Why I Stopped Finding the Way Out
A journey from clever escapes to necessary stuckness — in dreams and in leadership.
My psychoanalyst once remarked that in my dreams, which we discuss weekly, I never get stuck. I always find a way out. At the time, I took it as a compliment. Look, how fluid and resourceful my psyche is! Whatever the situation, it's workable!
Eventually, I started to get stuck in dreams. I would get into a frightening situation and wake up with my heart racing instead of finding a way out in the dream. Yet, it felt like progress.
In hindsight, what felt like never getting stuck was a skilful avoidance of the parts of psyche that I couldn't face, couldn't even come close to seeing them from the distance. We all have them. They're outside of our conscious mind but they can surface in the dreams, unless they're so deep and scary that we don't enter them even in the dreams.
That's why waking up with my heart racing felt like progress. I still couldn't enter them, but my psyche was getting ready for the showdown. Eventually, my dreams changed. I started to enter eerie, dead, shut-off spaces and then waking up from there, still being unable to go further for the time being. Take this dream: an abandoned building floating in some void, no chance of escape, with bored, angry people inside who've been stuck there for millennia without any hope. These were the parts of me I'd kept locked away.
Yet, even entering these spaces, trembling with fear, was progress. It was achieved not by setting goals or trying to get somewhere but by gently helping my psyche to look at what's scary. Bringing the light of awareness and attention to what's scary often works far better than trying to force some outcome or avoid the pain.
The Fantasy of Pain-Free Growth
What I learned in psychoanalysis about facing unconscious fears and letting go of fantasies continues to inform my coaching work.
The act of growing up is the process of shedding fantasies. They are countless; we all start with a big bag of them. One by one, we grieve them and let go.
One of the most persistent fantasies is that if only I find the right approach, the way forward will be pain-free.
The truth is that in some situations, the right way forward isn't going to be pain-free. It's not easy to let go of this fantasy, but we must do it.
Leadership and the Courage to Feel
Many years ago, as CEO, I dreaded emotionally loaded conversations with my team. For example, letting someone go. Or making a quarter of the team redundant. Like, looking someone in the eye, knowing that their wife is pregnant and it's covid outside, and telling them their job doesn't exist.
These situations aren't meant to be easy. There are playbooks for how to do them better, yes, but there's no playbook for being pain-free in that moment. We can dissociate from pain — and that's how some of the worst leaders in the world emerge, those without empathy, causing lasting damage to their teams, the world and to themselves, ultimately, in ruthless pursuit of corporate goals at the cost of personal wholeness — but that's not the right way forward.
Like in dreams, when we feel the pain of such difficult situations, a racing heart may be a sign of progress. It may well mean that we're finding strength to get closer to how emotionally tense the situation is for everyone, and that's a step closer to actually being with it.
Being with it, bringing conscious awareness and attention to the difficulty and not running away from pain is what heals that pain, even if it doesn't feel like that in the moment. In the moment, it hurts. But the adult question is not how to avoid pain. The adult question is how to be with it. How to stand still with your hair on fire.
The Work of Presence
The true work of a leader is not to give orders but to choose what's important and hard, bring their awareness there and stand still if necessary. When our teams see this, they understand what's going on in their heart even if their minds are unable to articulate it. They feel that it's possible for someone else, and that makes it possible for them, too.
This principle extends beyond leadership into all forms of growth and support. As a coach, I rarely discuss dreams with my clients. That's psychoanalytic work. But much of what I do as a coach mirrors what I learned in analysis: helping my clients to choose where to focus their attention, and stand still there — while I'm there with them. All the good things — decisions, plans, goals — follow from there naturally if we are able to ask the right questions and look unflinchingly at the answers, holding the gaze with ourselves.
The journey from never getting stuck to finally entering those abandoned, floating buildings in my dreams taught me something counterintuitive: progress sometimes feels like regression. The racing heart, the moment of being stuck, the pain of difficult conversations — these aren't obstacles to growth. They're signs that we're finally approaching the parts of ourselves and our responsibilities that matter most.
Getting stuck, it turns out, is how we get free.