Since I've been out of the classroom for five years, my most relevant examples come from teaching teachers.
As a former classroom teacher, I can attest to the fact that many of the lesson plans you create do not go as according to plan. Students do not follow a plan. Learning does not follow a plan. So, as educators, we have to be flexible. We have to be able to make amends to plans. By being flexible, we are taking risks.
Disclaimer: One educator's comfort zone is another's risk. It's critical to encourage, not judge, risks. Risks do not look the same for all.
Two years ago, I took a huge risk by starting the RRISD Google Ninja Academy. No one had done it before. We did not have funding. Our staff was unfamiliar with big tech conferences. I had never run a conference before. I had no experience. The only thing I had was a love for learning and a drive to bring in more high-tech conferences and exposure to our staff.
The result: a full-day event of nearly 500 educators from around the state learning and sharing. It was a huge success.
However, not all risks I take are successful initially. I took a risk in starting App-y Hour for our high school teachers. I dedicated time every Wednesday morning to teaching fun topics for teachers. The result: only two people ever showed up.
So, after two months, I changed it. I decided to hold conference hours for teachers. I had our students lead 30 minute trainings for teachers on topics the students deemed important. The result: higher participation and more change resulting from trainings.
Risks are important, but not as important as the changes you make as a result of those risks. Taking the risk is the first step - however big or small the risk is. The second, larger step, is making changes as a result of either a positive risk or a less-successful risk.
Take a risk - big or small. Then, follow-through. The follow-through is the most important step in making change and improving.