The Leader’s Paradox: Facing Reality While Shaping What’s Possible
We've all had one of those days. In meetings and emails, the updates come at you – and they are not what you would have hoped for. And yet, each one provides important information about the reality you’re being called to lead through.
On one such day, as I absorbed another unwelcome update, I was reminded of the perpetual tension leaders face:
We must take the world as it is, not as we think it should be.
And yet, we must make the world not more of what it is, but more of what we think it should be.
This is the paradox at the heart of effective leadership. We must simultaneously lean hard into understanding reality exactly as it is, while also working to transform it into something else entirely.
So how do we embrace "what is" while also striving for "what could be"?
Embracing What Is
Henry Cloud, in his book Integrity, writes one of the lines I most often repeat to myself:
"Reality is always your friend."
By which, of course, he doesn't mean that reality is always pleasant or convenient. He means that understanding reality is invariably more helpful than not understanding it—or worse, avoiding it altogether.
Reality is the only solid ground from which we can move forward. When we deny what's really happening, we build our strategies on quicksand.
A question I've been challenging myself with recently is this: "What am I trying not to think about?" The answer often reveals where there might be some reality I need to face. And when I do face it, that background anxiety my mind creates when pushing something to the edges of consciousness begins to dissolve.
The problem is that reality can be uncomfortable:
Sometimes it means accepting that an approach isn't working
Sometimes it means recognizing we’ve misjudged a decision
Sometimes it means acknowledging our own limitations
But here’s what I’m continuing to learn: the temporary discomfort of facing reality is always less costly than the prolonged pain of avoiding it. And like all of us, I’m still working on fully embracing this particular reality.
Envisioning What Could Be
Early in my undergraduate studies, I fell in love with Henry David Thoreau's classic, Walden, during an English Literature class. One line continues to resonate:
"The question is not what you look at, but what you see."
Reality is only the starting line—the vantage point from which we envision what could be. What, indeed, we believe should be.
This is where leadership begins to brim with possibility. Two leaders can look at exactly the same market conditions, the same organizational challenges, the same resource constraints, and see entirely different possible futures.
Where one sees only obstacles, another sees constraints that spark creativity. One sees problems, while another sees possibilities.
The difference isn't in what they're looking at, but in what they see.
From Here to There: The Leader's Journey
The space between "what is" and "what could be" is where leadership happens. It's where vision meets execution, where aspiration meets perspiration, where dreams become deliverables.
On that day of multiple pieces of unwelcome news, I asked myself a question that has become increasingly valuable: "What does this make possible?" Conditions had changed, and not in ways I would have chosen; but what new possibilities might have opened up as the pieces were rearranged?
This question helps me shift from passively reacting and feeling disempowered to actively imagining and shaping what might be possible.
It's also where we need to distinguish between wishful thinking and inspired vision:
Wishful thinking ignores reality. Inspired vision acknowledges reality but isn't limited by it
Wishful thinking is primarily emotional. Inspired vision engages both emotion and intellect
Wishful thinking waits for circumstances to change. Inspired vision creates the change it seeks
And then comes the real work—leading teams, developing strategies, implementing plans, measuring progress, adjusting course. Getting it wrong sometimes. Recognizing that now we have more information (my favourite mental go-to line when things don't go to plan), and moving forward again, this time hopefully a little wiser and better prepared.
The Beautiful Paradox
Perhaps this is leadership's most beautiful paradox—that powerful visions aren't built on fantasy but on the most unvarnished truth. The path to what could be begins with the clearest possible view of what is.
The tension of leadership lies not in choosing between realism and vision, but in holding both simultaneously. We embrace what is so we can create what could be.
So maybe the next time you find yourself in one of those days, when reality seems determined to test your resilience, remember that each piece of unwelcome news is not just a challenge but an invitation. An invitation to lift your eyes, see clearly, and step into the possibility space between what is and what could be.
That space is where our leadership comes to life.