Into and out of the Rabbit Hole

This is the true story of how my Macintosh ate Sleeping Beauty.

A couple of years ago, I don’t remember exactly when, my Macintosh started eating my email.

For many years, I had so much email I just ignored it. Thousands and thousands of emails. Spam. Business correspondence. Personal friends. Non-profits I founded or worked for. Non-profits asking me for donations. People trying to send me money.

It was too much. Literally, I let over 10,000 messages pile up, and it kept piling up.

I stopped reading email.

So I got SpamArrest. I got a new Mac.

Slowly, but surely, I started emailing people again. People started getting in contact with me again.

Because of other emotional scars I bore because of my c. 2000-2002 personal meltdown, I often got emails but was an utter slacker. Even to this day I have more emails inbound than outbound. Time management and email management is a critical, urgent, and important issue in modern communications.

For a man who used to pride himself for riding the crest of the tech wave, I have to admit I went under. This blog is called "8 days offline." Yet I was unplugged from most of the day-to-day world of reality for years.

Where was I?

I was in cyberspace playing games. Peter Panning. Not growing up.

I had enough in the bank to pay my rent for years. If people played Castle Marrach (c. 2001-2006, off-and-on), or perhaps World of Warcraft (Nov 2007 - Aug 2008) they'd find me. Otherwise, mail and email piled up like trash, or eTrash.

Since 2006, more or less, I have been on the wobbly road to data and information recovery. Getting in touch with friends again. Starting new businesses. I still have more dollars than sense, so I don’t “need” a job. Though I can see the end of that runway. I'll need to take off within the next year, and get one of these enterprises of mine, for-profit or non-profit, into a stable orbit.

Today, I saw an email from a friend, who I will identify only as Sleeping Beauty. Oh! I was so glad to hear from her!

Then the Mac ate my email. Gone.

Nooooooooo!!!!

It happens. It's been happening ever since I got my email started up again. Perhaps it was eating them the whole time.

An email will pop up at the top of the queue. Then vanish! I hit no key. I did nothing. Just.. poof! As suddenly as it appeared. No viruses as far as Norton can tell. No restarting the Mac does nothing. I’ll give a hairy eyeball to anyone who makes lame-brained suggestions for solutions. This is a difficult problem to detect, or I would have resolved it by now.

Is it my Mac OS? Is it the Apple mail client? Is it SpamArrest, my email spam-scraper? Is it the MobileMe (aka .Mac) email infrastructure that somehow retroactively killed it?

When you know that Sleeping Beauty is a lovely, lovely friend, and you'd like to get in touch with her after all these years, and when you want to archive her tender, sweet, friendship letters to you, you do what you can to get them back, don't you?

If this kept happening to all sorts of important correspondence, you'd want to solve the problem before you lost more precious, invaluable treasures, yes?

I called Apple.

The IVR failed again. These were the terms it could not understand:

Macintosh OS X ("Ecks")
.mac (“dot mac”)
Mac.com (“Mac dot com”)
Mail

None of them were recognized. The IVR kept trying to suggest I had a problem with an Apple Color Monitor. Uh... no.

Finally I got to speak to a human. Chris, he's a nice guy. He had an easy laugh, and offered no resistance to helping me.

He could see why I'd want to get back in touch with a Sleeping Beauty, and why one would call to get this sort of thing cleared up immediately.

Chris also thought it was funny how this was all happening, and the sort of oddball, humorous, but positive process it was. If we ever turn this into a book, Chris deserves a picture on page 118 or thereabouts as an example of someone who intuitively gets the concept of helping the customer achieve their goals.

To be fair, I am not surprised at the technical problem, nor am I surprised that Apple has good people like Chris to answer the call. I myself worked at Apple 1991-1992 on the System 7 AnswerLine. I am a lifelong Apple fan because of how they treat me as a customer. I owe a great chunk of my professional career, my personal fortune in life, and my happiness to the Apple Macintosh computer.

When I came out here in 1989, I tracked down Guy Kawasaki at ACIUS, where he worked at the time. He introduced me to his beautiful wife, and I shook his hand to thank him for writing The Macintosh Way. I still have that book on my shelf.

Part of what I am driving at in 8 Days Offline is that spirit. The good-natured, positive, progressive human contact component of one’s business. It is the holistic yet quintessential element of the overall product and support process.

Like I said, though, here, the ideal failed. I did not get IDd with the right product, and so I did not get routed to the proper team at Apple. But with Chris, I got to the right guy!

He understood it was not in the Apple IVR, and honestly admitted there had been a few problems with the IVR other customers had commented on.

I offered to work for Apple to help solve the problem. “For today, the first call is free!” I asked him to take down my email and phone in case anyone wanted to get back in touch with me.

Meanwhile, he succeeded in one more way. When I asked for a Ticket number, he took about one minute and then gave me Case ID 105306592.

I also told him an expression I learned from Paula Montgomery, a Customer Service manager at Cisco Systems. She was also, briefly, my roommate in Newark, CA.

“You're killing me smalls!”

It is a quote from the movie, “The Sandlot.” Chris laughed when he heard the expression. He remembered the movie too. I loved it.

Paula used to use it all the time, when we'd have to call Manufacturing to get something straightened out. Or when a process had a small failure we could get cleared up easily if we could get someone to just make the change, but someone was giving us a sort of “I didn’t say Simon Says” no-can-do.

“You’re killing me, Smalls!” was her way to make it a bit of light humor. Suzanne Vega, in more earnestness, has the line, “It’s so small to you, it’s so large to me. If it’s the last thing I do, I’ll make you see.”

How often in life are problems so small for one person, but so significant for another?

This was the issue with me losing an email from Sleeping Beauty. “So what?” others can say. It was not a million dollars. No. No lives were lost in the misplacement of the email. No nations crumbled and no species were directly extincted by the scattering of those electrons.

Yet it is part of a low-grade fever of miscommunications that can frustrate people and prevent communications. After all, I have spent more real time documenting this problem here on 8 Days Offline than it took to read the email before it poofed out of existence.

I am sure I can cobble together how to get in touch with my friend — this time — yet I can clearly recall other emails I lost recently. It keeps happening. Like a demon in my hard drive.

At this point, I want to exorcise my Macintosh, rather than exercise my demons, to make my operating system safe for Sleeping Beauty.