When to Use Optimism vs Pessimism as a Leader: Reflections from the Jump Offsite 2024

I like to think of myself as a glass-half-full kind of person. But if I’m being completely honest with myself, I’ve spent a lot of the last 3 years, since COVID lockdowns mired in pessimism and fear. Our world is warming at an alarming rate, economic inequality is deepening, and we seem to be constantly teetering on the precipice of a recession.

So thats why, on the second day of the Jump Offsite, I was surprised when I heard someone use the metaphor of childbirth to describe the pain many people are experiencing today. During childbirth, if you don’t know you’re having a baby, you’d think you’re dying . . .but if you do know, it helps you stay focused on the new and beautiful thing you are about to bring into the world. When thinking about that metaphor, I started to feel a lot more optimistic. Maybe our current pain means we’re on the precipice of a state change.

Now I know what you’re thinking. . . this is the part of the article where I’m going to give a trite, bubble-gum recommendation praising the virtues of optimistic vision and denouncing the perils of pessimistic fear. But that’s not the right message at all. Pessimism and fear get a bad rap. They can help motivate us to future-proof our businesses and avoid worst case scenarios. But the challenge with pessimism and fear is that they’re exhausting and sap motivation if experienced for too long.

I walked away from the Jump Offsite this year with a far more nuanced understanding of these two motivating forces and how to couple them in ways that can be uplifting while still driving urgency. Here are 3 things that are sticking with me.

1) “Pain Pushes until Vision Pulls”

This phrase stuck with me when one of the Offsite speakers referenced it. It brings together two conflicting points of view about motivation that I’ve often struggled to integrate. On the one hand, we’re motivated by pessimism? - pain and loss are far more motivating than opportunity and gain. That’s the foundation of the loss aversion theory Daniel Kahneman won a Nobel prize for. But on the other hand, people are motivated by optimism - vision and purpose help people see that their efforts are in service of something greater. That’s the foundation of Simon Sinek’s recommendation that everyone “Start with Why.”? So are we more motivated by optimism or pessimism?

What I realized at the Jump Offsite is that both models can be incredibly helpful . . .but they need to occur at different times. Too much pain and pessimism leads to disillusionment. Too much positivity and optimism leads to complacency. But if you stage things out so “pain pushes” people into action first, and then “vision pulls” them in a way that’s sustainable for the long term, that can be an incredibly compelling combination.

2) Play out both optimistic and doomsday futures

There are countless studies that show how poor we are at predicting what’s going to happen over the next 5 years. The future is inherently uncertain and that’s a big problem for most organizations. During periods of uncertainty most organizations freeze-up. But that’s where optimism and pessimism can help.??

Rather than arguing which future is more likely to happen and amassing ever greater fact bases, the best way for leaders to enroll others to take action in uncertainty is to play out multiple different futures. Play out the pessimistic doomsday scenarios where everything goes wrong. Play out the optimistic winning scenarios where everything goes right. By playing out a broad range of scenarios, people get more comfortable with the uncertainty. And better yet, they start identifying moves they can take today that are “no regrets,” or that increase the likelihood of the futures they want to see. This blending of pessimism and optimism helps teams more strategically navigate uncertainty.

3) Balance the signals you pay attention to

There are thousands of signals and datapoints coming at leaders every day. Based on a leader’s personal feelings of optimism or pessimism about a given topic, he or she will be more naturally drawn to some signals and less drawn to others. Our algorithmic media feeds and propensity for confirmation bias only exacerbate this challenge. So if you’re naturally a techno-optimist your brain is most likely to remember data about how AI is increasing creativity and minimize data showing how it’s propagating historical racial and gender biases. If you’re a climate-pessimist your brain will likely focus on how the rise in extreme weather events is killing more people than ever before, but forget about the new decarbonization solutions that are showing promise.

But whether your brain chooses to focus on it or not, all of those datapoints are true. And all of them are incomplete. A great leader can break out of their confirmation bias, and look for signals that actively negate their default optimism or pessimism. That helps them be more strategically aware, and better at enrolling others who have very different emotional biases than themselves.

When my business partner, Dev Patnaik, opened the Offsite, he swapped the word pessimism for pragmatism.? He said that all the people at the Offsite demonstrated the “Optimism of Mandela with the Pragmatism of Machiavelli,” and I really saw that come to life in the amazing conversations I had with everyone in Napa. The future is not set in stone. We get to shape it. And we have a lot of work to do over the next few years to do that. But I’m left with the feeling that if we can blend optimism and pessimism in ways that make our problems simultaneously seem urgent and solvable, we are capable of much more than we think.