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Do I Speak Up or Let It Go? Navigating Family Conflict

Adulting
with Jesse
Starting Nov 24, 2026 5PM UTC

About this Session

Holiday gatherings can bring people together while sometimes bringing out the most difficult parts of being together. A passing comment turns into an argument, a familiar disagreement resurfaces, or someone says something that goes against our values. We might feel the urge to challenge it, defend ourselves, or stand up for someone else. At the same time, we may worry about creating tension, ruining the gathering, or spending the rest of the evening in an argument. Knowing when to speak up and when to step away isn't always straightforward, especially when family dynamics are involved.

In this session, we'll explore how to navigate conflict with family and loved ones during the holidays. We'll talk about setting boundaries, responding to uncomfortable comments, deciding which conversations are worth having, and recognizing when engaging won't lead anywhere productive. Together, we'll consider how to stand by our values while being intentional about our energy, our relationships, and the situations we choose to engage in.

This session is for you if:

  • You dread certain conversations or disagreements at family gatherings
  • You struggle to decide whether to challenge a comment or let it pass
  • You feel responsible for keeping the peace, even when something bothers you
  • You want to stand up for your values without getting pulled into every argument
  • You find it difficult to set boundaries with people you're close to

You don't have to engage with every disagreement, and keeping the peace doesn't have to mean ignoring what matters to you. Let's explore how to make those decisions for ourselves and how to navigate difficult moments without losing sight of what we need. 💛

About this Space

Adulting is a space for figuring life out together without pretending you have it all together.

No one really explains adulthood.

One day you’re expected to know how to manage money, cook meals, navigate healthcare, build a career, maintain relationships, set boundaries, and regulate your emotions (all while somehow still having a five-year plan).

Meanwhile, most of us are quietly Googling things like “how often do you wash sheets?” and “is everyone else this tired all the time?”

This space is for the unglamorous, very human side of growing up — the responsibilities that pile up, the invisible labor, the comparison, the constant low-grade feeling of am I doing this right?

Through small, guided conversations, we talk honestly about what adulthood actually feels like. Not advice. Not productivity hacks. Not “fix yourself” energy. Just real people sharing what’s hard, what’s confusing, and what they’re learning along the way.

This space is for you if:

  • You feel like everyone else got a manual you missed
  • Everyday responsibilities feel heavier than they “should”
  • You’re navigating money, work, or independence and learning as you go
  • You’re tired of pretending you know what you’re doing
  • You want honest, low-pressure conversations about real life

Whether you’re 22 or 42, thriving or spiraling, starting fresh or rebuilding — you’re welcome here.

We’re all just learning in real time.

How Does it Work?

This is an open, guided discussion led by your Keeper, Jesse. Each participant will have the opportunity to listen to and share experiences on belonging, identity, community, and whatever else comes up during the session.

When and How Do We Meet?

We meet digitally every couple of weeks to make participation easy for those with demanding schedules. Cameras are optional, and you’re welcome to join from wherever you are, even between shifts. We only ask that you find a private place to join or use headphones to help maintain the security of everyone present.

Meet the Keeper

Jesse

Between Texas and Italy

Hey there! I'm Jesse. My professional background is in communications and advocacy and I'm passionate about making the world a safer, more just place to live in. I've studied and worked across issue areas and organizations.

Originally from Texas, I now live between the U.S. and Italy. Outside of work, …

Reach out to the Keeper: jesse@totem.org
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