I’ve had many a conversation in my head with someone, but not with them.  Most of us actually spend more time preparing what we’ll say than we do actually saying it.

We rehearse in the shower. We script it in our heads while driving. We imagine every possible response, every reaction, every way it could go wrong. And then when the moment comes? We say nothing. Again.

On my podcast I had Andrew Bryant as a guest.  He’s a global thought leader on self-leadership, and he shared:

“Sometimes in life we can be an observer and watch things go by but the moment we have skin in the game, the moment something is important to us, that’s when we find our voice.”

Skin in the game. What a phrase!

Most of us have been trained, conditioned, and rewarded for staying invisible.  And by that I mean staying quiet to keep the peace, or being the “easy” one, or not making waves.

And now we’re sitting in meetings with ideas that we don’t share. Or in relationships where we don’t express what we need. In our careers we watch other people get credit for thoughts that we wrote down ages ago in our little notebooks.

The question isn’t whether we have valuable things to say. We do. The question is: how do we get from observer to participant when everything in our conditioning tells us to stay quiet?

Why “skin in the game” changes everything

Andrew used this analogy during our conversation, and it’s one it’s a really useful and practical reframe for people who struggle with speaking up.

He said:

“Let’s say you’re the front seat passenger in a car and you look over at the driver and the driver’s eyes are starting to close and the car is crossing the centre line into oncoming traffic. Would you have the courage to speak up? Well of course you would because you’ve got skin in the game. You’re going to go ‘hey wake up, should we pull over for a coffee?’ “

When your life is literally on the line, you find your voice. Fast.

So we don’t need to change who we are to speak up. We need to reconnect with what matters to us. We need to find where we have skin in the game.

Start with Self-Awareness: What’s actually important to you?

Andrew explained self-leadership as having three components: self-awareness, self-regulation, and self-learning. And the first step is awareness.

He said:

“The awareness is to say: “Well, what’s important to me, where do I have skin in the game?”

This isn’t about speaking up in every situation. It’s about choosing where you engage.

Andrew gave this example:

“You might be at a dinner party and two people are arguing politics and it’s not important to you because neither of them is going to listen, and nobody’s belief is going to change. And so you go: ‘you know what I choose not to engage in that.’
Whereas you might be in conversation with a loved one around something which is very relevant today… and you might care about that person and say: ‘Look I want to listen to your perspective. I want to understand what your fears and anxieties are because I’d like to share my perspective too.”

You get to choose where you have skin in the game. You get to decide what matters enough for you to speak.

So start here: where does your silence cost you something that actually matters? Where would your voice create value that you care about?

Reframe humility so it doesn’t keep you silent

One of the biggest barriers I see, especially with my clients, is this belief that speaking up equals arrogance.

Andrew addressed this directly. He said:

“A lot of people didn’t want to speak up because they valued humility… humility comes from the Latin humilitas which means ground or dirt.  So it means we’re grounded and humility means having an accurate (neither overestimated nor underestimated) view of your own abilities.  And it means the ability to consider other people’s perspectives as equally valid as your own.”

Read that again. An accurate view. Not diminished. Not inflated. Accurate.

Humility doesn’t mean you stay quiet. It means you show up as yourself, with your real thoughts and perspectives, and you hold space for others to do the same.

Andrew continued:

“Why a lot of people don’t have the courage to speak up is because they think speaking up will put them immediately into conflict. Whereas if we can say: ‘okay I’m hearing this is your perspective, this is your thoughts, your feelings, your beliefs.  And these are my thoughts, feelings and beliefs.  How can we collaborate and work together?’
And so the courage comes from knowing that when we speak up, we have that opportunity for collaboration – that we’re not breaching our humility and being arrogant, we are being authentic.”

When you speak up and say “this is my perspective, and I’m curious about yours,” you’re not being pompous. You’re being humble. You’re being grounded.

Self-Regulate: How do I actually speak up?

Once you know what matters to you and you’ve reframed humility, the next question is: how do I actually do this?

Andrew talked about self-regulation as the bridge between knowing you should speak and actually speaking.

He said:

“The self-regulated say ‘How do I speak up?  And do I speak up in a passive way, an aggressive way, or perhaps more effectively in an authentic or assertive way.”

This is key. You’re not just blurting out your opinion. You’re opening a conversation. You’re framing your contribution in a way that invites collaboration rather than confrontation.

Authentic, assertive communication sounds like: “Here’s what I need, want, believe. Let me understand what you need, want, believe so that we can collaborate.”

You’re creating space for dialogue, not demanding agreement.

Living your purpose means speaking up

Andrew shared something about his own why that really shows what skin in the game looks like in practice. He said:

“My whole modus operandi,  my whole why that I exist, is that I see myself as a catalyst for change – as a coach, as a facilitator, as a writer –  I want to wake people up to their own leadership… their leadership of self and their leadership of others. And so if I don’t say something I’m not living my purpose.”

He continued:

“So I have to have the courage. Does that rub a few people up the wrong way? Absolutely.  Do I occasionally get a nasty message on social media? Yes of course I do.  But that’s more about them than it is about me. And so I continue to have the courage to speak my perspective.”

This is what having skin in the game means. Andrew cares more about living his purpose than avoiding discomfort. He cares more about the outcome than the risk.

When I asked him about a recent courageous conversation, he shared that he’d just told a CEO client:

“You’re behaving in a power play way… the moment you grabbed the marker you took the leadership position and that does unconsciously shut everybody down.”

That’s a career-risking conversation. That CEO could fire him. But Andrew had skin in the game. His purpose is to help leaders see their blind spots. If he doesn’t say something, he’s not living his purpose.

What helps you stay courageous when it’s hard?

I asked Andrew what helps him to be courageous in those moments. His answer was simple but powerful:

“I don’t have to please people. I have to be effective for people… I have a big heart for people and my heart comes from holding them accountable to be the best version of themselves.  So I don’t want to be nice… nice comes from the Latin and the old French which means ignorant… when we’re being nice, we’re not telling the truth.”

He continued:

“This drive to be the best version of myself and to be the best version of myself in a relationship with somebody – that’s what drives me to do that.  And if that relationship is broken because of that, then it wasn’t a relationship in the first place.”

You can be kind and still speak up. You can care about someone and still be honest. Being effective matters more than being nice.

Read the room, but don’t lose yourself

Andrew made an important point about context. He said:

“Context for self leadership is everything… if you speak your truth and say ‘hi, this is what I think, what I feel, what I believe, and what I need’ –  that’s actually aggressive communication. Assertive authentic communication is: ‘you know, here’s what I need, want, believe.  Let me understand what you need, want, and believe so that we can collaborate.”

Reading the room means you notice timing, audience, and approach. But it doesn’t mean you silence yourself completely.

Andrew explained how to frame conversations using how I framed a question to him:

“You let me know… you framed that this was going to be a personal question, you wanted a personal answer and you also generalized it to say ‘I ask all my guests’, which puts me under a little bit of a requirement to join the club.”

You can be strategic AND authentic. You frame your contribution in a way that the other person can hear it.

Your Starting Point

If you’re reading this and thinking “okay, but where do I actually start?” here’s the pathway Andrew laid out:

Step 1: Self-awareness – Ask yourself: what’s important to me? Where do I have skin in the game? Where does my silence cost me something that matters?

Step 2: Self-regulation – How will I speak up? Not passively. Not aggressively. But authentically and assertively. “Here’s what I need. What do you need? How can we collaborate?”

Step 3: Self-learning – After you speak (or after you don’t), reflect. What worked? What didn’t? What will you try next time?

Andrew said it this way:

“The self-learning is that when I do listen and when I do question and I do stay curious – that works better.  So that is the loop of self-leadership and how I’ve applied it in my courageous communication.”

The question you need to answer

Here’s what Andrew said about choosing where to engage:

“If it’s not my circus, it’s not my monkeys.”

You don’t have skin in the game everywhere. But you do have it somewhere.

So find what’s most significant to you. Find where your voice matters. Find where silence costs you something you can’t afford to lose.

Because as Andrew put it:

“The moment we have skin in the game, the moment something is important to us, that’s when we find our voice.”

You don’t need to become someone else. You don’t need to be loud or aggressive or fearless.

You just need to decide that your voice, your perspective, your contribution matters enough to be heard in the places where you have skin in the game.

Because it does.
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