Let the Higher-Ups Be Generous── Separating a worry from a risk

I often wish leaders would be generous. Not simply soft. It means telling a personal worry apart from an organizational risk, so you don't scoop up every scattered unease and tire everyone out. It means walking first toward a faint, far-off goal, and moving on without turning around. And if I never meet such a person, I can become one myself.

01The moment a "worry" turns into a "risk"

It was a Wednesday afternoon, at the regular meeting for material review. The person in charge picked up a proof of a promotional piece, stayed silent for a while, and let this slip: "Somehow, this one worries me." He gave no reason. Just worried. That was all.

I took a note on the spot. The next week, I opened the minutes that had been circulated, and was a little surprised. The phrase "somehow worried" was nowhere in them. Instead there was an item headed "Serious Risk," and under it three points to check, listed out. No one had decided to write it that way. The flow of the meeting had, at some point, made that translation on its own.

From the following week, the staff member started working late. To clear the three checkpoints, she wrote to another department inside the company, gathered documents, lined up the evidence. Not a bad thing in itself. But I couldn't stop wondering when, and where, that "somehow" had turned into a "Risk" with a clear outline.

The Danish philosopher Kierkegaard drew a line between two movements of the mind. One is fear. Here the object is clear. The dog in front of you is baring its teeth. The deadline is tomorrow. Because there is an object, you can deal with it. The other is anxiety (Angst = an objectless dizziness before possibility). You can't say what exactly, yet you feel unsettled. He wrote of it as "a dizziness before possibility." Standing at the edge of a cliff, you feel you might fall, and at the same time that you might throw yourself off — that unsteady feeling. Because there is no object, there is nothing to clear away.

That person's "somehow worried" was, I think, not on the side of fear but of this anxiety. An organization, though, cannot leave anxiety as anxiety. Heidegger called the working by which a person can't leave things alone, and ends up minding them, care (Sorge = the root movement of mind that makes a person unable to let things be). As long as a person is alive, it is always at work. In the meeting room, that care gets translated into a "risk item," a shape you can handle. You force an object onto something that had none.

The translating itself is not the problem. But the moment it is translated, you can no longer see whether the source was "anxiety" or "real fear." The words "Serious Risk" in the minutes line both up wearing the same face. And people trust the written words more.

02What is in your power, and what is not

Facing a piece before approval, I always draw one line inside my mind. Up to here is what my own hands can fix. Beyond that lies the other side's judgment, the market's reaction, the one call of the office that issues approvals (the regulator). Without this line, my hands freeze. If I carry all of it as my own responsibility, I can't move at all in front of a single flyer.

Two thousand years ago, a philosopher who had been a slave taught this line-drawing. Epictetus. A man freed from slavery who then taught philosophy. At the opening of his Handbook, he states it flatly: in the world there are things in our power and things not in our power. Telling these two apart he drilled into his students as the dichotomy of control.

His division is harsher than you'd think. What is actually in your power is little more than your own way of thinking, your choices, and your attitude. Your health, other people's opinion of you, tomorrow's weather — all sit on the "not in our power" side. And once you let your mind be captured by what is not in your power, you are bound to be thrown about. Pour your strength only into what is in your power, and the mind can stay still.

What I've seen again and again on the floor is this mix-up. A senior person's private anxiety — the "somehow" they can't quite explain to themselves — usually sits on the "not in your power" side. That in itself is natural. The more responsibility, the more worries pile up. The problem starts when that private anxiety slides sideways into a "Risk" the organization must manage. One person's uneasiness quietly turns into three people's overtime.

Marcus Aurelius, a Roman emperor, kept writing his Meditations addressed to himself. Carrying a greater weight than anyone, what he told himself over and over was: don't let your mind ripple at every thing that comes from outside. Self-command and calm in the one who leads. That is not coldness. It is a kind of embankment, so your own anxiety does not pour straight into your staff's workload.

You draw the line not to let go of responsibility. Quite the reverse: to keep from losing sight of the one point you truly should tend. Don't misplace worry over what is out of reach onto the shelf of what is in reach. This plain check might have cut a few of the three extra checkpoints that grew that Wednesday afternoon. That's what I believe.

03Scattered risks quietly bring people down

Once, checking a piece, I added yet another check item. The source of a figure, the placement of a footnote, the year of the paper cited. The moment of adding feels good. There's a sense that you're not cutting corners. Your body says you're doing the right thing. So you don't stop.

Before I knew it, the check items had passed twenty. Around then, the colleague who made materials most carefully of all fell ill. The most capable junior left the department without saying much about why. Neither had broken any rule. If anything, they were the ones who tried to keep every rule. At first I thought it was chance. I don't think so now.

There is a philosopher from Korea, Byung-Chul Han. He called our age the "achievement society". Old-style management took the form of a superior ordering an inferior to "do it." Now it's different. Even with no one ordering us, we drive ourselves. More carefully, with fewer gaps. Han called this self-exploitation. It leaves less room to escape than a whip from outside, because you are the one holding the whip.

Adding one check item is not an order. It's goodwill — the honest wish to miss fewer things. But goodwill stacks up. Those twenty-odd checks, born of no one's ill will but as the sum of everyone's conscience, press heaviest on the most earnest person's shoulders. People who cut corners ignore the added items from the start. The one who falls is the one who tried to carry all of it.

• The choice to add one risk costs almost no pain. So there's no brake on it.
• The added burden piles up not on the average, but lopsidedly on the single most honest person.
• When a strong person leaves in silence, it's a signal of the limit, not selfishness.

I was afraid to cut check items. If an accident happened after I cut one, I thought, and my hands froze. But a person falling because items were added is a fine accident too. To count only one kind of accident and not the other is not carefulness. It's just seeing only what you want to see.

04Generosity is neither softness nor letting things slide

When you hear "a generous leader," you picture someone who forgives anything. Doesn't fuss over details, gives you the benefit of the doubt. But the person I really leaned on at work wasn't that. He'd catch a mismatch in a figure's source in one look, yet cut off my small anxiety with "that one you don't need to count as a risk." He missed nothing, yet didn't scoop up too much. He stood right in the middle.

This is not timidity. The timid person, unable to pick anything, picks everything. Nor is it letting things slide. The one who lets things slide won't pick up even what matters. The senior I relied on was neither. He decided, case by case, what to pick up and what to drop. The measure of a person is not being able to forgive a great deal, but being able to decide what to keep and what to let go — that's what I learned then.

The ancient Greek philosopher Aristotle named this well. He explained a person's goodness through the mean. Courage lies between recklessness (too much) and cowardice (too little). The measure of a person is the same. Not one who carries everything, nor one who carries nothing, but one who stands between — this he called megalopsychia.

How to find the middle can't be written into a textbook rule. Aristotle thought so too. So he gave a name to the wisdom of looking closely at the situation and judging what is fitting here and now: phronesis. The middle has no fixed, set position. The other person's experience, the content of the piece, how near the deadline is — you look at all these particulars, and only then does it settle, each time. That's why a judgment that worked last year, brought over as is, misses this year.

This wisdom isn't gained from reading books. You get it only after seeing many pieces, passing through both kinds of failure — picking up too much and wearing people out, and dropping too much and drifting near an accident. Generosity was not a gentleness you're born with. It was the power to read a situation, gained at last after stacking up countless judgments. It sits on the opposite side from softness, and is the most laborious work of all.

05Stepping first toward a far-off point

In a material review meeting, you sometimes hit a case with no clear destination. Is this claim too aggressive, or within bounds? The data is there, but readings split. No one holds the right answer — that suspended time. In such moments, when someone speaks up first with "This is how I read it, so this is how I'd fix it," the air in the room moves. Even with the direction still hazy, when there's the back of someone who stepped half a pace forward, the anxiety behind thins out.

The interesting thing is that such people don't turn around to count heads. They don't check, "Everyone still with me?" They trust that people follow, and put their foot forward first. Even if the back of the line stirs, they don't stop for each murmur. This "walking at the front" comes, roughly, in three styles. It's not about which is right. The same step, but the motive for taking it differs.

What the three share is that the motive for standing at the front is not "to make yourself look big." ① steps forward to support, ② to show, ③ to hold the line. None of them is a step taken to count heads behind and feel reassured. That's why they need not look back. Serving first, showing a picture first, or quietly not breaking first — the order differs by person. But what reduces scattered anxiety was, without fail, "the back that stepped out first."

Back on the review floor, I think this: it's exactly when you can't point to the destination that a leader's measure shows. If you can't declare the direction, at least say first how you read it. That becomes a half pace. The people behind take reassurance not from the right answer, but from that half pace. Advancing beats counting. Trusting, and showing your back, moves the line forward in the end.

06The strength of not looking back

After you've decided "let's fix it this way" and started moving, if the leader keeps glancing back, the whole line stops. The same happens in material review. The person in charge keeps dredging up a point they'd already decided: "Is this really all right?" Then the staff halt their next move and start reading the boss's face. The power to go forward comes from not dragging along what's done and small anxieties. The habit of looking back after deciding looks like kindness, but it actually freezes the line.

A tightrope walker does not look down. The instant they mind the height under their feet, the sway travels into the body and they fall. Because they look only at one far-off point, they can bear today's single step. Where does the power to face forward come from? I want to check this against two thinkers' words. Difficult names come up, but the substance is not far from the feel of the floor.

One is Nietzsche. A thought he repeated is "self-overcoming." And another, amor fati. It's not making a past failure "as if it never was." Having admitted it happened, you take it on as part of your own road. So you needn't dig back through the past. His Thus Spoke Zarathustra has a tightrope walker in it — a parable that the meaning lies not in reaching the far side, but in the figure crossing, still on the way.

The other is Viktor Frankl. A psychiatrist who survived the concentration camps, he wrote that what holds a person up is not pleasure or power but "the will to meaning." His observation was this: a person who holds a far-off purpose can bear today's exhaustion. Those who lost their purpose ran out of strength first. When today's step is hard, what holds you up is not "today getting easier" but the sense that "there is a place ahead I want to reach."

Of course reflection is needed. Before you decide, look back all you like. Data and past cases of deviation should be checked stubbornly. But looking back after you've decided and started walking is a different thing in kind. It easily becomes not verification but the re-manufacture of hesitation. On the rope, you no longer look down. The farther the purpose, the more you can bear today's step. That one person can use both — caution before deciding, and the strength to face forward after — is what I'd call measure.

07If you can't meet one, become one

In reviewing a piece, I once wavered over a judgment. The data was correct, with footnotes. But the headline was one a reader might misread. Ask upward, and I'd likely be told "match the precedent." Ask sideways, and I'd get back "don't make waves." I was waiting for someone to show, clearly, "here's how to think about it." For someone generous, who'd walk at the front.

For a long time I kept looking for such a model. Calm like that senior, principled like that boss — I sought the ideal shape outside myself. But the model isn't always there. They're busy, or transferred, or simply never held the same trouble. While you wait, the piece halts. My judgment halts too. One day I stopped waiting. If the model won't come, I have no choice but to take on the judgment myself.

The American thinker Emerson, in a short essay called Self-Reliance, wrote this: stop imitating others, and trust the voice that comes from within. The "self" he means is not selfishness. It means standing on what you yourself have looked into and confirmed, not on other people's faces. That was exactly what I wanted to protect in the piece. I don't keep to the precedent because the precedent is right. I confirm with my own eyes the single point that the reader won't misread, and I stand there.

One more, the French philosopher Sartre, whose words land. He said "existence precedes essence." We usually think the reverse. A paper knife is made because the content "a tool for cutting" comes first. But a human is different. It's not that the mold "this is what a leader is" comes first and you pour yourself into it. You stopped waiting for someone's example, chose for yourself, and took on the responsibility. That accumulation becomes, afterward, "who that person is."

Strangely, from the moment I stopped waiting, I stopped being thrown about by other people's anxiety. Before, every time the person beside me murmured "I wonder if it's okay," my judgment clouded too. Now it's different. I take anxiety in as anxiety. But whether to pass or stop a piece, I decide by the facts I've checked. It's close to this: I'd handed the compass to someone outside, and I took it back into my own hand.

What I don't want misread is that this isn't a "do it alone" story. Asking others matters, and learning from a model is good too. Only, you must not hand the place where you finally set the judgment wholly outside yourself. You won't always meet a generous leader who walks at the front. Then take on that one person's role yourself, first. If you can't meet one, become one. From the day I decided that, the time I spend wavering at the review desk grew a little shorter.