Is truly its own special circle of hell, honestly.
I was just reflecting on this before my flight while we were being de-iced (about a 40 minute process from pushback to take off). I’ve historically had very few flight issues, but this winter season has made me a lot more cautious about how I structure travel for work.
For example, I had a FMTY to KCMO in December that turned into a full 15 hours of aviation chaos. Left my house around 7am and somehow ended up back in my own bed by 11pm that night. We had a last second go-around which is an aborted landing at MCI so we wouldn’t rear-end another plane. The unanticipated snow amount threw them so they hadn't prepped the runway or plowed it fully. We then got diverted to STL, which made zero sense because weather tends to travel west to east, three separate deplanings in STL, a broken de-icer, a 90-minute wait in the de-icing queue because STL wasn’t prepared, a crew timeout, and then a broken jet bridge for good measure.
By about 4pm I called the client and said, “I want to do this and normally I would pull all the stops, but they are looking for a crew and realistically, by the time I would get there, I don't think I'm going to be at my best.” I got on the last flight back to MSP and we rescheduled for the following month. Not ideal, but it was the safest and most sane option left.
Since then, I’ve been much more intentional in winter. Either the very first flight out to avoid cascading delays, or the very last flight so I’m not getting trapped mid-day. Driving can be more reliable in some cases and I've done it depending on the distance (like 5 hours or less), but then you’re trading airline chaos for time, fatigue, and wear and tear on your body (re: fatigue) and vehicle.
At the end of the day, stuff like this is part of traveling for work. You can do everything “right” and still get hit by circumstances completely outside your control. All you can really do is communicate early, be transparent, make the best call with the information you have in the moment, and hope the person on the other end is reasonable about it. I've heard the horror stories from colleagues about the people who are not so reasonable. Regardless, travel delays still suck though. Full stop.