the becoming: May 31, 2023

On the Edge of Kindness and Ambition

Hello, I’m Andi and this is the May edition of the becoming, a newsletter that shimmies in the border between the known and unknown.

The Edges of The Orb Image by my mind on Unsplash.

In my coaching practice I work with a wide range of people who embody beautifully unique ways of leading. Two things they all have in common, however, is ambition and sacrifice. Ambition acts as an animating force, moving them towards a specific outcome and playing a starring role in their success. Whatever stands in ambition’s way is sacrificed to the altar of achievement.

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Ambition is effective and highly rewarded in our society. Equal parts desire and determination, ambition brings clarity and purpose to an at times infuriatingly obscure existence. It gives us a degree of clarity in who we are, and makes it easier to share that with the world.

Ambition works, until the day it doesn’t. This is where I work with many of my clients - specific moments when the crystallized structures of ambition no longer serve the longings of the soul.

Up until my mid-twenties I was anything but ambitious. I loved to get lost in the woods, read books, and hang out with animals. I enjoyed school (at least until high school) but wouldn’t describe myself as a particularly inspired student. I had no idea what I wanted to “be” as an adult and wandered my way through college, taking courses with popular professors (good idea) and losing myself in works of fiction (not so good idea).

It wasn’t until a few years after graduation that anything like ambition showed up at my doorstep. While I was still meandering my way through life, my friends were notching big achievements in their careers. I found myself surrounded by advanced degrees, awards, fellowships, newspaper mentions, and other professional achievements that lit a fire under my ass. Not because I had any particularly lofty visions of my own, but because I did not want to be left behind.

Ambition entered my life as a strategy for belonging, and I committed myself with determination to “making it”. I didn’t really pause to get specific about the “it”, I just knew I had to move into action. When this nascent ambition emerged I was freelancing as a front-end developer so I just poured fuel on that fire and followed the energy. I moved to New York City, got involved in the start-up scene, started going to hackathons, and worked non-stop. My ambition felt unrelenting, a nuclear reactor of longing in search of recognition, success, and belonging.

The reactor was fueled by fear, and the vehicle for that fear was an inner voice that was critical and mean. For the sake of easy reference we’ll call it The Manager. The Manager told me horrible things about myself, shared unrelenting criticism of everything that I did, and constantly reminded me of where I was falling short. It kept me so deeply unsatisfied with where I was that I lost the ability to pause and take stock of things, to find respite from the frenzy of work, to celebrate what I had achieved along the way. The Manager’s strategy was to keep fear close enough that whenever I slowed down I could feel it, a discomfort so strong that only work could ease it. Ambition protected me from fear I was unwilling to face.

My clients often report similar experiences, that they have an internal voice that drives them to achieve big things through unrelenting criticism. They also share that without this voice they wouldn’t be where they are today. And this is true! At least to a degree. The job of this voice is to remind you of all the ways you are not enough so you will keep moving towards to learning more, doing more, and achieving more. It wants you focused on Big Hairy Audacious Goals because goals provide certainty, and certainty is squarely in the domain of ambition.

Ambition leaves no room for uncertainty, and while uncertainty may not feel great, it does contain important information. I’ve been thinking of uncertainty like rests in a piece of music - measures that call for an absence of sound. When the notes in a certain line stop we attune to a new soundscape and hear things that we couldn’t before. Uncertainty is a rest - a cessation of clarity that opens our ability to listen to a deeper knowing, a wisdom that comes from within and is connected to something bigger than ourselves. Where ambition is the size of a human, inner wisdom is the size of the world.

As a leader, you probably aren’t speaking to others the way The Manager speaks to you, though I suspect its presence is more noticeable than you imagine. Take a moment and reflect on the ways your relationship to yourself, and to The Manager, shows up in how you lead. It may be in the perspective you take, the conclusions you draw, the interpretations you make. In the ways frustration or pessimism leaks into interactions, into the edges of your words, and keeps you from being present with others.

The antidote to this inner harshness is kindness, compassion, and acceptance. Kindness releases the concentration of energy The Manager uses as fuel and creates space for more of who we are to become present. It can be uncomfortable to sit in the silence that was once filled with its critical voice and welcome more of ourselves home. After all, if we don’t have that relentless voice driving us, how on earth can we push ourselves to achieve everything we want? How is it possible that being kind to ourselves can become a foundation of our leadership practice?

A fundamental aspect of leadership is the inner game, becoming aware of how we have created constrictions in our thoughts, emotions, and body as a form of protection, and learning how to relax them. The Manager doesn’t have a big playbook - it has a single strategy that it picked up because it worked, and it ran with it. The Manager lives in these constrictions as a reactive program that executes whenever it is needed. As it relaxes we have greater access to direct experience. This access increases our ability to perceive and respond to the present moment, rather than to echoes of the past or hopes for the future.

I am starting to see how ambition, in many ways, is a response to fear and uncertainty. According to David Whyte “ambition abstracts us from the underlying elemental nature of the creative conversation while providing us the cover of a target that has become false through over-description, overfamiliarity or too much understanding.” I like this. Creative responses come from the ability to be in the unknowing and in conversation with what is emerging. And I think he’s right - ambition collapses complexity into something knowable, controllable, and hardened. It is a crystallization of a moment in the future that harnesses all our energy and focus into a single vector of movement.

A lot of high achieving individuals fear what will happen if The Manager stops doing its job, if ambition as a survival response ceases to be the default way of moving in the world. If we treat ourselves with kindness, how can we ever achieve the success we seek? The common assumption is that without ambition we become lazy, useless, self-indulgent. But if ambition is an abstraction that silences the intuition required to step into what is uniquely ours to do, then ambition can only bring us echoes of greatness that could have been. David Whyte continues:

No matter the self-conceited importance of our labours we are all compost for worlds we cannot yet imagine. Ambition takes us toward that horizon, but not over it - that line will always recede before our controlling hands. But a calling is a conversation between our physical bodies, our work, our intellects and imaginations, and a new world that is itself the territory we seek. A vocation always includes the specific, heartrending way we will fail at our attempt to live fully. A true vocation always metamorphoses both ambition and failure into compassion and understanding for others.

Ambition can get us to where we want to go, but it cannot take us any further. It acts only in service of the known and wants us to believe that we have more control than we do. With enough kindness, ambition loosens its grip and becomes one of many animating forces for how to move in the world. It can be used as a navigational tool, drawing boundaries around certainty to reveal the edges of the unknown. But ambition cannot go beyond the edges, into the new worlds we seek. For that we need kindness and compassion, qualities that can hold us softly in the discomfort of the unknown as we listen for the song of emerging worlds.


  • What has helped you succeed in your leadership career?
  • How do you experience your own ambition? What fuels it?
  • What internalized stories and voices keep you going?
  • How do you respond to not knowing/uncertainty?
  • What parts show up to protect you, and how do they do that? (e.g. Do they turn inwards with harshness and expectation, or do they turn outwards with irritability and blame.)
  • What is your ambition in service of?
  • What is the deeper longing beneath your ambition?

Worth Noting

As long as we are talking about what work gets automated in the Age of AI, why not extend that to the role of CEO? It seems like a pretty good candidate for automation - feed an LLM a few decades worth of market data, Financial Times articles, and case studies from HBR and you’d probably have a pretty good CEO. If you needed some mercurial decision making just modify with some DnD style character traits and introduce the potential for ‘botching’.

Looking for footing in turbulent times and don't want to do it alone? The Sanity Project might be for you. Even if you don't enroll, click on the link and check out the definitions in the green box titled, "What do I mean by staying sane?" Just reading the list helps me feel grounded, with more capacity to deal with the chaos whirling around me.

In grad school I learned about The Default Mode Network (DMN) and the Task Positive Network (TPN), two distinct subsystems in the brain responsible for getting things done and connecting with others (respectively). The two subsystems are anti-correlated, which means when one is active, the other one isn’t. I remember the professor making a comment about how switching between the two is hard, and doesn’t happen instantaneously. If we aren’t practicing moving between and using each subsystem, one can become dominant. It made sense to me, reflecting on how crabby I could be when people interrupted me during times of flow and deep concentration. More recently I’ve been thinking about the impact these two subsystems have on folks in the role of “Player-Coach” (however you feel about it), and what leaders, teams, and organizations need to know to set this role up for success. I’m in the process of writing something about this, but wanted to share Anne Betz’s post on the topic, “The Power of Dreaming, The Power of Action”. It is a useful introduction and has enough substance to support reflection on which network you hang out in more.

For me, summer has always been a time for reading (admittedly as is every other season - it’s always a time for reading). Summer Classics - a seminar program from St. John’s College - is an opportunity to read in community and the first week is entirely online. “The Incoherence of the Philosophers” looks stellar, and if I’m not totally off grid that week you’ll know where to find me.

Bayo Akomolafe recently spoke at the graduation ceremony for the California Institute of Integral Studies and his unlisted talk, which I am calling “The Wisdom of the Shush,” is on YouTube if you know where to look. I am always struck by Bayo’s perspective and poetic attunement to life - whenever he speaks, I listen. More than listen, I feel. This is not a comforting talk for a graduating class, but it is an important one. It unsettles the ego and soothes the soul, invites us to invert the stories we tell about ourselves and the world, to stop seeking clarity, and to find the cracks and dance with thresholds.


Leader as Coach

I’ll be running one last Vanguard cohort for Leader as Coach in June. The course will be on pause for the summer, returning in September.

If you, or anyone you know, has been wanting to integrate more of a Coaching Leadership Style into their executive or management practice, this is the course for you. The last day to apply is June 11th.

Members of The Vanguard receive 50% of the course price, have lifetime access to The Leader’s Little Book of Coaching (our course manual), and can join any future cohort at no cost. This is a pretty sweet benefit - the course changes from cohort to cohort based on feedback and student experience, each iteration honing in on what leaders need when it comes to building and supporting their teams. Plus, it’s always great to have space to practice coaching skills and get more comfortable facilitating a space for others to connect with their own knowing and agency.

Thank you for reading, have a wonderful 🌞 solstice 🌞, and see you towards the end of June!