inessential by Brent Simmons

That Enterprise App

Last night at Xcoders people asked me about the enterprise app I mentioned yesterday.

Here’s the story, condensed as much as possible:

In 2005 NetNewsWire was acquired by NewsGator, an RSS reader company with a deployed sync platform. I went along with NetNewsWire to that company. I continued to work on NetNewsWire for years.

Though that company started out as an RSS reader company, it later turned off its RSS reader software as it evolved into an enterprise software company that makes a business-oriented Twitter/Facebook-like-thing (plus extras) that runs behind the firewall. (Called Social Sites.)

I think that’s a pretty a good business. I have zero interest in it personally, but it makes sense, and I believe the company made smart choices, even though that meant it was a very different company from the one I joined.

Though the company had become focussed (quite rightly) on their main enterprise product, I remained working on consumer apps: NetNewsWire, then TapLynx and then Glassboard.

We sold TapLynx and NetNewsWire to other companies. That left me working on Glassboard, in a small spin-off company of six people called Sepia Labs. Sepia Labs was owned by NewsGator, and it had zero employees, but it actually existed as a company.

In all those years I had not been asked to work on the enterprise software. I didn’t want to.

But that changed in late 2012 — mainly because leadership really liked the work we’d done on Glassboard, and they wanted the same team to redo the iOS and Android clients for their enterprise app.

I could have said no, but I would have had to resign right then, and I was unprepared. So I said yes, knowing that I’d have some months to work things out, to either make peace with this somehow or move on.

But that meant actually working on software I didn’t care about or even like. (Not because it’s inherently bad, I should point out — it’s just not the kind of thing I like.)

We worked on it much the same way we had worked on Glassboard: Nick Bradbury did wireframes and I did the Photoshop mockups and assets.

The difference was that I didn’t write any code, where I had written 75% (or so) of Glassboard for iOS. Nick Harris wrote the iOS app and Nick Bradbury wrote the Android version. I was a designer only. (Which is like saying I tried enterprise software but didn’t inhale, I realize.)

NewsGator had treated me extremely well for many years. But a series of rational decisions on everyone’s part (mine and the company’s) meant that I was suddenly working on enterprise software, and I came to realize that I needed a change. There was no making peace with staying.

It was time to come home to indie life, where I’m happiest, where I do my best work.

* * *

I’m never going to be a manager. The fun of this industry, for me, is in making things directly, in getting my hands covered with clay.

And I’m not, at age 45, the best I’m ever going to be. That’s still in the future. But I’m getting closer. My peak isn’t 20 or 30 years from now: ten years is more likely.

As a teenager I read “Seymour: An Introduction” by J.D. Salinger. In that story Buddy, the narrator and a writer, had given his older brother Seymour a new story to read. Seymour liked it well enough as craft, but it fell short of being Buddy-worthy.

Seymour wrote to Buddy, “Keep me up till five only because all your stars are out, and for no other reason.”

I’ve kept that in my head every since. The work that happens when all my stars are out is the work worth doing.

* * *

More from Seymour, just because I like it:

Were most of your stars out? Were you busy writing your heart out? If only you knew how easy it would be for you to say yes to both questions. If only you’d remember before ever you sit down to write that you’ve been a reader long before you were ever a writer. You simply fix that fact in your mind, then sit very still and ask yourself, as a reader, what piece of writing in all the world Buddy Glass would most want to read if he had his heart’s choice. The next step is terrible, but so simple I can hardly believe it as I write it. You just sit down shamelessly and write the thing yourself.