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Befriending Dragons

For senior women in tech who are operating without a map in terrain that keeps changing. I'm Cindy Gross — leadership navigation coach, 25-year tech veteran, and the person who helps high-capacity leaders separate what's them from what's the system. Subscribers get tactical frameworks, named patterns, and honest intelligence on the dynamics most people won't say out loud: scope creep, political feedback, survival mode, and how influence actually works. Built for leaders who want precision, not pep talks.

Goose (left, unrepentant) and Zeke (right, still confused about what the fuss was about).
Featured Post

My cat was on fire. He still doesn't know.

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...

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. 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...

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...

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...

White and gold coffee mug with text "Befriend dragons every day" - sitting near a candle, a stack of journals, and a cozy white sweater in front of a window overlooking pine trees.

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...

Cindy Gross Befriending Dragons You're invited! 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...

NYT headline

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...

Green water with ripples

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...

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,...

Cindy Gross Befriending Dragons Even dragons need a place to rest. Even leaders need a place to just be. 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,...