How to build unshakeable confidence
This week's issue is in response to one of the most common questions I get from new clients:
How do I build my confidence?
How to build unshakeable confidence
"The moment you doubt whether you can fly, you cease forever to be able to do it." – J.M. Barrie, Peter Pan
I’ve played basketball my entire life. And as any player of competitive sports will tell you, the prerequisite to playing ball at a high level is believing you are the best. When I step on the court and know deep down I’m the best player there, I hoop. When I am uncertain, I play poorly.
Leadership is similar. If you believe you will win, you’ll win. If you believe you will lose, you’ll lose. Either way, you’re right. If you believe you will be the best company out there, or you believe you won’t be, you’re right.
Confidence is king.
So how do you build unshakeable confidence?
Defining Confidence
"Confidence comes not from always being right but from not fearing to be wrong." – Peter T. Mcintyre
Before we jump into how to build confidence, it’s useful to define the word itself.
Unshakeable confidence is not projected confidence. There’s no scarcity of folks who act like they know what they’re doing, puff out their chests, showboat, describe their accomplishments, and pretend to know all the answers. That’s peacocking. That’s BS.
Unshakeable confidence is not earned confidence. Even if you have built a successful company, hit 10 shots in a row, or hit quota six months in a row, you’re just one bad outcome away from second guessing yourself. So while this kind of confidence is often very powerful, it can still be brittle.
Unshakeable confidence is confidence from an alignment between your inner and outer worlds. It radiates from the person who has done the work to know who they are and who then faithfully communicates that person to the world through their words and deeds, even when it’s unpopular. Think Ghandi. Think MLK Jr. This type of confidence is the deepest and least fragile.
Confidence like this is not something you are born with. It’s something you work for. It’s something you earn not through achievement but through self-knowledge (achievement often follows, but it is incidental to true confidence). And because of this, it’s something anyone can have, if you’re willing to do the work.
Self / Words / Actions
To build the alignment that produces unshakeable confidence, a person must do three things: First, they must do the work to know themselves. Second, they must align their words with their inner self. They must speak their truth, even when it’s unpopular or shameful. And third, they must align their actions with their words. When they say they will do something, they must do it. Always.
That’s the recipe to build a lifetime of confidence. Let’s break down each step, so you can see specifically how a person earns their confidence.
Know yourself
"To be yourself in a world that is constantly trying to make you something else is the greatest accomplishment." – Ralph Waldo Emerson
The first step toward building alignment is getting clear on who you really are. As much as we might like it to be different, humans cannot sustainably align themselves to something they are not. You can live the life of a CEO and leader of a tech company (say), but if that is not who you are at your core, your life will be hollow and any confidence you have will be borrowed. And may come due at any point. Real alignment begins by discovering who you really are (apart from those parts of society you’ve internalized in an effort to feel safe/loved/accepted), and then accepting that person.
This process is outlined in detail in all the major wisdom traditions, and is the foundation of many contemporary approaches to depth psychology, from Freud to Jung to Adler. As it’s the neverending work of a lifetime, it deserves the reader beginning his own journey of self reflection at much greater depth than this essay, and I would refer you to the works in the Appendix to dive deep here.
However, suffice it to say the process of self inquiry is characterized by two basic steps.
First, you tease apart those parts of yourself that are authentically you from those parts you’ve inherited from somewhere else. The best tool I’ve found for this is the Enneagram – a framework that objectifies the developmental patterns on which your personality is constructed. Diving deep into the Enneagram has a tendency to demystify the complexity of personality to an alarming degree. The best resource I’ve found, and one I recommend regularly, is The Wisdom of the Enneagram.
And second, you embrace and love those parts of yourself that you find. Not only the parts that are fit for public consumption but the icky parts as well. Embrace them, love them, and integrate them into your whole being. This is as counterintuitive as it gets, because we’re so conditioned to resisting the parts of ourselves we don’t like or approve of (hence the idea of the “shadow”), but it is the path to self discovery. A fairly accessible (and really fun) resource to this approach is called Existential Kink, but the ideas behind this approach have been core to many branches of psychology for a century, and spirituality for millennia.
Whether you turn to old texts as I initially did or work with a trained professional (this is naturally a part of the work I do with founders, given how important confidence is to that role) or explore psychedelics or any other path, the important part in this step is that you begin the process of faithful self inquiry. You must ask “who am I?” with an open heart and allow sufficient space for an answer to emerge.
Over time, as you continue to know yourself more deeply, you can express yourself more and more congruently with your true nature, and as such build the foundation for greater and greater degrees of innate confidence.
Align your words with your inner self
"You gain strength, courage, and confidence by every experience in which you really stop to look fear in the face. You must do the thing you think you cannot do." – Eleanor Roosevelt
Regardless of where you currently are in your journey of self exploration — who you currently believe you are — the next step on the path to building inner alignment and unshakeable confidence is to align your words with your inner self.
You can begin this step immediately, even if you are still coming to know yourself. Whether you define yourself by your values, your experiences, or by an inner knowing, as a wave in the universe, whoever you are in this moment, you build confidence by speaking in alignment with who you know yourself to be. It’s the outer alignment with inner self, rather than the specifics of what is identified as Self, that determines confidence.
It’s easiest to demonstrate this in the negative, so imagine that you believe that your employee is not going to make it. She’s struggled, and despite your efforts she’s not turning it around. Now imagine that you haven’t said anything to her about this yet, so as a result every time you see her you must studiously avoid that subject. You talk about other areas of work, but pretty soon you see her struggles there so you avoid those areas, too. The areas in which you talk openly and unreservedly with her shrink and shrink, as does your confidence. Instead, who you are around her is someone who is filtering themselves.
A half-self.
Most people live their lives as this type of half-self, constantly filtering their own beliefs and knowing based on what they think will be palatable to others. Only presenting the parts of themselves that they believe will get them the results they want.
But most people are far from confident
You know who is confident? A first time founder who doesn’t know how hard their life is going to be. Who thinks they can change the world for $250k.
Why are they so confident? Not because of what they know. But because what they believe and how they’re expressing themselves are aligned. When a founder becomes less confident as their business grows, it’s not because they have somehow regressed as a speaker. No, it’s because their inner knowing, their self, has changed, and they are no longer acting in alignment with it. They know how hard things are, so they can no longer speak with naive authority about simplicity and ease. Their confidence must come not from presenting certainties of youth. It must come from truthfully presenting the facts as they understand them and showing why they are confident anyway. I’ve written more about how to fundraise like this here.
As a leader, the first layer of your confidence comes from fully expressing what you believe to be true. About yourself, and about any situation in which you find yourself. Yes, this means relationships, too. With others and with yourself. That relationship you’re not quite telling the truth in? At least not the whole truth? Each unstated truth creates landmines which, when stepped on, will destroy your confidence in areas of life well beyond it.
So how do you reclaim your confidence in this area?
Do a relationship audit. Evaluate all your relationships for anything left unsaid. Anything that is in the conversation that you believe to be true, that you haven’t expressed.
Express those things. This step can be terrifying, because it can include things that we feel may hurt ourselves or others. Things like “I don’t love you anymore,” or “I did something I’m ashamed of.” I’m not here to tell you those things aren’t hard, nor that they won’t hurt to finally bring them to light. But what I will say is that you have a choice: live a half-life of manicured okayness while constantly keeping the truth at bay, or come clean, be yourself (good and bad), and step fully into your real life. True confidence is only available through the latter path. Here’s the step-by-step process my clients use to clean up their relationships and reclaim their confidence.
Align your actions with your words
"Our deepest fear is not that we are inadequate. Our deepest fear is that we are powerful beyond measure. It is our light, not our darkness, that most frightens us." – Marianne Williamson
Once you’ve aligned your inner self with the way you present your outer self (self => words), the third step toward building confidence is aligning your words with your actions.
This is simpler than steps 1 & 2, but no less challenging.
To illustrate what confidence looks like at this stage, imagine that you’d lived a life in which you always, no matter what, did what you said you would do. After a lifetime of this, you’d have a certain relationship with your word. You would know it to have a great deal of power — experientially, not based on wishful thinking. Knowing the gravity of your word, you’d think carefully before saying something like “I’m going to be the President of the United States.” But if you did choose to say it, you’d know deeply that the world was about to change, simply because you spoke.
That’s the third stage of confidence.
And whether or not you want to be the President, you build this stage of alignment by developing your relationship with your word. You teach yourself, bit by bit, to relate to your word as precious and powerful. And in doing so, you imbue it with power, and yourself with the confidence of having true power in simply speaking.
Here’s how:
Keep an integrity journal. For a period of time, keep track of every time you give your word to anything, no matter how big (“I solemnly swear to do X by Y date so help me God”) or small (“I’ll be done in 5 minutes”). Log all of these in a notebook for a week or two, missing nothing.
At the end of each day, chart your batting average. For each time you gave your word, note whether you kept it with your actions or not. Be honest.
Over time, if you do this honestly, two things will happen: First, you’ll notice how often you give your word, and you’ll be more precious with it. And second, you’ll deliver on your word more often. Both start a virtuous cycle that builds innate confidence.
A final word on confidence
You can tell when someone has done the work to imbue confidence into their being. They no longer worry about how they appear to others, or needing to be successful at whatever the cost. They simply do what they know is right, and trust themselves to navigate whatever outcome comes of it.
No drama. No imposter syndrome. Just a fully aligned human being.
Confidence is a key to leadership, so it’s natural that it’s on the top of the list for leaders to create when they think of their inner game. But most versions of confidence are brittle and snap under pressure. True confidence, the kind that can weather the storms of building an organization or a movement, comes from alignment between your inner self and your outer self.
Creating this alignment, for most people, requires bravery, faith, and a great deal of hard work.
But it’s worth it.
Because when you are aligned inside and out, things simply work.
Appendix
The resources I suggest most to clients beginning their journey of radical self inquiry -- a journey that is the foundation of unshakeable confidence:
One: The midlife unraveling (Brené Brown)
An epic, world-framing take on the time in life most people are finally ready to dive deep and embrace their true selves. This is a must read if you're in your 30s or 40s.
LINK >>
Two: Soulcraft: Crossing into the Mysteries of Nature and Psyche (Bill Plotkin)
Psychologist Bill Plotkin's modern handbook, built on Jungian frameworks, for your journey inward. If you're into archetypes, vivid language and symbolism, this is your map.
Three: Let Your Life Speak: Listening for the Voice of Vocation (Parker J. Palmer)
A big part of this journey for many high achievers is learning to tell the difference between "work" and "vocation." Parker's short, wonderful book lays out an authentic path to your true calling.
LINK >>
Four: The Second Mountain: How People Move from the Prison of Self to the Joy of Commitment (David Brooks)
This was the book that first opened me up, as I struggled growing a startup with a conflicted heart. His book helped me recognize that I was transitioning from my first to second mountain, which was key in everything that came after.
LINK >>
Five: Reboot: Leadership and the Art of Growing Up (Jerry Colonna)
I wrote a love letter to this book, I loved it so much.
LINK >>
Six: The Wisdom of the Enneagram (Don Richard Riso and Russ Hudson)
Perhaps the most practically useful guide to understanding your subconscious patterns, also provides a roadmap to letting them go and regaining your freedom.
LINK >>
Want to dive deeper?
If you liked this, check out this list of my top posts, read and shared by thousands of entrepreneurs.
Here are a few of my favorites:
The secret to leadership (why authentic leadership is simply more effective)
How to pitch a big vision to investors without setting yourself up to let people down
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