You may have been taught not to fly too high and not to fly too low. Stay in the middle. Be careful. Do not draw too much attention to yourself, but do not perform so poorly that people begin to question you.
For many people, the middle feels like the wise place to be. You are not the winner, but you are not the loser either. You avoid the embarrassment of failure and the danger of falling from a great height. You remain safe, accepted, and difficult to criticize.
That may be a good way to avoid trouble.
It is not a good way to play to win.
The Lesson We Remember from Icarus
In the Greek myth, Daedalus warned his son Icarus not to fly too close to the sun because the heat would melt the wax holding his wings together. He also warned him not to fly too low because the sea could damage the wings. The instruction was to stay in the middle.
Most people remember what happened next. Icarus flew too high, the wax melted, and he fell into the sea. The story became a warning against pride, excess, and reckless ambition.
But stories do more than teach us what happened to one character. They shape what we fear.
Many of us grow up hearing our own versions of the same warning. Do not dream too big. Do not make yourself too visible. Do not challenge people who have been there longer. Do not reach too high because the fall will hurt.
The result is not always humility. Sometimes it is self-protection.
The Safety of the Middle
In some Filipino workplaces, people are encouraged to preserve harmony even when that harmony keeps the wrong person in the wrong place. You may be more capable, but someone else has served longer. You may have a stronger proposal, but presenting it too forcefully may be seen as stepping on another person.
The advice often sounds kind: do not hurt anyone, do not create conflict, and do not make others feel small. Those are good intentions. But they can become excuses for avoiding competition, delaying necessary decisions, and protecting arrangements that no longer serve the organization.
This way of thinking also appears in strategic planning.
Managers are asked to propose targets for the coming year. They do not want to submit a number so low that senior leaders become angry. But they also do not want a number so high that they may fail publicly.
So they choose the middle.
The Target Everyone Could Defend
During the strategic planning session of Company Z, Mara proposed a five-percent increase for her unit. She explained that the number was realistic. The economy was uncertain, competitors were aggressive, and her team was already busy.
Nobody could accuse her of lacking ambition. Five percent was higher than the previous year. It sounded responsible, and the team could probably achieve it without changing very much.
That was precisely the problem.
The target was not chosen because five percent represented a meaningful win. It was chosen because Mara could defend it. If the team achieved the target, she would look competent. If the team missed it, she could explain that conditions had been difficult.
The number protected her from being called a loser.
It did not require her to become a winner.
Fear Makes Success Smaller
Fear does not always prevent people from making plans. Sometimes it quietly lowers the meaning of success.
A manager begins calling modest improvement a strategic win. A company celebrates staying within budget, even though it created nothing new. A team completes every project on time because it accepted only projects it already knew how to do.
The reports look good. Nobody gets blamed. The organization survives another year.
But survival and winning are not the same.
A company can stay in the middle for a long time. It can remain profitable, respectable, and largely unnoticed. Its leaders may even say that this proves the wisdom of their approach. They lasted because they did not compete too aggressively.
What they do not see is the opportunity cost. They do not see the customers they could have served, the capabilities they could have built, or the future they could have created. The middle protects them from visible failure, but it also protects them from meaningful progress.
Change Your Questions
Mara was asking, “What number can we safely promise?”
She needed to change her questions.
What result would make this year worth the effort? What opportunity are we willing to pursue? What must we do differently to create that result? Which capabilities must we build, and what must we stop doing?
These questions do not encourage reckless ambition. Playing to win does not mean setting a ridiculous number and demanding that people somehow deliver it. A winning aspiration must still be honest about resources, risks, and reality.
But it must begin with the result worth creating, not the embarrassment worth avoiding.
When leaders begin with safety, they reduce the goal until it fits the organization they already have. When they begin with winning, they examine what the organization must become.
That is the shift.
Your Play-to-Win Challenge
Review one target you have set for yourself, your team, or your organization. Ask why you chose it. Does it represent a result worth winning, or is it simply high enough to avoid criticism and low enough to protect you from failure?
Then write a second target. Make it ambitious enough to require a different choice, a new capability, or a bold experiment. You do not have to announce it immediately. First, study what must change to make it possible.
The middle may keep you safe.
But when the game requires courage, being in the middle may only mean that you have chosen not to lose.
It does not mean you have chosen to play to win.
About Jef Menguin
Jef Menguin is a leadership development consultant, professional speaker, and founder of Strategic Learning Consultants. He helps CEOs, HR leaders, and L&D teams connect leadership development to business goals and turn strategic priorities into daily leadership behavior.
Explore his work in leadership training, learn about his motivational speaking programs, or connect with him on LinkedIn.