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In Captain Wentworth’s world, what you do is who you are. For example, we can look at how Wentworth viewed dear departed Dick Musgrove, who had served on Wentworth’s ship. When Dick comes up in conversation, Anne realizes from Wentworth’s smirk that as Captain he had "probably been at some pains to get rid of [Dick]" (8.28). Dick’s family background as part of the second-best family in the district doesn’t mean a thing onboard ship: what does matter is that he’s a lazy slob.
So when, in the novel’s backstory, Anne breaks off their engagement, Wentworth passes judgment on her character: obviously, he thinks, she must be a wimp to be so easily persuaded. He sees only how she acts, not the concerns behind it; she doesn’t reject him simply because Lady Russell says so, but because she believes it’s the right thing to do. Wentworth’s focus on action rather than thought causes him to get a false idea of Anne’s character. This is one of the reasons he doesn’t come back for her even when he’s rich.
When the paths of Wentworth and Anne do cross again he goes for a woman who’s the yin to Anne’s yang: Louisa Musgrove. While Anne tends to watch and listen, Louisa is the one who is being watched and listened to by others. Since Louisa goes out and gets what she wants, whether it’s fixing her sister up with Charles Hayter or arranging a family trip to Lyme, Wentworth thinks that’s a sign of her firmness of character. And firmness of character, in his mind, translates as reliability – he can trust that once she makes up her mind, she’ll stick to it, while with persuadable characters there’s no way of knowing what they’ll do next. Wentworth tells Louisa as much:
"It is the worst evil of too yielding and indecisive a character, that no influence over it can be depended on. You are never sure of a good impression being durable; everybody may sway it." (10.26)
Wentworth’s problem with people who are open to persuasion is that he can’t use their current actions to predict what they’ll do next, because they’re guided by other people rather than set internal principles.
Wentworth’s views get a jolt when Louisa decides to follow her principle of doing what she pleases and jump off the Cobb steps. Her recklessness, and Anne’s responsibility, tell Wentworth that something’s not right with the way he’s been seeing the world. Sticking to your guns isn’t a good idea if those guns are about to backfire, and swaying in the wind can be the best choice if that wind is blowing in a fair direction. In short, Wentworth has to learn about a little thing called context.
Wentworth’s development over the course of the novel owes a lot to Anne and her course in Appreciating Me 101. Would this self-made man have made the same advances without her help? Fortunately, he didn’t have to.
When Anne originally meets Captain Wentworth, he’s like a computer geek in 1975: he’s convinced he’s got big things ahead, but doesn’t have much to show so far.
Captain Wentworth had no fortune. He had been lucky in his profession; but spending freely, what had come freely, had realized nothing. But he was confident that he should soon be rich: full of life and ardour, he knew that he should soon have a ship, and soon be on a station that would lead to everything he wanted. He had always been lucky; he knew he should be so still. (4.4)
So what Wentworth has is a belief that he’s going to succeed, but not much more than that. His past success was based on luck, and while he thinks his luck will hold, we can hardly blame Lady Russell for not wanting to stake Anne’s future happiness on a spin of fortune’s wheel. Except, of course, if you don’t bet you can’t win, and win Wentworth does.
All his sanguine expectations, all his confidence had been justified. His genius and ardour had seemed to foresee and to command his prosperous path. (4.8)
It’s like Captain Wentworth has discovered The Secret two hundred years early: he believes he will be successful, and lo and behold, he is. But it’s not quite that easy, as it did take "genius," aka smart decisions, and "ardour," aka hard work, as well as luck. And also risk-taking, as we find out later, as Wentworth first finds success in the Asp, "a ship not fit to be employed" (8.12) and ready to sink at any minute. Would Wentworth have taken such a ship had he not been heartbroken at the time, but instead thought Anne was waiting at home to marry him? It’s impossible to say, but that impossibility just points to the dangers of getting too hung up on what might have been.
Whatever might have been, what we have by the time the novel itself begins is a Wentworth who is doing very well for himself. What he lacks in birth and family connections, he makes up for in wealth and charisma. His "air" (20.39) is such that even Lady Dalrymple admires him. His ability to make a convert of even Sir Walter by the novel’s end shows how far money and style can get you even in aristocratic society, and suggests that the social hierarchy might be more open to change than it initially seems. (For more on this, see "Overview" and "100 Words on Society and Class").