Back to Blog

Finding You in The Thick of It

in our own ways
we all break.
it is okay
to hold your heart outside of your body
at a time.

– heal

― Nayyirah Waheed


When the intersection of our life and work isn’t proving successful by some measure we feel it should be, we are quick to wonder if perhaps this isn’t what we’re supposed to be doing. Any moment like that can make us wobble in our own grounding sense of where we are and what we know right here. I’ve been there with my art. I’ve been there with other jobs. It can feel so crushing. Without ground, it can feel like you’re without a compass, unable to trust your read of the situation. It shakes up the faith we have in ourselves, among other things.

One of the books on my repeat playlist when I was a little human was the story of Louis Pasteur called The Power of Believing in Yourself. It’s worn pages retell the story of Louis Pasteur, whose unwavering belief in the concept of germs eventually led to a cure for rabies. Despite disbelief from others, hurdles, and the lack of enthusiasm he encountered along the way, Pasteur believed in what he knew and marched on, following his gut and his research.

When I think of him soldiering on, sworn to his convictions, I wonder what lessons in self-faith he could offer us in the moments we feel stuck in the corners of our passions. When we feel it’s right, but also find ourselves wondering why it feels so hard: Why am I not getting traction? Why is no one buying the product? Why am I not making any money?

“Am I wasting my time?” Michelle Haunold of Gearheads wondered in her conversation with Jerry in this episode. “Is there something else I should be doing?” Yet, right in the center of her gut, she feels an overwhelming need to keep exploring and unfolding the business.

I like to think that much of what we encounter in our lives, and perhaps most especially in our work-lives, offers itself up to our healing in some way if we choose to work with it as such. When work-life feels messy, or not working how we intended, it’s hard to think that anything beneficial could be happening. Yet I’ve learned to trust those sticky situations, like the ones that you’d rather cherry pick through, have a worthwhile kernel of experience and wisdom readily available.

When things feel messy, when you feel undone, frayed and frazzled, it’s a practice to see that there might be something emerging through all the chaos. If we can sit and stay in the thick of it, and inquire within from that place as a bit of a practice, we can work with what’s arising and what parts of us may be growing.

Personal growth and healing isn’t a tidy process. Sometimes it gets messier before it gets better and the good stuff shakes out. Molly Sheehan, entrepreneur and proprietor of Green Hope Farm, notes: “Just as walking in on someone in the middle of a surgery would not give us an indication of where the person is in the healing process or how things are going to turn out, the degree to which things look profoundly messy right now is not an indication that the situation is hopeless. It is a sign that we are deep into the healing, deep into the surgery.”

While each scenario of what looks like “deep, messy human healing in progress” bears a constellation of conscious and subconscious choices and motivations that got someone there, there are a few handy ways I’ve found to look at situations should you find yourself in the midst of one of those chapters of your Choose Your Own Adventure Story that feels circular or that isn’t that enticingly juicy. When I’ve been in those places, there are a few things that have helped me to reframe where I’m at so I can see things in a different light, and see myself differently within it.

When I have the wherewithal to inquire into myself in those moments (enter Radical Self-Inquiry), I hope to catch an awry glimpse of the psychological threads that hold me there. Feeling stuck, one part of me wants to move ahead and another part feels magnetized to repeat old patterns. Here I wonder: what does that hold for me in terms of what I need to move past, or unravel and heal before I am able to move past more harmoniously?

Life will tend to dish up the lessons until they are learned, or a new perspective is realized. When the path starts to feel familiar, or the dynamics at play bear a striking resemblance to the past (why do I always find these situations?), we can perhaps begin to realize that some conscious or most likely – subconscious – part of us keeps choosing this scenario. Who is that part of us? What does that part of us want for us? What’s important to him/her? What does he/she need?

My teachers of Transformational NLP Carl Buchheit and Michelle Masters at NLP Marin have offered this reframe: Imagine back to when you were a soul ready to incarnate into human form and you were choosing what kind of human experience you wanted to have. There you were, in the big lazy boy chair in heaven, flipping through the catalog of possible human experiences, and you choose this very experience — with the ups and downs and plot twists. As you are here now, what was it that you wanted to experience when you chose this experience? What was it that perhaps you wanted to learn? What is this experience offering you?

As entrepreneurs, we have ample opportunity to inquire deeply into what’s coming up for us in the moments we face. If we can withstand the moments that make us ask “Is this what I’m supposed to be doing?” we find ourselves in a growth moment. If we can return to our wise selves in those moments, we can ride the waves without losing faith in ourselves in the process. From there, the answers to those ungrounding wonderings can come to us as we find our way through the adventures we didn’t expect.


Embracing Leadership as a Reluctant CEO This essay is written by one of our first alums from our CEO Bootcamp, Sooinn Lee, CEO of LocoMotive Labs. Last fall, Sooinn also spoke at TEDxBayArea Women in a…
Connect. Think. Lead. Adapted from the forward I wrote to a friend’s new book… Connect. Think. Do. I’d first gotten the call, an inquiry call for coaching, two weeks previous. In a follow-up…
Up and to the Right I have a chai; he has a cappuccino. We sit outside, at the metal mesh patio tables, as the coffee house is about to close. “I can’t decide the path:…



The Reboot Podcast with Jerry Colonna, Team Reboot, and Startup Leaders

Check out the episodes

Social Media

Follow us on:


Follow our Medium publication for reflections on leadership and resiliency.

Subscribe to Medium