A Christmas game taught me the most counterintuitive truth about creating value—and it has transformed how I lead teams through pressure.
Years ago, during that restless week between Christmas and New Year's, we cracked open Settlers of Catan as part of our family tradition. If you've played it, you know the drill: manage resources, negotiate trades, build strategically, hope the dice cooperate.
After a couple of rounds, I did what any competitive dad would do—I read the strategy guide. One tip caught my attention: trade frequently.
Most players hoard resources. They calculate exactly what they need and guard it fiercely. But what if I took this advice to its extreme? What if I became the most generous trader at the table—even when I needed those same resources on my next turn?
I tried it. Won handily.
Surely a fluke. I tried again. Won by a larger margin.
Third game, same generous approach. Another decisive victory.
By now my family was getting frustrated. "What are you doing differently?" When I explained my strategy to our oldest daughter, her reaction was pure disbelief: "Really? That's what you're doing?"
We decided to test it together. Both of us played with extreme generosity, and for the first time, we were neck-and-neck at the finish. The secret was out.
What I discovered wasn't just a game hack; it was an economic principle. By being generous with trades, we were creating a secondary economy that flowed resources back to us outside the random roll of the dice.
Our generosity generated its own wealth.
Now, before any strategic Catan players start betting their winning streaks on this approach, I still played strategically. I just refused to be tight with my resources. I wanted to see how the experiment turned out more than I wanted to win, but I played smartly. I know many who have tried the same principle and lost spectacularly. We all know financially successful companies that foster environments of control or stinginess.
The difference is knowing how to be generous in good and tough times, not just being generous blindly.
I started seeing this pattern everywhere. My brother-in-law sold his trading company early in his career and has built multiple successful ventures since. He's also one of the most generous people I know. His generous attitude draws people to him, creating what I can only describe as an "economy of abundance" in everything he touches.
Let me share some specific examples of how generous leadership has created value in high-stakes situations:
The struggling employee: I once worked with a poor performer, a recent college grad so eager to prove his independence that he wasted weeks heading in the wrong direction. I had an open conversation, acknowledged his admirable qualities, and clearly but kindly showed him the problem (which I partially owned for letting him run too long without guidance). While he corrected his approach and check-in frequency, I gave lots of personal and team praise for what he was doing well. The result? He became one of our strongest contributors.
The difficult termination: When companies miss expectations, I prefer to handle layoffs personally. Being let go feels devastating. My approach is offering as much generosity as the situation allows; severance, references, transition time, so they feel they have an advocate in their corner during their career change, not just an executioner.
When I was on the receiving end: During a significant restructuring that affected me personally, I leaned into generosity with the CPO and HR team, recognizing that letting people go might be just as hard on them as on the hundreds being laid off. I offered to help communicate the changes to remaining staff, keeping waters calm during the transition. In return, I received dozens of unexpected recommendations, enabling me to quickly land a better leadership position.
The high-stakes negotiation: One client was negotiating with a strategic partner who held the upper hand. I suggested they offer almost scary generosity, a growing minimum seat commitment over time, then ask for generous channel support in return. The partner was so thrilled with the goodness of the offer that they rallied their entire large team to help my client grow. Both companies exceeded their goals by double-digit percentages.
These examples illustrate how generous leadership works in high-pressure environments where scarcity thinking usually dominates.
When private equity takes over, when investors demand results, when teams feel squeezed, the natural response is to hoard information, credit, and resources. But strategic generosity works better.
Generous leaders create their own economies:
I don't practice generosity for the monetary benefit, though I'm confident it has contributed to any financial success I can claim. The real return is different: emotional wealth.
It creates connections that are meaningful, not just transactional. It enables teams to move beyond failure and find value in setbacks that eventually turn to success. It creates hope. It creates peace and alignment—and alignment creates velocity, while division slows everything down.
As I think about the most influential people in my life, they're those who have been generous with me: who see good intent behind my sometimes poor decisions, who offer grace when I stumble, who make me feel better than I think I am.
These are the economies that create true wealth, and they have nothing to do with money.
In a world that teaches us to optimize, compete, and protect our advantages, the most powerful leadership strategy might be the most counterintuitive one: give first.
Not because you're guaranteed a return, but because generosity creates the conditions where value flows more freely: to you, to your team, to your investors, to everyone involved.
The dice will still roll randomly. Market conditions will still fluctuate. Investor pressure will still exist.
But when you've created an economy of abundance through generous leadership, you're not depending on luck to win.
At Upright Insight, I help SaaS executives create alignment and drive performance in high-pressure environments. Sometimes the most powerful business strategies come from the most unexpected places. Learn more about how generous leadership drives results.