Maybe You Can't Means Maybe You Can!
- Leadership
The Moment Leaders Get Stuck
Most leaders instinctively measure today against the version of today they imagined.
There is a moment that shows up in almost every executive coaching engagement. The leader across from me has a goal. A transformation they want to make. A capability they are trying to build. A version of themselves they are reaching toward. And somewhere between the ambition and the action, they get stuck. The calendar fills up. A reorg scrambles priorities. A key initiative stumbles. The question shifts from "how do I get there?" to "what is the point?"
That moment is the most interesting one in coaching. Not because I have a clever framework ready. Because everything that happens next depends on one thing: whether this leader is willing to operate as an optimist.
Optimism, Pessimism, and the Realism Confusion
People confuse realism with pessimism, but they are not synonymous. Pessimism is a disposition to expect the worst; realism is a commitment to seeing things as they are. You can be deeply realistic and deeply optimistic simultaneously—the best leaders I've worked with are both.
The pessimist concludes: "I knew this wouldn't work." The realist says: "This is where we are." The realistic optimist adds: "So what's the best we can do from here?" Realism and optimism are compatible.
Living in the Present
Coaching starts with the future — where you want to go, what you're building toward. But the actual work lives in the present, right here, right now.
The future is aspirational. The past is informational. Today is where capability gets built. Every insight that does not translate into a different behavior today is an interesting conversation and nothing more. The entire arc of a coaching engagement lives or dies on what a leader is willing to do on any given Tuesday, when they are tired and their inbox is full.
This is where optimism becomes a professional requirement. If you do not believe the work you are doing today is moving you forward, you will not do the work. You cannot sustain the discomfort of genuine growth unless you believe, at some foundational level, that it is going somewhere.
Pessimists do not change. Not because they are incapable. Because their operating assumption is that trying will not matter.
The Cost of All-or-Nothing Thinking
The all-or-nothing approach is one of the most common and most costly traps in leadership development. It turns every imperfect attempt into a referendum on the entire effort.
High performers are especially vulnerable to this: the belief that partial progress doesn't count.
It shows up as perfectionism — which sounds like standards but often functions as an exit ramp. If it can't be done right, why do it halfway? This logic feels principled. It's actually a way of avoiding imperfect effort.
The real cost is compounding. The leader who waits for ideal conditions doesn't just lose those days — they build a habit of waiting. Meanwhile, the leader who does the available work on the imperfect day keeps moving.
The Only Question Worth Asking
Realistic optimism is disciplined. It means accepting the situation as it actually is, then asking: what can I do today? Not what should I have been able to do — what is actually here, right now, that I can work with?
Progress is built on ordinary days. The Tuesday when the plan fell apart and you moved forward anyway. The week the energy wasn't there and you kept going.
Maybe you can't do what you planned. But you can still make progress.
“Maybe you can't” includes the possibility that “maybe you can”. You can do something. And something, done with intention and a willingness to learn from it, is something worth doing.