Thriving in Uncertainty: A Workshop with Scott Stirrett
On November 4, 2025, Scott Stirrett (SFS 2013), Founder & CEO of Venture for Canada and author of The Uncertainty Advantage, offered his thoughts on the importance of embracing uncertainty and learning to thrive in it. Laura Sheehan (Georgetown SFS) moderated the event.
In this interactive session, Stirrett drew from his Georgetown experience, efforts in raising $80M to help thousands of young people build entrepreneurial skills, and the latest research to give session participants a clear framework to turn uncertainty into their edge—and accelerate their careers.
He began his presentation by explaining that we all live in a time of “radical uncertainty.” Given the tremendous changes in our political landscape and the increased prevalence of emerging technologies—among other factors—Stirrett implored all attendees to be more aware of their relationship with uncertainty and become more comfortable with it. Indeed, uncertainty is a fact of life.
While Stirrett acknowledged that uncertainty is a primary driver of anxiety, he also stressed that incredible possibilities that simultaneously exist within it. In fact, he credits his greater comfort with uncertainty with his successful career across the financial sector and nonprofit space.
This message is resonates particularly strongly with him as a result of his lived experience: During the COVID-19 Pandemic, he was diagnosed with Obsessive Compulsive Disorder (OCD). Unsurprisingly, this diagnosis not only explained his previously wary attitude toward the unknown, but also sharpened his inclination to learn to accept it and thrive in such environments.
Stirrett’s OCD diagnosis taught him a valuable lesson: facing uncertainty directly is the only path to growth.
During this session, Stirrett maintained that learning to accept, embrace, and thrive in uncertainty is a skill we can develop, only requiring us to grow more accustomed to living with the unknowns and building our personal resilience.
Concerning this latter point, Stirrett identified six key aspects to building personal resilience (also as analyzed in his book, The Uncertainty Advantage):
- Nurture your self-compassion
In essence, this skill requires us all to be “kind to ourselves,” and Stirrett believes it possesses three key aspects: (a) speak to yourself in a positive and encouraging way; (b) recognize our shared, communal humanity; and (c) acknowledge when you are tough on yourself (as well as the reasons why you feel that way).
Considered together, these three aspects of self-compassion should allow us to self-motivate more effectively, contextualize our problems more fairly, and create a clearer and more well-formed sense of purpose and goals more easily.
- Maintain (and encourage) your adaptability
According to Stirrett, adaptability is a core skill that is instrumental in helping all of us overcome challenging circumstances (like that in which we all find ourselves today). This competency is also critical in a rapidly-changing world, where carefully crafted plans can change overnight.
He expanded on this idea by discussing three core aspects of adaptability that he found particularly meaningful in his personal journey: (a) It allows us to draft a personal mission statement to act as a “true north” to guide our job search activities; (b) in developing this mission statement, it requires us to reflect upon and ultimately identify our core values that can help us navigate potential professional decisions or ethical dilemmas; and (c) it encourages an iterative approach to planning, allowing for greater flexibility in both defining our goals and how we achieve them.
- Develop your anti-fragility instincts
Of course, sometimes disorder and confusion can be harmful (and certainly stress-inducing!), or more than an “opportunity in disguise.” In these cases, it is vital for us to learn to not simply “tolerate” uncertainty, but to benefit from it.
For Stirrett, anti-fragility goes beyond questions of survival, toward a more profound belief that we can be strengthened by it and harness it for our own gain. Stated in another way: capitalizing on the opportunity to pursue your true instincts and live your authentic self instills a greater comfort with risk-taking. While Stirrett doesn’t recommend recklessness, some degree of adventurousness is a core pillar that undergirds our personal resilience.
- Sharpen and lean on your generalist skills
As the name suggests, “generalist skills” are broadly applicable across a wide range of professional opportunities and sectors. Logically, enhancing our general skills will likely lead to us finding more job opportunities to pursue – Stirrett agrees. For him, not only can we lean on these competencies in a wide variety of roles but with AI’s emergence (and rewiring of our technical landscape), it is more important than ever to nurture a broad knowledge base across an array of domains to better distinguish ourselves from these new technologies.
In his presentation, Stirrett recognized three generalist skills that he encouraged everyone to sharpen: (a) collaboration, (b) communication, and (c) focus. When utilized effectively together, these three skills allow us all to work with anyone under any circumstance, communicate our needs and goals clearly, and to prove yourself to be a diligent and reliable colleague. Every job will prize these skills.
- Adopt an entrepreneurial mindset
An entrepreneurial mindset is an inherently crucial element in risk-taking, a behavior that can pay dividends in uncertain contexts. It also helps us understand the risks associated with not taking a certain action. Yet Stirrett believes that it is most important in the context of how we are able to identify and act on opportunities to create benefit or value for ourselves and others.
In this vein, this mindset allows us to better identify new opportunities worthy of our time and effort and, ultimately, act on these instincts. Opportunity-identification and decisiveness in action are invaluable skills to possess in times when professional opportunities emerge and disappear quickly. The present day is no exception.
- Commit yourself to network-building
At the end of his presentation, Stirrett identified effective network-building as a key aspect of personal resilience. For him, this skill cross-cuts across all the previous pillars: It not only helps us to identify new opportunities and places us to better seize these opportunities when they appear, but it also equips us with the tools and people needed to help guide us through challenging periods in our lives (job searching included).
Similar to Bill Fitzgerald , Stirrett emphasized the importance of nurturing both weak and strong ties to establish a community of people who will vouch for your skills and invest in your success. He also stressed the importance of “giving first,” and offer any value you have to others. The more you help others, the more likely they are to help you. Finally, he challenged us all to go outside our comfort zones. Doing so will let us meet new people who may be better-positioned to help us and can also help us identify new opportunities.
Throughout the discussion, Stirrett acknowledged how difficult embracing uncertainty can be, as well as how scary it can be in times of economic difficulty or personal stress. That being said, he also reemphasized that opportunity thrives in uncertainty. He believed that how we handle “not knowing” is more important than what you know. Despite the dizzying pace of change, there are more opportunities now than ever before. It is up to us how we confront this challenge.
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