And just like that, we missed our flight. That’s the conflict that results in the story and solution you’ll hear today.

It’s a story about a trip, but for many of you, an equally important story about negotiating the financial waters and getting your point across in a way that brings about a good result.

Watch the video or listen to the podcast. Then return for the takeaways and the same letters they reference.

Here is the letter we sent to JetBlue:

Here is the cover letter we sent to the travel insurance company:

Here is the letter we sent to the travel insurance company when we disagreed with the initial findings:

Here are 7 takeaways from our experience:

1. Pack a small carry-on containing medications and anything you would need anything you need to be “presentable” the next day.
2. Take pictures of your luggage. It’s easier to describe if it doesn’t arrive.
3. Have a place to trap all paperwork. It will all be in one place at the end of the trip.
4. Have a place to trap all. I use Evernote.
5. Write a cover letter that makes your case and your ask crystal clear. Then, include documentation on the following pages.
6. Dispute unfair credit card charges.
7. Have a good system for digital notetaking. (Another vote for Evernote.) Your memory is hazy. Elephants never forget.

“Here’s my Golden Rule for a tarnished age:
Be fair with others, but keep after them
until they’re fair with you.”

― Alan Alda, Things I Overheard While Talking to Myself

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