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Category: Befriending Dragons
Befriending Dragons Stories show how we transform, heal, and nurture our communities.
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This Is Why We’re Tired
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Closer to Fine
Cindy and Cindy enjoying Melissa Etheridge at Marymoor Park Hi Reader,
Last night, I stood in a sea of 50-somethings at Marymoor Park, dancing to the Indigo Girls and Melissa Etheridge under the shade of enormous trees as the sun slipped behind the stage. My friend Cindy (yes, two Cindys at an Indigo Girls concert—unapologetically perfect) and I had excellent seats, black outfits we didn’t overthink, snacks in our pockets, and zero desire to prove anything to anyone.
When the Indigo Girls stepped on stage, I felt a wave of rightness. Not nostalgia exactly—though I’ve seen them before several times, in younger versions of myself—but presence. At 56 (57 in September!), I wasn’t reaching backward to my 20s. I was honoring that person, sure—but I was fully rooted in the woman I’ve become.
And then we heard this from the stage: “We have to protect our friends—especially our queer, non-binary, and trans friends right now.”
The crowd roared. We stood. We screamed. It wasn’t performative. It was power—unified, raw, and real. There was no going back. We were moving forward together. When we work together, we can do the impossible. We can make it happen.
And then came the song “Closer to Fine:”
There’s more than one answer to these questionsPointing me in a crooked lineAnd the less I seek my source for some definitiveThe less I seek my sourceCloser I am to fineCloser I am to fineI’ve heard those lyrics for decades. But this time, they hit differently.
Because this time, I didn’t just hear them. I believed them.
The Old Map Isn’t Yours Anymore
There’s a version of me—of so many of us—who once believed we had to do it the hard way. Be busy. Be perfect. Be productive. Keep climbing. Keep proving. Keep collecting milestones like signposts to justify our path.
But last night reminded me: You don’t have to keep walking a path that was never meant for you. You don’t have to stay on a map someone else designed. And you absolutely don’t have to do it the hard way to earn the right to rest, to lead, to live.
My youth isn’t gone. She’s here, fully alive in me—but she’s not driving. Today, it’s the me of now who’s in charge.
What If Fine Isn’t a Finish Line?
What if “fine” isn’t some perfect version of you, waiting on the other side of burnout, overfunctioning, or endless performing?
What if closer to fine means:
- Letting go of what no longer serves you.
- Moving toward what’s aligned.
- Trusting yourself to define your own truth—on your own timeline.
Here’s a Way to Begin
Next time you feel the pull to prove, to push, to perfect—pause.
Pick one dragon part of yourself to listen to today:
- Your Head: What feels mentally clear—or what’s spinning?
- Your Heartfire: What lights you up, and what quietly drains you?
- Your Wings: Where are you ready to stretch or take up space?
- Your Scales: What boundary wants to be honored?
- Your Tail: What old pattern are you ready to steer away from?
- Your Spine: What truth are you standing in, no matter what?
You don’t need to answer all of them. Just pick one. Reflect. Gently. With care. Maybe in a journal. Maybe out loud with a trusted friend. Maybe with a coach.
If you’d like a deeper guide, I made this for you: Download the Leadership Culture Compass — it’s in my free Starter Kit.
It’s not a quiz. It’s a mirror.
You don’t need permission to lead differently. You don’t need to justify choosing ease, rest, or clarity. You’re already on your way.
I feel Closer to Fine – what about you?
With dragonfire warmth and enduring wisdom,
Cindy Gross
Founder, Befriending Dragons
Your Leadership Clarity Coach
🐉 https://befriendingdragons.com
🎁 Grab your Dragon Playbook Starter Kit
Start with:
- Leadership Touchstone – Create a one-breath reminder of who you are when you’re thriving
- Culture Compass – Define what you need to thrive in a work culture
- Boundaries for Thriving – Name, refine, and express values-based boundaries that protect your energy
Download the Starter Kit
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Your calendar is full—but where are you?
Hi Reader,
Back-to-back calls. Holding space for everyone else.
Delivering. Performing. Proving.
The days blur together—and so do you.If that’s you, you’re not broken. You’re at a threshold.
And something in you already knows: this isn’t sustainable.I’ve been there.
For me, the breaking point came not from failure—but from success that didn’t feel like mine.
I was performing the version of leadership I thought they needed.
Until my body—and my clarity—said enough.That’s what my coaching is for.
Not to help you hustle better.
To help you come home to yourself.I work with leaders—especially women and non-binary folks—who are done shape-shifting to fit systems that never fit them.
We name what’s true. We listen to the signals. And we build new ways of leading that don’t cost you your clarity, your boundaries, or your joy.And now, there’s a new way to start that process with even more clarity:
I’m now certified in the Leadership Circle Profile™ (LCP).
It’s a 360° leadership assessment that doesn’t just show what you do—it reflects why. LCP reveals your Creative strengths, your Reactive tendencies, and what might be shaping your leadership from behind the scenes.
Some clients may want to start their coaching arc with this mirror.
Others prefer to move straight into the Dragon Path.
Either way, if you’re curious, ask me.
We can tailor your journey together.Want to try a small shift this weekend?
So many of us say “yes” before we’ve even checked in with ourselves—yes to the meeting, the favor, the deadline, the emotional labor.
It’s not just overcommitting. It’s a pattern of giving away your power to stay safe, included, or useful.This weekend, try this instead:
Before you say yes—pause.
Ask yourself: Is this a true yes you can feel from your heart and body? Or a yes to avoid guilt, disappointment, or conflict?If it’s a yes from alignment, name it.
If it’s a no or a maybe, say: “Let me check on that and get back to you.”
Even that one sentence creates space—for your truth to have a seat at the table.Journal about it for one week.
What patterns come up? Where do you comply or accommodate by default?
Where did you try something new—and what shifted?This is how you begin to move from Reactive to Creative—one pause, one choice, one brave boundary at a time.
If you’re ready to stop performing and start leading from clarity—let’s talk.
Explore Executive Coaching & Dragon Path
Or just hit reply and tell me what’s top of mind or heart for you.With dragonfire warmth and enduring wisdom,
Cindy Gross
Founder, Befriending Dragons
Your Leadership Clarity Coach
🐉 https://befriendingdragons.com
🎁 Grab your Dragon Playbook Starter Kit
Start with:
- Leadership Touchstone – Create a one-breath reminder of who you are when you’re thriving
- Culture Compass – Define what you need to thrive in a work culture
- Boundaries for Thriving – Name, refine, and express values-based boundaries that protect your energy
Download the Starter Kit
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Burned out by layoff news? Here’s a live space to ask ‘What now?’
Hi Reader,
It’s a new week after a long weekend.
If you’re feeling the emotional hangover—not just from fireworks, but from burnout, layoff news, or the quiet dread of going “back to normal”—you’re not alone.
Maybe you’ve already been laid off.
Maybe you’re just waiting for the next round.
Or maybe something in you is asking the question no one else hears:
“What now?”This week, I’m holding space for exactly that.
Who Am I Now?
A live, 90-minute reset for folks in tech navigating layoffs, burnout, and identity shifts🗓️ Wednesday, July 9 at noon Pacific time
🕘 90 minutes | Free
🔗 Reserve your spotThis isn’t about bouncing back or fixing yourself.
We’ll speak the truth about what this moment really feels like.
You’ll use the Dragon Playbook Starter Kit—a tool from my Befriending Dragons framework—to name where you are and start reimagining what comes next.You don’t need to bring answers. Just bring yourself.
Yes, it’s 90 minutes. But it’s not a webinar.
It’s a breath. A reckoning. A return.If you’re burned out by the noise, come here for the signal.
With dragonfire warmth and enduring wisdom,
Cindy Gross
Founder, Befriending Dragons
Your Leadership Clarity Coach
🐉 https://befriendingdragons.com
🎁 Grab your Dragon Playbook Starter Kit
Start with:
- Leadership Touchstone – Create a one-breath reminder of who you are when you’re thriving
- Culture Compass – Define what you need to thrive in a work culture
- Boundaries for Thriving – Name, refine, and express values-based boundaries that protect your energy
Download the Starter Kit
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Independence and the Illusion of Normal: A Mythic Reclaiming
Dragons, fireworks, corn, and watermelon. Legacy, resistance, and the fire to grow bigger.
Hi [FIRST NAME GOES HERE],
“I’ll have the normal cheese on the regular bread.”
The woman behind the counter didn’t flinch. She knew exactly what that meant: American cheese. White bread.
Normal. Regular.
It stuck with me. My friend posted about overhearing that order, and someone else replied, “Oh yeah, I’ve heard that too—‘the normal cheese.’” Meaning American. Meaning white. Meaning default.
Let that sink in.
What we call normal—what we reach for without thinking—isn’t just habit. It’s culture. It’s the unspoken rules of belonging. And it’s often a story someone else wrote for us before we ever knew how to spell our names.
White. American. Normal. Regular.
As if anything else—or anyone else—is weird, exotic, other. Suspicious. UnAmerican. Not right.
I remember my own “regular.” I grew up poor in small-town Kansas and Missouri in the 1970s. Our meals often came from cans. The ham was marbled with fat, the bread was pillowy white, and fresh produce was a seasonal treat.
July 4th was special—not just because of fireworks, but because we got fresh corn on the cob and watermelon. A taste explosion eaten with our hands, juices dripping. Summer’s brief permission to enjoy without rationing.
I remember the first time I tasted kiwi in elementary school. It was part of a “cultural awareness” day. The tartness burst in my mouth like something from another planet. I loved it. Most of the other kids wouldn’t even try.
That moment stuck in my body. The thrill of trying something new, the disappointment of seeing others shrink away from it. That same feeling shows up now—in meetings, on stages, in boardrooms. Some of us lean in, hungry for truth and difference. Others recoil—still—though now with more polish, more power.
It’s not about food—it never was. It’s about fear. If they do it differently… am I doing it wrong?
But make no mistake—that disgust is taught. It is not mine. And it doesn’t have to be yours. We can unlearn it. We can decide, instead, to treat every human as fully human. We can see differences as richness and strength.
This is Independence Day. A celebration of freedom.
But freedom for whom?
The U.S. Declaration of Independence refers to my ancestors—Delaware and Cherokee—as “merciless Indian savages.” My presence is proof this country did not erase us. But it tried.
This holiday carries fire and contradiction.
Fireworks that split the sky. Barbecues and hot dogs and hands covered in ketchup and mustard—those are American. But rice eaten with hands? Too many say it’s gross. Uncivilized. Foreign. As if humanity can be revoked if it doesn’t come with a fork and a flag pin.
And those who hold power know this. They use that fear. They shrink the circle of “normal” down to a pinpoint, where only a few fit.
It’s why American white men invented the concept of whiteness in the 1700s—to stop poor folks from banding together by convincing lighter-skinned people they were closer to power than to their brown and Black neighbors. It wasn’t an accident. It was strategy.
Today, we get to choose.
I don’t perform loyalty to a version of America that’s allergic to truth.
But I do claim my right to exist, to thrive, and to tell the truth about this country—its stories, its wounds, and its possibilities.
We can stay small—clinging to what’s familiar, even when it no longer serves us. Or we can stretch. Not by pretending we’re all the same, but by recognizing that difference is the path to strength.
Systems built for sameness have never served us all. We grow as individuals, as communities, and yes—as a nation—when we welcome complexity, not erase it.
This is the work I do. Not just as a coach. As a human. As a woman who grew up poor and Indigenous and code-switching. As someone who finally said, “What if I stopped shrinking and just showed up?”
I believe we can build cultures—and countries—where authenticity is the norm. Where the regular cheese is whatever makes your body say yes. Where we lead with curiosity, not conformity.
We don’t grow by enforcing sameness. We grow by staying curious. We grow by embracing our dragons—those fiery instincts and inherited fears that rise when old rules no longer fit. Dragons don’t shrink to survive. We soar, rewrite, reclaim.
Let today be a reminder: independence isn’t about isolation. It’s about interdependence that honors every part of who we are. Including the messy parts. The parts that challenge. The parts that stretch us.
We can grow into something mythic. Something fierce. Something true.
That’s the path I choose. The Dragon Path. The one where we don’t erase difference—we fly with it.
Let this Independence Day be one where we choose fire over fear. Courage over comfort. Authenticity over assimilation.
Let us taste the kiwi again. Let us remember the corn and watermelon, sweet with memory and defiance—across borders, across histories. Let us trust that our differences aren’t threats—they’re invitations. They’re the start of something bigger.
Let the fireworks remind us: there is power in lighting things up. Not to destroy, but to illuminate. To grow.
We don’t need more regular bread. We need more permission to taste the kiwi.
Happy Independence Day. May you remember you’re already whole. May you trust that your difference isn’t a detour—it’s the way forward.
Shaped in conversation with AI—turning the fire in my bones into language on the page.
With dragonfire warmth and enduring wisdom,
Cindy Gross
Founder, Befriending Dragons
Your Leadership Clarity Coach
🐉 https://befriendingdragons.com
🎁 Grab your Dragon Playbook Starter Kit
Start with:
- Leadership Touchstone – Create a one-breath reminder of who you are when you’re thriving
- Culture Compass – Define what you need to thrive in a work culture
- Boundaries for Thriving – Name, refine, and express values-based boundaries that protect your energy
Download the Starter Kit
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When connection feels like leadership fuel
Hi Reader,
Last week I had one of those rare evenings that fills your cup in the best way.
I went with my friend and longtime collaborator Moni Giles, who’s doing powerful work around belonging and emotional intelligence through The Friendship Class. We showed up excited and ready to expand our networks.
We stepped into a room buzzing with powerhouse women—leaders, creatives, and equity-driven changemakers all showing up real, raw, and ready to connect. It felt like a deep exhale. A reminder that I’m not alone in wanting more from leadership—more authenticity, more impact, more alignment.
The event, hosted by Ellevate Seattle, was centered around mobilizing our networks—and it truly delivered. The space was built for meaningful conversation and real connection, not just small talk and drinks.
That’s the heart of what I do through Befriending Dragons.
I deliver a highly rated 1:1 coaching experience for women and non-binary leaders who are done performing and ready to reshape leadership on their own terms.
Here’s what we work through:
1. Name What’s True: We take stock. What are you done with? What’s calling to be reclaimed? This is your foundation.
2. Befriend the Dragons: Your patterns and instincts aren’t problems—they’re data. We learn how to work with them, not against them.
3. Integrate & Embody: You build your Dragon Playbook—your personal “Operating System of Me”—and start applying it in real-life moments of leadership, boundaries, and clarity.
4. Return & Realign: We reflect, recalibrate, and make sure what you’ve built is sustainable—even when life gets loud again.
Curious if this is the next right move for you?
Let’s talk. You can book a Threshold Call here:
🔗 https://calendly.com/befriendingdragons/threshold
And if you’re thinking about asking your org to cover the cost, I’ve got a clear ROI doc you can use—just reply and I’ll send it your way.
P.S. You don’t have to be in tech to be a fit for Dragon Path. If this message resonates, let’s talk. My mission is to be inclusive and bring more folks forward into thriving.
With dragonfire warmth and enduring wisdom,
Cindy Gross
Founder, Befriending Dragons
Your Leadership Clarity Coach
🐉 https://befriendingdragons.com
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Breaking Free from Perfection
𝗘𝘃𝗲𝗻 𝘁𝗵𝗲 𝗰𝗼𝗮𝗰𝗵 𝗻𝗲𝗲𝗱𝘀 𝗰𝗼𝗮𝗰𝗵𝗶𝗻𝗴 𝘀𝗼𝗺𝗲𝘁𝗶𝗺𝗲𝘀. 🐉
When I joined Alyona Brivkina aka Aly Breathe on her Brave Enough to Win podcast, I thought I’d be talking about leading as an entrepreneur.
Instead, I found myself face-to-face with one of my oldest dragons: 𝗽𝗲𝗿𝗳𝗲𝗰𝘁𝗶𝗼𝗻𝗶𝘀𝗺.
Aly saw straight through the strategies and stories I’ve used to protect myself — and helped me see how I still try to suppress and ignore the version of me who believes she has to earn her worth through flawless performance.
That part of me still whispers:
“Don’t speak yet, it’s not ready.”
“Fix it again.”
“Be better. Be perfect.”
And that part still sometimes wins… especially when fear and perfection-seeking tag-team to keep me from taking bold action.
But in that conversation, I remembered something powerful:
✨ I have my own Dragon Playbook.
✨ I know how to name, befriend, and disarm those dragons.
✨ I can choose not to let fear drive – by listening to it differently.
𝗕𝘆 𝗹𝗶𝘀𝘁𝗲𝗻𝗶𝗻𝗴 𝘄𝗶𝘁𝗵 𝗰𝘂𝗿𝗶𝗼𝘀𝗶𝘁𝘆 𝘁𝗼 𝘁𝗵𝗮𝘁 𝗳𝗲𝗮𝗿, 𝗜 𝗰𝗮𝗻 𝗮𝘀𝗸 𝗺𝘆𝘀𝗲𝗹𝗳 𝘄𝗵𝗮𝘁 𝗜’𝗺 𝘁𝗿𝘂𝗹𝘆 𝗳𝗲𝗲𝗹𝗶𝗻𝗴, 𝘄𝗵𝗮𝘁 𝗜’𝗺 𝗮𝘃𝗼𝗶𝗱𝗶𝗻𝗴, 𝗮𝗻𝗱 𝘄𝗵𝗮𝘁 𝗰𝗵𝗼𝗶𝗰𝗲𝘀 𝗜 𝗰𝗮𝗻 𝗺𝗮𝗸𝗲 𝘁𝗵𝗮𝘁 𝘄𝗶𝗹𝗹 𝗯𝗼𝘁𝗵 𝗵𝗼𝗻𝗼𝗿 𝘁𝗵𝗮𝘁 𝘀𝗶𝗴𝗻𝗮𝗹 𝗮𝗻𝗱 𝗻𝗼𝘁 𝗹𝗲𝘁 𝗶𝘁 𝘁𝗮𝗸𝗲 𝗼𝘃𝗲𝗿 𝘄𝗶𝘁𝗵 𝘀𝗼𝗺𝗲 𝗼𝗹𝗱 𝗺𝗲𝗮𝗻𝗶𝗻𝗴 𝗮𝗻𝗱 𝗮𝗰𝘁𝗶𝗼𝗻 𝘁𝗵𝗮𝘁 𝗻𝗼 𝗹𝗼𝗻𝗴𝗲𝗿 𝗳𝗶𝘁𝘀. 𝗠𝘆 𝗽𝗮𝘀𝘁 𝗱𝗼𝗲𝘀𝗻’𝘁 𝗵𝗮𝘃𝗲 𝘁𝗼 𝗿𝘂𝗹𝗲 𝗺𝘆 𝗳𝘂𝘁𝘂𝗿𝗲.
Aly helped me imagine my 2028 self, thriving on a well-earned vacation to Costa Rica. Surrounded by beauty, community, and clarity. Free to just be.
That version of me isn’t obsessed with proving. She’s at peace.
And today, I’m one breath, one choice closer to becoming her.
🎧 If perfectionism has ever kept you stuck, I hope this episode offers you a way through: https://lnkd.in/ggpcyAVc
💌 Thank you, Aly, for your insight, your heart, and for helping me remember who I am — dragons and all.
hashtag#BefriendingDragons hashtag#BraveEnoughToWin hashtag#Perfectionism hashtag#CoachingJourneyhttps://open.spotify.com/episode/1E57G0heJIy8UY3hcy4q14?si=087a3e52aab54b96Aly”
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Navigating Career Pivots in Midlife with Cindy Gross

Cindy Gross Featured on The Roller Coaster of Midlife with Lucie Q
Cindy Gross joined Lucie Q’s podcast, The Roller Coaster of Midlife, to discuss navigating career pivots, resilience, and embracing change in midlife. In the episode Midlife Pivots with Cindy Gross, she shared her journey—from overcoming workplace challenges to redefining success on her own terms.
Cindy explored themes of breaking gender stereotypes, setting boundaries, and transforming setbacks into opportunities. Her insights offer inspiration for those looking to reclaim their narrative and step into a more empowered chapter of their lives.
Listen in to gain practical strategies for navigating career and life transitions with confidence!
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Why hire a coach?
What keeps you from hiring a coach?
People facing tough environments and difficult people at work often come looking for advice, but I’ve learned a coach gets you further, faster. Get curious about YOU, tell me what keeps you from thriving and schedule time with me now. #BefriendingDragons #WorkplaceThrival #Thrive #AntiBullying #AntiHarassment #Equity #Gender #Race
Watch: https://lnkd.in/gRTpgh-4
Tell me what keeps you from thrival: https://lnkd.in/g-Sefh9G
Schedule time with Cindy: https://lnkd.in/g4S7e2Yx -
Land Acknowledgments
It’s becoming common to have “land acknowledgements” at justice focused gatherings. This is a way to recognize and respect Native peoples and their relationship with the land we colonizers stole from them. It also strengthens everyone’s relationship to nature, the lands we occupy, and the communities our dominant cultures often never take the time to see. Sometimes a land acknowledgement is simply asking people to name the traditional territory they reside on as part of their introduction, and sometimes it’s one person bringing a deeper discussion to the gathering. I delivered this land acknowledgement February 12, 2021 to a SheEO gathering. SheEO is a radically generous community supporting women + non-binary people working on the World’s To-Do List. It is an uplifting community for women + non-binary folks starting a social impact business and for anyone who supports social impact businesses through advice, caring, sponsorship, and funding.
Thank you for taking part in today’s land acknowledgement. I encourage those unfamiliar with the practice to learn more about why it is so important and incorporate it into your own communities. I encourage you to use one of the land maps such as https://native-land.ca/ to find what land you occupy, then visit those nations’ sites to get their thoughts on land acknowledgements and how we help each other thrive.
I am Cindy Gross. I reside in Issaquah, WA outside Seattle in the US – the stolen lands of the Duwamish and Coast Salish.
We, I, still benefit from institutions, including governments and schools, built on land stolen from indigenous folk, built with the labor of Black people ripped from their own indigenous homelands.
I am a descendant of both the colonizers and those they tried to destroy – the Lenape, now known as the Delaware, who greeted tired, starving travelers on America’s east coast, and welcomed them to this continent. Our society still suffers from the suppression of the matrilineal cultures of so many indigenous tribes, and we will grow and thrive when we reclaim more of those community focused traits we’ve coded as too feminine and therefore not valuable.
I am descended from the Lenape peoples, and I am a citizen of two Native nations. I know my legally defined blood quantum, but that doesn’t tell me which parts of my DNA are typically found in any specific Native population. DNA does not, cannot, indicate race, cultural connection, or citizenship. My tribal citizenship also doesn’t confer automatic cultural connections – I have few cultural touchstones with own my Native nations. It’s a complex situation – citizenship, DNA, lineage, and cultural connection are all distinct and often inappropriately mixed ways to talk about who is Native. The terms Native, or indigenous, or Indian are also problematic. If you know someone or are talking to or about someone who identifies as Native, use their terminology and where possible their specific Native affiliation.
Remember that native people are still here, still suffering from systemic oppression, and still loving, laughing, and thriving. Choose to honor them, don’t appropriate from them. Live by the idea of “Inspired Natives, not inspired by Natives.” Research when and where it’s appropriate for someone not a citizen of a given Native nation or tribe to use, buy, or wear Native items and imagery. My earrings today for example are made by Lakota artists and sold to support an Indian school. Honor the people behind the items and images you do use. Support Native owned and Native led businesses, community groups, and organizations such as the Navajo Water Project.
Thank you for pausing to SEE and LISTEN TO the Native folks around us.
My land acknowledgement is personal and action oriented. It acknowledges the past, sees Native peoples in the present, and envisions a more equitable future. Native peoples are still here. They are multi-dimensional, complex humans existing in countries that are often openly hostile to their existence as individuals and sovereign nations. This acknowledgement is specific and models good anti-racism practices. Where it was available and clear I used the language preferred by the people I refer to, even where it was inconsistent throughout my story. The bolded line above can be used as part of your introduction to any group – simple and straight-forward. Practice adding land acknowledgements and broaden what you know about Indigenous folks around you.
