“10 letters are slipped into a purple folder and put in the daily briefing book that is delivered to President Obama at the White House residence… The letters are read by the president, and he sometimes answers them by hand, in black ink on azure paper.”
—the New York Times

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Dear Mike,

Your letter reminded me of the old Abraham Lincoln quote: “Always bear in mind that your own resolution to succeed is more important than any other.” But I gotta say, a timeshare in Florida is not an investment. It’s just not. If you want go south for a couple of weeks out of the year, I think that’s great. You work hard, you deserve it. But you’re never going to be able to sell that timeshare for more than the purchase price. Never. Also, in my opinion, the whole process is a little suspect. Somebody offers you a free vacation, and suddenly there you are listening to a 90-minute sales pitch.

Look, here’s what these guys won’t tell you. There are annual fees that can range from a couple hundred dollars to over a thousand. So unless you’re really going to use your timeshare each year, and the cost of a hotel would exceed your annual fees, you might want to pass.

Then again, if that doesn’t sound like that will be a problem for you, maybe it’s worth considering. To be fair, the timeshare industry has changed a lot over the years, in many ways for the better. Let me know what you decide.

Sincerely,
Barack

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Dear Tommy,

Look, you need to trust Mrs. Klepperman’s academic timeline. If she has promised that you will get to dinosaurs before the year is out, you should believe her. Whereas I agree that the Cretaceous period is one of the more interesting eras—clearly any geologic system in which the Tyrannosaurus Rex flourished offers a sexier academic endeavor than, say, a time when eukaryotes developed flagella—I don’t want you to neglect the earlier epochs. The Cambrian period, for example, has an unusually high amount of deposits that offer extraordinary fossil richness and completeness. Yet in your letter you ignore this fact, and, with red crayon, have violently crossed out pictures of trilobites and fungi.

Tommy, please.

Though we may have a fundamental disagreement about how interesting one geological period is compared to another, the fact of the matter is that each era is a building block for the next. That’s just true. In order to properly understand, say, the Cretaceous Period, we need to have a working knowledge of the Jurassic, Triassic, Permian, Carboniferous, and so on.

And no, Mrs. Klepperman does not hate you.

Follow your dreams,
Barack

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Dear Marie,

Thank you for your letter.

Nice name, Marie. Reminds me of Molly or Martina. Not as nice as Marie though. Are you named after anyone in your family? Like a grandmother or an aunt? Some parents like to be more indirect when they name kids after their family members. They’ll stay away from the immediate family and go for a more obscure member of the extended family. I wouldn’t be surprised if you were named after your grandfather’s sister. I guess that would make her your father’s aunt, assuming that you were named after your grandfather’s sister on your father’s side. The funny thing is I bet your father didn’t even really know his aunt that well, but named you after her as a nice gesture to your grandfather. Maybe there was some tension between your father and his father that was smoothed out by naming you Marie. Something to think about.

Regards,
Barack

PS. What do you think of the color of this paper? It’s called Azure. It’s like a blue cyan.

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Dear Keith,

Thank you for your letter. I have thought long and hard about it and have been weighing the costs and benefits of your choice. Personally, I would stay in the band unless you have an individual project you are just dying to work on. It’s good money, right? And I got to say, as a huge fan, the highlight of any concert is when you come out and sing, “You Got the Silver.” Even if somebody has seen you guys 50 times, it’s always a welcome treat and breaks up the show quite nicely. Would hate to lose that.

Oh, and as for your other problem, try the Phillips and if that doesn’t work go to the hardware store.

Fondly,
Barack

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Dear Dave,

Hey, I hear ya, pal. People are idiots, and driving in Boston can be torture. What are you gonna do, you know?

Chin up,
Barack

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Dear Amy,

No.

Barack

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Dear Jarrod,

This is the 5th time I have written back to you and it appears that nothing has changed.

I shouldn’t be telling you this, but Jamie sends me letters too. I haven’t answered them because I thought it would be a conflict of interest. But here’s the thing: she loves you man. She really does. But hell, you know that. Everyone knows that. So if you don’t love her, you have to say something. Look, you can’t lead Jamie on. It’s okay if you don’t love her. What is not okay is dragging this out because you are too afraid to have a real conversation with her. She doesn’t deserve that. Then again, I’ve never done the long distance thing before so maybe I’m off base here.

Keep me posted,
Barack

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Dear Amanda,

I understand your concerns. Please talk to your classmate, Tommy, for my views on your study of prehistoric life, and the viability of Mrs. Klepperman’s lesson plans.

Follow your dreams,
Barack