Ask for More

Why Asking Feels Like a Threat

Before we begin, one promise and one disclaimer. The promise: by the end of this book you will be able to walk into a money conversation with a plan instead of a knot in your stomach. The disclaimer, because it matters and because I'd rather say it once, plainly, than bury it: this is general, evergreen education about how to talk about money and how to negotiate. It is not financial, legal, tax, career, or employment advice, and it is not a substitute for any of those. Every person, contract, employer, and market is different, and every name and number you'll meet in these pages is invented to illustrate a point — not a real case, not a benchmark for what you should be paid. When a real decision is in front of you, check your own situation against current, official, qualified sources: an accountant or licensed planner for money, an employment lawyer or labour authority for contracts and rights. Good? Good. Now let's talk about why this is so hard.

Here is something I've watched happen a thousand times. A capable, well-liked person — someone who is genuinely good at their job — sits across from me and says some version of: "I'm just bad at this." They say it the way you'd report a fact about your height. As if asking for money were a fixed trait, like being unable to roll your tongue. And I always say the same thing back: you are not bad at this. You are unpracticed at this. Those are completely different problems, and only one of them is permanent.

The reason the distinction matters is that "I'm bad at this" is a verdict, and you can't do anything with a verdict except carry it. "I haven't practiced this" is a diagnosis, and a diagnosis comes with a treatment. This whole book is the treatment. But before any technique can help you, we have to look honestly at what actually happens in your body and your mind in the seconds before you ask for money — because most people have never named it, and an unnamed fear runs the show from backstage.

So let's bring it on stage.

What you're actually afraid of

"I'm bad at asking" is almost never the real thing. It's a tidy lid on a messier box. When I open the box with people, I find the same handful of fears, again and again, in different outfits. See which ones are yours.

The first is the fear of seeming greedy. You worry that the moment you name a higher number, something shifts in how the other person sees you — that you'll go from "dedicated, reasonable, team player" to "in it for the money." For relational, conscientious people, this is the big one. You'd rather be underpaid and liked than fairly paid and suspected of being grabby.

The second is the fear of damaging the relationship. This is greed's quieter cousin. You're not worried they'll think you're greedy, exactly — you're worried the ask itself will introduce friction into a relationship that currently runs smoothly. Your boss, your client, your contact: things are warm now. Asking feels like dropping something heavy onto a clean table.

The third is the fear of hearing "no." Not the no itself, which is just a word, but what you imagine the no means: that you misjudged your value, that you reached and got slapped down, that now you have to keep showing up having visibly wanted more and been told you couldn't have it.

The fourth is the fear of being seen as not worth it. This is the deep one, and it wears a disguise. You tell yourself you don't want to seem greedy, but underneath, a colder thought is running: what if I ask, and they pause, and the pause says you actually aren't worth that? Many under-askers never ask precisely so they never have to hear that pause. Silence protects the fantasy that you could have gotten more if you'd only tried.

And the fifth, underneath all of them, is the plain fear of confrontation. Some of us are simply wired to find conflict — even mild, polite, businesslike disagreement — deeply unpleasant. A negotiation looks, from the outside of it, like a small confrontation. So we avoid it the way we avoid all confrontation: by going quiet, going along, and telling ourselves it wasn't worth the fuss.

Notice that not one of these fears is about being bad at math, or bad at "tactics." They are all social and emotional. That's the first useful truth of this book: under-asking is not a skills problem in the technical sense. It's a fear problem wearing a skills problem's coat. Which is good news, because fears can be examined, tested, and shrunk — and that's most of what we're going to do.

You are not your rate

Here is the single most important sentence I can give you in this chapter, so I'll set it on its own line.

Your price is a number for a service. It is not a score for you as a person.

We get these two things fused together, and the fusing is where most of the pain lives. When you say "my rate is £400 a day" and the client flinches, it feels like they flinched at you — at your worth, your competence, your right to take up space. But they didn't. They reacted to a number, in a context, against a budget you can't see, for reasons that mostly have nothing to do with your soul. A low number is not a verdict on you. A high number is not a moral failing. The number is just the meeting point of what you offer and what something is worth to someone right now.

When people undercharge, they often think they're being humble. They're not. They're confusing two different measurements. Humility is a fine quality for how you treat people. It is a terrible pricing strategy, because the market is not measuring your humility — it's measuring the value of the work. You can be a deeply modest person and charge a confident, fair number for what you do. Those don't fight. In fact, the calmest, most secure people I know are often the clearest about their rates, precisely because they've stopped treating the number as a referendum on their character.

So whenever you feel the dread rising, try this small mental move: peel the price off the person. Say to yourself, this is a number for a service. The number can be discussed, adjusted, anchored, traded — all the things we'll learn — without any of it touching who you are. Your worth as a human is not on the table. It was never on the table. Only the price of the work is.

The quiet cost of silence

Now for the part nobody warns you about. People assume that not asking is the safe, free option — that by staying quiet you simply keep things as they are, at no cost. But under-asking isn't free. It compounds.

Here's the mechanism. Almost every future number is built on your current number. Your next raise is usually a percentage of this salary. The next client asks "what did you charge the last one?" The new employer asks your current pay, or pegs their offer to it. So a number that's too low today doesn't just cost you the gap this year — it becomes the baseline that next year's number grows from, and the year after that. A small shortfall, left alone, quietly multiplies. The silence you thought was free turns out to have been the most expensive thing in the room.

This is why I get a little impatient with the phrase "it's only a few thousand, not worth the awkwardness." It's almost never only a few thousand. It's a few thousand, compounded, for as long as you stay on the low track — plus the slow erosion of how it feels to do good work for a wage you privately resent. That resentment has a cost too, even if it never shows up on a payslip.

Tomas, and the three years he didn't ask

Let me make this concrete with someone I'll call Tomas. He's invented — a composite, a hypothetical — but you may recognise the shape of him.

Tomas is a graphic designer, good at his job, the kind of steady hand a team relies on. Three years ago he had a private realisation: he's underpaid. He knows roughly what his skills go for. He knows he's taken on more than he was hired to do. And every year, around review time, he decides this is the year I'll ask.

And every year, the thoughts arrive on schedule. First: they've been good to me — they'll think I'm ungrateful. (That's the greed fear and the relationship fear, holding hands.) Then: the timing's never right — we're busy, or we're slow, or the budget's tight, or a project just went sideways. (There is, conveniently, never a perfect time, which is how you can wait forever.) Then, the closer: if I ask and they say no, I'll feel stupid, and I'll have to keep working here knowing they know I wanted more. (That's the fear of "no," and the fear of the pause that means not worth it.)

So he doesn't ask. Each year he tells himself he's saved himself an awkward five minutes. And each year his salary becomes the baseline for next year's tiny percentage rise, and the gap between what he earns and what his work is worth widens a little more. Three years of "the timing's never right" isn't a neutral pause. It's three years compounding on a number he already knew was too low. The awkward five minutes he kept avoiding would have been the cheapest five minutes of his career.

Tomas isn't weak. He isn't bad at his job. He's a thoughtful, relational person whose entirely normal fears were never named, examined, or tested — so they ran the decision every single year. That's the trap. And the way out of it starts with a distinction.

Discomfort is not danger

Your body cannot always tell the difference between a threat to your safety and a threat to your standing. So when you sit down to ask for money, you may get the full alarm: heart up, mouth dry, stomach tight, a sudden urge to leave or to fill the silence with reasons. That's a threat response. It is real, and it is unpleasant, and — this is the key — it is not evidence that anything bad is happening.

Discomfort is the normal, survivable feeling of doing something exposed and unpracticed. Danger is when something is actually about to harm you. In a salary conversation, you are experiencing the first and your body is reporting the second. Nothing in the room is going to hurt you. The worst realistic outcome of most money conversations is that someone says "no" or "not yet" — words, not wounds. You will walk out with the same job, the same client, the same life you walked in with, plus useful information.

Once you can label the feeling — this is discomfort, not danger — it loosens its grip. You stop trying to make the feeling go away before you ask (it won't; you ask anyway) and you stop reading the adrenaline as a warning to retreat. Brave isn't the absence of the alarm. It's asking while the alarm is going off, because you've correctly judged that the alarm is wrong.

What asking actually is

Let me also puncture the picture in your head, because I suspect it's wrong in a specific way. You imagine asking as an intrusion — as if you're interrupting the natural order of things to demand something you're not really owed, and the other side will be surprised and a little offended that you'd dare.

They won't. Across employment and freelancing and business, people who set prices and budgets expect the other side to discuss them. A hiring manager is rarely shocked that a candidate has questions about the offer; it's a normal step they've seen many times. A client who hears a rate is rarely scandalised; they've hired people before. The surprise and offence live almost entirely in your imagination, projected onto a person who is, in reality, just waiting for the next ordinary part of the conversation. Asking is not a breach of etiquette. It is the etiquette. It is simply how money is meant to be sorted out between adults.

Which brings us to the word I want you to retire. "Haggling." It carries the image of two people fighting over a fixed pie, each trying to grab a bigger slice at the other's expense — sharp, zero-sum, a little grubby. No wonder you hate it; it sounds awful, and it doesn't suit you. So put it down. For the rest of this book we're going to call the thing by its real name: a conversation about value. Not a battle to win, but a calm, prepared discussion of what something is worth and how to make a deal that works for both sides. That reframe is the whole foundation of what's coming — and the next chapter is devoted entirely to replacing the fight in your head with a far more accurate, and far more comfortable, picture of what's really going on.

Your first action: dread on the left, probability on the right

Every chapter in this book ends with one concrete thing to do, because reading about asking is not the same as being able to ask. Here's the first, and it's small.

Take a sheet of paper and draw a line down the middle. On the left, write the exact sentence you're afraid of hearing if you asked — the specific words, not a vague feeling. Something like: "We can't do that, and now things are awkward between us." Or: "Honestly, I didn't think you'd be the type to push for more." Whatever your particular dread whispers, write it down in quotation marks, as a real sentence a real person would say.

Then, on the right, write the most likely thing they'd actually say — the boring, realistic response, the one that happens far more often than your worst case. Usually it's something like: "Let me look into the budget and come back to you," or "I can't go that high, but here's what I can do," or simply, "Sure, let's talk about it."

Now look at the gap between the two columns. That gap — between the catastrophe on the left and the probability on the right — is the exact space your under-asking has been hiding in for years. You've been making decisions based on the left column and calling it caution. From here on, we're going to make them based on the right.

You're not weak for finding this hard. You're just unpracticed. Let's fix that.

It's a Conversation, Not a Cage Fight

Picture the last time you had to talk about money and your stomach dropped. Now notice the picture your mind made of it. For most quietly competent under-askers, it isn't a picture of two people sitting at a table solving something together. It's a picture of a fight. Someone is across from you with their arms folded. There is a winner and a loser, and you have already cast yourself as the loser — or, worse, as the one who has to turn nasty to avoid losing. No wonder you'd rather eat the underpayment than show up to that.

Here's the thing I want you to sit with for this whole chapter: the fight you're dreading is mostly imaginary. Not the conversation — the conversation is real and you should prepare for it. But the cage you've drawn around it, the bare-knuckle, one-of-us-walks-out-bleeding frame, is something you brought with you. You can put it down. And the moment you do, the entire skill gets easier, because you stop bracing for a war that the other person, in almost every case, doesn't want to have either.

In the last chapter we looked at why money talk triggers dread — and agreed it's a skill gap, not a flaw in your character. This chapter is about swapping out the single most expensive belief underneath that dread: the idea that negotiation is combat. We're going to replace it with something truer and far less frightening. Negotiation is a conversation. A specific kind, with a specific purpose, but a conversation all the same. And you already know how to have those.

Two pictures of the same table

Let me show you the two mental models side by side, because once you see them clearly you can't unsee the difference.

Model one: combat. There is a fixed amount of good stuff on the table — call it the pie. Every slice I get is a slice you lose. So my job is to take as much as I can before you take it from me. Strength wins. Flinching loses. The other person is an opponent, their gain is my loss, and the only postures available are attack or surrender. If this is your model, then of course asking for more feels grabby and aggressive — in this picture, asking for more literally is taking from someone. And of course you freeze, because you're a kind, relational person and you've just framed a normal work conversation as an act of plunder.

Model two: joint problem-solving. There are two people who each want something, and a set of variables they can arrange between them. The question on the table isn't "who wins?" It's "how do we both walk away able to say yes and mean it?" In this picture, asking for more isn't an attack — it's information. It tells the other person what you need so the two of you can find an arrangement that works. Your counterpart isn't an opponent; they're the other half of the puzzle.

Same table. Same money. Completely different conversation. And here's what I've watched happen a thousand times: the under-asker assumes everyone else is running model one — that the boss, the client, the hiring manager is a hardened combatant — and so they show up either over-apologetic or weirdly stiff, braced for an attack that never comes. They negotiate against a phantom. The phantom costs them money every time.

It's almost never a single, fixed pie

The combat model rests on a hidden assumption: that there's only one number, and it's fixed, and all you can do is push it up or down a few inches by force. That assumption is usually false, and seeing why it's false is the most practical thing in this chapter.

Most deals have more than one variable. The headline number — the salary, the rate, the fee — is just the loudest one. Look harder and you'll almost always find others sitting right next to it:

• Money in forms other than base: a signing bonus, a performance bonus, a deposit, a kill fee, faster payment terms.
• Time: start date, deadline, hours, a four-day week, time off, how long a rate is locked in.
• Scope: how much work, how many rounds of revisions, how many meetings, what's explicitly not included.
• Flexibility: remote days, control over your schedule, autonomy over how the work gets done.
• Title and standing: what you're called, who you report to, what you get to put on your CV afterward.
• Terms: the contract clauses, the review date, the notice period, the rights and protections around the work.

The instant you realise there are six or eight dials on the table and not one, the whole thing stops looking like a tug-of-war and starts looking like what it actually is: a fitting. We're adjusting a set of dials until the arrangement fits both of us. Maybe they truly can't move base pay this quarter — but they can move the start date, add a review in six months, and grant the remote days you actually wanted more anyway. Nobody lost. The pie didn't shrink for one of you so it could grow for the other. You just arranged it better.

(We'll come back to these variables hard, later in the book, because they're the raw material for trading — the fifth move of the Calm Ask, where a number only moves if something moves in return. For now I just want you to see that they exist.)

The other person wants a deal too

Now the part that under-askers chronically forget under stress: the person across the table usually wants this to work out. They are not sitting there hoping to humiliate you and walk away. They came to the conversation because they want an outcome too.

The hiring manager has a role to fill, a team that's stretched thin, and a boss asking when the seat will be filled. Every week it stays open is a week of work not getting done. They found you, ran the interviews, got everyone to agree — the last thing they want is to lose you over something they could have solved.

The client has a project that needs doing and a deadline breathing on them. They reached out to you. Starting over with someone new is expensive and slow and risky.

Your boss, when you ask for a raise, does not want to replace you. Replacing a good, trusted person is one of the most painful and costly things a manager does — the hiring, the ramp-up, the months of someone new not yet knowing how things work. Keeping you happy is very often the cheaper option, and a decent manager knows it.

I'm not telling you this so you'll squeeze anyone. I'm telling you because it reveals the real shape of the room. You are not a supplicant begging at a gate. You are one of two people who both have a reason to find a yes. That is a completely different posture to stand in — and it's the true one.

Soft on the person, firm on the number

Here is where the conflict-averse reader gets nervous, so let me say it plainly, because it might be the most freeing sentence in this chapter: warmth and clarity are not opposites.

You can be genuinely kind to the human in front of you and completely unmovable on what you need. Those two things live in different rooms. You don't have to trade one for the other. The trick is to be soft on the person and firm on the number.

Soft on the person sounds like: "I'm really glad we're talking. I want this to work." It's the warmth that comes naturally to you anyway — eye contact, good faith, an honest wish for both of you to come out well.

Firm on the number sounds like: "And for me to say yes, I need the figure to be sixty-eight." Said warmly. Said without an apology stapled to the front of it. Said, crucially, and then left there.

What kills under-askers isn't a lack of warmth — they have plenty. It's that they let their warmth dissolve the number. They get to "I need sixty-eight" and immediately soften it into nothing: "but I totally understand if that's not possible, whatever works for you is fine, I don't want to be difficult." The kindness leaks straight into the figure and washes it away.

You don't have to choose between being nice and being clear. Be lavishly nice to the person. Be quietly immovable on the number. A real "no, thank you" delivered with a warm smile is one of the most powerful and least aggressive things you will ever do.

Good negotiators are not who you think

Let me kill a myth, because it's been frightening you off this skill for years. You picture the good negotiator as a type: loud, slick, fast-talking, a little ruthless, the kind of person who could sell sand in a desert and enjoy it. You look at that person, you know in your bones you'll never be them, and you conclude that negotiation just isn't for people like you.

Good. Because that person mostly loses.

The slick, dominating style sets off everyone's alarms. It makes the other side defensive, guarded, eager to win one back. It poisons the relationship for the next conversation, and most money relationships are repeated games — the same boss, the same client, year after year. The aggressive negotiator wins the skirmish and loses the war.

The people who quietly do well at this are almost the opposite of the caricature. They are calm. They are prepared — they've done the homework, they know their number, they're not improvising. And they are comfortable being quiet — they can make an ask and then simply stop talking, which, it turns out, is one of the rarest and most valuable abilities in any negotiation. Calm, prepared, and quiet beats loud, smooth, and ruthless on most days of the week.

Read that list again: calm, prepared, quiet. That is not an alpha closer. That is a thoughtful, conscientious person who did their reading — which is to say, that is you, on your better day. The temperament you've been treating as a disqualification is closer to the actual qualification. You don't need a personality transplant. You need a method, which is exactly what the rest of this book is.

Collaboration is a stance, not a surrender

I have to guard one flank here, because the relational reader can over-correct. When I say "collaboration," some people hear "be agreeable, keep the peace, take what they offer so nobody's uncomfortable." That is not collaboration. That's just surrender wearing a friendlier coat.

Collaboration is a stance, not a concession. Being collaborative means you're genuinely trying to find an arrangement that works for both of you. It does not mean you accept less so the other person feels good. You can be the warmest, most problem-solving-minded person in the room and still hold your walk-away line like steel. In fact the two go together: because you're not treating it as a fight, you don't get rattled, and because you don't get rattled, you can hold your number without flinching. The calm is the strength.

So when you walk in collaborative, you are not going soft. You're choosing the posture that gets you more and keeps the relationship intact. You get to be the good person you already are and still get paid properly. Those were never actually in conflict. The cage was.

Devi and the question that flipped the room

Let me show you the whole thing in one scene. (Devi is invented, like everyone in this book — a picture to make the principle stick, not a real person.)

Devi is a freelance contractor, and she's good. A client comes to her with a solid project, and they set a call to talk money. Devi spends the day before that call sick with nerves. In her head she has built the full cage: the client is going to lowball her, push back hard, maybe make her feel greedy for naming a real rate. She rehearses her defences. She walks in braced for a fight, shoulders up around her ears, ready to be attacked.

And here's what she finds on the call: the client is nervous too. He's worried he can't afford what she's worth and that she'll think his budget is insulting. He's been dreading the call as much as she has. Two anxious people, each braced against an opponent who doesn't exist, circling a number neither wants to say first.

About ten minutes in, almost by accident, Devi says the thing that changes everything. Instead of defending her rate like a fortress, she asks: "What would make this easy for both of us?"

The room flips. The client exhales. He tells her the truth — his budget is a bit under her usual rate, but the timeline is flexible, he doesn't need the rush she'd priced for, and there's likely a second phase next quarter. Suddenly there isn't one fixed number being fought over. There are dials. They move a few of them together: she shifts the timeline, he commits to phase two, the rate lands somewhere they're both genuinely happy with. Nobody lost. The standoff became a problem they solved side by side — because one of them put down the cage and asked a collaborative question out loud.

Devi didn't win by being tougher. She won by refusing the fight.

Your takeaway: count the dials

Here's your one concrete action for this chapter, and it's the seed of real work later.

Think of one money conversation coming up — a raise, an offer, a rate, a client deal, anything with a number in it. Get a page. Write the headline number at the top. Then list every other variable on the table besides that number. Push for at least five. Use the categories from earlier if you stall: money in other forms, time, scope, flexibility, title and standing, terms. Start date. Revision rounds. Payment timing. Remote days. Review date. A bonus. Notice period. Keep going until you've surprised yourself.

Then keep the list. This isn't a one-off exercise — it's raw material. Every dial you found is something you can adjust, offer, or ask for when the headline number gets stuck. It's what you'll trade with later, so you rarely have to walk away empty-handed.

But the list does something quieter and more important right now: it dismantles the cage on paper. A conversation with six or eight movable parts cannot, by its nature, be a single-pie cage fight. You're not entering a duel. You're walking into a fitting, with a person who also wants it to fit — to arrange a handful of dials until you can both say yes and mean it. That's not a battle you have to win. It's a conversation you already know how to have.