The year-end email writers HATE receiving from publicists

Also, I'm seeking destinations to visit in Feb 2025

Dec 19, 2024

Hi friends,

Greetings from New York City, where I have a few days to recover from my Costa Rica trip and start adding my notes to the Lonely Planet content management system before I head to Wisconsin for the holidays. The vast majority of the work will have to wait until January because I insist on taking a holiday break! The pic above is an epic old-school suitcase I saw a guy carrying at JFK. Isn’t it fabulous?

First off - thank you SO MUCH to everyone who sent a thoughtful email (or left a public comment) on Monday’s post about my 2024 Review: Recap, Stats & What I Learned. It was a very data-dense post with some heart-wrenching personal shares that were hard to digest, and I’m grateful to know how helpful or meaningful the newsletter was.

I didn’t plan to send a newsletter today but I know a lot of people are still working — I heard from four different editors today, only one offered a confirmed assignment :( — so I figured some eyes may appreciate this update.

Happy holidays!

Cassandra

Seeking Asia Travel Destinations in 2025

As you may have read in my 2024 Review email, I am thoroughly exhausted and I’d like to dramatically cut back on travel in 2025. That said, I’ve been in discussion with Bhutan for six months and I have a confirmed trip there in late January - early February 2025.

Long-haul flights are the WORST so if I’m going to spend 23 hours flying somewhere (and another 23 flying back), I’m very likely to stack up trips on that side of the world because I’m probably not going to want to fly again for several months.

Do you rep a country in that part of the world? Nepal? Bangladesh? Myanmar? Can you even travel to Myanmar anymore? If so, I’d love to talk ASAP since I don’t have my flight to Bhutan yet and I’d love to coordinate.

Every Freelancer Hates Receiving This Year-End Email

At the end of the year, many freelancers receive reimbursement-related emails from tourism boards and destinations they’ve worked with regarding W9s and 1099s related to trips the writer took where they paid expenses out of pocket. The way this often works is that a writer may visit the destination and be told that they’d need to pay for meals, activities, admissions, and even the rental car out of pocket and then be reimbursed later.

In many cases, these expenses can be paid by the tourism board in advance (hotels, for example, are typically covered), but on independent trips, it can be hard for a destination to pre-pay meals because it’s not always clear which restaurants a writer will visit or how much their meals would cost. In my experience, rental cars are especially difficult to cover in advance so I’m often required to pay hundreds of dollars out of pocket to reserve the car. As long as a tourism board lets me know in advance (which is what Eau Claire, Wisconsin did), this works for me.

Taxable Income vs Expenses

The problem though, is what often happens later. Unlike Eau Claire, which confirmed in advance that I would NOT have to fill out a W9, many destinations require this. In some cases, the PRs have absolutely no control over the matter and they simply aren’t allowed to reimburse expenses without it. The issue with W9s and 1099s is that these are typically associated with taxable transactions that need to be reported to the IRS.

Say I take a press trip that the tourism board IS NOT PAYING ME FOR, and I pay $700 out of pocket for meals and the rental car, why on earth should I be expected to pay taxes on a $700 reimbursement? IT IS NOT INCOME! All caps there because this is a major annoyance for just about every freelancer I know and the topic comes up this time of year every single year. Consider this: if I pay $700 out of pocket to visit the destination, and then have to report income on that $700 reimbursement, I then lose several hundred dollars to Uncle Sam just because your destination couldn’t (or refused to) find another way.

On numerous instances, I’ve had destinations insist that they can only file the reimbursement request if they have a W9 on file. They assure me that they won’t process it as income so I won’t have to pay taxes on it. Guess what. On several occasions, I’ve still received end-of-year tax statements from the IRS, and I then have to spend time going back and forth debating with the destination to reverse. Now, I simply refuse to fill out W9s because I don’t want to deal with this headache at the end of the year.

A better way to issue reimbursements

The absolute worst reimbursement scenario I’ve ever encountered was a western state that required freelancers to fill out a complicated Excel spreadsheet detailing all their expenses in addition to submitting the actual receipts. Ugh!

My favorite way to have reimbursements handled is through gift cards. This way, I can go around a destination, happily swiping my expenses without having to come out of pocket. The added bonus is that in this scenario, I typically also don’t have to submit copies of all my receipts. T

So far, I’ve encountered three gift card scenarios that work well. Here’s a quick explanation, in order of my preference. If you know of other options, I’d love to hear about them!

1. Pre-Paid Physical Gift Card

In this scenario, the writer receives a physical gift card (which is usually left in the hotel room or handed off by the destination rep in person). This card is then used at restaurants, museums, bars, etc. No receipts need to be submitted.

2. Digital Gift Card

In this scenario, the writer is emailed a digital gift card, which can be used in person or online. I recently received a gift card like this and I don’t like it as much as the physical gift card because who wants to print out a copy of the card or have to zoom in on a screenshot on their phone to read off the numbers at a store clerk to be reimbursed? It’s not the worst option, but I wound up skipping using it at the destination and just used it for a separate online purchase where I could use up the entire amount in one transaction.

3. App Gift Cards

In this scenario, the writer receives a virtual gift card that’s sent through an app. To use the gift card, you open the app, tap, and pay. It sounds easy, but I’m one of those people who hates having to download an app for absolutely everything. Not only do apps clutter up your phone, but they typically track and sell your data so I avoid downloading apps at all costs. Some writers may not mind it, but it’s my personal least favorite.

Did I miss any fun or easy reimbursement options? If so, please share them with me!

Share Media Musings with Cassandra Brooklyn

Favorite Articles from 2024

Thanks to those of you who helped me source products, destinations, and quotes for these pieces. Here’s a sampling of what I wrote in 2024, which I think gives you a good idea of the sort of topics I cover for various outlets.

Thrillist: Spilling the Tea on This Indian Ocean Paradise

CNN Outdoors: The Best Bike Lights of 2024, Tried and Tested

Wall Street Journal Travel: For an Outdoorsy Vacation Without Massive Crowds, Look to Your Nearest State Park

Range Best (gorgeous print mag): Scotland Slowly - Why the Best Way to Explore this Rugged Country is by Water

Yahoo: FeatherSnap Scout Smart Bird Feeder Camera Review: An Intelligent, Addictive Addition to Your Backyard

Midwest Living: 11 Must-Visit State Parks According to Locals and Pros

AFAR: This Canadian Island is a Dream Destination Best Explored By Sea

Yahoo: 8 of Canada’s Best National Parks (which got 185,000 views!)

Hilton: Embrace the Season in These Worldwide Winter Wonderlands

AARP Travel: Traveling in Hot and Humid Weather? Here’s What You Need to Know to Stay Safe

AARP Caregiving: What I Learned from My Mom’s Move From Hospital to Rehab

Sierra Club: How Local Parks and Nature Centers are Putting Accessibility Front and Center