Every travel site will tell you how to do things the right way — but as every traveler knows, sometimes things go wrong. In his bi-monthly Mistake Monday series, TPG Contributor J. Keith van Straaten invites you to learn from his mistakes — his many, many mistakes. 

Collecting big sign-up bonuses on credit card offers is by far the most lucrative way to earn points and miles. In most programs, spending one dollar on a credit card yields one point or mile, so even if an average American making about $51,000 a year spent every dollar they earned, they still couldn’t generate the same number of points provided by a good sign-up bonus after spending only $3,000 or less.

In my early days of playing the points-and-miles game, I was excited to discover that I could get credit cards for both personal and business use, so I doubled up on every recommended offer … and soon ended up with eight shiny new points-earning accounts. One of my best scores was a sign-up bonus of 60,000 Ultimate Rewards points on the Ink Plus card; this was up from the usual 50,000, but certainly not as exciting as the rare 70,000.

Meanwhile, I put as much spending as I could on all my new cards so I could earn their promised bonuses. I switched to a dry cleaner that took Visa, and set my cell phone’s auto-pay option to my Amex Business Rewards Gold. I was really on a roll.

I became an evangelist for acquiring points and miles. I couldn’t take out a credit card at a restaurant without telling my date/friend/family/self how cleverly I was working the system, racking up hundreds of thousands of miles and points. I loved answering questions about which cards offered which bonuses, how to figure which card to use where and, of course, how I planned to spend my windfall on fabulous, practically free vacations.

About six months after my application binge, I was finally ready to use my earnings for some fun. However, when I logged onto the Ultimate Rewards site, I noticed that I only had about 4,100 points in my account. That’s weird, I thought, I should have at least the 60,000 points, plus whatever I put on the card (which included some 5x points earnings on bonus categories.)

I sent a message to Chase through their Secure Message Center, asking them to explain this surprising situation. Within a few hours, they replied with news that made my heart drop: I hadn’t actually met the minimum spend required to receive the Chase Ink’s sign-up bonus.

Madly searching for an error in their logic, I checked the numbers — but sure enough, the sign-up bonus offer clearly stated that I had to spend $5,000 within three months of account opening in order to receive the 60,000 points. Sadly, I’d thus far only spent about $3,200.

Somehow, amid all my excitement over all my accounts, I didn’t do the one thing I had to do in order to get the one thing I wanted.

I wrote back to Chase and asked the representative if she could make an exception for me. (As The Points Guy often says, it never hurts to ask.) I pointed out that I had several other Chase accounts and that I promised to spend $5,000 ASAP. She said she couldn’t — but in one of the only smart moves I made during this ordeal, I asked her to pass on my request to a supervisor.  The supervisor said he couldn’t change the terms of the offer, but as a courtesy would give me 10,000 points. I gratefully accepted and began downgrading my practically free vacation plans from Fabulous to Fair.

The lessons:

1. Make your minimum spend! It’s one of the basic rules of making these offers worthwhile, second only to: “Always pay your bill on time and in full.”

2. Keep track of your credit card bonus requirements. After this incident, I started putting reminders in my calendar, with alarms that gave me enough time to get the required spending done. Nowadays I use the TPG To Go app, with its TPG Tracker feature. It links to my bank accounts and keeps me current on my spend progress. (Full disclosure: I was using this app well before I became a contributor to this site.)

3. Don’t apply for more accounts than you can handle. This isn’t just true for what your credit score can handle, but also for what your attention span can handle. If you can’t pay attention to your accounts, your accounts won’t pay off.

4. Ask for mercy. The biggest lesson I’ve taken from every aspect of where travel and finance intersect is simply to ask politely for a break. Sure, 10,000 points isn’t as nice as 60,000, but it’s 10,000 more than I would have gotten without the request!