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Always Ask for What You Want: A Lesson in Asymmetrical Risk

TLDR: An asymmetrical risk is one where the potential reward greatly outweighs the potential loss. Identify and take more of these risks.

Every so often, a news article that offers "expert advice" on getting upgraded at the airport makes the rounds. Inevitably, the advice includes something about how you should "dress well and ask nicely."

Real travel experts always roll their eyes at such advice. These days, almost all upgrades are handled through computer systems based on elite status, travel disruptions, and other automated factors.

The travel experts then write their own articles explaining why the advice is dumb, and the process repeats a few months later.

I'm with the real travel experts: the advice on asking for upgrades is just clickbait. Yet I can't help but remember a time many years ago—way back in 2007, I think—when I was traveling from Copenhagen to Chicago.

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Do Hard Things Because They Are Hard

Last week I went to Utah to run an unusual marathon. My time was well over two hours slower than any marathon I've done, but that was by design—I was running with someone who was doing a series of extreme events back-to-back, every day for 100 days in a row.

The pace, therefore, was slow.

His name is James Lawrence, more popularly known as the Iron Cowboy. I'd heard of James a year or two ago after watching a documentary of his previous quest where he attempted (and accomplished, with a few small variations along the way) 50 Ironman-distance triathlons in 50 states in 50 days.

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How to Write a Novel

First up, thank you so much for your support of THE MONEY TREE! Despite the numerous challenges of current events, the book is getting out to lots of people.

Now that it's out, a number of readers have asked me to explain more about a big change I made. Specifically, my new book is unlike any of my six others: it’s fiction. I created an imaginary world of characters, and did my best to bring them to life.

It started partly because I wanted to do something new. The more I thought about it, the more nervous I felt ... which of course is often a good sign. A sense of nervousness and even feeling a little afraid can be helpful in showing you what you need to do next.

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201 More Stories of People with Day Jobs Creating Side Hustles

Listen to Side Hustle School:
-in iTunes or Stitcher
-on the website
On January 1, I began a new project: to share a story every day of someone who starts an income-generating project (a "side hustle") without quitting their day job.

The project failed and I decided to give up. Just kidding! We are relentlessly moving along, publishing story after story—and it's getting better and better!

I recently completed the first 100 200 300 days. There's much more to come, but I'm excited about everything I've learned since beginning back in January.

If you're just joining in, you can also catch up on any recent episode from the links below.

Download all episodes from each month:

JAN | FEB | MARCH | APR | MAY | JUN | JUL | AUG | SEP | OCT

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Instead of Manufacturing Hype, Just Start Doing Great Work

I got a call to do some filming for a marketing agency in Los Angeles. I had the date open and it sounded interesting, so I decided to go.

The filming took place in a Beverly Hills mansion, probably the largest single-person home I’ve ever been in. On the way in I waved awkwardly to the car valet who was hosing down a Porsche, then said hello to the personal chef chopping vegetables in the kitchen.

All over the studio, which looked a bit like what I’d imagine a porn set to be, there were whiteboards set up with verbal cues. Most of them related to the science of persuasion: scarcity, limited-time offer, feel better about yourself.

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If You Have No Challenges, Maybe It’s Time to Change Your Life

Have you ever walked around endless airport highway ramps for more than a mile? When it’s after 10pm and you’ve got your carry-on bags with you?

Yeah, so I did that the other night. Short version: when you arrive in DFW and are staying at the off-airport Hyatt Regency, you’re supposed to take the SkyTrain to the C gates, and then hike through the parking garage to the entrance. I’ve done it that way before, and it’s not terribly difficult.

This time I was hanging out in the D terminal, working from my favorite U.S. airline lounge, and I decided to walk outside and skip the whole SkyTrain thing. How hard could it be? I’ve been to DFW, oh, I don’t know—several hundred times if not more. Sure, it’s a big place, and there was that time I got lost trying to return a rental car and missed my flight, but still.

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“I am capable of more than I imagined”: On the Road with Elizabeth Glanzer

After experiencing many travel misadventures around the world, I love hearing other people's "silver linings" stories. This one (and other stories, too) comes from Elizabeth Glanzer in Los Angeles.

I'm a therapist and work with teens and young adults who feel misunderstood and out of place. I study psychoanalysis and neuroscience every chance I get.

Traveling is one of my favorite things to do. For me, it pulls everything together and shatters blind spots. People, culture, art, and "normal" is all relative when I go abroad, and I appreciate the ability to see how someone else lives and thinks.
Liz3

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The Modern Day Swiss Family Robinson: On the Road with Sheralyn Guilleminot

This is a traveler case study. (Read others or nominate yourself.)

Sheralyn Guilleminot didn't want to run the risk of never getting around to traveling the world. She and her husband Paul took to the road as a young family, home-schooling their sons while experiencing life in Southeast Asia. Here's their story.

Sheralyn-Guilleminot Tell us about yourself.

I've lived most of my life in Manitoba, Canada. It's where I grew up, got married, and worked. My husband Paul and I wanted to travel the world, but it seemed impractical. Once we had our two boys, though, I felt like there was never enough time to spend with Paul, with our family, or to indulge in being myself. And I didn’t see an end to being pulled in too many different directions. Something had to change.

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Adventures in Travel Hacking

Greetings from LHR Terminal 3, soon to be departing to San Francisco after a weekend in London for the U.K. launch of The $100 Startup. We've had a lot of new readers join our community over the past month (hi, everyone!) and I thought it would be good to provide an overview of travel hacking: the means of seeing the world in style while on a budget. For the past five years, I've been to at least 20 new countries a year on my quest to go everywhere. In addition to overland travel by bus or train, I get to many of them through a variety of paid and almost-free plane tickets ...

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Advanced Travel Planning: Looking Ahead to January-June 2009

Regular Readers: Please fill out my short feedback survey. Thanks to those who have done so already! (If you’re new, just keep reading the new post below.)

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Some of you have noted that I haven’t published any first-person travel adventures lately. I haven’t been to any crazy countries, slept in airports, crash-landed without a visa, etc.

Don’t worry – I’m not getting soft. I’ve enjoyed hanging out in Seattle, trying to make a living, get my book contract sorted out, and recover from a running injury that has bothered me for a while. The extended break has been good for me, but in January I’ll resume my adventures around the world.

Over the past couple of weeks, I’ve been planning out my trips for the first half of 2009. I tend to change things around a fair amount, but as of now, here is what I expect it to look like from January to June. If it seems overwhelming, first remember that I’ve done this a lot – I certainly didn’t begin with itineraries as complex as the ones I’ll show you here.

And of course, I’ll chronicle each trip in more detail as it gets closer. Cool?

JANUARY

In January, I’ll head to Northeast Africa, flying in to Ethiopia, then heading up to Somaliand (not Somalia; even I am not that crazy), over to Djibouti, and hopefully on to Eritrea and back out after about 12 days of roaming.

My fingers are crossed on this one, because the Eritrean embassy in D.C. has not yet given me a visa. If I don’t get one, I’ll have to scramble to figure something else out, because I already have a flight booked out of Asmara, the capital.

Earlier this summer, I learned that the Kurdish (Iraqi) government checked out this web site before deciding to issue me a visa at no charge. They even sent me a “Welcome Chris Guillebeau!” message which made me feel like a minor celebrity, at least in Kurdistan. Perhaps the Eritreans will be similarly kind – guys, if you’re reading this, please help me out. You can keep the $40 money order that I sent; I just need the visa.

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Southern Africa MapLATE FEBRUARY- EARLY MARCH

Assuming I get to Eritrea or at least get home somehow, in late February, I’ll head to Washington, D.C. for a conference, then fly out from there to Qatar to resume the Round-the-World ticket I began last year. That trip will take me to southern Africa – specifically Mauritius and Namibia. I also hope to take a side-trip to Swaziland and Mozambique while I’m over in that part of the world.

After I’m done there, the ticket takes me back to my usual Asian hub of Hong Kong, where I’ll need to figure out how to get back to the States for another four-week stay at home.

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The Three Mysterious CountriesAPRIL

One month later, I’ll be back on the road to visit Haiti and what I call the “three mysterious countries” of South America. They are Guyana, Suriname, and French Guiana. If you haven’t heard much about them, don’t feel bad – that’s why I call them “mysterious.” I’m not sure I’ll solve any mysteries, but I’ll try to at least get there and back.

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south-america-mapMAY AND JUNE

In May and June, I hope to wrap up the rest of South America, which for me includes Peru, Ecuador, Columbia, and Bolivia. I’m not sure I’ll get to all of them, but it would be significant to complete the whole continent, so I’ll give it a try.

Finally (are you getting tired of this?), I’ll travel to Jordan and then perhaps on to the Sudan. I say “perhaps” because Khartoum (KRT) is part of my current Round-the-World ticket, but I suspect it will be extremely difficult to get the visa. I hope I’m not disappointing anyone with this, but Sudan is not a place I am willing to attempt to fly to without a visa. As previously mentioned, I may be crazy but not that crazy.

If I don’t think it will work out a couple of weeks prior to departure, I’ll pay $150 to change the ticket – not really my preferred option, but also not the end of the world. If I have to drop Khartoum for now, I still have a couple of other options in that region that are less problematic for U.S. passport holders.

Planned Itineraries

For those who like these things, the itineraries for the trips are listed below. The parentheses are for transit stops, and the “x” refers to an overland segment.

Northeast Africa

SEA-(PDX)-(FRA)-ADD-xASM-(FRA)-SEA

By extreme travel standards, this is a fairly straightforward trip – all on Lufthansa, and the only complicated part will be the overland journey from Ethiopia (ADD) to Eritrea (ASM), assuming I get the visa sorted out. I also need to get to Djibiouti or Somaliland during the two weeks I’ll be away – preferably both, but nothing is for certain yet.

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Mysterious Countries

The next trip looks like this:

SEA-JFK-PAP-MIA-POS-???-POS-MIA-SEA

The ??? in this one is due to the fact that I’ll need to fly to one of the three mysterious countries (again: Guyana, Suriname, and French Guiana) and I don’t have that ticket yet. PAP is Port Au Prince, Haiti; and POS is Port of Spain, Trinidad – the jumping-off point to get to Guyana or Suriname.

(By the way, you can use this tool to find out what any particular airport code refers to, and the mileage calculator from the same site is also useful.)

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South America

The trip to Bolivia and elsewhere looks like this, tentatively:

SEA-(ORD)-MIA-LBP-LIM-BOG-(SCL)-GYE-(JFK)-(AMM)-KRT

Here I will be resuming last year’s Round-the-World ticket from Miami (MIA). I’ll need to buy separate tickets to and from Seattle, but that’s how I break up my trips to only be away from home for about two weeks at a time.

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A Colorful Array of MoneyHow Much Does All of this Cost?

I could go on about the flights for a while, but hopefully the above information gives you a good overview. If you have specific questions, post them in the comments and I’ll respond. For now, I’ll address the most frequently asked question I get about these kinds of trips: how much does it cost?

First, read this about priorities and how it all started. I don’t own a car, I have no debt, I didn’t take out a sub-prime mortgage when you could get one at 7-11, I spend about $150 a year on clothes, and so on. I honestly believe that most people (at least, those in Western countries who read this blog) who want to travel can find a way to do so. It may require you to make changes or sacrifices, but inertia is a much greater hindrance for most of us than lack of money.

That said, it does cost money to do this kind of thing, so it's only fair to give you the specifics.

Ethiopia & Beyond

I used Star Alliance Frequent Flyer miles for the first Africa trip, round-trip from Seattle. It took a big hit to my United balance (120,000), and I now have only 60k left. On the bright side, I got the flights I wanted, it’s in Business Class (important to me for long-haul and back-to-back overnight flights), and it would otherwise be fairly expensive to purchase a ticket to that part of Africa. The taxes were also cheap -- just under $150.

Cost: 120k Miles + $150 in taxes
Countries: Ethopia, Eritrea (hopefully), and presumably a side trip to at least one additional country in the region

Qatar & Beyond

My Qatar Airways ticket, another Frequent Flyer award, was 90,000 miles and $391 in taxes – and I’m also trying to add a free stopover to Yemen or Kuwait.

I didn’t have any Qatar Airways miles (I’ve only flown with them once, and I credited it to United), so I transferred points from American Express Membership Rewards into ANA Airlines (Japan) to book the partner award. It sounds a bit convoluted, I know, but it wasn’t that difficult in practice.

Cost: 90k AmEx Points + $399 in taxes
Countries: Qatar to resume another ticket, Yemen or Kuwait (side trip)

All of the South America stops, as well as the second trip to Africa (Mauritius, Namibia, Jo’burg, etc.) are part of my OneWorld Round-the-Word trip. This will also take me on to Hong Kong at some point in the early summer. That ticket was about $5,000, and I’ve received tremendous value from it. I have no idea how much it would cost if I were to try to book everything with round-trip flights – certainly several times more than what I pay when I effectively buy the flights in book with the RTW ticket.

Cost: Roughly $350 per country, prepaid last year
Countries: Mauritius, Namibia, South Africa, Hong Kong, U.K. (transit only)

The only “cash money” flights I need to sort out now are the entry and exit flights to the three mysterious countries, the flights within Northeast Africa, and the occasional cross-country trek to Miami or New York. Those will probably be a few hundred dollars each.

Cost: Variable, but usually $200-400 each
Countries: None, but allows me to come home and take side trips

After I complete all the trips mentioned above, I’ll start running out of prepaid flights, so I hope to begin at least one more Round-the-World ticket in the early summer. This one may be back on Star Alliance since I've earned more than 200,000 miles with OneWorld in 2008, and therefore don’t need to worry about elite status with them for a while.

I'm not 100% sure of what I'll do about the ticket, but whenever I sort it out, I’ll let you know exactly what I decide and what the next monster itinerary will be.

Well, You Asked for It

One request I’ve heard several times now is for more detailed travel planning notes. I have a question for you in return: is this progress? Is this the kind of thing that you guys want to know?

I cover even more travel planning details in the original Discount Airfare Guide, and I’ll be coming out with a more advanced Travel Ninja report soon… but I’m also happy to post information like this on the site whenever it seems like a good fit. As long as you give me good feedback, I’ll keep doing it.

Also, remember that next month we’ll look at my version of lifestyle design and annual planning. This includes travel planning, but also creating a structure for work, fun, learning, and more. I always look forward to doing the review in December, and this year I’m looking forward to sharing the process with you as well.

If you have any questions or feedback about the 2009 travel plans, simply leave a comment below. Thanks for reading!

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Related Entries:

Travel Hacking in an Unfriendly Enviornment
What I Talk About When I Talk About Travel (a Travel FAQ)
28 Things I Wish I Knew Before I Started Traveling
Why You Should Quit Your Job and Travel Around the World

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Unconventional Guides:

Working for Yourself: Creating Personal Freedom
Discount Airfare: Surviving Stress and Maximizing Fun

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