Minimizing Regret and Reframing Risks | Colleen Chang

In this episode we sat down with Colleen Chang, founder, writer, and builder, to explore her journey from engineering student to co-founder at Tuuli, a AI software start-up enhancing AEC workflows. She shares honest lessons about navigating risk, growth, and purpose.Rethinking Success and Compounding Small BetsColleen’s story begins during the pandemic, when she realized that the traditional formula of grades, graduate school, and a stable career did not align with the life she wanted to build. Instead of operating on autopilot, she began to think deeply about how to allocate her time toward experiences that mattered to her. This led to a series of small but significant pivots. Switching from civil engineering to computer science, seeking out fellowship programs, and pursuing opportunities outside of the classroom all became ways of moving closer to the future she envisioned. Rather than waiting for a single big leap, Colleen built momentum through a series of smaller choices that compounded over time.The Power of Community and Reframing RiskA key part of Colleen’s journey has been finding communities that inspired her to think bigger. Programs such as Cansbridge and Next36 placed her alongside peers who were prioritizing side projects, startups, and unconventional paths over grades and traditional markers of success. By putting herself in environments where ambition and experimentation were the norm, she was able to expand her sense of what was possible. Alongside this, she reframed her understanding of risk. What felt risky on the surface, such as pursuing a startup, was far less dangerous than the hidden risk of stagnation—remaining in a role that did not allow her to grow or create meaningful impact. Through this lens of regret minimization, she chose to bet on herself early, before life brought additional obligations that might have made such choices harder.From Exploration to MasteryColleen’s journey also reflects the balance between being a generalist and becoming a specialist. In her early years, she gave herself permission to explore broadly, testing different interests in sustainability, engineering, and design. Exploration helped her discover where her energy naturally flowed and what problems she cared most about solving. Once she found that intersection of skills, value, and growth potential, she began to dive deeper and commit fully. This has led her into the world of startups, where she has embraced not only the technical side of product development but also the surprising and deeply human aspects of sales and storytelling. For Colleen, sales is not about being the loudest voice in the room, but about practicing empathy, understanding problems deeply, and helping others find solutions that truly serve them. Storytelling has also become central to her growth, both in building her company and in shaping how others understand her vision for the future.The Importance of Rest and Human ConnectionEven in the intensity of startup life, Colleen emphasizes the value of rest and non-metric driven joy. Running, meditation, hosting dinners, and spending time with friends provide balance and creative fuel. These moments of slowing down remind her that not everything has to be optimized for growth or outcomes. They are essential for sustaining a clear mind, maintaining perspective, and nurturing a sense of purpose beyond work. Rest, she argues, is not wasted time but an investment in resilience and long-term creativity.Actionable TipAdopt a regret minimization framework. When faced with a decision, ask: Years from now, what would I regret more—taking this chance and failing, or never trying at all? This simple shift helps transform fear of failure into motivation to act.To practice, try thinking of times when it was difficult to make a decision, or when you felt very conflicted. If you used the regret minimization framework, how would you have made your decision? Would it have been similar, or different?Connect with Colleen on LinkedIn and Instagram (@colleen_sora)! This article accompanies our podcast episode featuring Colleen Chang. You can listen to it here on Substack, or through Spotify and Apple Music.References:* Strive: College Students’ Revelations During a Global Pandemic by Colleen Chang* Cansbridge Fellowship* Next36 Founder Development Program* Tuuli (startup creating AI tools for architects, which Colleen co-founded with Vit and Arpan) This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit thepragmaticdesigners.substack.com