In my case, I was late a lot because I resented having to do all the things I was late for. Even today, I’ve been known to wake up all pissed off, thinking “WHY DO THEY MAKE ME LEAVE MY HOUSE?”
Daniel Gilbert wrote in Stumbling on Happiness that the reason we have such a hard time being happy is that we are really bad at anticipating what our future selves will enjoy. This is why we own so much stupid shit. Furthermore, research into the brain also casts light on why we agree to do things we don’t really want to do when the time comes.
As it turns out, when we think about doing something in the future — say, climbing Mt. Kilimanjaro in five years — we think in very general terms: Adventure! Glory! Nature! When we think about doing the same thing in the near future, we think about specifics: Hard work! Bugs! No toilets! Thus, if you want to get people to agree to be bridesmaids in your destination wedding in Latvia, ask two years in advance — people will agree to almost anything that far out. You’ll get more assent to Latvia in 2013 than to dinner tomorrow — when it comes down to Friday night, people can anticipate whether they’re not going to want to go out. What a shlep! But Latvia in the winter? Fun! Adventure! Intrigue!
How to use this to your advantage: every time you consider adding something to your calendar, imagine that you have to do it tomorrow. Imagine the preparation you will have to do, and how much time it will take you to dress up or otherwise look appropriate. Imagine the transportation involved and how long before the event you will need to leave. Imagine waking up tomorrow and actually doing all of those things. Now, do you still want to put that on your calendar? (This, my friends, is why your social circle is not really going to visit you in Weehawken, even though they say they will).
The other big reason many people are habitually late is that they hate waiting, so they have decided that other people should wait instead. Don’t fool yourself: the only way to never have to wait is to make other people wait for you, also known as being an asshole.
In order to no longer be late for things, thus accruing the ire of others, you will have to make peace with waiting. Accept that committing to do something involves a time sandwich (the event is the filling; the commuting and waiting are the bread).
Five years ago, I lived in Bushwick, Brooklyn, where it takes an hour to get anywhere (“only 18 minutes on the train to Union Square!” doesn’t help much when the trains come anywhere between 7 and 29 minutes apart, depending on whether it’s Tuesday or they have PMS). [Editor's note: Moving away from the L train was one of the best life decisions I've ever made.] As a side effect of that unfortunate experience, I now sort of reflexively assume that it’ll take me an hour to get anywhere. (Also: an hour each way is a lot of time, so keeping that in mind makes it easier to decline dubious engagements — see also How to Get Out of Meetings, Permanently).
When you spend an outer-borough amount of time on the train, you of course find ways to redeem your train time. You can also find ways to redeem other wait times. For instance, when you buy a new album for your iPod, don’t listen to it: wait until you’ve got a serious wait on your hands. More productively, though, I postpone a lot of short to-do list items specifically for those five-minute blocks. If you’ve got a four-hour block in your day, don’t fritter it away on non-urgent five-minute tasks; save those tasks for your wait times. You can absolutely return phone calls outside of restaurants, which also gives you a fine excuse to keep calls succinct.
In sum, there are plenty of people out there blithely flitting through life, arriving places when they feel like it, and nothing bad seems to happen. Except that people hate you and are too polite to say so, or, at very least, they are keeping your friendship wholly in the hanging-out zone and specifically not recommending you for jobs, gigs, and all kinds of opportunities where they don’t want to get burned when you turn out to be irresponsible.
For years, I had a very talented friend in my own industry — a woman who could (patiently and with panache!) teach writing, logic, and research skills to a monkey. She was also routinely three or more hours late to everything, including a full-time job that no one could figure out why she still had. When a job came up that I couldn’t do, I would think of her literally at least twice a month — “Oh, I’ll bet so-and-so would write some amazing worksheets about verbs!” — and then I would say to myself, Oh, that’s a shame. Because I don’t work with any clients who want their work done “sometime.” And then we would hang out and have a lovely time, and I just wouldn’t mention any of the gigs she would’ve been (otherwise) perfect for and that I didn’t send to her.
That is — if everything seems fine, it’s very likely that it could’ve been a lot better than fine. Erring on the side of competence will really never do you wrong.