Carissa Potter owns a stationary and gift business called People I’ve Loved in Oakland, full of her work and other local stockists. But some may be surprised to learn she also writes a Substack called “Bad At Keeping Secrets” — a series of essays, conversations and artwork that talks about what it means to be human. 

On a cloudy October day at the Oakland Entrepreneur Retreat panel, she dove into how she cultivates community with her customers. 

The panelist’s questions provided insight into a larger landscape on how to build and maintain interpersonal relationships and explore what works and what doesn’t, a necessary asset that makes Bad At Keeping Secrets a special niche on the internet.

“I’m really attracted to complicated situations and messy people because I am one,” Potter said. 

Creations on her Substack and podcast, also called “Bad At Keeping Secrets,” consists of interviews with authors and psychologists whose work is currently on The New York Times Best Sellers lists. It includes conversations, essays, and graphics on being a gaslighter, exploring death, and feeling lonely.

And she’s messy. She fumbles over her words, mixes her colleagues up, and forgets the questions for the panel she is speaking on. But she is open and honest about what others might be trying to hide.

Bad At Keeping Secrets earned its title from Potter’s own experiences of not being able to differentiate between what is supposed to be a secret and what is for everyone to know. 

She writes in her work how in her eyes, hard conversations and feelings are already so heavy, adding shame into the mix can feel overwhelming. This shame can result in judgement being casted where there is no understanding, a vicious cycle that leaves everyone in its wake scathed.

But in an age when boundaries surrounding hard conversations are being discussed more than the discussions themselves, it is beginning to become more unclear for people to draw the line between what is trauma-dumping and what is simply confiding in a friend. 

Potter pushes back on this idea in her work, offering space in sharing the not-so-glamourous parts of human life that can evoke a sense of shame. The topic is explored in one of her Bad At Keeping Secrets pieces on Substack titled “How to know if you should de-friend someone?”

“If I have learned anything about myself during this pandemic is that people seem to push people away when they need them most,” Potter writes.

Some have complicated struggles with different relationships, another topic discussed at the panel. Growing older, dynamics and people begin to appear in shades of grey, and not everything is as black and white as they seem to be. 

Media, along with personal narratives like Bad At Keeping Secrets, broadcast personal life experiences for audiences across the globe to show difficult conversations and life experiences that are oftentimes universal but not discussed openly. 

Carissa Potter, writer of Substack series called “Bad At Keeping Secrets,” and other speakers in a panel at the Oakland Entrepreneur Retreat in Oakland, Calif. on Thursday, Oct. 22, 2026. (Gabriella Guerrieri/Bay City News)

“I’m just more interested in other people’s stories at the moment,” Potter said. 

And beyond romantic relationships, she also opens up on the panel about longing for friends and connection in that way–even suggesting friendship contracts in which individuals partaking in friendships agree to certain obligations and negotiate their role in this relationship. Initially, it sounded unromantic and unnatural — a contractually obligated friend. 

But as the panel went on, other Oakland entrepreneurs brought forward their own desires for friendship and comradery. 

One person even had their own form of a contract with 11 other people. This group of friends agreed to a monthly meeting for the past decade. Some months, only three people show up. But it’s in their contract. And when terms and conditions are not met in said contract, services are terminated. 

Potter also mentioned her Substack piece titled “Should you reach out?” It explores when to repair and when to let go of relationships. She uses her own experience growing apart from a longtime friend and making sense of the ending of a relationship that did not result from a direct consequence. She addresses her own shortfalls and how to tell when it’s time to move on.

At the retreat, conversation naturally gravitated towards building relationships since the panel focused on growing community with customers. 

In this same conversation, Candace Cui, the director of growth and marketing for Potter’s stationary business and an old friend of Potter’s from art school, talked about how, as she became older, a lot of what caused relationships in her life to end were not the result of a cataclysmic event or situation. They sort of just grew apart. 

“I don’t really recognize you anymore,” Cui said to the group. 

Another question asked at the panel was how to know the difference between a customer and a friend. 

Potter began the conversation about her longing for connection and a group of friends. But from this discussion, many audience members agreed that when they felt the most hurt was when someone said they were going to show up and didn’t.