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When I was a kid, I was pretty sure of whatever conclusions I came to. This used to irritate my father, who would say with exasperation when we disagreed, “You just think you’re right.” I found that an odd thing to say. Of course I thought I was right. Why would I have said it if I hadn’t thought I was right? Why should I question myself now?

My 12-year-old self would have really understood Barack Obama and various other politicians who seem puzzled when people want them to pinpoint the things they’ve been wrong about. I was reminded of it again a couple of days ago when I read these quotes from Obama when CBS News asked him about his mistakes as president so far. He sounded like a job applicant struggling to find an answer to a question about what he biggest weakness is.

“When I think about what we’ve done well and what we haven’t done well,” Obama said, “the mistake of my first term — couple of years — was thinking that this job was just about getting the policy right. And that’s important. But the nature of this office is also to tell a story to the American people that gives them a sense of unity and purpose and optimism, especially during tough times.”

See? He hasn’t actually made any mistakes. He just hasn’t sold his actions well enough.

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Life doesn’t come with convenient signposts letting us know which is the path to happiness and which is the path to misery, so we’re stuck taking blind gambles. Sometimes we choose well. Sometimes we don’t. Sometimes we have chances to change mistaken choices we’ve made. Sometimes we don’t.

But all along the way, we’re guessing and hoping, no matter how much thinking and reasoning we bring to bear on our choices. And we frequently end up with regrets that we carry to our graves.

I thought about this Saturday because of a woman I met and talked with. She’s consumed with trying to make a decision that will affect the rest of her life. Although the specifics of her story are very different from what happened to me, the feelings she described were enough to remind me of where I was four years ago this month.

We’re going to call her Ashley. She has two men who want to marry her, but she can’t decide what to do. She’s dated both of them, but the relationships have been very different. With one guy, she feels the magical connection that most of us want to feel and that a few of us have felt in a very real way. But that relationship had problems. It had great highs, but great lows. She saw things in him that she knew needed work — for both of them.

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Aaron Collins died last Saturday in Lexington, Ky. When his family got together to have pizza three days later, they weren’t just having lunch. They were fulfilling the last wish expressed by Collins in his will.

Collins’ written instructions to his family asked for the usual things — such as his debts to be paid with whatever he had — but they also had an unusual request. He wanted his family to go eat somewhere together and “leave an awesome tip” for the server. He suggested pizza and a $500 tip.

The 30-year-old didn’t leave much money and there wasn’t enough to fulfill the request, so the family set up a website in the dead man’s name and asked for donations for $500. They quickly reached the goal. On Tuesday, the family gathered at Puccini’s in Lexington. With a video camera rolling in the background, Collins’ brother told a stunned young woman that his recently deceased brother wanted someone to have the tip — and then he handed her $500. (See the video below. The audio isn’t good, but there are words on the screen to help.)

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