Jim Bailey on Rock Tree Sky and Experiential Education

This episode of the Getting Smart Podcast is a part of our New Pathways campaign. In partnership with American Student Assistance® (ASA), the Bill & Melinda Gates Foundation, Stand Together and the Walton Foundation, the New Pathways campaign will question education’s status quo and propose new methods of giving students a chance to experience success in what’s next. 

On this episode of the Getting Smart Podcast, New Pathways Senior Fellow Trace Pickering is joined by Jim Bailey, Director and Co-founder of Rock Tree Sky, a self-directed learning center in Ojai, California. Rock Tree Sky provides learner-centered, experiential education space where learners and mentors are supported to follow their unique learning journey. Rock Tree Sky cultivates an inclusive learning community with a goal of developing the whole self through learning in relationship with others.

Transcript

Trace Pickering All right, you’re listening to the Getting Smart podcast. I’m New Pathways Senior Fellow Trace Pickering, and today I’m excited to be joined by Jim Bailey, who’s director and co-founder of Rock Tree Sky, a self-directed learning center in Ojai, California. Rock Tree Sky provides a learner-centered, experiential education space where learners and mentors are supported to follow their unique learning journey. Rock Tree Sky cultivates an inclusive learning community with a goal of developing the whole self through learning in relationship with others. Jim, welcome. Yeah, so I’m going to give people a little bit of background on you here quickly, and then we’ll roll.

Jim Bailey Ah, it’s good to be here, Trace. Ah, glad to talk with you.

Trace Pickering Ah, Jim’s been teaching in the Ojai Valley for 22 years, and he brings his learn-by-doing approach from his science classroom setting, as well as years of youth mentoring through the Ojai Valley Youth Foundation, to his work in learner-centered education. His current work interests focus on the invention of community-based ecosystems of learning, learning space design, and the credentialing of off-site learning experiences. In his spare time, if there is any, he’s a certified California naturalist and enjoys studying the geology, insects, microinvertebrates, and birds of the Ojai Valley. His love of the natural world and of people is also expressed in his volunteer work as a member of the Upper Ojai Mountain Search and Rescue team, and he is an amateur astronomer and the father of four daughters. Why, you got me beat by two daughters. That’s good for you. Two is tough; I can’t imagine four.

Jim Bailey Yeah, I’m still waiting for the prize in the mail on that one, but I think it’s going to pay out later. But yeah, what a—you know, it’s just a blessing.

Trace Pickering Um, yeah, awesome. Um, so it seems like Ojai Valley’s been home to you for a long time. You spent most of your life there?

Jim Bailey It has. I got found at the local teacher job fair when I was graduating from Cal Poly, and I’d seen the sign for Ojai as I drove back and forth to visit family over the years. I always wondered what was there. I took a look around as a beginning teacher at the age of 31 and thought, “Wow, this could be a really nice spot to do this work.” And I wasn’t wrong. It’s been a blessing. It’s a lovely community and a great place to be a teacher—a lot of opportunities to share about the natural world, and the families are supportive and receptive.

Trace Pickering All right, great. Well, I’m super excited to talk to you. I’ve gotten to know Jim through our shared work with a group called Education Reimagined, and we definitely recognized pretty quickly we were kindred spirits. It’s been fun to get to know you. I’m really excited today to talk about Rock Tree Sky. It’s an interesting approach to transforming education because you’re kind of doing it outside the system, but it seems to be working fantastically. I would love to know the origin story. How did you and your wife start it, correct?

Jim Bailey That’s correct, and largely probably a little bit by accident. We were both teachers. I’d been teaching in the classroom for 15 years and had ended up at a progressive private school in town, where I met my wife. She was becoming a little disenchanted with the amount of worksheets coming home in the second grade for her daughter. She was invited to a homeschool parents group via Facebook and had a meeting. I thought, “I’ll tag along,” right? We went, and at this meeting, there were about 15 families, several of whom I knew from the school I was at at the time. It kind of turned into one of those standoffs like from the old spaghetti westerns—they were looking at me, and I’m looking at them. They asked, “Would you be the science teacher for this thing if we started?” This was before COVID—starting a pod support space. I thought, “I don’t know if we should both leave our jobs at the same time. I don’t know how intelligent that sounds,” but we did ultimately, after doing a little math on the back of an envelope.

We started with about 15 families in a 600-square-foot commercial space registered as an arts and crafts education space so that it could fly. I created a maker space; she had her reading nooks, we had the sewing, and we just started from there. That was in 2016, and little did we know we were just at the edge of a big shift. It just grew and grew, so now we have 200 learners, and we rent a school campus from the district that was surplused.

Trace Pickering Very good. So, is it privately funded, tuition-funded, public monies from the school district, a little bit of everything? How have you evolved? I’m assuming it’s evolved over time.

Jim Bailey Yeah, that’s right, it’s a super important question. It’s some of each of those. It’s fee-based primarily, and then in California, it turns out that independent study school Ed Code allows independent study schools to pay vendors for enrichment services. When we first started, families enrolled in California independent study schools began finding us. Sometimes these are called homeschool charters, although there’s really no state law related to homeschooling. It’s essentially an independent study school. They give families funds to use for approved educational vendors and enrichment support since they aren’t running a traditional brick-and-mortar space. We became an approved vendor for several of those programs, which helped some families with access. For families who truly wanted to homeschool independently, filing a private school affidavit and being out of the system, they could just pay out of pocket.

Currently, about 50% of our budget comes from a local public school district partnership, another 20% comes from these independent study charters, and around 30% is from families buying extra days of services.

Trace Pickering Excellent. So, what’s a student’s day like? Do they come during the school day? Do they get credit back at their school? Is it an after-school or summer program, or a bit of everything? What does it look like for a student?

Jim Bailey We’re open Monday through Friday, 9 a.m. to 3 p.m. Being an independent study program, learners do their education in a variety of places. Ideally, the independent study programs allow families to bring in experiences from all areas of a child’s life. Some teachers provide specific assignments, but many work flexibly with families to create meaningful projects.

Most students come to us two days a week. They might engage in a science activity with me or one of my mentors, work on an art project, or write a skit. If their teacher finds that creditable, they can use it for school credit. If not, they just enjoy the experience and take responsibility for other learning later at home.

A typical day looks like this: learners arrive around 9 a.m.—we have a soft start. Recently, we started offering school bus support from the lower part of the valley, so the bus gets in around 9:15 or so. There’s no official tardy time; it’s a smooth start. Each learner has a dedicated adult mentor—similar to a homeroom teacher—who begins the day with them. That mentor goes over the daily menu of activities and starts with intention-setting: “What are your goals for the day? Do you have any projects to carry over from last time?” This helps us know how to support them better.

After that, they start their activities. They might check in with friends, set up a game of Gaga ball for later, or jump into a project. We go until noon, and then everyone eats lunch together in a general area. By 12:30, they’re back at it. Around 2:30, we ring an old-school bell for cleanup. We don’t have an intercom system; we like it simple. After cleaning up, they go back to their groups, where they reflect on the day, share what they’ve learned, and address any unmet needs. It wraps up the day in a way that feels really good.

Trace Pickering That’s fantastic. How do teachers manage this approach? I imagine they might think, “Wow, every day I have to come up with things to offer.” How do you figure out what kids are interested in and ensure that teachers feel comfortable creating things on the fly or in short bursts?

Jim Bailey Good question. There’s a lot of emergent planning—those of us from traditional teaching backgrounds call it the “emergent lesson.” You need a toolkit of activities and resources you’re comfortable with. Finding the right staff who want to teach in this way is essential. There are some consistencies: many teachers will choose a theme or a challenge and stretch it out over the week since learners attend on different days. Some come Monday and Wednesday, others on Tuesday and Thursday. Only a handful come five days a week. Many are out doing independent study or exploring other interests with their families.

For example, if a child wants to work on a woodworking project, they might set an appointment with Spence, our builder. He’ll say, “Let’s meet in the woodshop at one o’clock.” So, there’s a mix of structured times—like studio hours—and open times where kids can jump into ongoing projects. Once they know the layout, many dive right into what interests them.

Trace Pickering That sounds amazing. So you’ve got all these learners working on different things at different times. How do you document their learning or keep track of what they’re doing?

Jim Bailey We rely heavily on reflection, journaling, and portfolios. Each learner has a portfolio that includes their reflections, goals, and examples of work. For example, if they’re doing a woodworking project, they might take photos of their work and write a few sentences about what they learned or the challenges they faced. This process helps them take ownership of their learning journey.

Each mentor also has a list of learners they’re responsible for and maintains a log of the projects, skills, or concepts each learner explores. We don’t grade traditionally, but we do assess growth. Our goal is to support kids in building a growth mindset and confidence in their abilities rather than focusing solely on content mastery. We meet regularly with learners and families to discuss progress and set future goals.

Trace Pickering That’s a really refreshing approach. How do families respond to this model, especially those who might be used to traditional education with grades and tests?

Jim Bailey Most families that come to us are already seeking something different, so they’re generally open to our model. They might have felt their child was getting lost in the traditional system, or they might want an environment that fosters independence and creativity. That said, some parents do initially struggle with the lack of grades or tests as benchmarks. But once they see the growth in their child’s confidence, skills, and joy in learning, they usually become more comfortable with it.

We also have regular family meetings where we talk about the learner’s portfolio, what they’ve been working on, and how they’ve grown. This gives parents a tangible view of their child’s progress, even if it doesn’t look like a report card. They see that their child is taking on challenges, developing new skills, and becoming more engaged. By focusing on these indicators of success, we help families understand the value of a learner-centered approach.

Trace Pickering It sounds like you’re really focused on helping kids find their passions and develop their sense of agency. How do you help kids who might not know what they’re interested in or who haven’t found that thing that lights them up?

Jim Bailey That’s a big part of our work. We start by creating a culture where it’s safe to try new things, make mistakes, and explore without pressure. Some kids come in knowing exactly what they want to do, while others need more guidance. For those who are unsure, we expose them to a wide variety of activities and let them experiment. They might try art, building, cooking, or coding—whatever sparks their curiosity.

We also work a lot with intention-setting. At the beginning of each day, learners set intentions, which can be as simple as “I want to learn something new today” or “I want to meet a new friend.” This practice encourages them to think about what they want to achieve, and over time, they start to uncover their interests and strengths. Our mentors are also trained to ask open-ended questions that help learners reflect on their experiences and identify what excites them. It’s a gradual process, but we’re there to support them along the way.

Trace Pickering That’s wonderful. It’s great to see kids given the freedom to explore in a safe environment. So, let’s talk about the community. How does Rock Tree Sky connect with the broader community in Ojai?

Jim Bailey We’re fortunate to be in a community that values alternative education and is open to supporting a learner-centered approach. We collaborate with local businesses, artisans, and organizations to create real-world learning experiences for our students. For instance, we have partnerships with local farms where learners can go and work. They learn about sustainable agriculture, participate in planting and harvesting, and get a sense of what it’s like to work on a farm.

We also partner with local artists and makers who offer workshops at our site. Some learners have even had the chance to intern or apprentice with these local artisans. These partnerships are mutually beneficial; our learners gain hands-on experience, and our partners get to share their expertise with the next generation. It’s a win-win for everyone involved.

Additionally, because we’re in a small town, our learners often bump into people they’ve collaborated with around town. This fosters a sense of community and helps them see that learning isn’t confined to a classroom. It happens everywhere, and everyone has something to teach.

Trace Pickering That’s fantastic. I think the community aspect is so important and something that’s often missing in traditional schools. You’ve created something really special. What advice would you give to someone interested in starting a similar program in their community?

Jim Bailey First and foremost, I’d say be prepared to listen. Listen to your community, to the families, and to the kids. Understand what they need and what they’re looking for. Every community is different, so what works in Ojai might not be the perfect fit elsewhere. Start small, build relationships, and let the program grow organically.

It’s also important to be flexible and open to change. When we started Rock Tree Sky, we didn’t have everything figured out, and we still don’t. We try things, learn from them, and adjust as we go. Being adaptable and willing to evolve is crucial, especially in a learner-centered environment.

Finally, find people who share your vision. Building a supportive team makes a huge difference. Our mentors are passionate about self-directed learning and creating meaningful experiences for kids. Without that shared commitment, it would be hard to keep the energy and momentum going.

Trace Pickering Great advice. I think people will really resonate with that. So, looking forward, what are your goals for Rock Tree Sky? Do you have any big plans or new ideas you’re excited about?

Jim Bailey We’re always exploring new ideas. One thing we’re excited about is expanding our outdoor education program. We’re located in a beautiful natural area, and we want to make more use of that. We’ve started doing more nature-based activities, like hiking, bird-watching, and studying local ecology. The kids love it, and it helps them develop a deeper appreciation for the environment.

We’re also looking into developing a mentorship program where older learners can mentor younger ones. This gives them leadership opportunities and reinforces their learning. It’s something that’s been happening informally, but we’re working on making it a more structured part of our program.

Finally, we’re considering ways to make Rock Tree Sky accessible to more families. We know our program isn’t affordable for everyone, so we’re exploring different funding options and partnerships to make it more inclusive. We believe that every child should have the opportunity to learn in a way that aligns with their interests and strengths, and we’re committed to making that a reality.

Trace Pickering Those are wonderful goals. It’s inspiring to hear about all the ways you’re expanding and improving. Before we wrap up, is there anyone you’d like to acknowledge who has been instrumental in your journey with Rock Tree Sky?

Jim Bailey Absolutely. There are so many people who have been part of this journey. I have to give a big thank you to my wife, who co-founded Rock Tree Sky with me and has been a constant source of support and inspiration. I’d also like to thank our incredible mentors, who bring so much passion and dedication to their work every day. And, of course, the families and learners who have trusted us with their education. We couldn’t do this without their enthusiasm and commitment.

Trace Pickering Well, Jim, thank you so much for sharing your story with us today. Rock Tree Sky is an inspiring example of what’s possible when we think outside the box and put learners at the center. I’m grateful for the work you’re doing and for your willingness to share it with our audience.

Jim Bailey Thank you, Trace. It’s been a pleasure to chat with you, and I appreciate the opportunity to talk about Rock Tree Sky. We’re always learning and growing, and it’s exciting to be part of this movement toward learner-centered education.

Trace Pickering And thanks to everyone listening. This has been the Getting Smart podcast. Until next time, keep learning, keep leading, and keep innovating.

Links:

• Rock Tree Sky
• Education Reimagined
• Free to Learn – Peter Gray
• John Holt
• John Dewey
• Iowa Big
• Karen Pittman and Gary Briggs Getting Smart Podcast
• Piaget