͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏

Forwarded this email? Subscribe here for more

👔 Coaching | 🎙️Podcast | ⏱️ Stopwatch | ⏰Off The Clock | & Guild | 📚 Books

Thanks for being here. I know your inbox is valuable, and your commitment to timeless ideals amid timely worries is admirable.

If you’d like more, please feel free to use this discount to join the & Guild with a discount:

Get 20% off for 1 year

Uncertainty & Unpredictability

We need assurance to make good decisions; four questions to keep us grounded

Scott Monty

May 21

READ IN APP

*King Lear* by Benjamin West, 1788 (public domain - Museum of Fine Arts)

“The oldest and strongest emotion of mankind is fear, and the oldest and strongest kind of fear is fear of the unknown.”
— H.P. Lovecraft, 1927

One of the constants of any era is uncertainty. In normal times, we don’t think about it often, because each day is similar to the previous, with a degree of repetition and predictability built in.

But what if each successive day is not like the previous, leading us to attend or expectations with fear, dread, or indecision because we don’t know what to expect?

Take the current state of tariffs. Since the inauguration on January 20, the administration has announced new or revised tariff policies more than 50 times.¹ On average, that’s a change every other day and it is having an effect.

Unsure about what to expect, small businesses are worried about the labor market and unpredictable trade policy.²

None of us should be surprised. Because as unpredictable as our current situation is, we’ve seen this kind of human behavior before.

This Stage of Great Fools

Shakespeare’s King Lear is one of the most powerful explorations of the consequences of poor leadership, especially when a ruler lacks clarity, consistency, and self-awareness.

The entire tragedy is set in motion by Lear’s failure to lead with wisdom, and it offers a textbook example of how a leader’s erratic behavior and shifting commands can plunge an entire realm into chaos.

Initial Act of Indecision and Misjudgment

At the very beginning of the play, King Lear makes a critical and impulsive decision: he plans to divide his kingdom among his three daughters based on who loves him most. This “love test” is a display of vanity and insecurity, not wisdom or political savvy, and it sets up the competing factions:

Cordelia, the daughter who loves him most, refuses to flatter him with flowery language. Lear misinterprets this as disloyalty and rashly disowns her.
He then divides the kingdom between Goneril and Regan, whose exaggerated declarations of love are purely manipulative.

This decision is not just poor judgment — it reflects a king who confuses personal emotion with statecraft, and whose sense of authority is dangerously unstable.

Erratic Leadership and Conflicting Expectations

After abdicating formal power, Lear still expects the privileges and authority of a king. He retains his cohort of knights and imposes himself on his daughters’ households.

When Goneril and Regan start restricting his authority and questioning his behavior, Lear reacts with fury, issuing curses and threats but with no real power to enforce them. He swings wildly between trusting one daughter and the other, unable to accept that his earlier decision was flawed.

This confusion increases as his expectations, both as a father and as a former king, clash with the political reality of having given up his rule.

When his daughters speak of his “unruly waywardness” and “unconstant starts” they indicate it is impossible to follow a leader who rules by impulse.

This instability results in a number of things:

Unclear political leadership: There is no firm ruler of the realm. We continue to see Goneril and Regan vying for control while Lear twists in the wind.
Confusion among the court: The dukes of Gloucester, Kent, and Albany are caught between shifting loyalties and unclear directives.
Civil conflict: The country descends into political chaos, with alliances formed and broken based on personal vendettas, not coherent leadership.

The Consequences

Lear’s initial and continuing indecisiveness spirals into madness, exile, and ultimately, civil war. His journey into mental breakdown mirrors the unraveling of his kingdom.

The lack of stable leadership creates a power vacuum that is easily exploited by opportunists like Edmund. The moral and political order collapses, symbolized by Lear wandering the heath in a storm, stripped of power, reason, and dignity.

By the end, nearly all major characters — including Lear and his daughters — are dead [oops, spoiler alert] and what remains of the kingdom is left to be picked up by the few surviving noblemen.

In King Lear, we see a narcissistic king challenged by adversity, but rather than learning and adapting, he doubles down on his self-absorption as others try to attend to him. It provides a valuable lesson.

Never try to satisfy the ego of a narcissist. It is a bottomless pit. Once you think you’ve filled it, the false bottom opens and there are two more chambers to be filled. And in the process, you may find yourself getting sucked into one of them as you and your services are suddenly deemed worthless to the narcissist’s ends.

Worse than the never-ending needs of a narcissist’s ego is the quicksand of his desires. You may think you’re on solid ground, but things can shift in a nanosecond, as a bruised ego may demand retribution or his gnawing lack of self-confidence may conjure up actions purely meant to overcompensate.

One of the greatest gifts leaders can provide is a clarity of vision and mission, communicated simply and consistently, and executed relentlessly.

Regular communication and transparency of your plan, updated with changes to reflect changing realities, is essential. When people lack information, they make assumptions based on confusion and fear.

Leading Through Uncertainty

So how should we lead when it is so difficult to predict what will come next?

The first thing is to realize this: there will always be elements of the world that are out of our control. And it’s fruitless to worry about them.

That doesn’t mean we ignore them; I tell all of my clients that the weekly business plan review meetings I help them conduct need to acknowledge the current reality.

Of course, we can’t keep altering our plans every other day based on “unconstant starts,” but we can build a plan with guardrails and assumptions.

There are some questions you can ask yourself and your team that help provide some grounding amid ambiguity — questions that work at both a professional and a personal level.³

What decision today will still make sense a year from now?
If a year from now this decision was used as an example of our leadership, what would it teach?
What if this isn’t the storm — what if it’s the climate?
What’s the cost of waiting?

The Secret Sauce

Amid all of these decisions and uncertainty, as a Timeless Leader, you have a secret weapon — something that no one else has.

Yourself.

Not just you, but how you show up.

That matters more than anything. Every day, how visible you are, how much you communicate with people, how much time you spend sharing what’s happening and why you’re doing things, and most of all, listening.

Listening to their concerns, their fears, their unspoken needs.

That’s what people need most when they feel unmoored. They need an anchor. A rock. They need you to be something for them.

Because, as Lear cautions us:

“Nothing will come of nothing.”