Daily writing prompt
How has a failure, or apparent failure, set you up for later success?
Failure is a strange thing. When it happens, it rarely feels like a stepping stone. It feels final. It feels discouraging. It feels like you’ve reached the end of the road.
But sometimes what looks like failure is really just a series of closed doors guiding you toward the one that’s meant to open.
Back in 2015, I was having a very hard time finding a job. Bills don’t wait patiently while you search for the right opportunity, so I did what I needed to do to help keep things going. In early December, I started substitute teaching in Duval County.
I’ll admit something right up front: substitute teaching is much harder than it looks. Students can be wonderful, but when you walk into a room where they know you’ll be gone the next day, you quickly realize that classroom management is a skill all its own. It was discouraging at times. Still, I kept at it. Between that first December and the end of the 2016–2017 school year, I think I worked in about fifty different schools across the district. One of those schools was Darnell-Cookman.
Somewhere along the way, probably in the spring of 2016, something dawned on me. Teaching might actually be a direction worth pursuing. So I went ahead and took the state certification exam for teaching English in grades six through twelve. To my surprise, I passed both sections on the first try. That felt like a good sign.
I started sending out résumés to schools all over the district. At first, nothing happened. No calls. No interviews. The silence was frustrating, but substitute teaching became my foot in the door. I began focusing my efforts on schools where I thought I’d enjoy teaching.
In the fall of 2016, I got what felt like my first real opportunity. I taught for eight weeks at a middle school where they were searching for a permanent teacher. I worked hard and thought I had a good chance. It turned out the principal had already decided she wanted someone under thirty years old. The job went to a brand-new graduate with a social studies degree who didn’t even want to teach English but needed the position.
Not long after that, another opportunity came along at one of the best middle schools in Jacksonville. I apparently did very well in the interview, and all I had to do was survive a three-day classroom audition. That sounded manageable enough. At the end of the three days, though, I was told it wasn’t going to work out because I didn’t have the “withitness” they were looking for.
“Withitness,” as I later learned from my brother-in-law who teaches, is a fancy way of saying you have eyes in the back of your head. I suppose that was their way of saying I didn’t see everything happening in the room. Of course, they had only given me lesson plans for two of the three days and expected me to create the third day’s lesson on my own without telling me ahead of time. Still, the result was the same: another opportunity that slipped away.
There were other interviews, too. At one school, a principal asked how I would teach writing and then narrowed the question to how I would teach “the conventions.” I had never even heard that term before, and my answer made it painfully obvious. At another school, the administrators peppered me with questions like “How would you teach RL.1.1?” and “What lesson would you use for RI.2.3?” When I admitted I didn’t have the standards memorized by number, I was told I probably didn’t really want to be a teacher.
Another summer came and went without a job.
Then, just before school started in 2017, I received a call from a teacher at Darnell-Cookman asking if I was still interested in teaching. Of course I was. She connected me with the assistant principal, Andrea Talley, and I was asked to substitute for a seventh-grade class on the very first day of school.
To prepare for that day, I met with another seventh-grade teacher named Linda Fralick. She walked me through the lesson plans, but she also did something else. She went over my past interviews with me and talked through the kinds of questions I might be asked. By the time the interview happened after school, she was actually one of the people sitting at the table.
She asked the first question.
“How was your day?”
That one was easy. The next question was one we had practiced together earlier. After that, the department chair, the assistant principal, and the principal all took their turns asking questions, and for the first time in this long process, I felt like I had the answers.
It felt good.
But not nearly as good as what happened next.
After the interview ended, I walked out of the building and started crossing the lane in front of the school toward the parking lot. My phone rang. It was Ms. Talley. She said she needed to tell me something, and then she handed the phone to Ms. Fralick.
Her voice came through the speaker with excitement that she didn’t even try to contain.
“You got the job!”
A moment later, I called Daryl.
“We did it, baby,” I told her. “We got the job.”
I didn’t say I got the job. I said we. Because through all of those interviews, all of those rejections, all of those uncertain months, we had been in it together.
As I stood there near the parking lot, tears streamed down my face.
Darnell-Cookman had been the school at the top of my list the entire time. I had loved every day I spent substituting there over the previous eighteen months, and now I was finally part of the team.
If any of those other schools had offered me a job earlier, I would have taken it without hesitation. And if that had happened, I wouldn’t be where I am today.
There have been highs and lows in the nearly nine years since then, just like there are in any career. But I love the students I teach, and I love the teachers I work alongside.
Looking back now, all of those “failures” weren’t failures at all.
They were simply the doors that had to close so the right one could finally open.
Copyright © 2026 Doug DeBolt.
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