Mind Vacation № 24: 5 Questions with People I've Loved

Thanks to People I’ve Loved for including us in their newsletter featuring 5 Questions for Inspiring Businesses. Honestly, we just love everything about the People I’ve Loved team—their vibe, their eye, their way of celebrating creativity, community and kindness.

We’re celebrating, too, with a giveaway! Enter here.

1. What is the origin story of Jenny Pennywood? 

Back in 2008, I gave myself an alter ego and named her Jenny Pennywood. At the time, my fine art career had some momentum. I was working with several galleries, making sales, and painting full-time. Then the economy crashed, and all of my gallery relationships fizzled due to galleries closing and sales being nonexistent. I needed to do something because everything I had been doing essentially disappeared.  I wanted to explore commercial work, but didn’t want to do it under my own name because I thought it would hinder my fine art path, so I thought, I’ll just make up a new one and work under that.

I definitely didn’t have a plan. Jenny Pennywood has been through many iterations, each one growing organically. That spontaneity has been both a blessing and, at times, a challenge. Right now, I’m in the process of rethinking and reshaping what Jenny Pennywood means. But that’s probably a whole other conversation.

2. What is your favorite part about running Jenny Pennywood?  

I love working for myself and coming to my studio every day. I even greet my studio as I walk in the door, “good morning studio”. I love having a studio space. If you are a friend, I’m sure you have heard me say something about working alone, and it might sound like I don’t love being alone all day, every day, but really, there is a deep part of me that loves it. I have wonderful people who work for me, but I do love being in my space, alone, all day, and puttering around the studio with my tasks and multitasking my way through my day.

3. Can you describe a recent project that meant a lot to you?

Well, I’d probably call this more of a life shift than a project. But here goes … 

I’d been talking for a while about making some big changes, but when my in-house assistant gave her notice, that kind of sealed the deal. I decided to move out of my fulfillment studio, hand over shipping to a third-party warehouse, and bring Jenny Pennywood back into my painting studio; I decided to go back where it all began. 

Technically, I made that decision in May of 2025. But if I’m being honest, it started way earlier. I recognized that there was a specific Jenny Pennywood vs Jen Garrido identity conundrum I had self-created. How was I going to bring the real me back to the forefront of all that I do? That is and was my desire. I also know that I needed to heal some stuff … you know. 

And if I trace it back a bit further, during a reading with a past life psychic (I know, super woo woo but that is me), this identity conundrum was present then too. Long story short, I was told that if I deepened my painting practice, I’d work through my karmic life. I didn’t know exactly what that meant, but something about it resonated with me. I kept thinking about it. Painting as a portal to take care of the business I needed to take care of – yes, please. 

And now, here I am… Some major weights have been lifted. The space that’s opening up in my life feels very real. I’m letting go of the old structure, trying to build something that leaves more room for the studio, for art, for less hustle. It’s a bit messy and full of grief, but that is fine. I know there is a bigger picture here, and while I don’t know what that is, I’m working on figuring it out. 

4. What are your customers like? Why do they shop with you?

My customers are the best and coolest community ever!  Truly. I think they shop with me because they care about supporting small businesses and real people. They are  not just looking for stuff, they’re looking for items that feel good and mean something.. They’re quality seekers who love color, shape, and a sense of play.

I want the things I make to spark joy in the simplest of ways. Like, you’re folding laundry and there’s a stack of Jenny Pennywood napkins, and you pause for a second and think, “wow, I love the way these colors look together.” That’s it. A tiny flash of joy. That’s what I want — for my work to live in people’s homes and add a little something good to their everyday lives.

5. What is a challenge facing “my” small businesses today? 

Lately, the hardest part has been managing debt and staying on top of bills. Every time I have to pay for something or someone, I feel like I’m on the verge of tears. And then there’s all the usual stuff everyone’s dealing with: Instagram being weird, slower sales, everything from production to packaging to shipping getting more expensive. Partners I’ve been in production with for years and years are raising prices by 500%, not an exaggeration. Figuring out how to pivot, constantly.

I’m trying to stay open to new possibilities, and I am excited about what could come next, but it’s hard not to feel the grief of what’s being left behind … especially the connection to my local SF partners and the freedom I used to have in how I created things. 

Enter to win a $200 Jenny Pennywood gift card and a $200 People I’ve Loved gift card here.