Dumb stuff I did early in my career
I worked for an entrepreneur early in my career who loved side projects. Who knows, over the course of his career may be enough of these paid off. But many I was exposed to were fun but ultimately fruitless diversions.
One such diversion was an idea they had about being able to pick some web content and compress it into an executable package that could be emailed to someone else who then could open it and view that content.
It was early in the growth of the web we began working on this — pre-year 2000. The tech for compressing and decompressing a bundle of files was something we had from our core business. Obviously, one fatal flaw right from the beginning was an idea based on sending executables via email!
This was totally an idea that was influenced a little bit by an imagined need and a lot about what was possible with the technology available. The components for grabbing web content we had the beginnings of from another project.
These ideas were not mine though so whilst these parts were likely a mistake they were not my mistake — I’d challenged them before eventually dutifully set out to build this tool.
The mistake that I owned and learnt the biggest career lesson on was of a similar nature. Given the whole project was an untested idea the important part was to test and see if real people would actually use it.
During the construction though I got hung up on the implementation of a few features. Firstly, I was very influenced by the popular apps such as WinAmp which had very stylised UIs that broke from the Windows UI conventions. I decided this was a must for our app given it needed to be consumer-friendly and widely adopted.
The other was the web-grabbing features. We felt that we needed to be able to pull web content online. The engineers quickly had a single-threaded web capture which would read a page and all of its referenced files. I didn’t think it was fast enough so I wanted a multi-threaded implementation. Fortunately, the engineers talked me out of it eventually but not before venturing substantially down that path.
I also thought there was potentially lots of content such a web capture mechanism would grab so I started designing an interface that would show the progress of what was getting sucked down and open up the opportunity to select what wouldn’t be included in the package. Quite over-the-top for a supposedly consumer-friendly app.
Ironically even after wasting some time on these features the requests from my boss kept coming thick and fast. Requests for templates for things such as birthday cards and other things we could build out of web content. Add UI wizards so these can be populated with custom content. Of course to make that work we had to add a template engine and so on.
It got to a point where this crazy app was desperately needing to be tested with real-world usage. This was a real point of contention with my boss as they had lots more ideas of functionality to add.
We had some decently trafficked sites from some other moderately successful products. We hatched a plan to use that traffic to advertise this tool aggressively. We pitched it to the boss. They said no, we did it anyway. Probably the one thing we did that wasn’t a mistake.
The initial telling-off I got was quickly rescinded once it was revealed there were 2500 downloads in under an hour. A few weeks later it was self-evident from the usage of the app that this was a collection of functionality that didn’t solve any problem that people who installed it had.
We soon wrapped up on that side-project and waited for the next one.
I don’t feel bad about my mistakes — in the whole scheme of things with this folly of a project they are fairly minor. I was young and frankly in the 90’s pretty much all software development was based on these sorts of gut decisions. I am proud that I recognised them and learnt from them.
In the years that followed such experiences led me towards agile software development, lean, lean startup methods and beyond.
What mistakes have you made during your career? Which ones were formative to who you are today? Please share your experiences in the comments. If you liked this post please let me know by hitting the ❤ — it means a lot as a writer to get feedback.
Originally published at https://wioota.substack.com on July 12, 2022.
