Grab Bag - Feature Requests for (Work) Travel
Traveling for work for the first time in a year is exhausting, but I'm full of ideas for making it better
For the first 2 years of my career, I flew out every Monday morning and back every Thursday night. Like most undergrads, I thought it would be glamorous. It wasn’t. At all.
After that, I traveled much less. But, I probably averaged a trip each quarter at least until the pandemic hit. And even after that, I traveled occasionally. 2022 was the first year of my life without work travel, and that’s changing in 2023. This week, I took 3 flights in 4 days and truly got back out on the road.
Work travel has certainly gotten better over the years. It’s still exhausting, but it’s better than it was. There’s still so much room for improvement, and I think there’s a good amount of money in it for the folks that deliver them. I won’t go into much detail on any of these yet, but here are 3 areas that stuck out to me this week that I’m going to put a lot more thought into soon.
Airport Reservations
No, I’m not talking about reserving your spot in the TSA security line. But, how telling is it that that’s pretty much the only live example of a reservation for a (non-flight) airport experience? If I’m AmEx, I’m embarrassed that the TSA has out-producted me. I’ve not used TSA Reserve, which is actually powered by Clear, but I’ve heard good things from folks who have.
This is telling: airports got busier than expected coming out of the pandemic, and the TSA has invested in improving the experience. Reserve is part of that, as is Digital ID. They’ve joined with tech-forward partners to make new products that get people through security faster and more efficiently. Clear is the big winner here, and I remain long on that company’s prospects.
Airports getting busier affects more than just security; it affects everything past security too. Lounges seem to be feeling that most acutely, and AmEx is responding by limiting guest privileges and…nothing else. They’ve made no product updates, though you can try to make a reservation in the app and it will do absolutely nothing for you. You have no way of knowing, until you show up at the lounge, how long it may take you to get a seat.
You can have a reservation to get through security, and nothing after that. You’re at the mercy of traffic for lounges, restaurants, and bars. The closest you can really get is app ordering at a few restaurants, and some airports have tried to do in-terminal delivery, but that still doesn’t get you a seat. Clear has a massive opportunity here to own much more of the airport experience once you actually get in.
Low-Dollar Digital Tips
I run into this when I’m not traveling to, but that seems to be ~half solved these days. Usually, low-dollar “cash” tips in Phoenix are for a valet since we drive everywhere and parking lots are too small to support that. Most of the valets have, wisely, started including their Venmo QR codes on the kiosk and you just scan that instead of fishing out a few bucks.
Traveling, this is generally encountered at hotels. I’d love to leave a few dollars for housekeeping staff and tip the doorman who loaded my suitcase into the Uber, but I don’t travel with cash. I feel cheap and mean, but it obviously doesn’t stick enough for me to remember to pack cash.
Some high-end resorts have a “no-tip” policy but then you can allocate a tip at the end of your stay as part of your bill. I’m not sure why that can’t extend that structure to every hotel, but it works great. The QR code hanging around in a hotel probably doesn’t work, but there’s a fix here. It just involves hotels investing in those folks more, which is…a tall order it seems.
1-Click Expense Tagging and Export
This one is a bit more niche, because most expenses are submitted against corporate cards/accounts and there’s a very defined process for pushing those through. That’s not my situation right now, and it’s not all that uncommon for expense reimbursement to just be against a self-generated report from items where you used whichever card you want. The smaller the company, the more common this is.
The problem with that is you need to record the expenses somewhere in near-real-time or you run the risk of forgetting that expense entirely. Sure you can go through your statement later, but if you ever mix personal and business expenses on the same account then that’s going to be tough. For me right now, that’s a Google Sheet that I add a row to every time I incur a business expense. It’s annoying.
If Chase (or anyone, I’ll switch) could send an alert for every transaction and ask me if it’s business or personal, let me respond, and then export anything business-tagged later I’d be ecstatic. It’s kind of like Mint, but with more proactive control over what’s in what category, and it doesn’t incur the very real expense of even lightweight solutions like Ramp.
Summary
Traveling for work is better than it used to be, but it hasn’t caught up with the digital transformation that’s sped up while travel slowed down. There’s fun stuff to build, and whoever does it stands to make some money. I’ll dive in deeper here soon.