I Was Losing Out Every Time I Paid a Bill

What’s my biggest regret?

You’re expecting something meaningful now, aren’t you?

You think I’m about to say something profound, something deep, something that explains the meaning of life.

You’re wrong.

My biggest regret is not having maximized the rewards from my credit cards for the first 20 years of running my practice.

Yeah, I’m not big on reflection. That’s what I’ve got for you.

The Game of Points

Over the last two years, I figured out the credit card/points game. It became an obsession. It’s complicated, interesting, and frustrating.

I think of it as golf for those who don’t want to go outside.

Since I started figuring this out, I’ve accumulated millions of miles and points. I’ve obtained free tickets (many in business class) to Rome, Paris, Bangkok, San Francisco, Chicago, San Diego, and a bunch of other places. I’ve still got nearly 2 million points sitting in my accounts today.

I’ve applied for and discarded more than 30 credit cards to get the sign-up bonuses. I’ve made countless trips to the office supply store to buy gift cards (there’s a whole thing where you can get even more points). I’ve stood in line at the CVS drugstore to buy tens of thousands of dollars in Vanilla reload cards.

I admit that it’s total insanity, but it’s awesome.

The free hotel rooms are amazing. I spent days in Sydney in a great room overlooking the harbor. The free week in the Conrad in Chicago was a blast. The week in Tribeca was terrific. I especially love it when my free room comes with a free breakfast: it’s a two-fer!

Yes, this is not an activity for those with anything important to do. This is an odd hobby for a peculiar type of person. I love it. It keeps me off the streets.

How to Score Points

The points are coming from three types of activity:

  1. Signup bonuses. The various banks sometimes seek to encourage the distribution of their cards. I only sign up for a card when it offers something extreme. Last month, I got 100,000 American Airlines miles for getting a Citibank card in a limited time offer (that’s a value of somewhere between $1,000 and $7,000 for filling out an online form). These offers come and go.
  2. Crazy schemes. The office supply store deal mentioned above is a good example. I’ve been known to walk into Office Depot and walk out 5 minutes later with $10,000 in Amazon gift cards. There are endless gimmicks that award points, and I’ve tried them all.
  3. Spending. Many of us pay our office expenses with checks. How last century. Most vendors will accept credit cards, and you can get points for all of those expenditures. Why not get what you can? Check all of your vendors and see whether they take cards. We’re even paying our office rent with a card.

I’ve got so many points now that I’ve switched over to a semi-cash back card. It gives me a credit for my travel expenses amounting to 2.2% of what I spend. That’s not quite what I’m getting when I use the points for business/first-class travel (5 to 7%), but I’m waiting to use the points before I go back to accumulating them again.

My guru for accumulating points is The Points Guy. He provides great advice along with alerts when special deals arise. His advice has served me well. There are a bunch of other bloggers in the points space (making their livings off the credit card affiliate links on their sites), but The Points Guy usually hits the important stuff.

This hobby won’t appeal to everyone. For some, it’s more trouble than it’s worth. However, for me, it’s fun as well as lucrative. It gives me a special thrill to get stuff for “free.” I accept that I might be a tad peculiar.

I hate to think about all the years I let pass without getting my fair share of the points. However, now I’m in the game, and I’m loving it. No more regrets for me.

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