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In Confidence

“Afraid that our inner light will be extinguished or our inner darkness exposed, we hide our true identities from each other. In the process, we become separated from our own souls. We end up living divided lives, so far removed from the truth we hold within that we cannot know the integrity that comes from being what you are.” 

– Parker J. Palmer

We humans carry a lot on our shoulders, in our minds, on our hearts. The entrepreneurs I meet and coach carry the normal human load plus the emotional load that comes from leading a team and running a company. For CEOs, it’s particularly lonely at the top. Yet no matter where we are, if we’re lucky, we have a trusted set of folks we can rely on and share our experiences with so as to build a bridge from the isolation we feel, which in turn can lighten our burdens. 

In this recent podcast conversation, Ryan Caldbeck, founder and former CEO of Circle Up, talks about the isolation he felt as had important things come up in his life as he was leading his company. He didn’t have a management coach, nor a CEO group, and didn’t feel comfortable talking to many people about the things that played a big role in the entirety of his days such as struggles with fertility and the reality of cancer, all on top of leadership issues. 

Finding a safe place to open up was a challenge for Ryan (something we hear from leaders often). For him, talking with friends and his partner proved to be not the listening audience he needed. Talking with other founders also felt risky to him. And he often wondered: would he be hurting the company by opening up about his own struggles? Yet, he had a need to be candid. 

We all have a need to be real and honest. We have a need to be heard and seen for the fullness of who we are and what’s happening in our lives. And what’s more: we all have a need to have our feelings and know it’s ok to have them. 

A few months ago, I was picking out fetishes from a favorite artisan shop in Santa Fe. (My altar at home is a bit of a zoo: I have a menagerie of hand-carved stone critters infused with totemic myth and magic.) That day, I found a two-toned horse carving called “Share the Load.” I felt the symbolic weight of that little one by one and a half-inch shape and put it in my basket for numerous reasons. At the time, I had a load on my heart that was burdensome and hoped this little buddy might help in some mythic way. 

While I too had something on my heart that felt big, mildly unruly, and wanted a safe place, I was thinking of our clients and the loads they carry. I was thinking of our CEOs and how lonely it can be at the top when you don’t have anyone to talk to, but are holding so much. There’s a trepidation about reaching out and speaking what’s true and alive for us, especially if those things are not highlight reels, or glossy, or even positive. Often, the things most laden with feelings can keep us from revealing them. And yet I’ve seen time and time again, at every Bootcamp by the end of the first evening of sharing challenges and struggles, the cohort sees each other in deep recognition and says, “Oh, you too? Your words could have been my words.” There’s relief and lightness in meeting kindred minds and hearts with similar burdens.

Reaching out to share our most vulnerable truth is challenging for reasons as varied as each of us are. When it comes to sharing what’s in our hearts, not every audience is able to hear what’s really going on for us. Sometimes when we do open up, the person we open up to isn’t meeting our need to be heard and seen. Real listening is a hard job that not many people in our lives are particularly good at all the time.

“When we honestly ask ourselves which person in our lives means the most to us, we often find that it is those who, instead of giving advice, solutions, or cures, have chosen rather to share our pain and touch our wounds with a warm and tender hand. The friend who can be silent with us in a moment of despair or confusion, who can stay with us in an hour of grief and bereavement, who can tolerate now knowing, not curing, not healing and face with us the reality of our powerlessness, that is a friend who cares,” the late Dutch Priest Henri Nouwen once wrote.

Historically, back when we were kids, if we were lucky enough to have space for our emotional lives, we may not have been met in ways that welcomed those emotions. Some of us had to shut down our emotional lives because there was no room for us to have our own experience. Now, as adults, this can make knowing what we feel and feeling safe to share what’s up for us a hard thing to do. Instead of reaching out to someone we can trust, we keep things close to the vest. 

Not only do we fear the inability for someone to hold and bear witness to what we bear, we fear that what we share won’t be held in confidence. One way we try to manage this by telling ourselves stories of what might happen if we do open up: “Oh, they are too busy to meet with me,” “What will they think of me if I share all of this,” and other renditions of “not pleasant or ideal things will come if I share what’s really going on for me.” We fear that if we show our vulnerability, we’ll be perceived as weak (or some other story of being banished and unsuitable for the human herd). None of which makes us feel safe enough to be real. 

Often our mind makes assumptions about the reaction we’ll get from an internalized stock caricature that’s an amalgamation of all of the honest conversations or vulnerable shares we’ve attempted in the past that went not so great. If we make assumptions, then we’re making stories. These stories of what could happen if we are real with someone can prevent us from reaching out. Here, in the realm of object relations, we think: “if I share X, then Y will happen.” Alternatively, the reality of how we can be received is more varied than the preemptive scenarios our mind will cast out of our shadow. If we can imagine a good, kind ear ready to hear our heartlines and all that quakes and wavers in our voice, someone who can hold what we’ve got and not annihilate our experience with their feelings, advice, or fixings, what happens to our sense of safety to reveal our heart? If we can get past what stops us, we have a chance to find a new reality and create a new experience for our nervous system in which we feel safe being real, honest, and true – in all its messy glory. That might be enough to talk to someone we trust about all that messy glory.

What stops us from showing up as our real honest truth? What does it take to feel safe and loveable and perhaps find belonging by being all that we are, as we are? Such ideas can be new to many a nervous system who’s not had that experience in spades. But if we can’t be true to how we really feel, without parsing that out to an audience or trying to make someone feel ok, we only enhance our isolation. As adults, what are the resources we can pull in or remember that help us feel safe and secure enough to say what we need to say in full confidence? 

And, on the flip side: what stops us from being the kind of person someone can come to in full confidence to share what’s closest to their heart?


A Good Ear “The beauty of listening is that those who are listened to start feeling accepted, start taking their words more seriously and discovering their own true selves.” – Henry Nouwen Long…
Where Spirit Meets Bone Almost anybody can learn to think or believe or know, but not a single human being can be taught to feel … the moment you feel, you’re nobody-but-yourself. To be…
Wondering About Wonder “May you experience each day as a sacred gift woven around the heart of wonder. ” – John O’Donohue Lately, I’ve been wondering about wonder. In talking to a friend…



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