We were lucky to catch up with Vivian Cobb recently and have shared our conversation below.

Vivian, thanks for joining us, excited to have you contributing your stories and insights. Can you share a story about the kindest thing someone has done for you and why it mattered so much or was so meaningful to you?

It is remarkable how much kindness I’ve been shown in my life. During one of the hardest times, a friend in particular showed up at my door with a $10,000 check. She loaned me that money interest-free and with no due date. It wasn’t the money that mattered most; it was her belief in me. Let me back up to give you the full significance of that act of kindness.

My husband had died very quickly after his diagnosis of colon cancer. Three and a half weeks to be precise. While he was in the hospital, I discovered our financial life was in crisis, which was especially shocking considering he was a multimillionaire and a successful entrepreneur. A trip to the bank revealed that we had $5,000 in cash. All the other savings and business accounts were virtually empty.

After he was gone, I learned just how dire my circumstances were. My credit was maxed out, I had no ability to borrow money, I wasn’t working at the time, and my house was in foreclosure. I was in a very precarious situation.

My friend was also a widow. But she’d been left in a very different position: life insurance, no foreclosure, financially secure. She knew I was dead broke. She knew I wasn’t working. She knew I couldn’t give her a timeline for paying her back. She gave me the money anyway.

It wasn’t the money that mattered most, despite the fact that I needed it desperately. It was her belief in me. She
believed I would pay her back and that I could get myself back on my feet to do so. That was enough collateral for her.

I had to borrow that belief from her because I didn’t have much in myself at the time. Borrowing that belief motivated me, inspired me, and helped me fully believe in myself. It took about two years, but I paid her back, dollar by dollar, whenever I had a little extra. Every payment was confirmation to her that her belief was not misguided, and more importantly, proof to me that I was making progress.

I’m not sure what I would have done without others’ belief in me and my ability to succeed. I’m grateful to this day for her generosity, not only with her money but also with her faith in me.

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.

Tell our readers about yourself.

I’m Vivian Cobb, an author and professional speaker. I guide individuals on how to have relationship-saving conversations, and I use money as the primary example because it’s not only my story, but it’s a difficult conversation most people avoid.

How did you get into your industry?

My journey into this work came out of personal devastation. As my husband was dying, I discovered that our entire financial life had collapsed. He didn’t tell me; we never talked about it. He avoided the conversation even as everything was falling apart. I was blindsided and unprepared. That silence cost me everything. But it also taught me something that shapes everything I do now: the conversations we avoid shape the lives we live.

Money conversations are my entry point because they’re loaded with everything that makes difficult conversations hard: fear, shame, conditioning, and the weight of what might happen if we speak up. I’ve realized something important in my journey: if you can learn to have an honest conversation about money with someone you love, you can have any difficult conversation. The skills are the same. The fears are the same. The patterns of avoidance are identical.

What I Do

I help people, whether in intimate, family, business, or organizational relationships, have the conversations they’ve been putting off. I show them that although these conversations may not be comfortable, they can be honest, respectful, and transformative.

Through speaking and my book, Unspoken Costs: How to Have Relationship-Saving Money Conversations, I equip people with the tools to have conversations they’ve been avoiding. I address the real barriers: societal conditioning around money and gender roles, fear-based thinking, shame, emotional patterns shaped by our upbringing, and then I provide the framework and language to move through those barriers and have the relationship-saving conversation anyway.

What Sets Me Apart

Most people approach difficult conversations as something to survive or “win.” I approach them as an opportunity to deepen trust and understanding. The goal isn’t to be right, it’s to be connected.

I also don’t pretend these conversations are easy. They’re not. But they’re possible. And the couples, families, and teams who learn to have them find that it can change everything about how they move forward in their relationships.

What sets me apart is that I’m not speaking from theory, I’m speaking from lived experience. I’ve been the person who didn’t ask questions and lost everything. I’ve been broke, rebuilding from nothing, and learning these conversations the hard way. When I talk about fear and shame around money, people recognize themselves in my story. And that recognition gives them permission to be honest about their situation rather than pretend everything is fine.

Why This Matters

When difficult conversations go unspoken, one person carries the burden alone while others may remain unprepared.

Two thousand seven hundred people die unexpectedly every day in this country. If something happens to someone and the people who depend on them lack crucial information, they’re devastated twice over, grieving while simultaneously trying to figure out what they don’t know.

The strongest relationships, the ones that survive hardship, that build real trust, that weather life’s storms, are built on honest conversations about the realities of life.

What I’m Proud Of

I’m proud that I’ve turned my devastating experiences into something that helps others avoid similar pain. I’m proud that I’m raising awareness about the importance of exchanging crucial information, even when it’s uncomfortable, and that my work gives people a framework for conversations they never learned to have.

What I Want People to Know

The conversations you’re avoiding aren’t actually about the topic itself. They’re about fear. Fear of being wrong. Fear of rejection. Fear of what you might discover. Those fears prevent you from having critical conversations with your partner, your kids, your parents, and your colleagues.

Silence doesn’t prevent conflict; it creates chaos. I learned the hard way that avoiding difficult conversations is much worse than facing the discomfort of having them.

We’d love to hear a story of resilience from your journey.

I was on my knees in my front yard in a full-on adult tantrum. I had just received a certified letter informing me that a creditor was attempting to have my house forced back into my late husband’s estate. They were accusing him of fraudulent transfer, legal-speak for signing the deed over to me after his terminal diagnosis.

That little guest house was the only thing standing between me and homelessness, and it was my last line of defense for my dignity.

So I ran outside and collapsed on the ground, pounding it, screaming, sobbing. “You’ve already taken everything from me. I cannot do this anymore.”

I had a fabulous cry, one for the record books. After a few minutes of this dramatic scene, I calmed down and caught my breath.

I was lying there face down on the ground, and I started to notice the blades of grass, covered in scurrying ants, clearly not happy about the pounding. I watched all the miniature movements of a world we rarely notice. I was struck by an overwhelming sense of life as I witnessed the ground teeming with it. It inspired me and reminded me that I had a lot of work to do and a lot of life to live.

I was exhausted from being in survival mode. My spirit was completely depleted. But lying there, I had to make a decision, both literally and figuratively: do I stay down, or do I get up?

It was a pivotal moment in my resilience journey. I realized that staying down wasn’t an option. I couldn’t even conceive of it. So, mustering all my strength, I slowly picked myself up from the ground, despite my sore hands, my tear-stained cheeks, and my weary spirit.

It took a few years, but that day was the day I committed to rebuilding my life from the ground up.

What’s the most rewarding aspect of being a creative in your experience?

The freedom. And I mean that in multiple ways.

First, there’s the freedom that comes from having rebuilt my life. I worked incredibly hard for years, twelve-hour days, seven days a week, to get to financial independence. That hard work bought me the freedom to do what I actually want to do. I can travel, I can write, I can show up in the world however I choose. That’s a freedom I earned, and it’s precious.

But there’s another kind of freedom that’s even more meaningful. For decades, I was the breadwinner, the mom, the wife, the caregiver. I was surviving and providing. I didn’t have space to be anyone but the person the roles demanded. Now I get to express my artistic soul, the part of me that’s always been there but was buried. I get to just be whoever Vivian wants to be.

And then there’s the healing part. Writing forces me to get the story out of myself. But sharing it, that’s where the real healing happens. I spent so much of my life bottling things up. Childhood wounds. Secrets. Grief. Loss. Now I get to take all of that and transform it into something that helps other people feel less alone.

That’s the most rewarding part, not just expressing myself creatively, but knowing that my vulnerability gives other people permission to be vulnerable too.

Contact Info:

• Website: https://HaveThoseConversations.com
• Instagram: https://www.instagram.com/vivian.cobb.9
• Facebook: https://www.facebook.com/viviancobbspeaking/
• Linkedin: https://www.linkedin.com/in/viviancobb/
• Youtube: https://m.youtube.com/@VivianCobbSpeaks
• Other: Substack: https://substack.com/@viviancobb, TikTok: @viviancobbspeaking, Facebook Group: facebook.com/groups/690510060811668