Category: Befriending Dragons

Cindy Gross

Befriending Dragons

Hi Reader,

My cat was on fire.

Yes, literally.

I was reading in my chair, and Goose – the orange menace – was walking through the tray full of candles toward me, tail twitching left, right, left, right, left… right into the one lit candle.

Readers, he still doesn’t know he was ever on fire.

My heart was racing, anxiety rising (Hollander, you are having panic attack! IYKYK). The last inch of his tail was flaming as Goose circled my lap looking for the perfect place to settle. I grabbed his tail, got the flames out, and was immediately rewarded with deep feline indignation — because I’d had the audacity to jump up and dislodge him. Then came the insult of a wet cloth running along his tail to remove the soot.

His brother Zeke sprinted in from the other room to see what the fuss was about.

Neither of them ever figured it out.

The soft top coat was gone. The undercoat never caught. Goose wandered off, mildly offended, and resumed his afternoon as if nothing had happened. Because for him, nothing had.

I’ve told this story a few times now, with a mix of horror and relief and genuine amusement at the audacity of that cat. And every time, I notice the same thing pulling at me.

Because you know what you almost never are? Goose.

You’re not wandering through the room unaware. You already know something is wrong. You’ve known for a while. You feel the friction, you see the dysfunction, you read the room faster than anyone else in it.

What you’re less sure about is whether the friction is a you problem, or whether it’s just the cost of doing business at this level. So you absorb it. You build it into your workload. You take on the translation, the smoothing, the managing of what nobody else wants to manage, and the project moves forward and nobody lights on fire and nobody ever quite connects that outcome to what you quietly did to make it happen.

There’s no retrospective on the near-miss. No recognition that the room almost looked very different.

The project lands. Goose is fine. You go back to your chair.

And you do it again next week.

It was just the tip. One inch. The soft top coat on the last inch of his tail took the damage, and the undercoat held. This time. One exposure, contained.

The problem is that complex workplaces don’t offer one exposure. The dysfunction cycles back. The friction is structural. The thing nobody else wants to manage becomes yours again next quarter, with a different name on it. And the soft coat doesn’t grow back overnight. Enough rounds of this and you’re not dealing with a singed tip anymore. You’re into the undercoat. You’re into the layers that were never meant to take that kind of heat.

That’s what sustained, unacknowledged friction actually does. It doesn’t announce itself. It doesn’t look like a crisis. It looks like Tuesday. It looks like you handling one more thing that shouldn’t be yours, absorbing one more round of dysfunction, smoothing one more thing over so the project lands and the room stays calm. Each one: just a tip. Just an inch. Perfectly manageable.

Until the undercoat is involved and you’re wondering why you’re so tired when nothing catastrophic has happened.

Nothing catastrophic happened because of you. Repeatedly. And that cost has to go somewhere.

The question isn’t whether you can keep absorbing it. You clearly can. The question is what it’s costing you in the places nobody sees.

What does this bring up for you? Hit reply. I read everything.

Cindy Gross

Befriending Dragons

Hi Reader,

Something I hear a lot right now, underneath the composed exterior:

“I don’t know if I trust my own instincts anymore.”

​

Not because she’s lost her edge. But because the signals have been contradictory long enough that the self-doubt has started to feel like clarity.

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If that’s where you are — or somewhere close — I’d like to talk.

Grab some time with me here: https://befriendingdragons.com/meet

​

I’m also asking a simple question: what’s the thing you’re navigating right now that doesn’t have a clean answer? The one where you’re not sure if the friction is yours to fix, or the system’s.

​

Reply and tell me. I read every one.

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The leaders I work with are not struggling because they’re not capable. They’re navigating the specific exhaustion of being highly competent inside a system that keeps asking them to be someone slightly different than who they actually are.

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That is a solvable problem. Not with inspiration. With infrastructure.

Cindy Gross

Befriending Dragons

Hi Reader,

The most capable woman in the room is often navigating the most alone.

Not because she lacks support — but because the systems around her weren’t built to see what she’s actually carrying. The scope that expanded without authority. The feedback that doesn’t add up. The political weather that shifted and nobody named it.

She’s not confused. She’s operating without a map in terrain that keeps changing.

That’s what I build.

I’m offering a Strategic Clarity Call — a working diagnostic where you bring one real situation and leave with a clear read and your first concrete moves. It’s not a consultation. It’s infrastructure.

If something is shifting for you right now — your role, your positioning, your next move — this is where we start:

→ Book your Strategic Clarity Call​

P.S. Know someone who’s navigating a reorg, a comp conversation, or a role that’s shifted under them? Forward this. The right conversation at the right moment changes everything.

Cindy Gross

Befriending Dragons

Hi Reader,

I just wrapped up a session using my new Untangle One Thing sprint format, and I want to share the shift that happened—because it’s a pattern I see in almost every high-performing leader I coach.

The client came in carrying a heavy mental load regarding a broken situation at work. It felt exactly like the knot above: a tight, chaotic loop that seemed to get worse the harder she tried to fix it.

A single conversation had gone wrong, and she was stuck in a cycle of offering data, explaining her intent, and assuming all the responsibility for the interaction.

She wasn’t being difficult. She was just caring more than the system did.

The invisible dynamic at play was simple: She was taking responsibility for a system that refused to be fixed.

In 90 minutes, we shifted her strategy from “repairing the unfixable” to “protecting her energy.”

She walked away with a Leadership Navigation Reset Plan that included:

• A “Stop” List: The specific efforts she is releasing immediately (without guilt).
• Decision Rules: A logic gate to help her know when to say “not my circus.”
• Exact Scripts: Language to protect her reputation without over-explaining.

The relief was visible. She realized she didn’t need to solve the problem to be safe; she just needed to stop carrying it.

This is for you if:

• You are replaying a specific conversation or conflict in your head at night.
• You feel like you are the only one trying to solve a problem that everyone else is ignoring.
• You are exhausted from explaining your intent.

If you are currently carrying a tangled loop that feels stuck, unfair, or endlessly draining—you do not have to carry it for another month.

I have 5 spots left for this January sprint at the pilot rate ($750).

​Book Your Reset Sprint​

​Read the full details

You don’t need to fix the whole system to find peace. You just need to untangle yourself from it.

Cindy Gross

Befriending Dragons

Hi Reader,

A small reframe I keep coming back to:

Overwhelm isn’t always “too much work.”
It’s often the cognitive cost of carrying too many unfinished things at once — half-decisions, outdated obligations, invisible responsibility, and the old scripts that keep running even when they’re no longer true.

This in-between week is a rare moment to release some of that before 2026 begins.

So I’m hosting a free, live reset:

The Let It Go RESET: A Strategic Capacity Workshop​
​Monday, Dec 29 | 11:00 AM – 1:00 PM PST​
Free (my gift to your nervous system)

We’ll do four things together:

• Reflect on what mattered this year
• Release 3 things you’re leaving in 2025 (one physical item, one mindset, one obligation)
• Clear one small area in real time (cords / papers / expired meds — your choice)
• Protect your new capacity with a simple Q1 “Navigation Anchor”

If you want to start 2026 lighter, I’d love to have you.

Register: https://luma.com/uwngib2x

P.S.: I’m considering a short series that decodes workplace dynamics through scenes from Heated Rivalry — using my “befriending dragons” lens (the conversations we avoid until they cost us). If you’ve watched, reply with your favorite scene and the workplace moment it reminds you of.

Cindy Gross

Befriending Dragons

Hi Reader,

I’ve been thinking a lot lately about the invisible loads we carry.

We all know someone—maybe it’s a colleague, a dear friend, or maybe it’s you—who is holding everything together at work. They are brilliant and indispensable, but they are also navigating a system that wasn’t built for them. They are tired, not from the work itself, but from the friction of just trying to lead authentically.

For a long time, the conversation has been “should I stay or should I go?”

But I believe what we really need is direction. We need a compass, not just an exit sign.

That deep desire to help—to be the guide I wish I had—is why I am focusing my work on The Befriending Dragons Leadership Navigation System.

This isn’t just about business strategy; it’s about human sustainability. It’s about ensuring that the people we care about don’t just survive their roles, but navigate them with clarity, intention, and their health intact.

I am ready to help, and I’d love your support in reaching the people who need this most.

I am opening up space to support leaders in two specific ways:

1. Deep 1:1 Navigation: For the individual leader who needs a confidential strategic partner to map their path.
2. Organizational Cohorts: Partnering with companies to support groups of “Keystone Leaders” so they can navigate together.

Come say hi (and see the system) – I’m hosting a few 45-minute Strategic Briefings this week to walk through this approach. I’d love to see your face, catch up, and share how we can “befriend the dragons” in our professional lives. You can RSVP here: [Eventbrite]​

How we can help each other You are often in rooms I am not in, and you see the struggles of friends that I don’t see. I would be so grateful for introductions to the people who are currently looking for a guide:

• Leaders navigating new or expanding roles who need a strategic partner to find their footing.
• HR and L&D teams who are trying to grow leadership capacity but aren’t sure how to support their senior talent.
• ERG and affinity group leaders who are working hard to build inclusive cultures.
• Conferences or podcasts exploring strategic leadership and the future of work.

If someone comes to mind—or if you are feeling the need for better navigation right now—please just hit reply.

I’d love to hear how you are doing and how I can support you.

Cindy Gross

Befriending Dragons

Hi Reader,

A recent, provocative headline in The New York Times asked if feminism ruined the workplace.

This question is fundamentally flawed. It’s a distraction that points the finger at a group of people instead of at the systems that weren’t built for everyone. It invites us to debate which type of person is problematic, rather than asking the far more useful question: Why do our workplaces still generate so much friction for so many people?

The problem isn’t, and has never been, a specific identity. There is nothing inherently wrong with any gender, race, or background.

The problem is the rigid, narrow, and often unspoken expectations our workplace systems have bolted onto the concept of an ideal employee—expectations that have been unreasonably tied to gender, race, disability status, communication style, and cultural background. For decades, the default operating system for success was based on a very specific archetype—an in-group. This created a set of invisible rules about what a leader looks like, how a leader sounds, and how a leader acts.

This is what I call Leadership Friction.

It’s the invisible, systemic force that creates drag on individuals and organizations. It’s the tax paid by anyone and everyone who doesn’t perfectly align with that default in-group model.

And this friction isn’t just paid by those whose authentic style doesn’t match the default. It’s also paid by those in the in-group who, operating from a different starting point, often can’t see or understand the friction points that are painfully obvious to others. This creates massive organizational blind spots, miscommunication, and inefficiency, where countless hours are wasted managing misalignment that stems from these different, unexamined experiences.

Leadership Friction is the invisible battle a leader from an out-group fights when their confidence is called aggression while the in-group standard is called authoritative. It’s the unrewarded glue work disproportionately shouldered by those expected to be collaborative, work that is critical for team cohesion but mysteriously absent from performance reviews. It’s the constant, exhausting background process of having your competence questioned in ways others are not.

This friction is the real saboteur. The true ruin isn’t that diverse professionals are in the workplace. The ruin is the staggering amount of energy, talent, and innovation we waste navigating this friction.

Think of the sheer volume of brilliance that is lost—not to a lack of skill, but to Environmental Exhaustion. This is the exhaustion that comes from pushing against a system that was simply not built for you. It’s the exhaustion that leads your most indispensable, high-impact Keystone Leaders to a stay or go crossroads, not because they can’t do the job, but because they are tired of paying the friction tax required to do it.

Bringing a diversity of people into the workplace didn’t ruin it. It simply held up a mirror and exposed the systemic friction that was already there, slowing everyone down. The discomfort some feel isn’t from the ruin; it’s from the revelation.

Stop asking if any group ruined the workplace. Start asking how we can finally address the systemic friction that drains our best people. The goal isn’t to fix people to fit the system. The goal is to diagnose the system and equip all leaders with the tools to navigate it, turning that friction into strategic leverage for themselves and their organizations.

That is how you build a workplace that doesn’t just survive, but thrives.

This is a conversation I’m passionate about, and I’ve just posted this article over on LinkedIn to get a wider discussion going.

My question for you is: How much of your team’s energy is spent navigating friction versus doing the work?

I would be honored if you would bring your voice to the public discussion. https://www.linkedin.com/pulse/real-workplace-saboteur-isnt-identity-its-friction-cindy-gross-pcc-2yklf​

I’ll also be exploring these themes in person this week (Nov 19-21) at the PASS Data Summit in Seattle. If you’ll be there, please find me at my talk, “I got the role… Now what?”, or at the Community Experts Clinic.

Cindy Gross

Befriending Dragons

Hi Reader,

“I’m tired of acting like I’m okay when I’m not.”

This was shared by a leader in my Befriending Dragons community, and it perfectly captures what I’m hearing in dozens of private conversations right now.

My new article on the “Layoff Echo” is striking a nerve. We’re all seeing it: the burnout of indispensable “Keystone Leaders,” the isolation, and the immense, unspoken pressure to just… keep performing.

If this resonates, I want to invite you to a space where you don’t have to pretend.

On Tuesday, November 11th, I’m hosting the Befriending Dragons Roundtable.

This is not a webinar. It’s not training. It’s not a performance of strength or strategy.

It is my free, monthly, confidential space for women and non-binary leaders to connect with peers who get it. It’s a space to process what’s real—the grief of layoffs, the weight of being “the strong one”—and learn to lead without abandoning yourself.

You don’t have to arrive with clarity or confidence. You just have to come as you are.

The Roundtable is free for all members of the Ember Circle (my private, no-cost community).

If this is the space you’ve been looking for, I invite you to join us.

Click Here to Join and Get the Zoom Link for Tuesday https://community.befriendingdragons.com

I hope to see you there.

P.S. If you missed the “Layoff Echo” article that sparked this conversation, you can read the full analysis here. https://www.linkedin.com/pulse/layoff-echo-hidden-crisis-your-workforce-cindy-gross-pcc-jrkxc

With dragonfire warmth and enduring wisdom,

Cindy Gross | Founder, Befriending Dragons
Your Leadership Navigation Coach

🐉 ​https://befriendingdragons.com

Cindy Gross

Befriending Dragons

Hi Reader,

What if clarity cost less than staying stuck?

Two weeks from now, you could already have clarity — or you could still be circling the same dragons.

What will it cost you to wait?

Yesterday, Pete Hegseth — an underqualified man posturing like a reality show host — turned a room of admirals and generals into a stage for political theater.

He lied about DEI. He distorted “woke.”
And here’s the truth: the opposite of what he said is real.

Diversity, Equity, and Inclusion don’t cost us — they save us.
Because unfair workplaces bleed talent.
Replacing one tech employee? Over $200,000 lost in productivity, recruitment, and retention.

DEI is risk management. DEI is retention. DEI is smart business.​
And the best orgs already know it.

But let’s be real — whether the system shifts or not, the work begins within.

The self-doubt.
The dreams.
The coping strategies that now hold us back.
The brilliant ideas we’ve held too close.
The critic that says we’re too much and not enough.
The longing to be valued — in systems that weren’t built for us.

Fighting these dragons drains us.
Befriending them changes everything.

When we stop slaying or silencing our dragons and listen instead, we make room for something legendary.
That’s where clarity lives.
That’s where power begins.

It’s not a coaching commitment. It’s a conversation.

One hour to set something heavy down, explore what’s possible, and see if coaching is right for you.

Bring a friend. Refer someone. Tag someone in.
However you need to show up — show up.

And here’s the truth:​
Coaching underestimated leaders — whether that’s you or someone you lead — pays for itself.
Research shows an average 7x ROI.
And breakthroughs in clarity, confidence, and influence often happen in just 3–6 months.

3 ways to step across the threshold this October:

🔥 Clarity Call — Just you and me. Let’s talk.
👉 Book here​

🌱 Befriending Dragons Roundtable (Oct 7) — Put something heavy down in community.
👉 RSVP here​

🌀 Layoff Renewal Circles — A 6-week reset for folks between roles.
👉 Join here (payment options available)

Don’t lead like the people you don’t admire.​
​Don’t bleed energy into systems that were never built for you.​
​Lead like your dragons are your fuel.

I’ve got ~10 clarity call spots left before Oct 15 to explore coaching together.
​Claim yours.​
👉 Schedule here​

Cindy Gross

Befriending Dragons

Hi Reader,

If you’ve been carrying more than you let on lately — you’re not the only one.

The Befriending Dragons Roundtable is a 60-minute, no-agenda space for women and non-binary leaders navigating complexity, burnout, and the quiet ache of performing strength.

We gather not to fix, but to feel. To remember we’re not broken — just tired of pretending we’re fine.

Next Roundtable:​
​Tuesday, Sept 2​
​2:00 PM PT​
​Join here:https://community.befriendingdragons.com​

You don’t have to show up with clarity.
You just have to show up.

Not your space?​
If this doesn’t quite describe you or resonate, you’re still welcome in the wider Befriending Dragons ecosystem. You can join a Dragon Drop-In Circle or meet with me 1:1:
→ https://befriendingdragons.com/meet​

P.S.​
I’m currently in a season of deep listening — doing quiet market research with thoughtful leaders who are navigating complexity, shaping culture, or asking meaningful questions. If someone comes to mind — anyone you admire or think I should meet — I’d love the intro. Feel free to hit reply or send them tohttps://calendly.com/befriendingdragons/listen.