Mind Vacation № 21: Pondering What’s Next
Mind Vacations are a space to share and pull back the curtain. This post isn’t so much an interview as it is an open look at where Jenny Pennywood stands today—navigating the ups, downs, and in-betweens of running a business in a challenging world.
A business advisor once told me that scaling to the next level is especially hard for operations like mine: tiny team, lean everything, high standards. I felt that then, and I feel that now. At the moment, Jenny Pennywood is essentially me, one part-timer, and a few freelancers helping out where they can. But to truly grow? I’d need more full-time support—and the bandwidth to even dream of that. Instead, I feel like I have a lot of a little bit of things. Never quite enough of any one thing to leap forward.
I’m a stickler for quality and ethics, always have been. But as prices climb across the board, I’ve had to make tough decisions. I’ve resisted raising prices as long as possible, but in order to maintain the integrity of what I make, some increases are inevitable. Home goods, especially, are hard to reimagine. I’m still committed to keeping production as local as I can—California, ideally San Francisco—but I’m also open to new possibilities if it helps me stay afloat without sacrificing values.
If I could wave a magic wand and change one thing about the textile industry, it would be this: make it easier for small makers to stay. The system is designed for big operations—MOQs, pricing structures, supplier policies—it all favors scale. For someone like me, trying to operate with intention and stay small-but-mighty, it can feel like the harder I work, the less room I have to breathe. So instead of chasing someone else’s idea of growth, I’m trying to redefine what expansion looks like. For me.
And somehow, despite everything, there are still bright spots. Working with other women-owned businesses has taken on new meaning—it feels like true community care. My non-negotiables are clearer than ever, especially when it comes to making space for my art. My painting practice is shifting, evolving, and I know it needs time and trust to grow into what it’s becoming.
So where is Jenny Pennywood headed next? Honestly, I don’t know yet. The questions are still forming: Can I keep going under these financial constraints? Can I pause long enough to imagine something bold? Can I stay true to what makes this brand feel like me?
Biggest dream? An angel investor who believes in the vision—and gives it wings.
This is where I’m at—how to hang on, figuring out what growth even means, what’s worth holding onto, and what’s next. If any of this hits home, I’d love to hear from you. Keep an eye out for a survey soon—I want to include your thoughts in what happens next for Jenny Pennywood.
