Getting Into the Discomfort Zone: Lessons from Scaredy Squirrel
Scaredy Squirrel was one of my favorite books to read to Owen, Izzy, and Charlie when they were young. We were lucky enough to benefit from Dolly Parton’s Imagination Library. Simply by being born in Tennessee, our children received a free book each month until they reached kindergarten. There were many wonderful ones, but the story of Scaredy Squirrel always stood out to me.
Written and illustrated by Melanie Watts, the story centers on an anxious squirrel who refuses to leave the safety of his familiar tree. The outside world, as he imagines it, is filled with danger: sharks, germs, killer bees, and poison ivy. He thrives on routine and preparedness, carefully assembling an emergency kit for every possible threat. From the security of his tree, he observes life at a distance rather than participating in it.
One day, something unavoidable happens. A “killer bee” forces Scaredy Squirrel out of his tree. What follows is an unexpected discovery: he is, in fact, a flying squirrel, capable of far more than he ever imagined.
I thought about this book recently after a conversation with friends who also remembered the books from Dolly Parton’s program. As I reflected on fond memories of reading to the kids, I was reminded of the powerful and relatable message of Scaredy Squirrel.
What a metaphor for life.
I remember reading the book again and again to the kids. I encouraged them to take chances and push beyond their comfort zones to reach their fullest potential. I had no idea how much I would one day need to heed that same advice myself.
Last week, as we celebrated Izzy’s 20th birthday without Owen, I was reminded how important it is to keep moving forward, even when it feels impossible. Recently, I spoke to a group about the importance of filling up our tanks: staying off technology, staying active, getting outside in nature, and perhaps most importantly, cultivating kinship.
Kinship is more than connection. It is community.
Since Owen’s death, conversations can sometimes feel awkward. I can find myself present on the outside while carrying pain and sadness on the inside. No one can fully understand our loss, but I am deeply aware of those who reach out, even when there are no words to heal the pain. In those moments, we simply feel seen. That is kinship—connection and community.
Loss of any kind is often accompanied by, at times, almost unbearable pain. Healing also requires discomfort. Personal growth requires taking chances: talking to a stranger in an elevator, saying yes to a trip with friends, going out to dinner, or taking a walk or hike. When we find ourselves in darkness, the safest place often feels like staying home, alone under the covers. But there is no personal growth there.
At The Goldfinch Foundation, this belief shapes everything we do. We create opportunities for young people and adults to gently step out of isolation and into connection—through creativity, movement, time in nature, and shared experience. Not because it is easy, but because healing and resilience are most often found just beyond the tree.
We can all benefit from taking a chance, as Scaredy Squirrel did, and leave the tree occasionally. It is only then that we realize we just might be able to fly.