The travel hacking index card

I popped by the library this week to pick up "The Index Card," the famously slender volume of personal finance advice by personal finance columnist Helaine Olen (author of "Pound Foolish," a previous entry in my pretty good book review series) and University of Chicago professor Harold Pollack.

It's a pretty good book about personal finance, although not spectacular. The authors' "model portfolio" is invested in small-cap and international index funds for reasons that are not made clear, presumably in order to keep the book as simple as possible. But people who don't understand why they're doing the right thing are just as vulnerable to persuasion from hucksters are people who are doing the wrong thing. So while their model portfolio isn't terrible, it also doesn't have a straightforward evidence-based argument presented for it.

Reading "The Index Card" got me to thinking about what would go on a travel hacking index card. There's plenty of information about individual rewards programs and "sweet spots," which makes it easy to get bogged down in specifics — and difficult to tell the difference between real values and credit card sales pitches.

So what kinds of simple rules can keep a travel hacker from making expensive mistakes while developing a travel hacking practice that helps them achieve their financial and travel goals?

Here's what I came up with, with a few words about each.

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1. Start slow

When you're just getting started, there's absolutely no reason to sign up for more than a single new credit card as you get a feel for how credit card rewards programs and travel loyalty programs really work.

This rule also applies to experienced travel hackers testing out new techniques. I'm happy to take a loss by putting $5 on a prepaid debit card with a $5 activation fee, so I can find out whether it's PIN-enabled before I start filling up shopping carts with them.

2. Keep good records, but don't get hung up on a single system

When you're dealing with thousands of dollars in financial products or merchandise, you obviously want to keep good records. But the system you develop when you are just getting started might not serve you well as you scale up or down. A reseller handling $50,000 in merchandise per month has different record-keeping needs than one who just jumps on the biggest deals. When a system starts to get clunky, take a step back and think about how you can improve or simplify it.

Likewise, an envelop in the glove compartment may work great when you're handling a few thousand dollars in money orders, but may start to become unwieldy when you're handling a hundred thousand dollars.

3. Build relationships

The overwhelming majority of travel hackers love this game and love helping people think about the myriad problems we encounter on a daily basis. The rest are ornery bastards, but you'll learn to identify them pretty quickly.

I'm always reminded of the couple that spent a million Starpoints on a paid American Airlines flight using SPG Flights, instead of transferring a small fraction of that number to AAdvantage and booking award tickets. If they'd known to ask anyone in the travel hacking community, they'd have half a million Starpoints left in their account! Don't be them.

4. Every deal dies eventually

I like to joke on Twitter about bloggers killing deals, but the simple fact is, most bloggers of any merit are fairly circumspect about deals they believe are fragile, and most credit card affiliate bloggers either don't know or don't care about real travel hacking deals, since there's no money in it for them.

Bloggers don't kill deals; time kills deals. So when your favorite deal dies, take a moment to mourn, but don't lash out at the blogger you're certain is responsible for its passing.

5. Treat employees calmly and with respect

Let's stipulate that you're always right. You know a store's point-of-sale system better than any of the cashiers there. You know a chain's purchase limits by heart. You have a Christmas card from the CEO clearing you to purchase an unlimited number of cash equivalents using the payment method of your choice.

If you cannot explain yourself briefly, calmly and with respect for the employee you're dealing with, you will fail, you will be remembered, and you will draw attention to techniques that will become harder to implement. Service employees don't work for you: they work for their supervisors, managers and, ultimately, for faceless corporations that they know are completely indifferent to their well-being.

Customer service employees have more to lose than you do.

6. Spend cash last

Once you've dug deep into the travel hacking weeds, you're going to have some unavoidable expenses (or investments, if you prefer): annual fees on your most valuable credit cards, activation fees and liquidation costs, losses on reselling mistakes, postage on 94 envelopes, and so on.

The last thing you want to do is unnecessarily add to those expenses by paying cash for your travel while you hold out for some "ideal" points redemption! You've already paid for the points — now use them. Save your cash for expenses that can only be paid for with cash.

7. Be realistic about your travel goals

In other words, earn the points you redeem and redeem the points you earn. I'm not saying you should think small: if you want to go to the Maldives, travel hacking makes that possible, if not exactly easy. But don't build a travel hacking strategy around something amorphous like "this blogger made the Maldives sound nice."

If you have an ambitious goal, then pick a date (or range of dates, since award availability can be tough), pick a strategy (Hilton or Hyatt?), earn the points you need, then stop. Enjoy your vacation.

If you have less-ambitious goals, then focus on earning the miles and points you find yourself redeeming most often. Consider using fixed-value points currencies like US Bank Flexpoints. Earn points you're likely to be able to use across a range of destinations, like Hilton HHonors.

8. Don't structure transactions

It's against the law, and if you do it the government will ruin your life.

Conclusion

The travel hacking index card isn't a travel hacking strategy: it's a strategy for developing a practice that will achieve your travel and financial goals with mistakes as few and cheap as possible along the way.

So what did I miss — what would my readers add to a travel hacking index card?