Caitlin's Corner

A Women's Money Workshop, In My Friend's Kitchen

At a time when horrific events are unfolding across our country and so many are feeling the weight of fear and uncertainty, it feels especially important not to ignore that reality, but also to lean into our shared humanity, compassion, and care for one another. I had an experience this week while facilitating a workshop that made me feel deeply human, even while talking about a rigid and unjust system that our lives depend on. I want to share that glimmer of humanity, compassion, and hope with you.

Two nights ago, I stood at the edge of a long dining table under the cozy drop lights in my friend’s kitchen. The table was crowded with crackers, dip, wine, Lindt truffles, and a dozen women. I glanced down at my timer and felt a flicker of panic. I was facilitating my first in-person workshop in over two years. We were already an hour in, and we were still doing introductions.

My nerves kicked in. Instinctively, I grabbed my pen and prepared to gently interrupt and suggest more concise intros, but something stopped me, and I read the room.

Every face was turned fully toward the woman speaking. I looked around and saw pain. Love. Recognition. Understanding. Over and over again, the expressions on the faces around the table said the same thing: This is me. You’re telling my story. It finally makes sense.

We carry so many assumptions- about strangers, our neighbors, even about the people we think we know well. And that night, we quietly shattered them.

This wasn’t meant to be a therapy session or a vulnerability circle. It was a women’s money workshop. Or at least, that’s what it was supposed to be.

I’m used to hosting sessions online, where Susan and I have worked hard to cultivate community and connection over Zoom. But this, this in-person connection, was something else entirely.

I began the workshop by sharing a bit of my own story. Then I asked each woman to introduce herself and respond to one prompt:

What’s one thing you’re hoping to get out of tonight?​
-OR-
​What’s the biggest feeling you have when you think about money?

Fifteen minutes later, the room was alive with nodding heads and soft murmurs of agreement. We talked about uncertainty about the future. About money trust issues shaped by the past. About wanting to be more involved, but not knowing how to do that without conflict. About overwhelm.

Different stories, but many of the same emotions.

No matter where we are on our wealth-building journeys, we all carry some version of fear, hope, guilt, shame, and longing. And for the first time in a long time, no one was holding those feelings alone.

Eventually, we did make our way into the nitty-gritty. We worked through exercises to help each woman understand her monthly and yearly finances, and how to use that information to begin shaping a future picture. We talked about looking at money neutrally (not judgmentally), spotting patterns, and putting simple plans in place.

By the end of the night, everyone had a sense of her next steps and the beginnings of a financial system she could actually live with. But more than that, something had shifted.

Each woman looked lighter, as if she had set down a weight that had been occupying her mind for far too long. The feeling of being behind, of being the only one who didn’t quite “get it,” faded into the cold night air. Our group was glowing with connection- neighbors seeing one another fully.

Here are a few of the themes and learning moments that stayed with me:

“Whenever my husband and I review our spending together, we end up fighting or resenting each other.”​
This resonated deeply. Managing money with a partner is one of the most common friction points I see. The solution isn’t for one person to take over; it’s to design a process that works for both people. Sometimes that means one partner handles the detailed review, while both zoom out to look at broader categories like groceries, dining out, or clothing. Other couples prefer separate spending accounts with agreed-upon rules and equal monthly amounts. Don't aim to do this perfectly. Aim to have a system that leaves both partners feeling empowered, not defensive.

“I have a 13-year-old son and a lot of student debt. I haven’t saved for college, and it stresses me out every day.”​
The empathy in the room was palpable. Even without identical circumstances, every woman understood the emotion behind this fear. We talked through FAFSA considerations, including how current rules treat parent assets but not student debt, and how that may influence decisions around paying down debt versus holding non-retirement assets before applying for financial aid (e.g. sometimes it might be wise to pay off student debt with cash rather than keep that cash, since it's counted as an asset for FAFSA considerations- always depending on personal situations).

“My new employer doesn’t offer a retirement plan. Am I just falling behind?”​
This question captured a broader sense of overwhelm. When employer-sponsored plans aren’t available, the number of choices can feel paralyzing. We discussed options like IRAs, both pre-tax and post-tax, and the importance of maximizing tax-advantaged accounts when possible. And we also talked about this fact that often alludes us: even without tax advantages, investing is still investing. Money set aside for retirement doesn’t lose its purpose just because it lives in a brokerage account.

That night wasn’t highlighted by any single strategy or worksheet. It reminded me that money isn’t just math. It’s memory, emotion, and identity. And when women are given a safe space to talk about it- like really talk about it, breakthroughs happen.

Sometimes, all it takes is a kitchen table. 💛

What I'm Reading

📕 Please don't listen to Elon Musk when he tells you not to save for retirement.

📘 CEOs of big banks are already using AI to generate investment recommendations, make portfolio tweaks, and inform shareholder voting. With more of our money being automated, it's even more important for us to understand our own finances, ask good questions, and not outsource our own thinking.

📗 A reminder that rest is not only important, but a partner to our work. Making boundaries between work and personal time is paramount to making both effective. I appreciate the reinforcement of the idea I hear over and over again that scheduling my work around periods of "uninterrupted, highly focused blocks of 90-120 minutes, followed by rest breaks of 20-30 minutes" is a better solution for me, rather than accepting that I just can't focus anymore.

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