The Match | Forward
Word: Forward
Sentence:
Sometimes the thing that moves us forward is not success, but what failure shows us.
Passage:
In my third year as principal, Mayor Rahm Emanuel asked us to take part in XQ, a national high school redesign challenge backed by Laurene Powell Jobs. We would be the only Chicago school to submit a proposal. Ten schools across America would each receive ten million dollars to bring a new vision for high school to life.
So we went to work.
For six months, we listened. Students. Teachers. Parents. Community. We asked what young people needed from high school that they were not getting. We asked what school could become if we stopped settling for what had always been.
Our idea was rooted in problem based learning. Freshmen would explore themselves. Sophomores would take on problems in their city and community. Juniors would study national issues. Seniors, through a partnership with United Airlines, would explore a global problem and travel to see it firsthand.
It was one of the boldest things I had ever been part of.
When we found out we had made the top 50 out of more than 1,000 applicants, it felt like affirmation. Like maybe this was it. Maybe this was the thing that would take our school from good to great. Then they asked for more, and we gave more. More time. More thought. More vision. More heart.
Two months later, we found out we did not make the final cut.
I was devastated.
I remember sitting alone with that loss, feeling like I had let everybody down. My team. The city. The organizations that had helped us. I had convinced myself this was the answer. That this was the thing that would unlock everything we wanted for our kids.
And then it was gone.
But with time, I came to see that we had not left empty handed.
The money would have helped. No question. But the process had already shown us something deeper. It showed us our capacity. It showed us the strength of our ideas. It showed us the assets already sitting inside our school and community. It reminded me that we did not need a prize to prove we were capable of doing meaningful work.
We did not get the grant.
But we were not where we started.
We had more clarity.
More conviction.
More belief in what was already possible.
That is the thing about failing forward. Sometimes you lose the opportunity you thought you needed, only to realize the process revealed what you had all along.
Sometimes the thing that moves us forward is not success, but what failure shows us.
Your Turn:
What has failure shown you that success never could?
Help us grow The Match community by sharing this with someone that needs to hear it today.
2 Comments
Leave a Comment
About The Match Weekly
The Match Weekly is one of the ways I can help provide a small spark each week to help you lead with heart and keep your fire lit. It's sometimes all we need to keep going.
Get the spark by signing up
2 Comments
-
on April 3, 2026 at 4:38 am
Chad… another great message/word this week. This reminds me of the concept that “the journey is considered more important than the destination, because “the process, not the final result is where we gain experience, personal grown and lasting memories” (from AI Overview)… many theorists and philosophers have written similar themes, but you have given a very tangible and resonating example of this in “real life”. Each one of the teachers and students involved with the process benefited and took those experiences with themselves for the rest of their lives. However, I really think that these lessons need to be practiced by the organization time, and time again. I have seen the disappointing disappearance of benefit when new leadership (in this case, leadership, teachers and new student body) don’t have the same institutional memory from that time, and the lessons are not practiced… and, of course, situations change over time, and new concepts need to be explored and new solutions need to be formulated. How does that occur? How do we get sustained benefit? How do we get that practice ingrained in the institution? All good questions, Your weekly newsletter will help answer the questions.
-
on April 5, 2026 at 8:31 pm
Thanks for this reflection Chuck! A breakthrough moment can move an organization forward, but if the lessons are not practiced, protected, and passed on, they can fade as people and circumstances change.
That is why culture matters. It is not enough to experience something once. We have to build ways of working that outlast a moment, outlast a person, and keep evolving with the needs of the time.
It’s really make it me think that progress only lasts when it becomes practice.
Really appreciate you adding this layer to the conversation.
-
Chad… another great message/word this week. This reminds me of the concept that “the journey is considered more important than the destination, because “the process, not the final result is where we gain experience, personal grown and lasting memories” (from AI Overview)… many theorists and philosophers have written similar themes, but you have given a very tangible and resonating example of this in “real life”. Each one of the teachers and students involved with the process benefited and took those experiences with themselves for the rest of their lives. However, I really think that these lessons need to be practiced by the organization time, and time again. I have seen the disappointing disappearance of benefit when new leadership (in this case, leadership, teachers and new student body) don’t have the same institutional memory from that time, and the lessons are not practiced… and, of course, situations change over time, and new concepts need to be explored and new solutions need to be formulated. How does that occur? How do we get sustained benefit? How do we get that practice ingrained in the institution? All good questions, Your weekly newsletter will help answer the questions.
Thanks for this reflection Chuck! A breakthrough moment can move an organization forward, but if the lessons are not practiced, protected, and passed on, they can fade as people and circumstances change.
That is why culture matters. It is not enough to experience something once. We have to build ways of working that outlast a moment, outlast a person, and keep evolving with the needs of the time.
It’s really make it me think that progress only lasts when it becomes practice.
Really appreciate you adding this layer to the conversation.