The Unsure Leader & CEO: Dealing with Insecurity

“You sound like a 17-year-old teenager looking at the world and feeling insecure about what he wants to do with his life!” my friend Matthias exclaimed to me in a most affectionate tone as I was feebly talking about this and that and mostly about how I couldn’t figure out what I wanted to do or even how I felt.

Time and again I’ve come to find one of my most hated states of all: when I feel unsure and insecure about myself in my own body. It’s most cunning and often affects me over days and sometimes weeks. Mainly because I struggle to name it and to include it in my range of acceptable human experiences and as a part of my existence. So I end up walking around feeling insecure and unsure without being able to recognize it. That’s doubly taxing to my nervous system.

When my friend pointed it out in that phone call, I immediately relaxed and felt a sense of peace. Oh yeah, insecurity! As much as I don’t like that state and have shame, disgust, and anger when it comes up, as well as all kinds of stories and ideas around how it’s not a good thing to feel insecure, something shifted. Naming it was like the beginning of releasing a bondage rope wrapped around my chest and belly.

On top of that comes another layer of shame that through my profession as a coach and with my experience in meditation and other kinds of healing and wellbeing modalities, this shouldn’t happen to me in the way that it does.

The vulnerability of insecurity

There’s been a powerful shift I see many people go through of leaning more into our vulnerability in recent years around different feelings and experiences. Yet, I find that the vulnerability around feeling insecure is a double-whammy:

• It first requires us to be in touch with our true selves: the experience of being vulnerable
• And then to recognize that the thing that is there is a shaky, uneasy, quivery experience of ourselves, which is an extra layer of vulnerable yet again.

It seems natural that our brains have built protection around us going into this two-fold level of vulnerability. It already screams “It’s not safe!” from far away. And staying from being in touch with those experiences seems like a safer, easier option. But only on the surface!

As long as we don’t find the courage or the space to go into our experience, it will continue to drive us from the unconscious. Our choice lies in the naming and feeling of it, to be freed from its bonds, not in the choice of having it or not.

The unsure CEO

What I can’t do for myself, I sometimes find a lot easier to support other people with. D’uh! We often teach what we ourselves struggle with and need to learn the most a coach I’ve learned a lot from tells me.

And on a number of occasions I’ve introduced my clients to the concept of “the unsure CEO”. At first, this is deeply terrifying and goes against everything they’ve read or heard about how a CEO should act. And yet, it’s such a striking counter-archetype. Simply imagining what an unsure CEO would look and feel like if she accepted herself can bring a lot of resolution.

Most of my clients that have included the unsure CEO as a part of their persona toolkit have reported that it has brought them ease. Counter to their fears, they haven’t ended up being only the unsure CEO.

If you’re a CEO struggling to ever acknowledge your own self-doubts and wavering feelings of commitment, try on the hat of the unsure CEO. See what it’s like to make that a persona that is allowed to have space in your life and experience of things.

The thing that’s right in front of you

The puzzling experience of feeling unsure is that most of us haven’t learned to identify it as a thing. When we say “I can’t decide if I want to do A or B!” what eludes us that the thing right in front of us is that we can’t decide. That we’re unsure whether A or B is the thing that’s best for us. And that unsureness of ourselves is something and not nothing. Conventionally we’ve just overlooked it and I’d argue it’s something of a collective blind-spot. I know very few people who are comfortable in their unsureness about themselves or a situation.

Once we bring it into our awareness, we’ve gained a massive opportunity to unfold into our aliveness. One that is three-fold:

• you get to integrate an important human experience into your tool-belt: that of being unsure.
• you get to explore and be present to sensations, feelings, and thoughts you’ve previously had running through you on auto-pilot. For me, it’s a shakiness in the belly and a slight headache around the temples. Then there is constant chatter weighing multiple options in my mind and raised shoulders, just to name some parts of it. It’s a unique cocktail of experiences, that if I drop my story around how it’s not a good or bad thing to be feeling it, I can almost get to enjoying and appreciating it.
• you get to support others and not feel scared or feel the need to “fix” or “advice them” out of their situation if they themselves are feeling unsure too.

How to be with being unsure (or any other emotional state)

This, as usual with most of our experiences, is the easy part once we’ve identified what it is that we need to be with that’s right in front of us in the first place.

• Notice: When it comes up, my most trusted method is to notice, simply notice. And to begin noticing most pointedly how my body is feeling. That is where I usually find the bulk of the experience is coming from. The thoughts and feelings that accompany the body seem to be something like second-order items, important, but often influenced by my bodily state.
• Accept: Usually I have to expand my noticing to include also my relationship with what I’m noticing. With the sense of feeling unsure for example, I’ve also felt angry, disgusted, annoyed, and ashamed. Since those are present in relation to feeling unsure, it’ll be hard to let them have space if they are not also noticed and accepted as being present. My experience is that unless I can come to my emotional state with a sense of warm curiosity, through the help of a trusted friend or professional, it’ll be difficult for it to actually expand and have room to flow through me.
• Follow: Once I’ve noticed something or enough things, there’s usually an opportunity to follow an experience, feeling, or thought. The shakiness in the belly wants to expand into the legs. From the legs, it turns into a tingling in the feet. From there, it becomes a warm sensation of feeling peaceful and at ease.
• Rest: After a process like this that can take anywhere from 5 minutes to 2 hours, there can be a good point to rest and do something entirely different, not related to what I’ve just felt into. This might be going to the sauna, have some food, go for a walk, spend time with friends or spouses, what have you, you know yourself best around what brings you restful relaxation.
• Optional: Integration/Analysis: If I’m most present with myself, I steer away from self-analysis for as long as I can. That means putting questions like “Why am I this way?” or “Where did this come from?” to the very end of my exploration. Too often they aren’t helpful when introduced early on, since it leads to little expansion or resolution and just thoughts turning in on themselves more and more, furthering the constriction around what we’re already haven’t spent enough time to just be with, instead of analyzing it. True integration and analysis have the experience of feeling fresh and new, coming from the unfolding of things that happened before. The fresher the insight feels, the more I’d trust it as guidance. The more familiar it feels, the more I might wonder if I’ve truly touched into what’s going on for me.

PS: a big thanks to my friend Matthias for pointing me towards my sense of feeling unsure and sparking this article.