The single most important thing you can do to succeed in travel hacking is stay organized. That's true of every single aspect of the game:
- If you're booking your hotel stays through a portal like Rocketmiles or Pointshound, you have to make sure the correct number of miles post for each and every reservation: miles posting incorrectly or not at all means foregoing hotel loyalty points in vain;
- If you're chasing elite status, you have to make sure you know the number of elite-qualifying miles you need each year and game out each and every flight you plan to take: falling short by a few hundred — or even just a few — elite-qualifying miles is in most cases a catastrophic failure;
- If you're manufacturing spend across a number of credit cards, you need to keep track of the statement closing and payment due dates of each and every one of your cards: a single missed payment will result in interest and penalties that can wipe out the returns on months of manufactured spend.
I use a variety of methods to track my manufactured spend, but just one to track my actual income and expenses: Mint.com.
Mint can download most transactions from most banks most of the time
Most major banks and many reloadable prepaid card accounts can be added to your Mint master account. When you do so, each time you refresh your Mint account your balances and transactions are downloaded from each bank's server.
The system's not perfect, and I find that Mint's servers are unable to download transactions from some banks most of the time. US Bank is a particular offender — don't bother using Mint to track business credit card accounts with US Bank.
Tracking transactions is nice in and of itself, but the real genius of Mint is allowing you to recategorize transactions, which is to say reassign them from the category Mint guesses they belong, to the category where you know they really belong.
Recategorizing transactions gives you a concrete sense of your actual income and expenses
Here's a deposit to my primary local credit union checking account. Mint originally categorized it as "Income," but I knew better and recategorized it as "Transfer:"
That keeps Mint from adding that amount to my monthly income statistics.
In addition to recategorizing transactions, Mint also allows you to "split" them. Here's a recent purchase I made at one popular merchant:
Mint, naturally enough, originally categorized the $504.94 transaction as an expense. But, knowing better, I categorized just $5.64 of it as "Fees & Charges," while the remaining $499.30 has no effect on how Mint reports my income and expenses since I recategorized it as a "Transfer."
As a final example, for tax reasons it's necessary for me to track my self-employment income. But I also want to treat things like credit card retention bonuses, statement credits, and cash back as positive income flow. To do that, I use Mint's "bonus" category (you can create your own categories to help refine transaction reporting even further):
Don't worry, I'll be paying self-employment tax on Andy's subscription come April.
Do you need to keep track of your manufactured spend expenses?
This practice gives me an instant grasp each month of every penny I spend on fees while manufacturing spend, and also lets me see at a glance how much of a cash return I get on those fees.
It's also a pain in the ass.
Don't get me wrong: I do all this coding while in bed each morning sipping a cup of coffee or three. But you don't get to sleep in every day, sipping coffee. You have a job. Hell, you may have two jobs!
So should you keep track of your manufactured spend expenses as closely as I do? There are strong arguments on both sides.
On the one hand, as I hopefully made clear, Mint can only keep track of dollar-denominated expenses and returns. It won't tell you how valuable your Hilton HHonors points or United Mileage Plus miles are; it will only tell you how much you paid for them. Since you aren't recording income each time you redeem your miles and points, why should you record your costs each time you earn them?
On the other hand, you really are spending cash money when you manufacture spend. That's money you can't put towards a down payment, towards tuition, or towards retirement. It's gone, and if you use Mint to track your expenses, logic demands that those expenditures be recorded somehow as well.
Ultimately, I come down on the side of meticulously tracking manufactured spend expenses, not because they make a huge impact on my net worth, but because I find it risky to dispense with absolutely rigorous honesty when so much is potentially at stake. I can't help but think that if someone doesn't face the concrete costs they pay when manufacturing spend, they'll be more likely to ignore similar expenses elsewhere in their financial life.
That being the case, I'm happy erring on the side of scrupulous honesty when it comes to my own income and expenses.