Balancing Optimism + Reality

Wow. I got a lot of great feedback on last week’s newsletter. A biiiiiiig thank you to everyone who reached out. As a follow-up, my aunt is doing well so far. She can breathe, and she is sleeping well. My cousin said, “Best of all, the chip has fallen right off her shoulder!”— which made me laugh out loud.

For anyone who missed it, in the newsletter, I pointed to a truth we all already carry: At any given time, any one of us— and the people we lead— are dealing with something sad, or difficult, or demoralizing, or depressing.

I heard from one subscriber (Thank you, Alan!) who said he’s been a longtime readers of Stoic philosophy. (Google it— it’s pretty cool stuff. Practical, too. One of the tenets is to differentiate what we can control with what we can’t, and being able to accept fate as an outcome. Ummmmmmyesplease.)

One quote has been stayed with him, Alan said. It came from POW Admiral James Stockdale in an interview with Jim Collins in the book Good to Great.

Collins had been reading Stockdale’s memoir, In Love and War, and found himself depressed by the sheer brutality and uncertainty Stockdale faced. He asked the Admiral how he dealt with the reality of his situation when he didn't know the end of the story. How did one survive seven years as a prisoner of war? Collins wondered. Who did survive? Who didn’t?

The optimists didn’t survive, Stockdale answered. These were the men who would say, "We’ll be out by Christmas." Christmas would come and go, then they’d say, "We’ll be out by Easter." Then Thanksgiving. Then Christmas again. Ultimately, these faithful optimists did not survive. Their hearts were broken, their hopes were repeatedly shattered by reality.

That’s why, Stockdale said, “You must never confuse faith that you will prevail in the end—which you can never afford to lose—with the discipline to confront the most brutal facts of your current reality, whatever they might be."

When I read these words in Alan’s email, I literally put my pen down and stared at the screen.

I felt both peace and inspiration.

Peace because it is permission let go of the idea that optimism is that dreaded “toxic positivity.” Optimism can be seen as faith— a genuine belief that things will be okay. It is internal (resilience), while toxic positivity is external (ignoring others' pain).

Inspiration because it describes a critical psychological balance. As leaders, we can be a bridge between optimism and realism.

Let’s be real— optimism and realism can appear to conflict with one another.

But Stockdale is essentially telling us that the two must exist at the same time.

As a POW, instead of saying, “We’ll be out by Christmas,” Stockdale’s approach was to accept the reality: "We are not getting out by Christmas; in fact, we might be here for years.” He let himself see that the days were going to be very difficult. Yet he maintained his optimism— “I will get out eventually, and this experience will be the defining turning point of my life."

This mindset reminds us that hope is not a stand-alone strategy. You cannot simply "positive-think" your way out of a crisis. You must have the courage to acknowledge exactly how bad things are right now, while simultaneously holding onto the belief that you have the power to overcome in the long run.

I don’t have to point this out to you, but the application to school leadership is pretty aligned.

Optimism is that deep, fundamental belief that you will prevail. That things will be okay. That you shouldn’t give up; you should keep willing yourself to move forward.

Realism is the discipline to look at your current situation, no matter how bad it is, and see it for what it is. It’s the willingness to look at difficulty right in the eye.

So, as we navigate the rest of this month, don't feel the need to ignore, sugarcoat, or breeze over the staffing shortages, the budget constraints, legislative mandates, or the heavy hearts in your hallways. Look at those facts with clear, honest eyes. But as you do, hold fast to that underlying faith and optimism—the knowledge that your work matters, your school is resilient, and you will prevail.

Being a leader doesn't mean having all the answers right now; it means having the discipline to face the truth today while never losing sight of tomorrow.

With gratitude to all of you, you leadership champions—

Jen

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P.S. Keep sharing this newsletter with your colleagues.

P.P.S. As a weekly reminder, no AI is used in creating this newsletter. It’s just me and my keyboard!