Why are some conversations uncomfortable, or interesting?

Or, how to learn from every conversation, and why we picked these topics.

Why do we avoid (possibly) uncomfortable conversations?

There are conversations we hesitate to have: talking to our kids or parents about sex, holding a team member up to expectations, bringing attention to something we don’t like, asking for help when we’re having trouble.

Why do we avoid these talks? What makes uncomfortable situations uncomfortable?

It’s taboo (we’re not supposed to talk about it)

Bad words. Sexy words. Emotional words. There are things we’re not supposed to say, for fear of seeming rebellious, arrogant, dirty, or weak. We’re asked to suppress our curiosity along with our fears. We’re gotten used to not talking about it, and we’ve come to terms with dismissing our intrigue.

Fear of judgement (you may think I’m weak or different)

We want others to see us as smart, impressive, strong, interesting, “normal,” etc and feel that the wrong question or a sensitive story will change that perception. Sometimes, we are indeed judged. (And sometimes, we see someone being vulnerable and call them courageous.)

I’ll need to be vulnerable (not sure if you’re ready)

We want to share with you, but we’re not ready to share with the world. We trust the other person, and we think they might too — but what if they’re not? We’re afraid to ask because asking makes us vulnerable to rejection. Just sharing makes us vulnerable to shame.

Fear of conflict (what if we start arguing?)

When we think about talking to someone about their poor quality work or insensitive behaviour, we start to imagine the anger that comes after that “confrontation.” Anger or tears can be uncomfortable to face because we feel righteous, but also responsible, guilty, and unsure of what to do.

The good news? Often when you acknowledge what makes a conversation uncomfortable, it goes away.

Why are interesting conversations interesting?

There are conversations where we feel we just live for moments like that. This is when we feel connected to that other person, fully seen and heard, communicating on the same wave length, fascinated and exploring new old topics.

What makes these moments so interesting? (And how can we have more of them together?)

We come in with curiosity and openness to learn

We just want to know more. We realise that there is so much breadth and depth to what we’re talking about — that although we’ve asked so many questions, there’s an infinity to choose from. We can ask questions without fearing stupidity or being wrong. “Right” and “wrong” are irrelevant, because we can learn from anything.

We have willingness and permission to be vulnerable

We know that everyone in the conversation is here to entertain new ideas, and to ask without judgement. We notice nods of support or curiousity, and that people are ready to share and listen fully. We can defend ourselves without being “defensive” or shutting down. We give everyone and ourselves permission.

We’re excited to challenge norms, able to participate

We’re not here to show off technicalities. We’ll talk about the world as we see it. Failure is not about a specific story but about facing our fears, respecting our pain, and rising up again. Open relationships and divorce are each about living with another, choosing love, defining boundaries, dealing with conflict. We are excited to question everything.

Why did we choose these crucial, taboo topics?

Because these topics affect us everyday. They’re about how we relate to and interact with each other. They’re about how we are when we are alone with ourselves. They affect how we deal with conflict, money, love, intimacy, shame, and much more.

Because shining a light on what is unsaid allows us to be more courageous, self-aware, understanding, and thus more innovative, creative, resilient, and happy. We know that articulating what we think or feel helps us make sense of it, which lets us integrate it, rather than reject and suppress it. When we know of our fears, we can respect and overcome them. When we know of our weaknesses, we can grow stronger. When we know how to be curious, we are happier.

For ex, what might we learn from…

Open relationships

We make some assumptions about ideal relationships and how they should work, but in practice, we might desire something more customised. Open relationships is one area in which people have to define their own terms for love and boundaries. Kink is another, where permissions granted and ideas of arousal are very different. Whether or not we support these choices, what can we learn here?

Marriage, divorce

We expect a natural progression from dating, to living together, marriage, having children, etc — but what if those are not the defaults? What if we get to define what we do by default? Divorce — it’s taboo because it shows that we and our choices aren’t perfect. But let’s talk about family after divorce. Let’s talk about how we and our children understand and talk about love.

Business failure

We’re all about the high value exits, innovative ideas, working with friends in a garage, and awesome culture. But what about when the business is going well but you just don’t want to get out of bed? What about when you’re in a hard place, and you’re just trying to get everyone out safely? How do you take risks, and recover from mistakes? We need to know how to land the plane.


What does it signify when we’re angry, passionate, defensive, ashamed, or annoyed? Often it means we hit something we really value — and that what we each think is important is different. Conflict might be because we’re defensive — that we’re running away from a harsh truth, illusion, or insecurity. What if we could approach those moments with just curiosity?

Think about something you find interesting. What’s interesting about it?

Angela OgnevWhat’s interesting?