Learning Optimism as You Lead

Ever felt like you are pushing a boulder uphill, only for it to roll back down the moment you think you have made it? That feeling is familiar to anyone who has led creative projects, built teams, or tried to bring new ideas into established institutions. I have been there more times than I can count. Optimism has never been about blind positivity for me. It is about seeing things clearly, recognizing challenges, and still choosing to move forward.

Early in my career, I was leading an ambitious cultural project in a new market. We had a clear vision, a dedicated team, and what felt like momentum. Then, without warning, a regulatory change put everything at risk. The project stalled, tensions rose, and months of work seemed like they might be wasted. It was one of those moments that make you question everything. Why fight for creativity in spaces that resist change? Why push forward when roadblocks seem endless? But after the initial frustration, something shifted. Instead of seeing the situation as a failure, we focused on what we could still control. We found a new approach that not only worked but ultimately made the project stronger. That moment changed the way I think about optimism. It is not about ignoring difficulties. It is about engaging with them and finding opportunities within the challenge.

This idea has stuck with me. It also connects with Stoicism, a philosophy that has influenced my work in curating, strategy, and leadership. Stoicism is not about detachment or suppressing emotions. It is about control. It is about resilience. It is about asking, what is within my power to change? Then focusing all effort on that.

Here are a few ways I have applied this mindset to management, leadership, and innovation:

• Embrace the pivot. Plans fall apart. Strategies that seemed solid suddenly do not work. Instead of resisting change, build flexibility into your approach. Be willing to shift course while staying true to the vision.

• Create a culture of trust. The best ideas emerge when people feel safe enough to take risks. In my work with clients, I have seen that the most innovative teams are not necessarily the most talented ones. They are the ones where people feel comfortable challenging assumptions, experimenting, and learning from failure.

• Focus on what is next, not what went wrong. It is easy to dwell on setbacks. The real leadership challenge is shifting the focus toward what is possible. Instead of asking why this happened, ask what can we do next.

• Celebrate small wins. Progress rarely follows a straight path. Acknowledging each step forward builds momentum and keeps teams motivated.

• Lead with empathy. Leadership is not about pushing relentless positivity. It is about creating a space where people feel supported even when things get tough. Optimism, at its best, is about seeing the reality of a situation and choosing to find a way through.

I have applied these principles in strategic planning for clients across industries, from cultural institutions to global brands. The most effective teams are the ones that acknowledge obstacles but do not let them define the work. Optimism, in its truest form, is about looking at the world as it is without illusions and still seeing the possibilities.

What challenges have tested your optimism? How did you find a way forward?