How to bankrupt a successful software company

Interesting:

Quark 5 and OS9 was what we were used to, but it was pretty miserable. The things that stick out:

Restarting your computer and losing your unsaved work over software freezes was a regular part of your day. Like, many times a day.
We had all these crazy workarounds to achieve certain effects like drop shadows or change-and-repeat. It was all pretty rudimentary and hard to standardize across many designers in a department.
Shapes were pretty much a non-issue, so we had to do everything supplementary in Illustrator. Text and image display were awful. We printed to see what we were doing.
We were, of course, still importing images directly into boxes by browsing for files from Quark. [Quark only got drag and drop with version 8. Let me reiterate—8 as in “eight.” That’s not a typo.]
Those things are all quantifiable productivity sinks that should have been addressed in Quark 6, but Quark was so comfortable in its position of power that it missed its chance. It put out a mediocre release that forced everybody to upgrade just so they could have a few overdue meager enhancements like compatibility with OS X (for real, that was the big sell, as if it was a treat) and, I think, drag and drop image placement from a finder window. Maybe a drop shadow? The thing is, there could have been more, but nobody remembers stuff that doesn’t impact their daily workflow. I think everyone who cared felt like they’d been disrespected by that release.

And then InDesign CS2 was released in 2004 or so, and I remember being at an AAN (Association of Alternative Newsmedia) conference in a room full of production managers from all over North America at a session comparing Quark 6 to the new InDesign. InDesign had so many beautiful, necessary features that it really felt like Adobe had locked users (like us, our people) in a room for a year until they came up with all the right ideas: stability, autosaves, shapes and paths, real image and type representation, drag-and-drop, customizable keyboard shortcuts, effects, repeats. All our habits had been supported and standardized and simplified.

We all actually got emotional. The room was nuts. The Quark reps were humiliated. It was so obvious that all this stuff was going to take the friction out of our departments, which sometimes moved up to 200 ads a day. I remember this PM from Brooklyn sitting beside me who grabbed my arm partway through the demo, and we actually held each other while we listened. CRAZY.

The thing is, the effort and risk of changing a whole company to a new piece of software is so great that that release still wouldn’t have swayed us if Quark had actually done its job with Quark 6 and made a competitive update. But it didn’t, and the time, job happiness, and financial implications of switching to CS2 were super crystal clear. Everybody did it.

I did it for the Santa Barbara Independent, and it was a months-long process of testing, file conversion preparation, and training to make sure that our conversion week wouldn’t implode when it happened. But once you’ve switched, you’re done. As Quark should have known in the first place, it’s almost impossible to get people to go back again without a super compelling reason. Maybe they implemented all those awesome things in a later version, but we would never know.