Never transfer points before finding the seat

If you remember one rule about points, make it this one: the seat first, the transfer second. Always.

Why this matters. Credit card points, Chase, Amex, Citi, Capital One, are flexible. They can become airline miles in a dozen different programs. That flexibility is most of their value, and it survives exactly until the moment you hit transfer. Transfers are one-way. Once your Amex points become Aeroplan miles, they are Aeroplan miles forever. There is no undo button and no customer service agent who can reverse it.

How the mistake usually happens. Someone reads that Aeroplan has great business-class prices to Europe, moves 150,000 points over, and then goes looking for flights. The award space on their dates doesn't exist, or exists at double the price they read about. Now their points are stranded in a program that doesn't have the seat they want, and the flexible currency that could have gone to United, Air France or British Airways instead is gone. I've talked to people who did this two or three years ago and still have the miles sitting there.

The right order of operations. Find the actual seat in the airline program first: real availability, on your dates, at a price you're happy with, bookable right now. Then, and only then, move the points. Most transfers from Chase and Amex to major partners are instant or near-instant, so you can find the seat, transfer, and ticket within the hour. A small number of partners take a day or two, which is exactly why the search comes first, so you know before committing whether you have that kind of time.

One more trap: the phantom seat. Sometimes a search site shows an award seat that isn't really there; the booking fails at the last step. It's rare on the sources I trust, but it's another reason to confirm the seat is bookable in the actual airline program, not just visible in a search tool, before any points move.

This ordering discipline is invisible when it works and very expensive when it's skipped. It's also, frankly, half of what people are paying for when they hire me: I don't just find the seat, I sequence the transfer so nothing gets stranded.

Sitting on points and not sure what they can get you? That's the exact conversation my free 10-minute call is for.