Beyond “It Should Be Fine”

How I work

Beyond “It Should Be Fine”

Before a trip with my wife, I asked a travel agent whether where we were going would be okay for us. The answer I got was that it should be fine.

Whoever says that doesn’t know. That’s what the sentence means, and I’ve thought about it a lot more than they’d expect. I opened Clark & Co. Travel in May 2026, and that answer is a decent part of the reason.

Updated September 2026

Jessica Clark

“Should” is a prediction

It sounds like reassurance and it carries almost no information. Someone who says it has told you they like the odds. They haven’t told you what the law says, what a hotel’s policy commits to about names and documents and who can share a room, or what happens at a front desk when a card and an assumption don’t match.

All of that’s knowable. Somebody just has to go and find out, and when nobody has, “should” is what you get instead. I’d rather do the finding out. It’s most of the job.

What I go and check

Before I tell you a place works, I want to know what the law actually says and whether anyone enforces it, what the hotels commit to in writing, what the walk back to your room is like at eleven at night, and what people who have actually been say when they’re writing somewhere no tourist board is reading.

A place having a reputation doesn’t take it off the table by itself. It usually means the answer gets more specific than yes or no. Sometimes it’s a private transfer from the airport instead of the taxi rank outside it. Sometimes it’s one hotel in that city and none of the other four. Sometimes it’s that the week you had in mind is the wrong week. And sometimes I think you shouldn’t go, in which case I’ll say so and tell you why.

When my wife and I travel, I don’t pretend to be anyone other than her wife. I’m not going to build you a trip where you have to.

The explaining is the part nobody wants

What people tell me they’re tired of is the explaining. Working out in advance how much of it a place is going to take, then doing it again at the front desk, then again with the driver.

That part is finished before we talk. If you don’t need it, it costs you nothing. If you do, it saves you a conversation you’ve had too many times already.

Start here

Fifteen minutes, free, nothing to sign. Long enough for me to tell you whether I’m the right person for what you’re planning. Bring a destination, or bring the three you can’t decide between. If you’d rather write first, send me your trip and I’ll start looking.

Frequently asked questions

How do you check a place for queer travelers?

Law first, and whether it’s enforced or just sitting on the books. Then the specific hotels and what their policies actually commit to in writing. Then people who have been, writing somewhere no tourist board is reading. If I can’t get a straight answer about a place, I tell you that.

Are conservative destinations off the table?

Usually not, but the answer gets more specific. It becomes which hotel, which transfer, which week, and occasionally which country next door instead. Where I think you shouldn’t go, I’ll say so.

Do I have to explain myself to you first?

No. That’s the part I’ve already done. Tell me where you want to go and who’s coming.