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Hope, Expectations, and Winning the Lottery

" Most people know that the lottery is not a good investment plan. It’s not rational to invest large amounts of money in lottery tickets, because you’re almost certain to lose no matter how much cash you spend at the gas station or convenience store.

Buying a single lottery ticket or two, however, is actually quite rational. Most of us don’t play the lottery as an investment in anything other than dreaming. For a few minutes after you buy the ticket and before you scratch off the numbers, or maybe even for a few days if the winning numbers aren’t announced until later, you have the opportunity to walk around with a dream in your pocket.

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“What do you do for a living?” “I confound expectations.”

Grammys

Bob Dylan gave a rare 35-minute speech at a MusiCares event for the Grammys last night. It's all interesting, but here's my favorite part:

"Critics have made a career out of accusing me of having a career of confounding expectations. Really? Because that's all I do. That's how I think about it. Confounding expectations."

"What do you do for a living, man?"

"Oh, I confound expectations."

You're going to get a job, the man says, "What do you do?" "Oh, confound expectations."

And the man says, "Well, we already have that spot filled. Call us back. Or actually, don't call us, we'll call you."

Here’s the full transcript.

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There’s a Good Reason Why We Keep Repeating the Same Mediocre Experiences

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I loved this story from a reader in response to why I enjoy the routine of visiting a hotel that’s consistently bad:

"Years ago my in-laws would drive me crazy by complaining about the food at a (now defunct) restaurant chain that they would unfailingly stop at numerous times when traveling from Pennsylvania to Florida each year. It was a major topic of discussion; how not-good the food was, service was terrible, etc. But the food wasn't bad enough to stop them from going back to the chain (and same locations) year after year. I asked them why they went there at all when all they did was complain and when there were probably so many local restaurants they could try along the way.

They finally came up with the answer "We know what to expect."

As you have said, it's easy to get into a rut. Some ruts are good, some not so much. I try to remember this story anytime I find myself sliding into a rut. It doesn't always work, but at least I've made a conscious decision and then I can't complain however it turns out."

I also always visit the Waffle House whenever I'm in the southern U.S. But of course, the Waffle House isn't mediocre. It's amazing!

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Why I Keep Returning to My Least Favorite Hotel in London

Sheraton-Heathrow1 Many years back, I checked into the Sheraton Heathrow after winning a bid on Priceline. It was incredibly cheap—something like $30-40 for the night, as I recall.

At the time I was still new to the world of branded hotels. A few times a year, I might stay in a Starwood or Hilton property. I spent the rest of the nights in hostels, guesthouses, or on the couches of kind hosts. Arriving at the Sheraton Heathrow for the first time, I remember thinking, huh, this hotel is a little weird—but hey, it’s a hotel!

Everything about it was dismal, from the carpeting in the public guest floor areas to the tiny, unclean rooms, right on down to the attitude of the staff, who didn’t seem particularly pleased to be working there.

As I traveled more and more, I returned to the Sheraton Heathrow a couple times a year. Each time I had more experience in staying at other hotels, and finally I came to the realization: it's not me—this place is just really bad.

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Video Update: Expectations Management and the Worst Hotel in All of Guyana

Hey guys,

Greetings from Georgetown, Guyana - the launch point for the second part of my trip.

For the past couple of days I've been staying in what TripAdvisor calls the worst hotel in all of Guyana. Is it really that bad? Check out the video.

Also, a note from the director (that's me): I recorded this video outside at 6:00 p.m., thinking that sunset would be half an hour later. It turns out that sunset in Guyana starts about 5:45. Who knew? Anyway, I had to rush to get this going. I did a second take afterwards, which was a bit more concise, but the sky was too dark. I know, I know - it's a work in progress.

See you next from Suriname, a 10-12 hour journey from here via ferry and a combination of buses. Thank you for the great feedback last week; I have read all the comments and wish I could be more responsive.

I'll hole up in the Dominican Republic at the end of this trip and get back up to speed. Have a great week!

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