“It is not uncommon for people to spend their whole life waiting to start living.” ~Eckhart Tolle
Whenever I’m tempted to play it safe with my life, whenever I start talking myself out of the risks I really want to take, I think about something my friend Jesse said years ago, when we were on a work-sponsored retreat.
After a day of travel, activities, and settling in, we were left with a free evening. As the darkness deepened, a group of us stood together, discussing our options. What would we do on our first night in the woods?
There was a pause. And then, with a look of inspired wildness, Jesse said, “Let’s go for a walk and scare ourselves alive.”
And so we walked out the doors and into the night. We carried flashlights, but we didn’t turn them on; the moonlight gave us just enough light to see by. We walked down a hill and into a valley, weaving through the trees and underbrush.
Except for the leaves crackling underfoot and the owls crying in the distance, the night was silent. The walk was just daring enough to feel dangerous, just safe enough to feel like the right risk.
Here are 3 key lessons I learned from that moonlit walk in the woods:
1. Sometimes, you need to lose control to find closeness in your relationships.
And yes, absolutely, that includes your relationship with yourself.
When I arrived at the retreat, I was feeling tired, lost, and disconnected. I’d been working hard to prove myself on the job, and though I loved my role, my self-confidence was low.
When Jesse dared us to walk out into the woods, I felt something stir within me.
As Anne Lamott writes in Plan B: Further Thoughts On Faith, “…they say that the soul rejoices in hearing what it already knows. And so…pay attention when that Dr. Seuss creature inside you sits up and strains to hear.”
Deep down, I knew that I needed to stop proving, striving, and playing it safe. My soul needed a healthy dose of daring. Prior to that retreat, I’d mistakenly believed that if I just tried harder and did what I was supposed to do, then I’d feel safe. Then I’d feel okay about myself.
Walking out into the woods was an unexpected medicine; it cured me of my false belief. It reminded me that I wasn’t made to feel flawless. I was made to feel alive. And on that night, being alive felt scary, but it also felt right.
When Jesse proposed the idea of walking in the woods, I felt a shiver of fear. What if we got lost? What if I tripped and fell? What if a ravenous bear suddenly appeared?
I considered the possible negative outcomes. Yet my considerations couldn’t compete with the enthusiasm in my friend’s expression. In the moment of decision, I chose to take up his excitement and let go of my fear.
This is a choice that you can make. The next time you’re faced with a risk you really want to take— a calculated risk that will move you a step closer to where you want to be—acknowledge your fear, but look toward your excitement.
Imagine the expression on your face if you actually went ahead and did whatever it is you’re scared of. If the risk you’re considering is in line with your values and your true self, chances are the expression on your face will be one of surprise and delight.
Too often, we focus on our fear, and we give our enthusiasm nary a second glance.
3. Sometimes, you need to see the riskbehind the risk.
My best friend Brooke Law recently realized that making enough money to live wasn’t enough for her. Showing up every day for a job she couldn’t stand wasn’t enough, either.
True, quitting her job to work as a freelance consultant and writer felt risky, but Brooke realized that staying in a stifling situation presented risks of its own. Risks like depression and anxiety. Risks like never doing what she’s meant to do.
So, after a season of careful planning and cultivating opportunities, Brooke struck out on her own.
How’s she doing now? As Brooke wrote, “I’m still a little anxious about what comes next, but I no longer dread waking up in the morning. And that’s a gift that’s priceless.”
I know what she means. When I woke up the morning after that walk in the woods, I felt different. Braver. I felt that, in some small way, the act of daring had redefined me.
After that night in the woods, I took more risks on retreat: I went for a run in the rain with a top marathon runner. I stood next to a family of deer. I performed in a skit and laughed until I cried.
Though years have gone by, I can still remember how it felt to walk through the woods that night, that specific mix of adrenaline and excitement. I can still see Jesse’s silhouette walking in front of me, leading us into the woods.
And I’m still learning from his words, still scaring myself alive.
Photo by rowland_rick
Caroline McGraw is the creator of A Wish Come Clear, a personal development blog that gives you carte blanche to change your life. Visit and receive free copies of her three digital books, designed to support you as you make mistakes, fall down, and dare to rise again. You can also follow her on Facebook and Twitter.
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