On communities and responsibilities

I try not to get too worked up over other bloggers' behavior. If you want to throw up a generic Wordpress template with a creditcards.com affiliate link, you'll never hear a peep out of me.

Of course, I make an exception for the very small number of credit card affiliate bloggers who dominate the credit card affiliate space, because the nature of the internet tends to concentrate their popularity and wealth far beyond their contributions to the genre. So when a Thought Leader From Behind misbehaves, I'll sometimes throw out some well-deserved snark on Twitter.

Yesterday was interesting

I spent most of the day yesterday in the car, so it wasn't until I got home in the afternoon that I discovered that a minor affiliate blogger had written a post describing how, in the course of manufacturing spend, she was splitting up and concealing money order deposits in order to avoid federal transaction reporting requirements.

The internet being the internet, the comments section of that post exploded with criticism, mockery, and derision. Likewise apparently the entire Twitter travel hacking community chimed in on various sides of both the substantive question of whether what she was describing was the federal crime of structuring and with more emotionally-charged personal attacks.

Individual responsibility is a weird concept

Two sentiments stood out to me in the course of that wide-ranging conversation. First, in two tweets Matt from Saverocity tried to explain to the blogger that she needed to "stop arguing and start thinking if your post can do harm to your readers" and then reiterated "This isn't about you."

The second sentiment that stood out to me was that the blogger wasn't responsible for what her readers did, and that it's everyone's individual responsibility to do their own research to determine if what they're doing is legal or not. That's something I see frequently when larger affiliate bloggers are criticized for peddling bad advice: readers have only themselves to blame if they follow the advice of these jet-setting clowns.

There's an obvious tension between those two sentiments: either we are in a constant war of all against all and answer to no one, or we're responsible for the consequences of our actions — particularly when they cause harm to others.

If you know anything about me, you can guess I fall on the side of taking responsibility for the consequences of our actions.

People have been recording their thoughts, ideas, and experiences for a long time in private and professional journals, diaries, and logs. And a diarist who never publishes a word of her diary really can write anything they want and answer to no one!

But publishing those logs online, and especially doing so for commercial purposes, moves you into the public sphere and embeds you in a community of people. To then suggest that you're not accountable to anyone for anything you write, and placing the onus of judgment entirely on your readers, strikes me as a deeply cynical approach to life.

The blogger's aggressive reaction to criticism treated that criticism as a personal attack on her strong lady blogger identity. But Matt wasn't trying to convince her to get married, pregnant, and join the PTA; he was trying to convince her to take responsibility for correcting her error as quickly as possible, to avoid additional harm to innocent people who might take her advice at face value!

Conclusion

There are as many different approaches to travel hacking as there are travel hackers, and it's not surprising that different bloggers will take a variety of different approaches. In that context I think everyone has responsibilities: bloggers should exercise judgment in putting their readers' interests first, and readers should exercise judgment in both identifying and sharing the blogs they find helpful and steering others away from blogs that are mercenary, unhelpful, or, as in this case, downright dangerous.

Entitlement is only the start of a loyalty conversation

Sometimes travel hacking is about figuring out what you're entitled to and how to get it. It's not unusual to read blog posts about Starwood Preferred Guest elites searching for suites right up until the minute they check in, to make sure that the front desk staff give them the very best room they're entitled to.

Likewise, you're entitled to use Delta voluntary denied boarding vouchers for other passengers, as long as the person the voucher was issued to is one of the passengers on a single reservation. In practice, Delta makes that difficult, but not impossible.

Other times, what you're entitled to is just the starting point of a conversation.

Background: tour of Central Europe, 3 nights at a time

Before the June 1, 2015, Club Carlson devaluation, I booked a 9-night trip through Central Europe, with 3 nights at the Radisson Blu Beke Hotel, Budapest, 3 nights at the Park Inn Danube, Bratislava, and 2 nights at the Radisson Blu Style Hotel, Vienna.

The 3 nights at the Park Inn Danube cost 18,000 Gold Points total, for one 2-night reservation and one 1-night reservation.

The Park Inn Danube closed out from under me!

On Tuesday the manager of the Park Inn Danube e-mailed me to say:

"We hope this mail finds you well and we take this chance to wish you a fantastic start of New Year

We are happy to inform you [editor's note: I have no idea why he's "happy" to inform me of this] that our property, Park Inn Danube Bratislava, will go under full refurbishment from 1st of March 2016 until 1st of September 2016.

Due to this we are, unfortunately, not able to provide you with hotel accommodation as per your reservation...as the hotel operations will be completely ceased for the mentioned period.

We suggest you cancel your reservation trough Club Carlson in order to retrieve your Club Carlson points and we apologize for the short notice.

If you will still be interested to come to Bratislava, we strongly suggest booking the Radisson Blu Carlton that is located in the same area of Park Inn Danube."

How to turn 18,000 Gold Points into 84,000 Gold Points

When I found out my hotel had been closed, I immediately sized up the situation: I had 18,000 Gold Points locked up in my existing reservation. Bratislava doesn't have a ton of hotels in the old city, but as the general manager of the Park Inn Danube pointed out, it does have another Club Carlson property about a block away. Without the last-night-free benefit, three nights at the Radisson Blu Carlton Hotel would cost 84,000 Gold Points.

When I first called the Park Inn reservations line, the best suggestion the representative came up with was to cancel my existing reservations, and use the points for a cash and points reservation at the Radisson Blu. That would have left me out 15,000 Gold Points and $300.

And in fact, that's likely all I was entitled to.

So I took off my travel hacker hat and put on my civilian hat. If a civilian had a 3-night award stay planned a year in advance, and the hotel closed out from under them, they wouldn't agree to replace 3 free nights with a $300 paid stay! Instead, I explained the situation to the phone representative again, and told her I expected Club Carlson to reaccommodate me at the Radisson Blu Carlton Hotel.

She transferred me to their "Customer Care" department, and after a mere 30 minutes on hold, Club Carlson had deposited 66,000 additional Gold Points into my account and made me a 3-night reservation at the Radisson Blu:

Conclusion

Whenever I get a points windfall like this, I take the opportunity to think through my existing reservations to see if there's any way to optimize them for price or comfort.

For example, I could cancel the new award reservation, rebook the hotel with cash (about $300), then use 70,000 of the Gold Points for a third night at the Radisson Blu Style Hotel, Vienna. But hotels in Vienna aren't that expensive! The Park Hyatt Vienna costs just $250 in Ultimate Rewards points or $269 for a Points + Cash redemption (plus a Diamond suite upgrade, naturally).

In fact what I'm likely to do is cancel my existing 2-night reservation at the Radisson Blu Style Hotel, Vienna, upgrade our stay to a premium award redemption at the Radisson Blu Carlton Hotel, and book all three nights in Vienna at the Park Hyatt.

On false economy

[editor's note: my worthless MacBook Pro has finally stopped working completely, so I'm using an aged clamshell laptop for my blogging this week. Grammar and punctuation will suffer, and pictures will be minimal/nonexistent.]

After dropping off my MacBook Pro at the Apple Store on Sunday, I started poking around the current batch of gadgets and saw the 2 terabyte Time Capsule, currently retailing for a mere $299 before taxes and portal cash back (if you signed up in time to double your Discover cash back, you can get 5% cash back now and another 5% cash back at the end of your doubled year).

My current backup solution is a $54.99, 500 gigabyte external USB hard drive, and it works fine, except for three problems:

  1. I have to remember to plug it in;
  2. I have to remember to plug it in;
  3. and I have to remember to plug it in.

As long as I remember to plug it in, it backs up my hard drive. The longer I forget to plug it in, the more out of date the backup becomes, and the more data I potentially lose.

This got me thinking about the question of false economy, which happens to be very relevant to travel hacking, in several ways.

Thinking critically about false economy

It's easy — and dangerous — to fall into sloppy thinking about false economy, and the best defense is to carefully define our terms. For me, false economy doesn't mean "paying less for an inferior product." That's just economy — we expect things that cost less to be of lesser quality! For me, false economy means specifically saving money upfront in a way that ultimately ends up costing more money, by some order of magnitude, than the amount saved. Further, it helps if the larger, future costs are somehow foreseeable, but irrationally ignored for the sake of saving money upfront.

The best illustrations of my vision of false economy are when amateurs try to make do without the help of professionals. Regular economy is using masking tape to fix a plumbing problem. False economy is leaving town, the masking tape bursting, short-circuiting your refrigerator and causing a devastating fire (it happened to Edward Norton).

It's simply impossible to imagine saving enough money on plumbers in the short term to rationalize losing your home to fire in the longer term.

Think holistically to avoid false economy

There are two popular options college students use to save money when flying from South Central Wisconsin:

  • a $46 roundtrip bus to General Mitchell International Airport in Milwaukee, which is served by Southwest Airlines.
  • a $60 roundtrip bus to Chicago's Midway (served by Southwest) and O'Hare airports (served by Alaska), which occasionally have lower fares.

You can see the appeal of both options (especially if you're the parents paying to bring your kid home or, worse yet, send them to Cancun for spring break): if a Southwest ticket saves you $47, why not put your munchkin on the bus for an hour and make them fly out of Milwaukee? It's not like you're the one sitting on the bus.

When the travel hacker is the one traveling, the calculus suddenly changes dramatically:

  • Flexpoint redemption bands means more expensive local flights may cost you the same number of Flexpoints as flights which require a bus ride;
  • Discounted point redemptions mean even more expensive flights don't cost as much as they would when paying cash. For example, to justify paying $60 for a bus trip you'd have to save $75 in airfare if redeeming Ultimate Rewards points out of a Sapphire Preferred or Ink Plus Ultimate Rewards account (1.25 cents each), $85.80 when using "pay with points" in an American Express Business Platinum Membership Rewards account (1.43 cents each), or $96 when redeeming Citi ThankYou points from a ThankYou Prestige card on American Airlines (1.6 cents each).

As a mid-career white collar professional you might find these examples ridiculous: why would anyone take a bus instead of flying out of their local airport? The reason I raise them is that I want to take the idea of economy seriously, because spending tens or hundreds of dollars for "convenience" is really out of the question for a lot of people in this country.

And let me tell you: the busses to Milwaukee and Chicago are full, all day every day, with people doing their best to save a few dollars on airfare.

Avoiding false economy isn't an excuse to splurge

I think it was Matt from Saverocity who quipped on Twitter after reading yet another first class trip report that he couldn't justify paying $1,000 for an $80 bottle of champagne (well, he said "champers").

And that's the way I feel about a lot of so-called "aspirational" travel. It's not that there's anything wrong with getting a good night's sleep on a plane, or flying across the world to spend a week at the beach, it's that the marginal benefit of doing so over a far cheaper vacation (or many, many far cheaper vacations) isn't worth it to me personally.

And I think that's a real risk: once you recognize that false economy is a problem, there's a temptation to err in the opposite direction. If a $299 2-terabyte Apple Time Capsule is a good deal, well it's just $100 more for a 3-terabyte Time Capsule. That's just 33% more money for 50% more storage space (whether you need it or not)!

Yesterday's post on chasing Delta elite status illustrates the point nicely: booking a $350 first class ticket instead of a $250 economy class ticket with Flexpoints is a no-brainer: both tickets cost 20,000 Flexpoints, but one includes free checked bags, making elite status worthless.

But booking a $550 first class ticket instead of a $350 economy class ticket isn't a no-brainer: you're paying $100 (the cash value of 10,000 more Flexpoints) and saving just $50 in roundtrip checked bag fees. $50 in cash isn't a lot of money to pay for a roundtrip first class upgrade, but it's also not free.

You don't have to make rational decisions all the time

One of the advantages of paying such a small fraction of retail for our travel is that mistakes don't have catastrophic consequences. If you forget to book through a cash back portal, you might lose a 4% cash back payout on paid Hilton stays, but your reservation won't be canceled, you won't be arrested, you'll just pay slightly more than you could have if you'd remembered to click through.

But thinking through these questions in advance will help you develop the analytical tools you need to make better decisions, more often, than you would if you approached each decision from scratch each time you have to make a reservation.

I haven't bought a 2-terabyte Apple Time Capsule yet. But I'm thinking about it, and the reason I'm thinking about it is that a 2-terabyte Time Capsule doesn't have to save me very much time, stress, and money to be worth $299.

Miles and points as an (irrational!) commitment mechanism

One of the reasons I started blogging, all the way back in the long long ago, was that I was disillusioned and furious with bloggers who each week or month would run through a whole spectrum of airline or hotel co-branded credit cards, explaining why each in turn was the one readers absolutely had to have.

Of course it can't be the case that the Marriott Rewards Premier credit card (annual Category 1-5 night certificate!), IHG Rewards card (annual night certificate!), Citi Hilton HHonors Reserve (annual weekend night certificate!) are all the best co-branded hotel credit card.

So I build this website and started writing this blog with the goal of providing as much true information as possible, and the truth is the Hilton HHonors Surpass American Express is probably the best co-branded hotel credit card, if you're willing to manufacture spend furiously, with the possible exceptions of the Club Carlson Business Rewards Visa (if you can stand their rundown properties) and the Wyndham Rewards Visa, which earns a free night at any Wyndham Rewards property in the world every time you spend $7,500 with the card.

People really don't like paying for their travel

What I didn't understand when I started writing is that people really don't like to think about the money they spend on travel. For example, when I point out that a 30,000-point Hyatt Gold Passport redemption costs $300 per night, the comments section quickly fills up with people explaining that they paid much less than $300 for their Ultimate Rewards points, so it's not fair to say they're paying $300 for their Hyatt stay.

Ultimate Rewards points are worth 1 cent each when redeemed for cash. A 30,000-point transfer costs $300.

I don't mind paying for travel

I've loved to travel for as long as I can remember. Long before I learned about travel hacking, I was taking the Chinatown bus to Boston, DC, and New York City, spending Spring Break in Ireland, getting an English-language teaching certificate in Prague, and teaching English in Moscow.

And I just paid for it. I searched for the best prices, then I booked tickets, then I traveled.

If you don't like paying for travel, travel hacking is a convenient way to hide the cost

What I've come to realize is that one thing people like about travel hacking is that it gives them permission to travel.

If you earn $250 in cash on some bank account signup bonus, then you treat that $250 like cash, as you should.

But if you manufacture $10,000 in spend on a Hilton HHonors Surpass American Express and earn 60,000 HHonors points, you don't have to think about the $200 you've given up by not using a 2% cash back credit card. Instead, you're stuck with 60,000 HHonors points you have to use on Hilton hotel stays.

If you need a commitment mechanism, then go for it

In the economics literature, a commitment mechanism is a way to "commit" your future self to some action that you're not sure you'll do in the absence of the mechanism. A typical example is the 10% withdrawal penalty on IRA balances as a way to commit your future self to not touch your retirement savings until you reach the penalty-free retirement age.

When deciding between a cash back card and a travel rewards card, you may have legitimate concerns that your future self will use cash back to make mortgage payments, save for retirement, or buy a flat-screen TV, when you know that what your future self will really value is a trip to Italy.

One way to commit your future self to the Italy trip is to make it so unreasonably expensive to convert miles or points to cash that they're compelled to use them to travel instead.

You know yourself better than I do. If that's you, then leave the cash on the table and pay a little more to commit to the travel that's really going to enrich your life.

Conclusion

This post is my way of making peace with people who really do need to "lock up" a certain portion of their earnings in order to give themselves permission to travel.

On the other hand, that will never be the approach I take to travel, or to travel hacking, so I'll keep writing about the cheapest, easiest ways to earn as much value as possible, and I'll leave it up to my readers to decide how much needs to go into a lockbox rather than into a checking account!

My top 10 most popular (and one least popular) posts of 2015

In the spirit of shamelessly ripping off Frequent Miler, I thought it would be interesting to see what my most popular new posts in 2015 were. Since I don't use Google Analytics for, well, anything, it took me a little while to figure out how to assemble this list. In other words, accuracy not guaranteed, but I found it interesting and thought my readers might as well.

Without further ado, here are my 10 most popular posts written in 2015, ranked by total unique pageviews. I've placed an asterisk(*) next to the techniques that are still working or relevant today.

Any lessons here?

I basically write whatever I feel like writing about, so it's pretty much luck of the draw when that coincides with what readers want to read about. With that in mind, are there any lessons to be learned from this list?

  • Lots of people want to read actionable tips for upping their travel hacking game. My post on the Chase Sapphire Preferred is the only popular post that was more analytical than action-oriented. None of my posts on imputed redemption values or other methods of analyzing miles and points redemptions made the cut.
  • No one wants to read about my award redemptions. My most popular "Anatomy of an Award Trip" post in 2015 got just 363 unique pageviews.
  • The game is always changing. Of my top ten posts of 2015, only 6 are still actionable or relevant: it's become much more difficult to automate American Express offers over Twitter; American Express gift cards are no longer a lucrative method of manufacturing spend; Amazon Allowances now have a minimum of $5, making them less useful for meeting transaction requirements; and Uber no longer allows anyone to purchase gift credit.

What was my least popular post of 2015?

Just for fun, I thought I'd scroll down to find my blog post with the fewest unique pageviews. For whatever reason, that post was:

In fact, 5 of the 10 least-viewed posts were "Do this now" posts about registering for various promotions.

Expect this to have absolutely no effect on the content of my blog in 2016. Old dogs, new tricks, etc.

Use Hipmunk to find positioning flights

There are a lot of websites you can use to search for paid flights. Kayak is one of the most popular, but Orbitz, Expedia and Priceline will all find you tickets as well. If you're booking paid flights with Ultimate Rewards points you'll need to use their internal search engine, and the same is true of US Bank Flexpoints.

All those sites work, and they all have roughly similar search features: you can search for specific dates or flexible dates, you can specify your cabin of service, and you can filter by airline and time of day.

What none of them let you do is filter by different times of day depending on the day of the flight. Let me explain.

Award availability often requires positioning flights before or after the award segments

Award availability is the aspect of travel hacking that we have the least control over. Whether or not an airline makes seats available on the dates we need them is entirely at the discretion of the airline. While much digital ink has been spilled over the best ways to find award seats, ultimately it's not something we can predict in a reliable way.

Further, when award availability does become available, it may not exactly suit our needs. There may be award seats from an alliance hub city, but not on flights from your home airport to the hub. If you're committed to booking the award seats, that means you'll need a positioning flight: either a paid flight or an award on a different carrier that gets you to the airport in time to take your award flight.

Of course, positioning flights can be necessary at the beginning or end of a trip.

Use Hipmunk to find positioning flights

When you search for flights with every other search engine I know of, you can filter by time of departure, but that filter applies to every day searched. For example, on ITA Matrix filtering by "early morning" departures returns early morning departures for every day within the search range:

HIpmunk is the only flight search engine I know of that lets you filter by departure times across day boundaries. For example, I have an upcoming award flight booked on Air Berlin between Berlin and New York City. But I don't live in New York City, and there's no oneworld award space between New York City and my hometown, which means I need a positioning flight.

Since we don't want to go into the city (we'll be getting back from 17 days in Europe), I'd like to search for the cheapest flight that leaves either the evening we arrive in New York or the next morning. In other words, I'm fine staying overnight at the airport if it saves us some money, but I'm not willing to wait to fly out until the next evening.

Lo and behold, Hipmunk found me the perfect flight:

We'll stay overnight at JFK, leave early the next morning, and be back home early that afternoon.

"Pop Finance" is a pretty good book

This is a review of "Pop Finance," by Brooke Harrington. You can find all my previous book reviews here. If you're interested in buying a copy, I hope you consider using my Amazon Associates referral link.

I first heard about "investment clubs" from my Italian immigrant barber back in New England. He and some of his business associates and cronies get together once a month and contribute a nominal sum to a common pot. They then vote on which stocks to buy with that month's contributions.

My barber seemed to realize that this was a strange way to invest in the stock market, but explained that the real point wasn't necessarily to pick winning stocks, but as a forced savings vehicle: if you wanted to hang out with your buddies, you needed to find $50 to save each month, which was enough incentive to get people to save money who otherwise wouldn't bother.

With that in mind, I was excited to stumble across "Pop Finance," an ethnography of investment clubs in the San Francisco Bay Area written by Brooke Harrington. The principle research behind the book was conducted over the course of 1998 — in other words, at the peak of the 1990's tech bubble — with followup research in 2004, in the midst of the Bush Administration stock market doldrums.

Mass participation in the stock market is something that requires explanation

Today, popular ownership of publicly-traded shares, either individually or through mutual funds, is so common that it seems part of the natural order of American economic life. So it's worth pointing out that this isn't the only way that it's possible to save money, whether for retirement, health care, or educational expenses.

To this day, it's perfectly legal to simply save half your salary from age 25 to age 65 in FDIC-insured vehicles like savings accounts and certificates of deposit that earn market interest rates on the money saved. That volume of savings would allow you to then continue spending the same amount of money (half your lifetime salary) from age 65 to age 105, with a little left over depending on where market interest rates happen to fall during your lifetime.

Of course, Social Security exists, so you don't need to replace your entire annual consumption through savings — Social Security will replace 18-90% of your income (depending on your lifetime earnings), so you only need to replace the remaining portion, meaning you can spend more than 50% of your income and still spend the same amount during your working life and your retired years.

A private pension replacing even more of your income would mean even less savings would be required to smooth out your consumption over your entire lifetime.

Harrington convincingly argues that mass participation in the stock market, in her case in the form of investment clubs, was the result of two factors that made the above logic fall apart in the 1990's:

  • Corporate defined benefit pensions were replaced with defined contribution plans, often self-directed and invested in stocks and bonds;
  • Between 1985 and 1995, real wages declined while corporate profits tripled. In other words, for the average American, saving half their salary in FDIC-insured savings vehicles would mean a decline in living standards in retirement, while purchasing "the market" would mean an increase in living standards in retirement, or even early retirement.

Finally, I'll add that obviously the overwhelming majority of Americans today are incapable of or unwilling to live on half their salary. There are many reasons for this: status anxiety, a feeling that they've "earned" the right to enjoy their money, and of course in the case of prosperous coastal cities, the accelerating cost of living.

Ultimately, that means either settling for a much lower standard of living in retirement, or investing in riskier assets with a higher potential rate of return than FDIC-insured savings vehicles.

Day trading is a very intuitive way to invest in the stock market

Once you've decided that the stock market is the only way to secure the lifestyle you envision for yourself in retirement, day trading is the obvious method of doing so: since different stocks move in different directions on a daily basis, by buying stocks before they go up, and selling them before they go down, you can earn more on a daily basis than in a whole year of FDIC-insured interest.

In fact, if your wins are big enough and your losses are small enough, you don't even need to be right a majority of the time! After all, one 10% gain offsets four 2% losses with 2% left over as your profit, not annually, but daily!

Investment clubs are day trading by committee

Investment clubs, like day traders, also purchase individual stocks for short term profits. The problem is that unlike an actual day trader, investment clubs can't react quickly to changes in the prices of their stocks. At the beginning of March a club may vote to buy Pfizer, the stock may peak in mid-March and be lower than where they bought it by the time they get together again in April. And at that point, they have to vote on whether they think it'll do it again!

One club Harrington profiles attempts to deal with this problem by putting stop-loss orders on all their stock holdings: if a stock declines by 20%, they sell the stock — then frequently buy it again at their next meeting, when the price has had time to recover!

This is not a good way to invest

I believe virtually all people should save for retirement in Vanguard target retirement date funds.

But even if you have a different risk tolerance than the ones reflected in Vanguard's target retirement date funds, you probably should implement that risk tolerance through low-cost indexed mutual funds.

But even if you believe that you're preternaturally gifted at predicting the short-term movement of stocks, you should simply act on your gift by buying and selling stocks, not waiting weeks at a time and then spending time convincing your fellow investment club members that you know which direction a stock will move before your next meeting.

But creative forced savings mechanisms are pretty cool!

That brings me back to my Italian barber. He is really convinced that many members of his investment club would save nothing if they weren't saving $50 a month in monthly club contributions.

And at the same time, over a working lifetime, $600 per year invested in the broad stock market really will return more than the same $600 invested in FDIC-insured savings vehicles.

So I'm all in favor of crazy schemes to force yourself to save! Here a few I came up with that make at least as much sense as investment clubs:

  • Every time you withdraw money from an ATM, withdraw an extra $20 and set it aside for a monthly retirement savings contribution;
  • Deposit your credit card cash back rewards into a designated retirement savings account;
  • When you redeem your miles or points for an award trip, deposit the cash value of the trip into a designated retirement account — be your own mileage broker!

A final note on tax-advantaged accounts

It's no secret that I'm a strong advocate for simplifying the US income tax code. Not simplifying it and reducing rates, just simplifying it, full stop.

One reason for that is that the current configuration of tax advantaged savings vehicles (employer-based retirement and health savings accounts, traditional and Roth Individual Retirement Accounts, and the mortgage interest deduction) leads people to spend extraordinary amounts of time gaming the tax code instead of simply saving money.

In other words, once you've maximized your tax advantaged savings vehicles by contributing to a 401(k), IRA, and buying an unnecessarily expensive house, you feel like you've done all the savings necessary (perhaps adding a 529 College Savings Plan as icing on your tax-advantaged cake).

But that's ridiculous: it's perfectly legal to simply buy stocks and bonds. You can invest in a Vanguard target retirement date account in a taxable account, and it will generate the same long-term returns as the identical fund held in your tax-advantaged accounts. You just have to pay long term capital gains on the returns when you eventually sell (although you avoid the 10% early withdrawal penalty on the exact same fund if held in your IRA).

Portland is a city where young people go to retire

I go to Portland, Oregon, three or four times a year. I think it's a little slice of paradise, so I thought I'd share some of the things that make it so special for me.

How to get there

  • Amtrak. Take the Empire Builder west from Chicago or the Coast Starlight north from Los Angeles. The first costs 40,000 Amtrak Guest Rewards points in a bedroom (or family bedroom), and the second costs 25,000 points in a bedroom until January 24, 2016. A single redemption includes tickets for up to the maximum occupancy of the room, e.g. 2 adults and 2 children in a family bedroom.
  • Portland International Airport. PDX has flights operated by the big 3 US carriers and Alaska Airlines, as well as Southwest. From PDX the MAX light rail will take you downtown in about 40 minutes for just $2.50 ($5 for a day pass).

Where to stay

  • Downtown. I usually stay at the Hilton Portland & Executive Tower (30,000 HHonors points November-March, 40,000 HHonors points April-October), although they sometimes play games with award availability. If you're a Gold or Diamond HHonors member, you can use your continental breakfast voucher for about $12 off anything on the breakfast menu, which I recommend since the continental breakfast is terrible. If you have Starwood Preferred Guest points, The Nines is a very fine hotel, and Urban Farmer is one of the best restaurants in Portland, located on the 8th floor of The Nines. Other than that, Marriott dominates the downtown hotel scene, and their properties are overpriced, unless you're able to get an especially good deal using Priceline.
  • AirBNB. AirBNB offers two advantages over staying at hotels: you'll often pay much less than you would staying at a downtown hotel, and you can stay in the neighborhoods, which are one of the things that make Portland so great. Three fantastic neighborhoods to check out are Northeast Alberta, between perhaps 9th and 33rd Streets; Southeast Hawthorne almost anywhere East of Grand St; and North of Burnside in the Pearl District or what's charmingly called "Nob Hill."

What to do

  • The 4T Trail. Do a loop around Portland taking the MAX light rail train, the trails between the Portland Zoo and the Oregon Health & Science University, the aerial tram down to the river and the Portland Streetcar Trolley back downtown. You can do the loop in either direction, but the aerial tram is only free going downhill. Warning: bring a printout of the trail segment, or you might get very, very lost (not that I'm speaking from experience or anything).
  • ZooLights. Speaking of the Portland Zoo, every winter the Zoo is open late and lit up with holiday lights. Fun for all ages.
  • Ground Kontrol Classic Arcade. Classic arcade games from your youth and your parents' youth, plus new additions like Killer Queen, the world's first 10-player arcade game. There's a huge selection of classic and new pinball games, as well.
  • Dante's Sinferno Caberet. Sundays at 11 pm until the wee hours of the morning, a mixture of nudity, profanity, and feats of strength. The pizza joint in the corner is now operated by Lonesome's Pizza, which is excellent.
  • Clinton Street Theater's Rocky Horror Picture Show. One of the longest-running screenings in the country, doors open at 11:30 pm on Saturday nights.
  • Laurelhurst Theater and Pub. $3-4 second run movies and classics, cheap beer and great pizza. Each seat has bar space to place your pitchers, pizzas, and salads, so you don't have to juggle your dishes.
  • Look for inspiration. Part of what makes Portland so magical is that you don't need a plan to have a good time. You can walk around, make friends, check out the local alternative weekly, and wait for inspiration to strike.

Where to eat

  • Pine State Biscuits. Three locations, always lines at all 3, but always worth the wait. Go at weird times for shorter waits, go during brunch for hour-plus waits.
  • Pacific Pie Co. Two locations. Great meat and vegetarian savory pies, sweet pies, and craft beer. Save money by going during happy hour, Monday-Friday 3-6 pm.
  • Bunk Sandwiches. Five locations. The Marinated Garbonzo Beans sandwich at Bunk Downtown is way, way spicier than it has any right to be.
  • Food carts. Portland food carts are clustered into groups called "pods." Make a food cart pod the beginning or end of a walk around town and you're guaranteed to find something delicious.
  • Anywhere. Portland bars are generally required to serve hot food, and it tends to be fantastic, or at least greasy, which can be almost the same thing.

Where to drink

  • Distillery Row. Portland's craft distilleries are clustered in Southeast Portland. Visit any one to try a flight of craft liquors, or buy a Passport and drink many flights of craft liquors.
  • Swift Lounge. Craft cocktails served in large or very-large mason jars. Great food.
  • Binks. Great cocktails made with house-infused spirits.
  • Ash Street Saloon. You will never find a more wretched hive of scum and villainy.
  • Craft breweries and brewpubs. There are a lot of them, including nationally known breweries and brewpubs like Widmer Brothers, Hopworks Urban Brewery, Full Sail, and Deschutes.

Conclusion

Remember, the dream of the 90's is alive in Portland.

American Express cards I'm thinking about

Introduction

When I say that I don't chase signup bonuses, it sometimes gives readers the impression that I don't apply for new cards or that I don't think signup bonuses are a good deal. Nothing could be further from the truth!

If I need a new card, I'll apply for it, I'll call reconsideration lines, and I'll move credit around like anyone else hungry for approval. Likewise, if I'm planning to sign up for a card, I'll do my due diligence and hunt down the highest signup bonus available.

The difference, as I see it, come down to what cards I think I need. Since I earn the miles I redeem and redeem the miles I earn, I won't sign up for a new card just because it has a high signup bonus; I need to have a sense of where and when I'd redeem those miles. Otherwise, I might never redeem them and be left with a worthless novelty balance.

That being said, here are a few cards I'm currently thinking about adding to my collection.

Starwood Preferred Guest Business

I recently met the $50,000 spend threshold on my Platinum Delta SkyMiles Business American Express card, which makes the card all but useless for the rest of the calendar year. Last week I called American Express to ask which cards I was eligible to product change my card to, and was given two options: the Starwood Preferred Guest Business card, or the Blue for Business.

The latter product earns 1 non-flexible Membership Rewards point everywhere, which isn't very interesting, while the Starwood Preferred Guest card earns points that can be transferred to Delta, Alaska, or American (among others), in addition to booking Starwood hotel stays.

The main reason I'm interested in the Starwood card is for hotel stays. While Hilton is my primary hotel program because of their enormous footprint and the high bonused earning rate on the Hilton Surpass American Express, there are times when Hilton rooms aren't available or their properties are inconveniently located. At times like those, it's helpful to have points like Ultimate Rewards (for transfers to Hyatt) or Starpoints for booking alternatives.

On the one hand, requesting a product change to the Starwood Preferred Guest card would save me a hard credit pull and the risk of having my application denied. On the other hand, it would permanently cost me the 25,000 Starpoints I would earn if I applied for the card from scratch.

Ultimately, given the choice between canceling my Delta card, keeping it, or product changing to Starwood Preferred Guest, I'm leaning towards the product change, even if that means leaving 25,000 Starpoints on the table.

New "Old" Blue Cash

While my pre-devaluation "Old" Blue Cash card was closed by American Express in December, the "Old" Blue Cash card is still available, albeit in stunted form, and still earns up to $2,240 in annual cash back on purchases at supermarkets, gas stations, and drug stores. It's not as outrageously good a deal as it was before bonused earning was capped at $50,000 in yearly spend, but it's still low-hanging fruit, and I'm considering applying for another.

Amex EveryDay Preferred

While I'm not thrilled about the $95 annual fee, the EveryDay Preferred earns 4.5 Membership Rewards points per dollar spent at grocery stores (on up to $6,000 in spend) and 3 Membership Rewards points per dollar spent at gas stations (uncapped) when you make 30 purchases during your statement cycle.

I don't find Membership Rewards points to be particularly valuable, but this card would be a highly efficient method of earning Delta SkyMiles compared to my Delta Platinum Business American Express, and with a much lower annual fee. Delta is my primary airline program for domestic travel, so being able to earn those miles faster means paying less for the redemptions I already know I'm going to make.

The tradeoff, assuming I product change my Delta card to a Starwood card, would be giving up the opportunity to earn 20,000 Medallion Qualifying Miles per year through credit card spend.

However, I've already secured Silver Medallion status for 2016, and I don't trust Delta enough to pay a $195 annual fee purely in the hope that the SkyMiles program will retain value in 2017 and beyond.

Conclusion

When thinking about my credit card applications, as you can see above, signup bonuses play virtually no role in deciding whether to apply. If the Amex EveryDay Preferred is worth getting, it's worth getting in order to manufacture spend on the card year-round, not because its signup bonus was temporarily raised to 30,000 Membership Rewards points.

Likewise, for the convenience of a product change (keeping the same account number, avoiding a credit pull, etc.) I'll go so far as to permanently give up the chance to earn a 25,000 Starpoint signup bonus, because I believe the card is worth spending money on year-round, not just in order to trigger a one-time payday.

Having a routine is fantastic. Also dangerous

Back in September, Matt at Saverocity wrote this post about the potential problems of a travel hacker getting so "locked in" to one or two loyalty programs that they're unable to take advantage of other, potentially more lucrative programs sitting right under their nose.

Conveniently, I was name-checked in the post, so I guess I'm entitled to respond.

Matt thinks our limiting factor is time and attention; I think it's value

Here's the marker Matt laid down, challenging us slackers to rise above the hobgoblins of our little minds:

"I don’t think anyone would have the gumption to do this. But what if you had to drop all your existing programs for 6 months. The world wouldn’t end, and if you were dedicated, you’d be forced to learn a lot about other things outside of your knowledge base. Humans are notoriously good at adapting and evolving when forced to do so, but if you give us the choice...we’d rather not."

Today, I can manufacture up to $120,000 per cardmember year on a US Bank Flexperks Travel Rewards card and earn 2 Flexpoints per dollar (at gas stations or grocery stores) or 3 Flexpoints per dollar (in charitable spending), worth up to $4,800 or $7,200 in paid airfare.

I have unlimited time and attention (this is my job), but what I don't have is the willingness to give up concrete, quantifiable value in favor of spending months diving deep into alternative rewards programs on a speculative basis.

Having a routine is fantastic

Much of my monthly manufactured spend proceeds according to a familiar routine. I know which merchants will sell me which products in which quantities, and I buy them with the cards that give me the most value, starting with bonused spending categories and working my way down.

Far from limiting my frame of reference, I find a consistent routine, developed based on the actual credit cards and loyalty programs that I use to pay for my actual travel, gives me more mental bandwidth to dedicate to studying new techniques and calculating how I can integrate them into my travel hacking practice.

Having a routine is (can be) dangerous

What Matt gets exactly right is that if you focus on a single method of manufactured spend, or on credit cards issued by a single bank, or on a single method of liquidation, then you're making yourself vulnerable to local, regional, or national policy changes.

If you travel hack recreationally, that may not be the end of the world; a lot of people who were manufacturing huge volumes before Vanilla Reload Network cards became harder to buy stopped completely once they became increasingly restricted, and never thought about the game again.

No deal lasts forever

At the time of writing, I understand that Target stores are not allowing Prepaid REDcards to be loaded with debit cards. Is this the end?

Honestly, probably not.

But if it is, did you convert all your Serve and Bluebird cards to Prepaid REDcards in anticipation of the deal lasting forever? Why? Serve cards can still be loaded at Family Dollar stores using any PIN-enabled debit card. Bluebird cards can still be loaded at Walmart with US Bank-issued MasterCard and Metabank-issued Visa cards sold at Staples.

The most lucrative deal, the biggest secret you're keeping, even from your fellow travel hackers, won't last forever. When it ends, you can either have a range of unrelated deals to fall back on, or you can find yourself scrambling to learn about other techniques to meet your ongoing travel needs.

Conclusion

There are only 6 programs I earn miles and points in with any intensity:

  • US Bank Flexperks
  • Hilton HHonors
  • Chase Ultimate Rewards
  • Delta Skymiles
  • Barclaycard Arrival+ miles
  • Alaska Airlines Mileage Plan (for crediting paid flights operated by American and Delta)

On the one hand, Matt is right to point out that any constellation of miles and points programs that are earned to the exclusion of other programs raises risks: the risk of devaluation, the risk of increased attention to accounts, the risk of available techniques changing or drying up.

On the other hand, a simplified routine based on the actual value of the points you're earning and, even more importantly, the points you're redeeming, may give you the cognitive freedom you need to stay on top of new and developing techniques.