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Sometimes It Doesn’t Work, But You Still Have to Try Anyway

16484981468_a7a7c1e677_z You always hear about the people who took a chance that paid off. You always hear the try, try again stories—those case studies of overcoming what seems to be an insurmountable challenge.

You know how the story goes: so-and-so encountered failure a dozen times, but on the thirteenth attempt, they made it!

Then so-and-so says, “Thanks, everyone. I’m so glad I kept going. Victory was never guaranteed, but look at me now."

Sometimes, though, you head into a situation knowing that there’s a high likelihood of failure. I'm not talking about the possibility of failure, I'm talking about odds that would make a free-wheeling Las Vegas roulette player back away from the table and head straight for the buffet.

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WDS 2015: Initial Batch of 1,200 Photos Now Online

Hi, everyone! I’m still on blogging hiatus but am looking forward to getting back to daily writing very soon. Thanks for your understanding.

Here in Portland, WDS week has come to an end and you can view more than 1,200 photos in the official media albums.

I'll be sharing more about WDS in the weeks to come, and I'll be linking to posts written by our attendees. For now, here are just a few highlights.

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One Log Cabin and 800 Yoga Mats: Some Unconventional Tax Deductions from My Life in 2014


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My tax return is complicated for a lot of reasons. First, I run several different businesses which all have their own set of accounting. WDS, our annual gathering, has its own legal structure, including a foundation that is completely separate from all my other projects. Last year we started an all-new event that also has its own legal structure.

So yeah, it’s complicated. It takes about 20 hours just to prepare all the info for my accountant, and as with most tax-prep tasks, it’s not usually a fun process. But I do enjoy seeing some of the charges on my statements from the previous year. They remind me of the crazy life I have, and the many fun experiences that I'm fortunate to participate in.

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Bonus Miles from All 12 “Dining Dash” Visits Have Posted (AKA “Yes, It Works”)

Two weeks ago, the travel hacking crew and I went on our 2015 Dining Dash, an attempt to visit 12 restaurants in a day. As explained in the recap post, we did it!

And I just noticed that we really did it, because the miles posted up for all 12 of the stops. When I logged into my AA account this morning, I was greeted with this update:

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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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This Magic Journey

Everything begins with a crazy idea, and this particular crazy idea comes to you in stages.

You don't decide to visit every country in the world when you haven't been out of your own neighborhood. First you go to a dozen countries in Africa, then a dozen more in Europe, and before you know it you've reached 50-country status.

That's when you start thinking about goals, and that's when you first decide to visit 100 countries before you die.

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