Chapter 5: Step 2 — Defining Where You Want to Go (D)

The Temptation to Leap

"So now I know my D′," Sarah said, reviewing our work from the previous session. "I stay quiet in leadership meetings — that's how it shows up: I defer to whoever spoke last, and I look down at my notebook when the CEO calls my name. What's next — figuring out what I want instead?"

"Exactly. We need to define D — where you want to go."

"Easy." She sat forward, decisive for the first time in our conversation. "I want to be the kind of leader who walks into that room and is heard. The one the CEO turns to first. A voice that holds its ground."

I paused. "That's a beautiful aspiration. But it's not D."

Sarah looked confused. "Why not? That's what I want."

"I know. And that's exactly why it's dangerous to start there."

The Aspiration Trap

Here's where most people go wrong—and where the Perry Approach diverges sharply from conventional wisdom.

When asked "What do you want instead?", our minds leap to ideals. We imagine the finished product, the transformed self, the perfect outcome. Sarah pictures herself as the commanding voice she's admired in others her whole career. David envisions being a calm, secure leader who lets his team rise. Each of them has a vivid picture of who they want to become.

These aspirations feel motivating. They give us something to strive for.

But they're traps.

Why? Two reasons:

1. Aspirations Contain Assumptions

When Sarah says "I want to be the voice the CEO turns to first," she's already assumed she knows what success looks like. But does she? Her model of "being heard" comes from watching others — people whose internal experience she cannot know. Perhaps those leaders she admires are terrified inside. Perhaps their "presence" comes from a different source entirely than what Sarah imagines.

Starting with an aspiration means starting with assumptions about how to get what you want. The cloud process is designed to surface assumptions, not begin with them embedded invisibly in your destination.

2. Aspirations Limit Solutions

This is the most counterintuitive point, so stay with me.

When Sarah defines her goal as "being the voice the CEO turns to first," she's already constrained her solution space. She's decided what success looks like. But what if the most powerful version of Sarah isn't a commanding voice at all? What if her breakthrough is something entirely different — a quieter authority, a particular timing, a way of holding the room that doesn't look anything like the leaders she's been modelling? Something she can't currently imagine because she's been fixated on one picture of what "being heard" means.

By specifying the end state too precisely, you close doors before you know they exist.

The Power of Negation

So if D isn't your aspiration, what is it?

D is simply NOT D′. It's the negation or reduction of your current behaviour.

Let's make this concrete:

Notice what's happening here. D isn't a grand vision. It's simply NOT what you're currently doing. This might seem underwhelming compared to "commanding presence," but it's actually far more powerful.

Sarah Finds Her D

"Let me try again," Sarah said, putting aside her vision of being the voice the CEO turns to first. "My D′ is that I stay quiet in leadership meetings. So D would be..."

"Just negate it. NOT D′. Don't reach for something that sounds better."

"NOT stay quiet in leadership meetings?"

"Exactly."

She looked uncomfortable. "But that doesn't tell me what to do."

"Precisely. And that's the point. We don't know yet what you'll do instead. That's what the cloud process will reveal. If we decide now that D means 'speak with measured authority,' we've already assumed we know the answer."

Sarah's D: NOT stay quiet in leadership meetings.

Notice: no mention of "commanding voice." No vision of being a transformational leader. No assumptions about what "speaking up" looks like in practice. Just NOT what she's currently doing.

"This feels... incomplete," Sarah admitted.

"Good. The incompleteness is the doorway. If it felt complete, you'd have closed down the possibilities before we've explored them."

David, the Other Side of the Same Step

The same trap catches David from the other direction.

When we worked his D′ in Chapter 4 — I take back work after setting up delegation — and asked him to define D, he didn't reach for a commanding image. He reached for a virtuous one.

"I want to be the kind of leader who trusts his people," he said. "Who lets them rise. Who can sit with the discomfort of not controlling the outcome."

A beautiful aspiration. And the same trap.

"David, what's the assumption baked into 'trusts his people'?"

A pause. "That trust looks like not intervening."

"And what if trust looks like something else? What if your breakthrough isn't 'trust' as you currently imagine it, but a different relationship with the work entirely — one we can't picture yet?"

He sat with that for a moment. Then, slowly: "So my D is just... NOT take back work after setting up delegation?"

"That's it."

David's D: NOT take back work after setting up delegation.

Where Sarah's aspiration was about acquiring a voice she doesn't yet have, David's was about embodying a virtue he doesn't yet feel. Different textures, same trap. Both versions of D close down the discovery before it begins.

The NOT — for both of them — keeps the door open.

Having, As Not Having

There is something deeper in the NOT than a technique for keeping your options open, and it is worth naming, because it changes how the whole method feels to live with.

Nearly two thousand years ago, Paul of Tarsus wrote a line to a community in Corinth that has intrigued readers ever since. Those who have, he said, should live as not having; those who mourn, as not mourning; those who deal with the world, as not engrossed in it. The phrase in his Greek is hos me — "as not." He was not telling people to give up what they had, nor to pretend they did not have it. He was pointing to a third posture entirely: hold what you have without letting it close around you as final. Have it, but loosely. Be it, but not only it.

That is precisely what the NOT in D asks of you.

When Sarah writes NOT stay quiet in leadership meetings, she is not abolishing the careful, considered self who learned to stay quiet — that self is real, and it kept her safe for years. Nor is she pretending it was never there. She is holding it as not final. The quiet is still hers; she is simply no longer only the one who stays quiet. The behaviour is named, honoured, and loosened — held open rather than defended or destroyed. A positive aspiration ("a commanding voice") would slam a new identity shut just as firmly as the old one had. A simple opposite ("speak up constantly") would do the same. Only the NOT keeps her in the open posture — having her current self, as not having it — long enough for something genuinely new to arrive.

This is why the NOT is not a half-measure, and not a placeholder for the "real" answer we will supply later. At this step, the open hand is the answer.

And there is one more thing to notice, because it reaches well beyond this chapter. You will return to this move. Once Sarah has shifted — once not staying quiet is simply how she now works — that new way becomes, in time, her new current state: her new D′. Life will surface its next cloud, and she will negate again. The NOT is not a gate you pass through once and leave behind. It is a posture you come back to, again and again, for as long as you keep growing. We follow that spiral to its conclusion in Chapter 15. For now it is enough to see that the small, uncomfortable NOT you are writing at Step 2 is a rehearsal of something you will be doing for the rest of your life: holding who you are with an open hand — as not the whole of who you might yet become.

The Language of D

How you phrase D matters. The key principle: D is NOT D′.

Keep the NOT Explicit

D should explicitly negate D′. Don't convert it to a positive alternative.

• D′: "I take back work after setting up delegation"
• D: "NOT take back work after setting up delegation"

The NOT does important work. It points away from your current behaviour without assuming you know where you'll land.

Avoid Identity Statements

D should negate a behaviour, not claim an identity.

• Wrong: "I'm a trusting leader" (identity/aspiration)
• Wrong: "I let my team complete their work" (positive alternative)
• Right: "NOT take the work back before completion" (negation of D′)

Identity statements are aspirations in disguise. Positive alternatives assume you know the solution. NOT keeps the door open.

Match the Grain of D′

D should negate D′ at the same level of specificity.

• D′: "I revise emails repeatedly before sending"
• D: "NOT revise emails repeatedly before sending"
• D′: "I delay all decisions until forced"
• D: "NOT delay all decisions until forced"

Mismatched grain creates confusion and makes the cloud harder to work with.

Avoid Overcorrection

A subtle trap: don't swing to the opposite extreme.

• D′: "I work until midnight" → D: "NOT work until midnight" ✓
• D′: "I work until midnight" → D: "Leave precisely at 5 PM" ✗ (overcorrection)
• D′: "I stay silent in meetings" → D: "NOT stay silent in meetings" ✓
• D′: "I stay silent in meetings" → D: "Speak up constantly" ✗ (overcorrection)

NOT D′ is simple negation. Overcorrection is a new behaviour that swings to the opposite extreme. Stay with NOT.

Why This Feels Uncomfortable

If you're feeling frustrated that you can't define your grand vision as D, good. That frustration is data.

It means you've been carrying an image of your transformed self—a picture of who you want to become. That picture isn't wrong. It's valuable. But it doesn't belong in D.

It will reappear in A, the unified outcome we'll discover in Chapter 8. That's where your deepest aspirations live. That's where the purpose behind both D and D′ reveals itself.

But we have to earn our way there. First, we need to understand what D gives you—that's B, the benefit of NOT doing your current behaviour. Then what D′ gives you—that's C, the benefit of your current behaviour. Only then can we discover what both are really trying to achieve.

The Perry Approach is a journey, not a leap.

Your D Discovery Process

Let's work through finding your D. Return to the D′ you identified in Chapter 4.

Step 1: Write Your D′ Again

State your current behaviour clearly. This is your starting point.

Example: "I accept meeting invitations automatically without assessing their value against my priorities."

Step 2: Add NOT

Simply put NOT in front of your D′. That's it. That's your D.

Example: "NOT accept meeting invitations automatically without assessing their value against my priorities."

Step 3: Resist the Temptation to "Improve" It

You'll want to convert this to something that sounds more actionable—like "I evaluate meeting invitations against my priorities before responding."

Don't.

That positive alternative assumes you know the solution. The NOT keeps the door open for discovery.

Step 4: Check for Overcorrection

Make sure you haven't jumped to an extreme alternative.

• "NOT accept meeting invitations automatically" ✓ (simple negation)
• "Decline all meetings" ✗ (overcorrection)

Step 5: Test for Aspiration

If your D sounds like a grand vision of transformation, you've slipped into aspiration. Return to NOT D′.

• "NOT accept automatically" ✓ (negation)
• "Be disciplined about my time" ✗ (aspiration)

Final D: "NOT accept meeting invitations automatically without assessing their value against my priorities."

Common D Formulations

A few well-formed D statements for common patterns from Chapter 4:

The Over-Deliverer

• D′: I take on more work than I can sustain
• D: NOT take on more work than I can sustain

The Pleaser

• D′: I agree to requests and adjust my position
• D: NOT agree to requests and adjust my position

The Avoider

• D′: I delay addressing difficult issues until they become unavoidable
• D: NOT delay addressing difficult issues until they become unavoidable

Notice how each D is simply NOT D′—no grand visions, no transformed identities, no assumptions about what you'll do instead. Just NOT what you're currently doing.

What Sarah Realised

By the end of our session, Sarah had something far more valuable than her vision of being the voice the CEO turns to first.

She had openness.

"I've been carrying this picture of the leaders I admire," she said. "But I never stopped to ask what I'm actually doing that's different from them. I just assumed I needed to become a different person."

"And now?"

"Now I see it's about NOT doing what I'm currently doing. NOT staying quiet in leadership meetings. What I actually do instead — that's what we'll discover."

"Exactly. And here's what we don't know yet," I said. "We know you want to stop staying quiet. But we haven't yet named what speaking up would actually give you — and it's almost certainly more than you can picture from inside the old pattern."

Her eyes lifted, curious. "More than just being heard?"

"Far more. Naming what change would give you is where the energy to make it comes from. That's what we explore next — in Chapter 6."

Sarah's cloud was beginning to take shape. She had her D′ (where she was) and her D (NOT D′). David's was taking the same shape from his side of the room. But the real work — understanding why each of them was stuck between D′ and D — was just beginning.

Chapter Reflection

You've walked through the discovery process with the meeting-invitations example. Now do the same with your own D′ from Chapter 4.

Add NOT in front of it. That's your D.

Before moving on, sanity-check:

• Have you slipped into aspiration? Return to NOT D′.
• Have you overcorrected to an extreme alternative? Stay with simple negation.
• Have you tried to "improve" the NOT into a positive alternative? Resist — the NOT is doing the work.

Write your D statement:

"D′: [current behaviour]. D: NOT [current behaviour]."

Looking Ahead

You now have two pieces of your cloud:

• D′: Your current behaviour—specific, observable, positively phrased
• D: NOT D′—the simple negation of your current behaviour

But clouds don't dissolve just by naming endpoints. The real insight comes from understanding what each position gives you.

In Chapter 6, we'll surface B — the benefit of D, what NOT doing your current behaviour would give you. Then, in Chapter 7, we'll go after C — the benefit of D′, what your current behaviour is already giving you. This is where transformation becomes possible.

The Perry Approach reveals this: You're not stuck because you're weak or broken. You're stuck because both D′ and D are serving you—and you haven't yet found a way to honour both.

What's Next

In Chapter 6, you'll surface B — what change would give you. Then in Chapter 7 you'll uncover C — what your current behaviour is protecting. This is where transformation becomes possible. Everything you need is in the next chapter. You can work through it on your own, at your own pace.

Support for this step

Staying with NOT D′ — resisting the pull toward aspiration, overcorrection, and positive alternatives — is simpler to describe than to practise. The temptation to leap to a grand vision of your transformed self is strongest at exactly this point, because D feels incomplete. That incompleteness is doing the work.

RIC — the Rapid Improvement Coach is an AI agent built specifically to support you through the process. RIC holds the NOT with you, catches aspiration when it slips in disguised as clarity, and tests your D against the traps this chapter names — overcorrection, identity statements, positive alternatives. You choose when the formulation feels right; RIC keeps the door open until you do.

The Rising Above the Clouds course includes RIC, a discussion tab with the author, and membership of the Conflict Club.

Rising Above the Clouds - The Course