5 Tips for Doing Stuff That Scares You

I love change. I like learning new things, challenging myself in new ways, meeting new people, and, to be honest, I like to be thrown far out of my comfort zone. When I was in college, I completed the second half of my student teaching requirements at a sports high school in Sydney, Australia. As I was finishing college, I applied to two overseas positions: teaching English in Japan with the JET program, and teaching social studies (my certified area of teaching) at the American School in Tegucigalpa, Honduras. I didn’t know anyone who had done either of these things, but had met a bunch of international 20-somethings while working at a summer camp throughout college. These international youth seemed very glamorous and worldly, so I figured that if I could work and travel, I would also experience this fabulous lifestyle.

Fast forward twenty years, and I’ve lived in Australia, met my husband at that school in Honduras, added a library master’s degree, had two daughters while working as a school librarian at an international school in Jakarta, Indonesia, moved back to the U.S., moved overseas again to Manila, Philippines, then moved back once more to Chicago. I got my first administrator position, and then I got my next (current and wonderful) administrator position.

All that to say, I’m still looking for ways to keep myself off balance. Not in a self-punishing way, but I feel like I’m at my best when I’m a little uncomfortable. I think this is a good thing– reflecting on my life, I’ve been at my best when I’ve done something brand new, something I wasn’t sure was going to be 100% successful. I definitely had no road map for success in Honduras, or library school, in Indonesia, or in this brand new job, but what I know for sure is that as long as I’m not attached to achieving pre-identified results, and as long as I’m willing to be open to learning from others and making mistakes along the way, everything seems to work out okay.

Over the past three months, I’ve counted five separate circumstances into which I’ve placed myself VOLUNTARILY, and due to which I’ve experienced varying levels of discomfort– sometimes asking myself, “What are you doing??? Don’t you remember how this is hard and scary??”

First, I gave a presentation at a state conference this past February. I’ve presented at conferences before, but the topic of this one was especially personal and a little out of the ordinary. But I was driven to create and present it, in the hopes that sharing my experiences might help other people. I spent countless hours creating the best slideshow, talking points, and presentation that I possibly could, largely out of fear of failure (which was actually the topic of my presentation– I get the irony). I felt a great sense of accomplishment because I did it even though, and maybe because, I was really afraid.

The second voluntary situation is this blog itself! I want to write in it regularly as a way to develop my own thoughts on a variety of topics and to challenge myself to add to the work/life, education conversation, but the entire time I’m writing I’m trying to silence the voice in my head saying, “Does anyone really care about this?” It’s a small but powerful voice! From what I’ve read, and the advice I’ve gotten from others, is to just keep writing without attachment or expectation of outcome.

On a lighter note, the third voluntary circumstance I’ve thrown myself into is golf. My dad has been a huge golfer my whole life, but aside from a forgettable stint on the 9th grade girls’ golf team, I have not made an effort. After beginning my new job, however, something clicked– and I feel great motivation to at least be good enough to play at a very basic level in case of the occasional golf outing (even if it’s just a few holes before moving on to riding around in a golf cart, heckling the real golfers). It’s been fun taking lessons and assuming a beginner’s mindset, having no expectation of skill save that of what I may have remembered from the previous week’s lesson. It’s refreshing to look to someone else as the expert, and freeing to be able to ask any question that comes to mind without worry that maybe I should have known the answer. Not that in my current district leadership position I feel that I have to have all the answers– far from it– but there is an underlying sense (completely self-determined)  that I should have at least some idea or prior knowledge of everything I do.

The fourth situation evoking mild terror is the first annual district-wide technology conference that I’m planning. I’ve ALWAYS wanted to do something like this, and am extremely thrilled and grateful to my district leaders for supporting it. It’s scary though, because having never done it before, I have no idea how it’s going to turn out. I think it will be successful, as we’ve got 21 amazing staff members presenting on a variety of exciting topics, but still, I can’t control the number of staff signing up and it’s hard to predict what hiccups might occur that in hindsight should have been completely obvious. This one is especially looming large in my head right now, as it’s happening in less than a week! Stay tuned for a post-conference reflection :-).

Finally, I’m presenting at a big conference (ISTE– International Society for Technology in Education) at the end of the month. It’s in a format I’ve never tried before, and I could have said no, but it seemed like a new experience and, as I’ve established earlier in this post, there’s nothing I love more than being thrown in the deep end. So I said, “Sure, why not?”


  1. No ones cares. No ones cares like you do. This might seem really hard to believe, especially if you’re in a high-pressure environment like a conference presentation or some other circumstance where it feels like all eyes are on you, but it’s true. Your biggest nightmare (messing up your presentation, hosting a lame conference, whiffing your drive in front of colleagues) will very barely register in someone else’s mind. They might have a negative or critical thought skitter across their mind, but they will soon be back to focusing on their own worries.
  2. You’re growing your brain. Trying something new, practicing new skills, learning new concepts, all of these help stimulate the neuroplasticity of our brains. The very act of new physical or intellectual efforts helps our brains grow and form new pathways. You might never achieve greatness at these new skills, but your brain benefits all the same.
  3. Have no attachment to the outcome. This one is probably the thing that helps me the most. I won’t pretend that I don’t check the stats of this blog in the days after a new post is published, but I try to remember that I’m not writing to raise my stats or to receive some sort of outside acknowledgement– I am writing for myself. Once I hit that publish button and send it out into the universe, I’m done. I can release attachment from any further expectation. Same for the golf, or the presentations, or the conference– I want to do the very best that I can do, with the information that I have, and create circumstances with the greatest chance of success. But once you have done that and given it your best effort, you can release any further attachments to achieving specific outcomes.
  4. Examine your thoughts. Freaking out? Caught in a worry cycle? Wondering why you ever did this in the first place? Explore that. Follow your thoughts about the very worst outcome. What if it did happen? Would it really be all that bad? What might you learn if that did happen? Will people really judge you or laugh at you? This is highly doubtful. What I’ve found is that people tend to admire those who try stuff– even if they’re not successful. People regret what they don’t try– they don’t regret having tried something that failed.
  5. Have fun. Because new stuff is fun, and you often to get meet some pretty awesome people along the way! Take it from Ferris Bueller– life does move pretty fast and if you don’t stop and look around once in a while, you could miss it!

What have you tried? Are you doing something new right now? Leave a message in the comments and let me know!

The Mentor

“What’s in it for the mentor?” George Costanza asks in a classic Seinfeld episode. “Is there money involved?” When Jerry lists the benefits of mentorship (“Respect, admiration, prestige”), George scoffs and asks if the protégé would “pick up stuff for the mentor… laundry, dry cleaning?”

I’ve never picked up anyone’s dry cleaning, but I have been lucky in my career to have had a number of mentors in both official and unofficial capacities. I can trace the lasting effect they’ve had on my career and how they shaped my understanding of what it means to be a professional. Additionally, because of their very different personal and professional styles, I learned something unique from each of them.

What follows is a list of people who both believed in and challenged me, and who consistently demonstrated the highest levels of professional ethics. I want them to know what their time and attention meant to me.

First there was was BF, my wonderful headmaster at a small international school in Indonesia. I was a newly-minted school librarian and eager to learn and grow in my position. BF was widely admired by the school community for his empathetic and supportive personal style and his unwavering commitment to doing whatever was best for kids. He also responded to every email in a timely fashion– regardless of how insignificant the question or request. Responding promptly to email is something that I have also tried to incorporate into my professional practice, because I remember how much I appreciated his quick responses. I thank BF for teaching me the importance of empathy and timely communication.

Next was DF, who was perhaps the most directly influential mentor that I had, as she and I worked together on a daily basis as we led a high school library. She and I are still close, which reflects the strong, positive nature of the relationship we built. DF has the most impressive work ethic of anyone I’ve ever met. She has boundless energy and the willingness to pitch in and do what needs to be done in order to accomplish a task, no matter how large or small, whether physical or mental in nature. Even though she was the head of our library, DF was willing to let me create programs and try new things– and would then jump in to support me every step of the way. She had no discernible ego about her position of leadership, and was also truly committed to supporting the goals of the school district through her work in the library. I thank DF for teaching me the value of encouraging others as well as the value of hard work and pitching to help until the job is done.

At the same school, I met TS, PB and KS, all of whom mentored me in important ways. TS was hands-down the most intensely passionate educator I have ever met. He was an administrator who was so supportive of teachers and students that he was willing to allow both to take risks and try new things if the purpose was to grow. When I came up with an idea for a new staff PD program, I pitched it to TS and received so much support and encouragement that there was no way I was going to fail. I thank TS for showing me that there is a place for intense passion and even argument in education as long as the goal is to help students succeed.

PB was also an administrator at the school and spent many hours of her time with me as I worked through my Master’s degree in educational leadership, for which she was my official mentor. PB and I had many long conversations, and I felt that she did take a special interest in supporting me and my career. Several years later, when I was contemplating a move back to the U.S. and looking for another job in education, she actually offered to talk to me on the phone about interviewing and job searching while I was still overseas. I of course took her up on it and received valuable insight. She was also one of the people who, when I expressed fear for my career when my family and I decided to leave our jobs and move overseas, consistently told me that “Good people land on their feet.” She never doubted me, and for that I thank PB.

KS was also an administrator at the school, and was a mentor who always challenged me to get better and do more. When he came to the school I was in a great position, but after we started working together he really leveled-up the content and quality of my work. I always enjoyed our conversations because he challenged me to deepen my understanding of school leadership and of my own capabilities. He believed in me to a degree that my own vision of what I could do in my career expanded exponentially, and for that I thank KS.

Finally, there was DH. DH was an official mentor, assigned to me in my new role as a district administrator. DH himself was a former longtime administrator, who possesses a wealth of experience in education and in educational coaching. Being a new district administrator comes with a learning curve, as it’s inherently different than working in a school building, and the ways in which communication needs to occur at this level are uniquely important. As an outsider to the organization, DH was able to help me understand how to work within the district office system and to become more effective in my approach. I experienced some significant challenges during the year we worked together, but was able to maintain both perspective (most days) and a commitment to my professional path largely due to his wise observations, recommendations, and unwavering professional support. I thank DH for teaching me how to design and maintain a successful career in educational administration, and for embodying the essence of a great mentor– even without the dry cleaning pickup.

My advice for prospective mentees: Don’t wait for an official mentor– look around you now and ask, “Who do I admire? Who is doing this right? Who has mastered skills that I’d like to have?” You can observe them in action, see how they handle various scenarios. You can also ask to meet with them occasionally. Come prepared with questions you’d like answered: “How do you manage x, y, z? What would you do if x, y, z happened?” Have no ego. You can learn from anyone, even someone in a lateral or lower position than you on the organizational chart.

My advice for prospective mentors: Be generous with your time, know that others may be watching and learning from you without your being aware, and have a firm understanding that a small gesture, word, or note from you may have unknown positive affects on someone still making their way. The benefits of being a mentor may not impress George Costanza, but mentoring’s value can yield truly immeasurable rewards for the rest of us.