Reminds me of my small time spent at a startup that focused on OCR scanning Medicaid documents (not going to name anything).

My friend and I worked for some random local millionaire in our area who wanted to create an automated system for processing Medicaid-related documents. We bootstrapped a bunch of Python/C# code to create an illusion of a website that did something. In reality all it did was take document uploads, run a Tesseract OCR program, and regex through text. That worked for about one document out of a hundred on average.

Initially we started as contract workers, but then the millionaire decided to create a "real" company/startup with an office. I started commuting to work, and the millionaire brought in his newly-grad MBA son not much older than us to lead the company. The son also brought his best friend on-board who was another Stanford grad. So we did a bunch of back-breaking coding while these guys ran a skeleton business hiring new people and letting us slowly hire our college friends to do "work". Our friends were barely fresh out of college comp sci students and didn't know much about developing in a professional setting at all, so we hardly meshed and collaborated on anything.

We didn't use teamwork tools like Git properly, didn't set up issue tracking, and we hardly ever communicated in a group. My friend who I worked with was focused more on infrastructure, and I was stuck trying to figure out how to read PDFs and documents in a secure fashion that wouldn't leak data for fear of HIPAA violations (we even had a HIPAA training class at some point in office, which I don't think most of us took seriously).

Our software wasn't improving and we had a ton of issues hitting benchmarks and passing on test documents we had. After our HIPAA training, my friend and I had a dilemma where we wanted our systems to be secure. He said we shouldn't want to write things at all to disk, because if servers were compromised, all of those Medicaid docs would be exposed. He was kind of right, but we had users log into accounts to view what they submitted, so this was highly baffling. Instead he wanted to store things to memory temporarily, but I really didn't know how to do this part at all. Our OCR and document uploads went to disk, so parts of our systems had to be modified. He tasked me with securing this all by myself while he set up deployment and general infrastructure.

I didn't know anything about solving these issues. I was hardly a security expert. I wrote Django and some Linux shell scripts, but my experience in security was none. At the time I didn't know how to create memory-file mappings in Linux, so I was stuck trying to modify an OCR program to read and write from and to memory. Tesseract OCR was written in C++ and I am by no means an expert in C++ at all. None of our classes had taught that, so really I only had my Java experience to fall back on.

Eventually I started feeling pressure at work and not being up to the job. In meetings I had to say that I wasn't going to meet a deadline for a task and that I would need assistance. I would get told to "Google it" and figure it out and have it done by next time. I would actively look for tasks from my coworkers to avoid doing my own work and tried to look busy and active and helpful. Impostor syndrome started creeping up, and I started having breakdowns after work. I knew I had to do something.

I left on my own volition and I haven't spoken to my friend ever since. I felt better because I wasn't confident in my skill-set. I started going to therapy, and was happy writing my own little software hobby projects while pursuing much less intense jobs.

This was almost 8 years ago and I haven't written software professionally ever since. I figured the company would flop because it had bare-bones leadership and the millionaire investor was sketchy as hell and had too many demands. The company is still going strong it seems and re-branded themselves to a new name. I think they still do document processing. They have a fancy office now in New York City. My friend who I no longer speak to anymore left that place a while ago and works in DevOps at a new company. He was a really good friend for trying to get me into the tech world like this.

I learned a lot since then about comp-sci and software development, but I still feel impostor syndrome when I try to apply to jobs now.