The Power of Knowing When to Walk Away · Annie Duke
36 highlightsIn book order (loc 209–2,273)5 disciplines synthesized
🎯 Your 5 — the quitting disciplines to build
Fable’s read of your 36 highlights — ranked, most leverage first. Each card grounds the discipline in what the book actually argues (with the passage numbers it draws from), then carries the system to install — trigger, anchor, forcing function, metric, weekly rep.
1
Set kill criteria in advance — states and dates, decided outside the storm
The career decision you’re weighing is exactly the decision Duke says gets made worst “in it” — inside the daily noise of the job itself. So don’t try to make THE decision; write the criteria that will make it for you: “If by <date>, I have/haven’t <state>, I walk.” Decided in advance, on a calm day, the exit stops being a test of nerve and becomes a tripwire you already agreed to honor.
In the book
Duke’s starting point is Kahneman’s: the worst time to make a quitting decision is when you’re “in it” — the work should be done long before you face the choice (5). Her tool is a set of kill criteria: imagine, at entry, what you could learn that would tell you the road is no longer worth it — “What are the signs that, if I see them in the future, will cause me to exit the road I’m on?” (30). The best generator is a premortem — cast yourself into a failed future and look back at why (31). The workable format is states and dates: “If by (date), I have/haven’t (reached a particular state), I’ll quit” — developed for the highest-stakes decisions and, she stresses, broadly applicable to personal ones (32, 34). The payoff is mechanical: criteria set in advance plus a precommitment to act on them get you to no faster, limit the losses you have to absorb, and make follow-through likelier exactly when you’re losing (33).
Build the system
When…thenWhen the career question surfaces — in my head or in a conversation — I don’t re-litigate it; I check it against the written kill criteria, and only a tripped criterion reopens the decision.
Cue + anchorThe Friday thinking block you already run. The criteria live at the top of the decision doc — opening the doc IS reading them.
Forcing functionUntil they’re written, the doc’s first line reads: “NO KILL CRITERIA YET — deciding ‘in it.’” Every criterion must carry a date and a measurable state — no vibes.
TrackCriteria surviving Friday review unchanged, and decisions referred to them vs decided ad hoc. Stable 4–6 weeks = they’re real.
This week’s repFriday, 15 minutes: premortem the move (“it’s a year on and it failed — why?”), then turn the top three causes into “If by <date>, <state> → I walk” lines.
Sunk costs are a katamari — only the next year is on the table
The years in, the seniority, the “go‑to” reputation — that is the katamari, and it votes for staying every time you weigh the move. Your highlights are blunt: the spent years are gone whichever path you pick, and knowing the fallacy does NOT immunize you against it. The only question with information in it is which option buys the better NEXT year — so ban past‑investment arguments from the decision entirely.
In the book
Given the chance to quit, we don’t just decline — we back up the original decision by spending even more to save it (20), the escalation of commitment Duke calls robust and universal, in individuals and organizations alike (21). Sunk costs snowball like a katamari: everything already invested adds mass that makes quitting harder, which invites more investment, which adds more mass (22). The mechanism is mental accounting — we hate closing an account in the losses, though the only thing that matters is expected value across the whole portfolio (23). Her hardest reframe: what matters is whether the next resource — the next year, the next unit of effort — is worth putting at risk, not the ones already gone (24). Her summary names your exact sentence — “If I don’t make this work I will have wasted years of my life!” — and warns that knowing about the effect doesn’t keep you from falling prey to it (25). Two more weights sit on the stay side: identity — quitting a career means quitting part of who you are, and that is painful (35) — and the endowment effect, demanding more to give up what you hold than you’d ever pay to acquire it (36).
Build the system
When…thenWhen I catch a past‑investment argument — “the years I’ve put in,” “my standing here,” “so close now” — I strike it and restate the choice: starting from zero today, which option wins the next 12 months?
Cue + anchorThe tell‑phrases are the cue: “already,” “wasted,” “after everything.” Hearing one leave your mouth = the fallacy is live, right now.
Forcing functionThe decision memo bans backward‑looking sentences by rule — every argument must be about the future. A two‑column “next 12 months” table is the only allowed comparison format.
TrackKatamari catches per week — each one logged is the bias surfacing instead of steering. Expect the count to start embarrassing and fall.
This week’s repWrite the two‑column stay/switch memo — next 12 months only, zero references to anything before today. Note where identity (35) tries to sneak back in.
Decide in expected value — happiness units, whole portfolio
You already think in expected value when it’s money — the move is to run the career on the same math, in the units Duke insists on: happiness, time, self‑fulfillment. The dialogue you marked at 13 is practically a script: if staying is unhappy with near‑certainty and switching is only maybe unhappy, the comparison is already over. Whether this quarter feels ahead or behind is noise; the EV of the path is the whole signal.
In the book
Thinking in expected value is how you figure out if the path you’re on is worth sticking to, and EV “is not just about money” — it can be measured in health, well‑being, happiness, time, self‑fulfillment, satisfaction in relationships (16). The goal is to persist when EV is positive, regardless of whether you’re currently ahead or behind — ahead/behind is just the lazy signal we substitute for the real question (18). Her career case is the one you highlighted — in short: stay = one hundred percent unhappy; switch = sometimes unhappy, sometimes real fulfillment, and that has to be better (13). What corrupts the math is prospect theory: loss aversion makes us quit too early in the gains and stick too long in the losses — Kahneman’s sure‑loss aversion (17). Even expert investors get selling wrong; and once we quit something we stop tracking it, so the feedback that would train our quitting never arrives (19).
Build the system
When…thenWhen weighing stay vs switch, I write probabilities, not adjectives: P(still unhappy in 12 months | stay) and P(unhappy | switch) — plus what each path pays in time and energy, not only in money.
Cue + anchorAny “how’s work feeling” moment — the Friday block, a run, the commute — converts the feeling into a number while it’s fresh.
Forcing functionThe memo’s verdict line is an inequality, not prose: EV(switch) vs EV(stay) in named units. No inequality → no verdict.
TrackRe‑estimate the two probabilities monthly and keep the dated series. The drift IS the data — three months of P(unhappy | stay) pinned near 100% answers the question by itself.
This week’s repAnswer your own highlight 13 in writing: the two probabilities, dated, in the decision doc. Ten minutes, done.
Expect on‑time to feel too early — a close call means go
Nothing dire is happening — the pay lands, the reviews are fine — and Duke’s point is that this is exactly what the RIGHT moment to leave looks like from the inside. You highlighted the rule: a close call between staying and going means going is likely better, because every force in your head — certainty’s siren song, sure‑loss aversion, grit itself — leans on the stay side of the scale. Expect on‑time to feel early; expect others to call it early too. That’s the bind, not a verdict.
In the book
When quitting is objectively the best choice, “things generally won’t look particularly grim” — and we rationalize away the clues that tell us how bad things really are (10). The management heuristic you marked cuts the same way: the right time to fire someone is the FIRST time it crosses your mind (11). Intuition says walking away slows your progress; Duke says the reverse is true — every month on a path no longer worth pursuing is when you actually lose ground (12). Certainty’s siren song — persevere and you’ll at least know — is what lures you onto the rocks (8), grit sticks you to hard things that are no longer worthwhile (2), persistence is not always the best decision because context changes (1), and hindsight’s “winners stuck with it” never implies that sticking makes you win (3). Hence her rule — a close call likely means quit (15) — her bind — on time looks too early to everyone, including you (16) — and her tie‑break: listen to the messages your past self sent you (14).
Build the system
When…thenWhen I hear myself offer “it’s not that bad” as the case for staying, I log it as a CLUE per 10 — the absence of drama is what on‑time looks like.
Cue + anchorThe close‑call feeling itself is the cue, and it points OUT, not in (15). The “people will say it’s too early” flinch = the bind operating, not information.
Forcing functionOne permanent line at the top of the decision doc: the DATE the move first crossed your mind (11). Every week since is visible bind‑tax, staring at you on open.
TrackWeeks between “first crossed my mind” and a written decision either way. This metric exists to shrink.
This week’s repWrite that first‑crossed‑my‑mind date down. Then reread highlight 16 — the whole bind in one paragraph — the next time the feels‑too‑early flinch hits.
Monkeys and pedestals — test the hardest unknown of the move first
A career move has one monkey — the question that actually decides it: would the new track fix what this one can’t? — and endless pedestals: polishing the CV, one more exploratory coffee, one more market read. Pedestals feel like progress, quietly add sunk cost, and delay the no. Find the conversation or fact that could kill the move fastest, and go get it first.
In the book
Astro Teller’s X runs on this: quitting gets you where you want to go faster, because the sooner a dead end is declared, the sooner the resources move to something fruitful (26). The model: if the goal is a monkey juggling torches on a pedestal, train the monkey first — building the pedestal is solving what’s already solved (34). Pedestal‑building creates the illusion of progress rather than progress, while stacking up sunk costs that make quitting harder just as you learn the monkey may not be trainable (27). Worse, when the monkey proves difficult, we instinctively retreat into more pedestal‑building rather than admit the no (28). Her compression: figure out the hard thing first, solve it as quickly as possible, beware false progress (29). It’s the same discipline as the book’s thesis — success lies in picking the right thing to stick to and quitting the rest (4) — and quitting is the “primary skill” of a good decision‑maker precisely because it lets you react when the landscape changes (6, 7), while you keep surveying that landscape for something better (9).
Build the system
When…thenWhen I plan any step of the move, I tag it monkey or pedestal — if I already know I can do it (CV polish, another coffee chat), it’s a pedestal and it queues BEHIND the monkey test.
Cue + anchorThe comfort of a task is the tell: feeling productive and safe = probably a pedestal. Friction and fear of the answer = probably the monkey.
Forcing functionSection one of the decision doc is titled THE MONKEY: the single question that kills or confirms the move. Nothing else gets worked while it stands unanswered.
TrackHours on monkey vs pedestal per week — the ratio is the discipline. Second number: days until the monkey has a real answer.
This week’s repName the monkey in ONE sentence, then book the one conversation or test that could return a hard no. A fast no is the win here, not the failure.
From your highlights: 4 · 6 · 7 · 9 · 26 · 27 · 28 · 29 · 34
All 36 highlights
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1Loc 209
Persistence is not always the best decision, certainly not absent context. And context changes.
2Loc 211
That’s the funny thing about grit. While grit can get you to stick to hard things that are worthwhile, grit can also get you to stick to hard things that are no longer worthwhile. The trick is in figuring out the difference.
3Loc 228
By definition, anybody who has succeeded at something has stuck with it. That’s a statement of fact, always true in hindsight. But that doesn’t mean that the inverse is true, that if you stick to something, you will succeed at it.
4Loc 238
Success does not lie in sticking to things. It lies in picking the right thing to stick to and quitting the rest.
5Loc 387
quit should be done long before you are facing the quitting decision. It recognizes, as Daniel Kahneman has pointed out, that the worst time to make a decision is when you’re “in it.”
6Loc 466
That’s why, if I had to skill somebody up to get them to be a better decision-maker, quitting is the primary skill I would choose, because the option to quit is what allows you to react to that changing landscape.
7Loc 483
Quitting is the tool that allows you to make that different decision when you learn that new information. It gives you the ability to react to the way the world has changed, your state of knowledge has changed, or how you have changed. This is why it’s so important to skill up on quitting, because having the option to quit is what will keep you from being paralyzed by uncertainty or being stuck forever in every decision you make.
8Loc 533
When you are weighing whether to quit something or stick with it, you can’t know for sure whether you can succeed at what you’re doing because that’s probabilistic. But there is a crucial difference between the two choices. Only one choice—the choice to persevere—lets you eventually find out the answer. The desire for certainty is the siren song calling us to persevere, because perseverance is the only path to knowing for sure how things will turn out if you stay the course. If you choose to quit, you will always be left to wonder, “What if?” Just as the Sirens of mythology lured sailors toward their song, we are lured to persevering because we want to know. It’s the only way to avoid those “what ifs.” The problem, of course, is that sometimes, the siren song lures you toward a rocky shoal that breaks your ship apart. Or it leads you to your death at the top of Everest. In fact, the only time you can be sure you should quit is when it’s no longer a decision, when you’re at the edge of the abyss or you’ve already stumbled into it. Then you have no choice but to abandon course.
9Loc 550
As the world changes, we should be quitting stuff that isn’t working or is no longer what people want or what we want. We should be surveying the landscape, both to understand when that may happen as well as to find something better we can turn our attention to.
10Loc 729
If you quit on time, it’s not going to seem like anything particularly dire is happening at that particular moment. That’s because quitting is a problem of being able to glimpse at the range of ways the future might play out and see that the likelihood that things will turn out poorly is too high to make it worth your while to continue. At the moment that quitting becomes the objectively best choice, in practice things generally won’t look particularly grim, even though the present does contain clues that can help you figure out how the future might unfold. The problem is, perhaps because of our aversion to quitting, we tend to rationalize away the clues contained in the present that would allow us to see how bad things really are.
11Loc 752
There is a well-known heuristic in management consulting that the right time to fire someone is the first time it crosses your mind. This heuristic is meant to get businesses to the decision sooner, because most managers are reluctant to terminate personnel, hanging on to them too long.
12Loc 769
We are reluctant to walk away when we should because we have the feeling that doing so will slow our progress or stop it altogether. But it is the reverse that is actually true. If you stick to a path that is no longer worth pursuing, whether it’s a relationship that isn’t going well, or a stock that you’re invested in that’s losing money, or an employee that you’ve hired who isn’t performing, that is when you lose ground. By not quitting, you are missing out on the opportunity to switch to something that will create more progress toward your goals. Anytime you stay mired in a losing endeavor, that is when you are slowing your progress. Anytime you stick to something when there are better opportunities out there, that is when you are slowing your progress.
13Loc 871
“Imagine it’s a year from now and you stayed in the job that you’re currently at—what’s the probability you’re going to be unhappy at the end of that year?” She said, “I know I’m going to be unhappy, one hundred percent.” I followed up by asking, “If it’s a year from now and you switched to this new job you’re considering, what’s the probability you’re going to be unhappy?” She said, “Well, I’m not sure.” “Is it one hundred percent?” She said, “Definitely not.” At that moment, she realized, “Oh, wait a minute. I’m always going to be unhappy if I stay. If I switch, sometimes I’ll be unhappy, but sometimes I won’t. Sometimes, I’m going to find real fulfillment in the job that I’m switching to, and that has to be better.”
14Loc 904
When you are making a decision about whether to quit, you need to listen to those people from the past who are giving you important advice. Sometimes, the person sending you a message is someone who has traveled a similar path before you. And sometimes, the person traveling from the past is an earlier version of yourself.
15Loc 932
If you feel like you’ve got a close call between quitting and persevering, it’s likely that quitting is the better choice.
16Loc 996
Quitting on time usually feels like quitting too early. The hardest time to make a quitting decision is when you’re in it. Our intuition is that quitting will slow down our progress. The reverse is actually true. If you walk away from something that is no longer worthwhile, that frees you up to switch to something that is more likely to help you achieve your goals—and you’ll get there faster. When the time is objectively right to quit, nothing particularly dire will be happening right at that moment. Getting the timing right means looking into the future and seeing that the chances things will go your way are too slim. Thinking in expected value helps you figure out if the path you are on is worth sticking to. EV is not just about money. It can be measured in health, well-being, happiness, time, self-fulfillment, satisfaction in relationships, or anything else that affects you. If you feel like the choice between persevering and walking away is a close call, it’s likely that quitting is the better choice. In hindsight, we can see when someone has waited too long to quit, and we tend to be harsh in our judgment of those people. But when someone quits before it seems obvious to others, we mock them for quitting too early. That’s the quitting bind.
17Loc 1,091
When we are coming to a decision fresh, having not yet incurred any losses or gains, loss aversion creates a preference for options associated with a lower chance of incurring a loss. It makes us risk averse and stops us from getting started, from choosing options where we might lose. But when we have already accrued losses on paper, we become risk seekers. Daniel Kahneman subsequently characterized this as sure-loss aversion.
18Loc 1,158
Our goal, obviously, should be to persist when we have a positive expected value, regardless of whether we have already won or lost to a prior course of action. Because these decisions are made under uncertainty, we rarely know for sure whether sticking or quitting is the best choice. In the same way that it’s easier for the cab drivers to see if they’ve met a daily goal, it’s easier for any of us to see whether we’re ahead or behind so we use that signal to determine whether or not to persevere.
19Loc 1,245
A key finding of prospect theory is loss aversion, the phenomenon whereby the emotional impact of a loss is greater than the corresponding impact of an equivalent gain. Loss aversion creates a preference for options associated with a lower chance of incurring a loss. It makes us risk averse. When we are in the gains, we have a tendency to quit too early in order to avoid the risk of giving those gains back. In other words, we like to quit while we’re ahead. When we are in the losses, we become risk seekers. We want to keep going, hoping we can avoid ever having to realize the loss. Daniel Kahneman has characterized this as sure-loss aversion. In other words, we like to stick when we’re behind. Quitting on time usually feels like quitting too early, and the usually part is specifically when you’re in the losses. Retail investors show this pattern of quitting when they’re ahead and sticking when they’re behind. Even expert investors don’t get their quitting decisions just right. They outperform on their buying decisions but underperform on their selling decisions. We naturally track and get feedback on the things we are doing. But once we quit something, we also quit keeping track of that course of action. This creates a problem with getting high-quality feedback, which in turn makes it hard to hone our quitting skills.
20Loc 1,472
There are all sorts of ways we get stuck in our decisions. Presented with the opportunity and the relevant information, we will over-persist, rejecting the chance to quit and backing up our original decision by spending even more resources to try to save the endeavor.
21Loc 1,482
When we are in the losses, we are not only more likely to stick to a losing course of action, but also to double down. This tendency is called escalation of commitment. Escalation of commitment is robust and universal, occurring in individuals, organizations, and governmental entities. All of us tend to get stuck in courses of action once started, especially in the face of bad news. Escalation of commitment doesn’t just occur in high-stakes situations. It also happens when the stakes are low, demonstrating the pervasiveness of the error.
22Loc 1,647
Like the katamari, rolling around collecting debris, which makes it grow in mass and collect more and even bigger debris, there is a self-reinforcing aspect to the sunk cost fallacy that we really need to watch out for. When we embark on an endeavor, we also accumulate debris—the time, money, and effort we have spent. As we accumulate costs, the mass grows, escalating our commitment and making it more and more difficult to quit. That decision to persevere then makes us accumulate more costs, which then makes us even more likely to continue the next time we consider quitting. And that keeps adding weight to the scale in favor of persevering. The whole thing snowballs.
23Loc 1,736
What really matters is maximizing your expected value across all the things you start, across all of your mental accounts. If you’re investing in a number of stocks, some are going to win and some are going to lose. What matters is whether you’re winning across your whole portfolio not whether any one investment is up or down. But that’s not how we naturally think. We don’t think about the whole portfolio of stocks we own. Each is associated with its own mental account that we don’t want to close out unless we are in the gains. What’s true for one stock or one hand of poker is just as true for an individual decision or a project, or climbing a mountain, or opening a discount store in a converted chicken coop. When we start any of these things, we open a mental account. When things start going poorly, we don’t want to quit because we don’t like to close accounts in the losses.
24Loc 1,758
But the reality is that when it comes to decisions about whether to continue or withdraw, what matters is whether the next life is worth putting at risk, as much as we instinctively want to take into account the lives already lost. If we continue, are our chances of getting the outcome we want worth risking additional lives and imposing those losses on other families?
25Loc 1,804
The sunk cost effect is a cognitive illusion where people take into account resources they have previously sunk into an endeavor when making decisions about whether to continue and spend more. The sunk cost effect causes people to stick in situations that they ought to be quitting. When deciding whether to stick or quit, we are worried that if we walk away, we will have wasted the resources we have spent in the trying. You might be experiencing the sunk cost fallacy if you hear yourself thinking “If I don’t make this work I will have wasted years of my life!” or “We can’t fire her now, she’s been here for decades!” Sunk costs snowball, like a katamari. The resources you have already spent make it less likely you will quit, which makes it more likely you will accumulate additional sunk costs, which makes it again less likely you will quit, and so on. The growing debris of your prior commitment makes it increasingly harder to walk away. We don’t like to close mental accounts in the losses. Knowing about the sunk cost effect doesn’t keep you from falling prey to it. You can’t trick yourself into not taking sunk costs into account by trying to view the situation as a new choice. Asking whether or not you would continue if the decision were a fresh one doesn’t mitigate the sunk cost effect the way you might intuitively think it would.
26Loc 1,891
Astro Teller clearly understands that quitting gets you where you want to go faster. The sooner you figure out that you should walk away, the sooner you can switch to something better. And the sooner that happens, the more resources you’re saving, which you can then devote to more fruitful endeavors.
27Loc 1,901
One of Teller’s valuable insights is that pedestal-building creates the illusion of progress rather than actual progress itself. When you are doing something that you already know you can accomplish, you’re not learning anything important about whether the endeavor is worth pursuing. You already know you can build the pedestal. The problem is whether you can train the monkey. On top of that, Teller realizes that when you’re building pedestals, you are also accumulating sunk costs that make it hard to quit even as you find out that you may not be able to train the monkey to juggle those torches. By focusing on the monkey first, you naturally reduce the debris you accumulate solving for something that’s, in reality, already solved.
28Loc 1,912
Astro Teller also understands a subtler but no less important point, that we have a tendency, when we butt up against a monkey that is proving difficult to solve, to turn our attention to building pedestals rather than giving up. We prefer that illusion of progress to having to quit and admit defeat.
29Loc 1,924
Figure out the hard thing first. Try to solve that as quickly as possible. Beware of false progress.
30Loc 1,931
If we can identify in advance what the signals are that we should pay attention to and make a plan for how we will react to them, we can increase the chances that we’ll cut our losses when we ought to. Essentially, when you enter into an endeavor, you want to imagine what you could find out that would tell you it’s no longer worth pursuing. Ask yourself, “What are the signs that, if I see them in the future, will cause me to exit the road I’m on? What could I learn about the state of the world or the state of myself that would change my commitment to this decision?” That list offers you a set of kill criteria, literally criteria for killing a project or changing your mind or cutting your losses. It’s one of the best tools for helping you figure out when to quit closer to on time. Kill criteria could consist of information you learn that tells you the monkey isn’t trainable or that you’re not sufficiently likely to reach your goal, or signs that luck has gone against you.
31Loc 1,991
In general, this idea of casting yourself into the future, imagining a failure, and then looking back to try to figure out why is called a premortem. Using a premortem is a great tool to help develop high-quality kill criteria.
32Loc 2,053
The importance of thinking about states and dates in setting kill criteria in advance has been developed and tested in situations with the highest possible stakes, affecting large numbers of people and gigantic, world-changing decisions. But the concepts are broadly applicable to your personal decisions, where you are trying to spend your resources on things that matter and avoid pedestal-building when you ought to be quitting.
33Loc 2,103
mental model and kill criteria help us overcome our aversion to closing accounts in the losses. First, they both get you to no faster, which naturally limits the losses that you have to absorb when you quit. And the less you are down, the easier it is to walk away. Second, when you set out clear kill criteria in advance and make a precommitment to walk away when you see those signals, you are just more likely to follow through, even when you are losing. Anytime you can make a decision about cutting your losses in advance, you’ll do better at closing those mental accounts.
34Loc 2,109
Monkeys and pedestals is a mental model that helps you quit sooner. Pedestals are the part of the problem you know you can already solve, like designing the perfect business card or logo. The hardest thing is training the monkey. When faced with a complex, ambitious goal, (a) identify the hard thing first; (b) try to solve for that as quickly as possible; and (c) beware of false progress. Building pedestals creates the illusion that you are making progress toward your goal, but doing the easy stuff is a waste of time if the hard stuff is actually impossible. Tackling the monkey first gets you to no faster, limiting the time, effort, and money you sink into a project, making it easier to walk away. When we butt up against a hard problem we can’t solve, we have a tendency to turn to pedestal-building rather than choosing to quit. Advance planning and precommitment contracts increase the chances you will quit sooner. When you enter into a course of action, create a set of kill criteria. This is a list of signals you might see in the future that would tell you it’s time to quit. Kill criteria will help inoculate you against bad decision-making when you’re “in it” by limiting the number of decisions you’ll have to make once you’re already in the gains or in the losses. In organizations, kill criteria allow people a different way to get rewarded beyond dogged and blind pursuit of a project until the bitter end. A common, simple way to develop kill criteria is with “states and dates:” “If by (date), I have/haven’t (reached a particular state), I’ll quit.”
35Loc 2,192
In large part, we are what we do, and our identity is closely connected with whatever we’re focused on, including our careers, relationships, projects, and hobbies. When we quit any of those things, we have to deal with the prospect of quitting part of our identity. And that is painful.
36Loc 2,273
He described the endowment effect as “the fact that people often demand more to give up an object than they would be willing to pay to acquire it.”