How We’re Building Risk-Taking and Resilience into our Work
One of CITY’s key objectives is to foster skills in risk-taking and resilience among our students. The importance of risk-taking and learning from failure is a familiar refrain in innovation and entrepreneurship circles, from Silicon Valley’s “fail fast” mantra to the popularity of failure-focused story nights. Beyond cheery slogans, however, it can be harder to see what that looks like in practice — and how students can balance thoughtful work on real-world problems with a comfort around the possibility that their ideas or efforts may not work out. Particularly on a campus like Yale, at which many students have arrived thanks to a sustained series of successes, how does CITY approach creating a space in which acknowledging, learning from, and moving forward from setbacks is given more than just lip service?
I talked to a few CITY team members to get their thoughts on creating this space, and on the tangible efforts they’re making to build a culture of risk-taking and resilience into their programs and day-to-day work.
Justin Freiberg, CITY Mentor in Residence and Yale Landscape Lab Director
As a CITY mentor in residence and director of the Yale Landscape Lab, Justin Freiberg leads programs and initiatives that focus on innovation and experimentation within the contexts of the natural environment, from food entrepreneurship to plant-based health. His recent and upcoming projects with CITY include Intensives on fermentation and on ethnobotany and traditional foods, and a series of community gatherings about food’s role in our society.
In your fermentation Intensive this past fall, you advised students that the Intensive was a space where they could “let go of perfection and learn from the process.” How have you tried to build that approach into your programs?
So many students have gotten to this point in their lives through meeting targeted expectations on output. In turn, we have to make it particularly clear that paying attention to — even highlighting — moments of problem-solving during the process can sometimes be the most useful, strength-building thing they can be doing. Firstly, it helps to reframe the process as the product. And, of course, defining why this is useful is key: I often stress that students’ ability to handle future problem-solving moments will be enhanced by this shift in focus.
There are a few elements of program design where this shift in focus can be furthered as well; most obviously, when we bring in experts in one field or another, we often ask them to speak to the shaping nature of their struggles just as much as their successes. In other programs, where the students are approaching a specific problem and building solutions, allowing time and structure for multiple attempts initially validates the change in focus. And lastly, trying (and failing) alongside the students doesn’t hurt.
At the Landscape Lab, you often work with elements that have lives of their own and can be unpredictable, from sourdough starters to plants and ecosystems. How do you hope students will engage with innovation — and with risk-taking and resilience — in that context?
That the Landscape Lab is filled with elements that have lives of their own — plants, ecosystems, honeybees, the occasionally cultivated bacteria or yeast on a fermented product — can be useful in making the effects of one’s innovations and successes clear, tangible, and rewarding. It can also be a nice reminder of the fact that these greater systems which students hope to affect are inherently hard to work with and understand.
Elements of YLL are seasonal and ephemeral; there is constant, yearly failure. Resilience is key for students to innovate in such systems with so many unknown, interconnected variables. Complementary to that idea is that the elements of these systems — whether they be the behaviors of honeybees or the compounds within certain plants — are in and of themselves the products of innovation. There are lessons to be found there for the careful observer.
You were a student entrepreneur while at the Yale School of Forestry & Environmental Studies, founding a company that ultimately folded. How do you draw from this experience in developing programs and mentoring students?
That my company eventually folded initially obscured the countless successes along the way and the lessons I would take from the experience. I began to appreciate just how rich and useful the experience of starting that business was when I started to realize how differently I was approaching issues and problems after my team had left the business behind. In turn, in developing programs, I often try to allow students some version of that experience when possible; a healthy amount of independence is generally part of this, as is allowing students to see processes through from start to finish with room and time for errors, learnings, corrections, and new iterations.
In terms of mentoring students, I often find myself asking them hard, simple, probing questions about their ideas — all with the aim of helping them pressure-test what they’re creating. This approach, which some of my own mentors took during my time with my startup, was fundamental to our improvement. I was thankful for it, and with a bit of a cushioning introduction to students that I am going to try to “break” their idea a bit to make sure it is strong, I think it is often helpful for them too.
Abdul-Rehman Malik, CITY Mentor in Residence, and Abby Winslow, CITY Operations & Events Manager
Abdul-Rehman Malik, a mentor in residence at CITY, is an award-winning journalist, educator, and cultural organizer. At CITY, he mentors students across these areas and more, often with a focus on social justice and storytelling. This spring, he and CITY operations and events manager Abby Winslow collaborated to launch a new program: Fail Night. “Fail Night first popped into my head as an event after seeing the success of our pitch slams [low-stakes events that invite students to pitch any idea to an audience of peers] and given our directive to fail. I envisioned an event similar to a pitch slam, but themed around failure,” says Winslow.
She soon found out that Malik had also been thinking about creating programming around failure, and the two joined forces: “When I saw Abdul-Rehman’s vision for a failure workshop, it was one of those ‘aha!’ moments,” Winslow explains. “His ideas for the structure and types of activities that we’d facilitate in the workshop, inspired by his studies and teachings in drama, were going to have so much more impact on the students than a pitch slam-style event.” Together, Malik and Winslow planned a small-group event that would encourage students to share and celebrate their failures — not always an easy task on a campus full of high achievers.
As a warmup, Malik opened the program by leading the group through a few low-stakes theater games. From there, the program moved into a series of “keynotes” — failure stories told by CITY team members — and small story circles, in which groups of students took turns telling two-minute stories in response to questions like, “What’s your earliest memory of failure?”
As the event unfolded, it became clear that it had carved out a space in which students felt comfortable leaning into vulnerability, telling their peers about times they had fallen short of expectations, let themselves or others down, or tried to make a misguided idea work. Towards the end of the event, Malik asked each person to come to the center of the room and assume a pose that embodied the feeling of moving forward after a failure; when everyone was assembled, they collectively created a powerful tableau of setbacks and resilience. The event then wrapped up with a joyful celebration of everyone’s failures — complete with cheering, kazoos, and a cake decorated with an enthusiastic misspelling: “No Regerts.”
Kassie Tucker, CITY Managing Director
Beyond cultivating meaningful risk-taking and resilience among our student body, we also aim to support these qualities within our staff. Kassie Tucker helps lead these efforts as CITY’s managing director, shaping both CITY’s programs portfolio and our team’s internal processes and culture.
At CITY, we aim to encourage risk-taking and resilience not just among our students, but among our staff as well. Why do you see this as important?
Taking risks is such an integral part of the innovation process. In order to move an idea forward, you need to constantly put yourself and your ideas out there, testing them, learning from that experience, and then iterating to the next improved version. As CITY strives to be a thought leader on supporting innovation, it is important for our team to experiment with different ideas, formats, and concepts so that we can develop the best possible models to support our community.
What‘s one way you try to support risk-taking and learning from failures among our team?
A small example of how we encourage risk-taking and learning from failures is a weekly exercise we do as a team called “Looking Back/Looking Forward.” We dedicate time in our staff meeting for anyone on the team to celebrate a success or share out a failure they’ve recently had. Having that space to acknowledge when we failed and, most importantly, talk about what we learned from that failure has helped our team normalize taking risks in our roles and has helped us iterate and improve faster as an organization.
What have you learned as you’ve led a team with this approach?
Talking about your own failures is must. Being open that even in your best efforts you too sometimes miss the mark, and then articulating what you learned from the experience, helps normalize the concept of failing forward for the team.
Learn more about CITY’s mission and objectives here.
By Laura Mitchell Tully
