providing learning support to students and academic coaching. It felt like a solid step, and it was right up my alley. But freelancing, I soon realized, brought a whole new set of challenges: You’re building a reputation (or creating a portfolio), forming relationships, collecting testimonials… and it doesn’t happen overnight. Clients weren't arriving as I'd hoped, and the disappointment was palpable. Each day that passed made me question my resolve.

Eventually, I started to get more work. Even then, I noticed a pattern: I’d get a new client, and then another one would need to reduce the times their child met with me. And, they go on vacation. Suddenly, there was this ebb and flow I wasn’t used to. Some months were strong, others were slow. You don’t have the kind of consistency you get with a salary, and that got to me. I’m someone who likes to plan and predict. As much as I wanted more clients, it doesn’t mean they are going to appear.

That’s when I realized I couldn’t rely solely on the companies I was freelancing for. I had to start finding clients on my own. Well, that opened up a whole new learning curve: marketing myself, navigating proposals, and following up. These weren’t things I’d needed to think about in the classroom, but now they were essential. My old nemesis came knocking on the door- impostor syndrome. If you struggle to project confidence, people usually aren't keen on using your services or products. I've found that consciously focusing on the value I bring and reminding myself of my expertise, even when it feels uncomfortable, has been key to starting to shift this.

So here I am.

Still freelancing. Still figuring it out. Yet, more grounded than when I started.

I’ve come to accept that the path isn’t linear, and it’s definitely not predictable. But I’m learning to sit with that uncertainty without letting it shake my confidence or cause me to question my decision.

If you’re in a similar place, navigating the in-between, this messy middle, here is my message to you:

There will be ups and downs. You’ll doubt yourself. But that doesn’t mean you’re doing it wrong. It means you’re growing. Professional growth can be messy. So, embrace the journey. Starve the doubts. Lean on your support system. Reach out for help. And trust that something is taking shape, even if you can’t fully see it yet.