Some of my friends and family members who stopped working when they had kids are trying to reenter the workforce now that their children are in school for much of the day. Because flexibility is hard to find in most offices (and career pauses are generally frowned upon on résumés), these women all seem to be flooding the same fields. In other words, they are becoming travel agents. Succeeding in that job is almost entirely dependent on having a strong personal network willing to pay for your services and suggest you to others -- and my friends have not been shy about asking me to help them. I'd rather continue to use a trusted travel agent instead. I want these women to succeed, but I also don't particularly want to mix business with friendship, and truth be told, I'd prefer to use someone more experienced. The problem is I'm afraid of them finding out that I booked a trip -- for example, via seeing me on vacation on social media -- and didn't use their services. How do I handle that?

Your question made me do some hard thinking about what exactly we owe our friends, but first I had to find out what a "travel agent" even is. I had naïvely assumed that this profession had gone the way of "milkman" and "newsie."

Thirty years ago, everybody used to have to buy their plane tickets via travel agents, who were paid a commission by the airlines. These days, of course, you can buy tickets directly from the airline or from any number of travel websites. Many "higher-end" travel agents now prefer the term travel adviser, and -- as a very nice travel adviser with 20 years of experience named Howard informed me -- people who are planning non-luxury domestic travel don't really need one. If I'm, say, renting a house for a week on Cape Cod or heading to my cousin's wedding in Chicago, I'm perfectly capable of planning those trips on my own (and I totally will, when I get around to it). Where a travel adviser like Howard would come in handy is if I were traveling internationally, to a country or countries where I'd never been before and there was a language barrier, and I was going to need guides to show me around and rides to get me where I was going. In that case, I would pay Howard a deposit up front, which would then be applied to the cost of the trip. The adviser would get a cut from the hotels, guides, and drivers they'd book. The other instance in which I might want to use a travel adviser is if I, say, sold the film rights to my next book for a huge amount of money and got an executive-producer credit and then wanted to reward myself with a stay in a White Lotus-type luxury resort. Booking that trip via Howard would mean I'd get lots of cool perks since his business is a member of organizations like Four Seasons Preferred Partner and Virtuoso. Room upgrades, free meals -- that kind of thing. Honestly, it sounds really nice!

It also sounds as though there are a lot of very good reasons why you wouldn't want to use a less experienced travel agent. If someone is just starting out in the business, Howard says, they might not be as well traveled -- they wouldn't have the firsthand experience of the trip you want to take that would give them access to the connections with third parties that could make the trip easier for you. There are also lots of things that can go wrong during travel: missed connections, delayed flights, hotels that lose a booking via human error, etc. Those things might not even be your friend-travel agent's fault, but she'd still be on the hook if you had a bad trip. Not to mention the things she might screw up on her own -- a strong possibility if she's new to the business. Howard says that his co-workers make a point of not working with people they know socially: "It's not a company policy, but they don't want to be in an awkward position where if something happens, their friend doesn't know how to tell them that something stinks or they don't like it. And so we tend to kind of just nip it in the bud by saying, 'Sorry, we don't work with friends.'"

Not mixing money and friendship is a great all-around policy, but it's always going to be tempting to make an exception to the rule. When a friend is starting a new business venture, of course you want to help her out, whether it's by spreading the word about her services or using them yourself. But I can personally attest that it's wise to think twice before you do so, whether we're talking travel agents (most of us are not talking travel agents, I think we've established) or something that seems lower-stakes. For instance, I once paid a friend's husband to design my professional website. Now they're divorced and estranged and I have no idea how to update the stupid thing, but I don't want to get in touch with that guy to ask him how, so my website is permanently trapped in 2020. It would have been better to hire a rando or to go with Squarespace, like the podcast ads are always telling me I should do. What it boils down to is this: You owe your friends who have just become travel agents (or website designers, or accountants, or therapists, or lawyers, or sex-toy designers) your emotional support and encouragement. "I'm always here to listen to you if you need to kvell or vent about your new gig!," etc. But you don't owe them your business.

So have an honest conversation with your newly minted travel-agent friends before you go on your next trip. That way, they won't find out you went to the Four Seasons San Domenico Palace, Taormina (where season two of The White Lotus was shot), via Instagram. "I would love to support your business, but our friendship is valuable to me, and I don't want to run the risk of damaging it if something goes wrong on my trip." There! Now you can relax by the infinity pool in Sicily with an Aperol spritz, taking in the view of Mt. Etna over the ocean with a (mostly) clear conscience.