I've always been a get to the airport with plenty of time to spare person to avoid the stress. But I briefly worked for someone in downtown Boston in the late 90s who I would sometimes travel with. I'd be looking at my watch in the office maybe a half hour before flight time and be like "Joe. Don't you think we should be headed to the airport now?"

Pre-COVID I traveled frequently to see family on the opposite coast, this is still possible with TSA Pre and only carry on bags at most major airports.

However, it's risky now because airlines are under much more pressure to get flights off the gate, and they'll gladly close the door on you if somehow they have a quick boarding process.

Yeah. I’ve gotten to a gate 30 minutes ahead of time because I’ve been in a lounge or just had a connecting flight and basically gotten a cross “Why are you so late?” at the gate.