25 Feb 2026
Lessons from Failure: Shaping Social Enterprises | Part 1
Failure is often where the most valuable learning happens. In this candid conversation, social enterprise leaders share personal stories of setbacks, tough decisions and unexpected lessons. Together they explore resilience, risk, leadership and how embracing failure can strengthen both impact and long-term sustainability.
Summary
This webinar brings together experienced social enterprise leaders to share honest reflections on failure, uncertainty and learning. Through stories spanning start-ups, scale-ups and established organisations, speakers discuss the realities of balancing social impact with financial sustainability and the challenges that emerge when things do not go to plan.
The conversation explores a wide range of experiences, including unsuccessful business models, expansion efforts that failed to gain traction, difficult decisions to close programs, and the personal toll leadership can take. Speakers reflect on the importance of asking difficult questions, recognising warning signs early, understanding opportunity costs and avoiding the temptation to continue investing in initiatives that are no longer working.
A recurring theme is the need to normalise failure as part of innovation and growth. Rather than viewing setbacks as something to hide, participants encourage leaders to share challenges openly, seek support from peers and use failure as a source of insight and improvement. The discussion also highlights the role of boards, funders and trusted networks in helping organisations navigate uncertainty and make informed decisions.
Learners will gain practical insights into risk management, stakeholder communication, leadership resilience and the importance of creating organisational cultures where experimentation, reflection and learning are valued alongside success.
Show notes and quotes:
Kevin Robbie: “On the surface, we were seen as successful. We were growing, we were getting big. But it brought us to the brink of one of our almost biggest failures.”
Sofiah Mackay: “There's a spectrum. Failure is not binary. It's a spectrum. There's a certain degree of failure at one end of the spectrum that you actually want to encourage, because it's about innovation, it's about trying things and then working out the better way to do it.”
“It's interesting, the questions that I'd often find myself posing as a coach when I was working with a lot of social entrepreneurs were things like, what's the worst that can happen? But also, what's the best that could happen? So helping people when there is that fear of failure. Helping people rather than avoiding that fear or that thing that's sitting there, really just going into it.”
Ifrin Fittock: “We know we’ve failed in something, but as a leader, you often think, I'm going to put on my brave face. I'm going to still appear confident, but actually inside you're crumbling down…more and more I realised that that brave face and hiding it yourself is not helping. That is actually really killing you from the inside.”
“Usually, as a CEO of a social enterprise, a leader or a social change leader, you feel that you can't fail. You have to be able to do this, and you have to put on a brave face all the time. I think that is wrong. I started off like that, but I got to the realisation that, no, you don't have to be like that. In fact, I think it makes you more human if you just say, well, I made a mistake, sorry…”
Jaison Hoernel: “If you can give yourself permission to sit in that failure, it's okay. The better you get at sitting in that failure, as you said, being able to emotionally hold that, the stronger that you become at being able to do it, because we should be able to accept failure.”
“If you're trying to make change, which is what you're doing, none of this is easy. You have those moments of gutting disappointment, disappointment in yourself, disappointment for the people around you.”
Mick Cronin: “And that's what I did. I brought in people around me in the team who actually had experience doing that. It took a lot of resilience. I had to dig in a little bit, but I had a lot of determination, and fight to go, yeah, I'm not going to go out this way. I'm going to at least give it a go and see if I can take this social enterprise out of what it's facing.”
“I think it's relationship-based. I think it's being able to have honest conversations. Over time, you'll work with different funders who will have different expectations of what you are trying to do with your social enterprise and the outcomes you're trying to seek.”
Pablo Alfredo Gimenez:. “I think one of the things is just continue to share the failures and what you've learned from them and where you're going to go with those learnings.”
“... if you run a small business, you have sweat equity.”
Explore more:
For those who are keen to dive deeper and do differently, here are some links to learnings and resources mentioned by the speakers and/or related to the open learning topic:
We’d love to hear from you!
Reach out to one of our team members, and share input and ideas about how we can evolve Understorey.
Get in touch