Nothing Is Ever as Good—or as Bad—as You Imagine
One of the hardest parts of leadership is making decisions when the outcome is unclear.
We want hard decisions to be obvious. We dream of a moment where the right answer appears fully formed. It is right in front of us and guaranteed to work out exactly as we hope.
At the same time, we fear the opposite. We imagine the worst-case scenario: a single decision cascading into failure, criticism, or lasting damage.
Here’s the truth most leaders learn the hard way:
Nothing is ever as good as you can dream it—or as bad as you can imagine it.
And that truth changes everything when you’re making tough decisions.
The Trap of Imaginary Outcomes
When leaders struggle with decisions, it’s not because they lack intelligence, experience, or good intent.
It’s because they are measuring today’s decision against an imaginary future.
- A perfect outcome that likely doesn’t exist
- Or a catastrophic failure that probably won’t happen
Both are distortions.
When we compare real, imperfect decisions to imagined perfection or imagined disaster, we paralyze ourselves. We hesitate. We delay. We over-optimize. Or we avoid deciding altogether.
That’s not leadership. That’s fear disguised as analysis.
Decision Quality Is Not Outcome Quality
One of the most important lessons I’ve learned from combat operations to nonprofit leadership to higher education is this:
You cannot judge a decision solely by its outcome.
Good decisions can lead to bad outcomes. Bad decisions can sometimes get lucky.
What matters is the quality of the decision at the moment it was made.
That means asking:
- Did I act based on my principles?
- Did I seek clarity, not comfort, when I ask for input?
- Did I bring in dissenting views rather than protect my ego?
- Did I decide when it was time to decide?
If the answer is yes, then you made a good decision, even if the outcome wasn’t what you hoped.
Stop Chasing Certainty
Certainty is seductive and often unavailable.
Leaders who wait for perfect information usually wait too long. In complex environments, the data is incomplete, the variables are changing, and time is a constraint, whether you like it or not.
Instead of chasing certainty, focus on disciplined decisiveness:
- Anchor yourself in clear principles
- Maintain the humility to invite other perspectives
- Accept that ambiguity is part of leadership
- Decide and own the decision
Decisiveness does not mean arrogance. It means accepting responsibility when there is no "good" option. Often, you must accept that you are choosing the least worst option and moving on.
Make the Best Decision You Can—Then Lead Through It
The goal is not to guarantee the best outcome. The goal is to make the best decision you can at the time and then lead well through whatever follows.
That includes:
- Adjusting as new information emerges
- Taking responsibility rather than assigning blame
- Learning without self-flagellation. No one likes a leader who does that.
- Moving forward instead of replaying the decision endlessly
Leadership is not about avoiding risk. It’s about making principled choices in imperfect conditions.
Final Thought
If you’re facing a hard decision, here’s a simple reframe:
Stop measuring yourself against an imagined future, good or bad. Start measuring yourself against your values, your preparation, and your willingness to decide.
Because in the real world of leadership:
Nothing is ever as good as you can dream it.
Nothing is ever as bad as you can imagine it.
But indecision is almost always worse.
