The Pickle: A Conversation About Making Digital Books
4: The Struggle (Sorry)
Eep! “Why in the world would anyone do this?” I’ve been asking myself forms of that question for the last two years. I’m sure Eli’s been asking himself the same thing. We’ve definitely asked each other. But, isn’t it weird that the heady days of startups and The Valley and Unicorn Companies mean we’re all in disbelief at the prospect of creating software that doesn’t mold itself to optimal financial success? That’s not to say we wouldn’t take our $20 million, or that we’re not very actively thinking about how to sell and market this thing now, but maybe it just feels nice to whittle away at a project with a buddy and make something weird?
If we have to get deeper — and I guess we do — maybe we should actually circle back to Craig’s cry that building apps is still too difficult. It is. Building any type of software is stupendously difficult. Not because it requires comprehension of code and commands and syntax, but because of the breadth of required skills, the team management, the interdisciplinary communication, the specifications, the refactoring of those specifications, the testing, the endless bug fixing. It’s a struggle. I’ve been building software my whole life — as a lone(ly) programmer, as a professional software developer, as the boss of a small agency, as a product manager at a corporation. All of it’s a struggle due to software’s inherent flakiness — no matter how much process and formality you sling at it — but despite how personal it feels at times, it’s ultimately all planned, phased engineering.
What makes projects like The Silent History and The Pickle Index different for me is that I throw out all (most) of my favorite software-engineering principles — the ones I use every day to build “real” software — and instead I free-code, I free-design, I free-requirements-plan. Then Eli edits me, we figure out story logic, Eli writes, we stress, we doubt, and we carry on. This next bit is going to sound pretentious and ungainly and I hate myself already, but the struggle I feel like I overcome in these projects is the same personal struggle as making art, not engineering software. That hopefully doesn’t mean my code is sloppy or suboptimal, but — am I explaining this at all well? — it’s a very different mental process for me and therefore a different reward.
In maybe-less-obnoxious terms: there’s no way we could have created Pickle by agile-methoding a team for six months. It ended up nothing like we discussed at the start, nothing like what we had at the one-year stage. And that wasn’t because we were pivoting to market feedback or business scope. We were in our own heads, trying to sculpt something until we felt it was good and in service to the objectives of the project, which — for me at least — was to make a book (that’s my view on the other debate) that told Eli’s story in an entirely new way, and challenged people’s perceptions of what fiction/novels/literature could be. Everything I’ve just said is a terrible way to make commercially viable software — because the outlay is always so huge and the risk so great — but I think that’s the only way Pickle, as it exists today, could have gotten made.
Eli and I keep referring to the app as “bonkers,” because I don’t think either of us really know what we just brought into this world. It’s very nice of you both to pin praise to it, but mostly I feel like I poured myself over the page/canvas/un-sculpted rock and now it’s in public and people are (rightly) kinda baffled that we spent so long making this oddly shaped thing that isn’t an actual recipe-sharing network we can sell to Pinterest.
Note to readers: This is (going to be) a long, loopy conversation. The Pickle Index is crisp and compact. Consider sampling its tangy delights.
The Indexed Pickle
- Opening Salvo [Robin Sloan]
- Blank Slates![Craig Mod]
- Opportunity Cost [Robin Sloan]
- ➡︎ The Struggle (Sorry) [Russell Quinn]
- Self Selection & The Jaws of Venture Valley [Craig Mod]
- The Many Futures of Storytelling [Eli Horowitz]
- Recruitment [Robin Sloan]
- Blarp [Eli Horowitz]
- That Oracular Feeling [Robin Sloan]
- Benevolent Leaders of the Frothy Kingdom [Craig Mod]
- The Left-on-the-Floor Weirdness [Russell Quinn]
- Territory of the Book [Eli Horowitz]
- At This Moment [Robin Sloan]
- Make a Book, Even Just One [Craig Mod]
