I realize passwords can be stolen. Maybe I’m a sucker and was phished. Maybe one of the various public Wi-Fi networks I’ve been on in the past few months of traveling was compromised. It doesn’t matter. I should be changing my password more often.

But it also got me thinking. How was it so easy for these guys to send out a few hundred emails from my Gmail account? If Gmail is so good at filtering incoming spam (and it definitely is), how are its outgoing spam filters so poor? There are things Gmail could do to help this problem.

For instance:

The “Wait, What Are You Doing?” Filter

By my count, 47 emails were sent from my account between 3:14am and 3:17am, each without a subject line, each containing just a link, each to alphabetically sequential addresses from my address book. Maybe Gmail should raise a red flag at some point? Maybe after the first five are sent? How about a “hey, we love you and all, but maybe you can send the next five after a few hours” alert? I woke up at 6:19am to an email from a friend alerting me to the spamming. I could have shut it down at that point.

The “You’ve Let Go Of Your Ex-Girlfriend…I Guess We Can, Too” Feature

Gmail is to email addresses as cell phones are to phone numbers: no one has to remember them any more. Just type in a couple of letters from an address, hit tab, and move on. That’s awesome. What’s not awesome is that clients, co-workers, and random people I happened to email five years ago got a link from me this morning asking them to buy Viagra. To top it off, each note had my signature, so they were reminded which idiot from their past lives was being hacked. So I’m asking Gmail to be dumber: after six months or a year, if I haven’t emailed my junior year accounting professor, do me a favor and forget his email address. If I need it that badly, I can do a search for his name within my mail.

The “We Know You Hate Taking Your Medicine, But It’s That Time Again” Lab

The previous two features I mentioned could not be part of Gmail Labs; it would be too easy for outgoing spammers to turn them off. But what if Gmail had an optional feature that reminded you to change your password everythree months? Too few people would use it. And it’s something we can remember to do on our own (I just added it as a recurring event on my calendar). But if “Go Back To Gmail Beta” is a Lab feature…surely we can add this one, too.

Maybe these are tougher features to implement than they seem. The product managers and developers at Google who work on Gmail are significantly smarter than I. But I woke up this morning and found that a few hundred of my closest random acquaintances got an email from me with a link to buy pills online. And that’s frustrating. My wife pointed out that most online users understand that spam happens. But each one of those emails had my website in them (which is how I know the hackers were using the Gmail web interface), and who knows what the readers of those emails will now think about me and my work.

Here’s to hoping Gmail’s outgoing spam catches become just as smart as the incoming.

Have you been hacked? Got any tips or tricks to keep it from happening? Any more outgoing spam features you’d like to see in Gmail? Hit those comments.

Of particular note in the not-so-excellent column was the first session I caught featuring reps from a couple of Boston’s biggest ad shops, sitting on stage with their large financial clients (the companies are large…not the clients themselves). I had an overall positive experience that day, so I’m not going to harp on the negative too much here, but let’s briefly review why this panel was brutal:

Did anyone learn anything here? How can we trust anything either of these parties say? Clients gush over the agency, agencies gush over the clients.

Financial clients. Behind car accounts, these are the cornerstone of the traditional agency model. And if not for some amazing fumbling by a large British oil company right now, they’d still be the target of some serious public ire. But there they are, sitting, smiling, pretending like they could do no wrong, as long as their trusty agency partner sits by their sides.

We got to watch a bunch of TV spots. And who doesn’t love TV spots? Especially when discussing this town’s ability to innovate. To be fair, they did show a few iPad screenshots. iPads are hip and innovative, right?

Ok, so I’ve gone on a bit longer than I hoped. And please don’t get me wrong: while I don’t work for a big shop, I can’t say I never will again (some of them know what’s up). But these guys were pretty rough to sit through.

In stark contrast was the small agency panel featuring founders from PJA, Pod Design, Small Army, and Beam: this one falls under the excellent category. The four guys up on stage were smart and – most importantly – candid about their shops, their clients, and their industry. My only disappointment was where the panel was scheduled: right after a brutally out of place session on socially responsible architectural design and right before a coffee break that those who hadn’t left yet couldn’t wait to take.

The juxtaposition between this and the big agency panel was made even more evident by a couple quotes I thought were quite poignant. First, David Batista of Beam pointed out that “it’s easy to please clients…what’s hard is to make something that humans actually want to use.” Can’t say that when your client is sitting right next to you. Secondly, Jeff Freedman of Small Army pointed out that “the traditional model is dead, traditional media is not.” And he’s right.

But what both of those quotes really bring to light is the fact that small shops get it: this isn’t about just trying harder at what has been done for years. This is about doing what’s been done for years in a different way.

Remember that time I spent days getting you just right? Remember how I tweaked every little pixel, molded your PHP, your CSS, your JavaScript? I gave you my heart. And you’ve completely thrown it on the floor and stomped on it.

Ok, I realize I may have stopped updating you for a bit. Maybe I should have paid more attention to you, and less attention to my new job, or my new fiancée. Maybe I should have traveled less. But that’s all behind us now. I am looking at the future.

Or am I? How can I consider a future with you, my dear blogging software, when you keep screwing me over here. First your iPhone app loses posts randomly, removes UI elements when it feels like it, and ultimately breaks. That was hard to take. I wrote out a nice long rant about it. But I hit delete. Why? Because I felt it wasn’t worth the anger. It was time to move past it.

But now – now I must speak up. You ask me to update you to 2.8. Easy! I click a button, I wait a few minutes. Just like that, you’re as good as new. But perhaps you’re TOO new! Where is the overly-muted black and white theme? Where is the skinnier-than-necessary Chalet Nineteen Sixty typeface (implemented via sIFR)? I spend all this time morphing you in to what I want in a blog, and you go off and do your own thing.

Of course, there’s nothing I can do but go back to the beginning now. Pick up the pieces. I won’t be switching to MoveableType or Tumblr or the like. They may be better. But I will never know. I’ve commited myself to this relationship. My only request is that, this time – please – get your shit straight and behave.

Because I love you. I do. But only when you do what I say.

Lovingly yours,

Gabi.

Agency Spy does a superb job of laying into this ridiculously unnecessary, too-much-but-too-little-too-late move, so I’ll leave the ranting to them.

But come on. Really? Forget about being about ten years behind the curve in the ad business…what a poor business move in general. AIG much?