I started with a small (10-12 people) company whose main business was wage management. One day the boss said, "The web is the future!" and that's more or less how I was hired.
Main issues? They were all working with AS/400's (backing up their data for 8 hours every night, on tapes) with a terribly outdated development workflow:
As soon as I learnt how modern development was like, I introduced SVN to the company and I ended up being... its only user.
I was a junior and I grew in a culture with no automated tests, so I wasn't writing them either, although I loved the concept... but then again: "We don't have time for those, the client will tell us if there are any issues!"
And it didn't stop there. Even though I was the only front-end developer in a company of just 14 people, I wasn't allowed to talk with the clients. Everything went through a non-technical account that reported to me, from client requirements to answers to my questions.
Not to mention some requirements were just out of my reach. Example: "... and if you catch an error on the page, take a screenshot and send it to the server".
"Huh, I can't do that, boss. The browser doesn't allow me."
"I want solutions, not complaints, Max!"
Conference participations were a no-go. Surfing the web outside coffee breaks was frowned upon.
My observations like "We need an exit strategy from iSeries" or "We can't let the users wait 1.5 seconds to retrieve a list of items", were mostly ignored.
After 5 years, when I was finally considered "almost a senior" but still the low man on the totem pole, the company went into troubles. Commissions plummeted, the environment grew darker and darker. Boss said we needed to save every dime, but I understood lately that he actually wanted to lay off employees. And that included me, because I wasn't part of the company's core business (also because the boss changed his mind and believed mobile apps were the future).
Relationships became harder for me. I was once reprimanded because I used to leave my PC on stand-by during the night, instead of turning it off (to save on electricity!). After I was accused of wasting time while developing an interface (I actually was working hard as always), and a newly hired junior colleague helped stabbing me in the back, I was fired.
That actually came for the better. I already decided to leave the company, but that saved me a couple of months and earned me an exit bonus. I started the first of my OS projects on GitHub that reached 100+ stars (it's currently at 331), then I landed on much greener pastures.
But thinking about back then, all of my insecurities, and being laid off, almost led me to depression. I knew I was capable, but maybe not a good employee. And I had to earn a salary, somehow.
After two more difficult years, my former company went bankrupt and was acquired. Half of the (already very small) workforce was laid off in the process.
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