Taking a position to do a big-bang rewrite of a large system. Project was shelved after 2 years. I should have taken Gall's law to heart.

A complex system that works is invariably found to have evolved from a simple system that worked…A complex system designed from scratch never works and cannot be patched up to make it work. You have to start over with a working simple system.

• John Gall

Agreeing/attempting a big-bang rewrite was definitely a mistake. But things turned out alright in the end. After the project was shelved, I used what I learned to make system improvements. Then led a team to make new cloud products. And we're still working on the legacy system. Carving off pieces to modernize one-at-a-time.

Taking the position was also a mistake if I had known the whole picture. But there was a change in leadership. And that changed the whole working environment and available opportunities.

So I guess you never know.

I used to be a Top Rated freelancer on Upwork taking my pick of fixed-price jobs. Last year I was lured into an hourly contract by an enticing offer. I ignored the (obvious in hindsight) red flags and ended up regretting it.

The client treated me like his employee, monopolized my time, ignored my advice, and altered the scope of our arrangement one too many times. I refused to bend over backwards any father and ended the contract. He left me a scathing review and my Job Success Score dropped significantly. Meanwhile, he's now in the process of hiring a 4th person to take on the tasks I was handling alone and has made essentially no progress in 2x the time.

Before that debacle I was at the top of my field, now over half of my proposals go unread and the rest get ignored. I should have forged ahead on my original path... I spent years building a stellar reputation and all of that was obliterated by one unreasonable client. I should not have let the temptation of steady income override my intuition. Taking on the role of Tech Lead for a startup has always ended up being a bad experience for me. If you're not a founding member of the company, you'll just be a tool for them to exploit as they see it.

Perhaps not exactly what you mean, but I have history of pretty poor choices regarding what technology to focus on between two that seemed to have similar chances to become popular. For example:

• Textile vs Markdown - I bet on Textile, not no one remembers about it
• D vs Rust - D seemed to be much more natural choice and Rust too complicated to become mainstream. Well...
• Rails vs Merb - Merb was just better. Was.
• DataMapper vs ActiveRecord - I think you can guess at this point
• Pylons vs Django
• Mootols vs JQuery
• Ractive vs React

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Stopped learning after I got the my first Job as a Front End Developer. Should've not stopped the learning and updating myself. Now I'm starting again after a year and a month to learn/ trying to build something for fun.

Tried management — really wasn't for me.

Ignored some opportunities thinking there will be better coming in future and I can skip them. Believe me life is something that always proves that it's uncertain no matter how good you are or how talented you are individually.

Never ignore an upcoming opportunities as when life gives you lemon make lemonade .

Not sure I would call this a wrong turn, rather I just hit a dead end.

I started my technology career at the ripe age of 15 with an apprentiship at my local school district. I would continue down that path through college and into my first FTE role at a non-profit org in Chicago. It was there I realized my growth prospects were limited, I could not make significant changes to my responsibilities that would translate into meaningful comp adjustments. When I worked my ass off, I only received a cost of living adjustment (COLA) and when slacked off, I received the same adjustment. This led to apathy and with it, a decline in performance.

Knowing I was thirsty for a greater lifestyle, I began the painstaking process of transitioning career paths, this time into engineering. This was before things like Bootcamps were common and popular, so I spent about 18 months self-teaching myself to the point where I could get hired for contract work. A few successful contracts later and I was once again getting hired for FTE roles, but this time with real growth prospects. I've since tripled my earning potential and I'm no where near the upper limits of what I can do with my current skillset.

I once dropped out of my IT degree thinking I would not get a job. There always a lot of chatter around me that IT was a bad career. It was one of the worst decision of my career. So after a two years I started the degree again and completed it. I have been a software developer for 5 years and counting. So don't give up on something you're passionate about.

Another wrong turn, much earlier in my career. I worked as an employee doing software development consulting work for a consulting company. The company wanted to train in other consultants to do OS/2 software development, since at the time there was a big demand for OS/2 developers.

Since I had just done a big single-developer job with ISDN integration on OS/2 platform in C++, they asked me to train in other co-worker consultants at the company.

I naïvely thought, "Sure, sounds like fun!" Hoo-boy, I didn't realize that I had jumped into the deep end of a cold pool. I had a week to prepare.

What I came to appreciate is:

• teaching is a skill, and I have zero experience in that skill
• preparing a curriculum is a huge undertaking
• teaching a subject needs to be laid out and presented such that it is a logical progression, so the students can consume and digest the information
• people can be categorized by the way that they learn; not everyone learns in the same one way (I learn by following along with tutorial books, and futzing around, and branching out to do other things extrapolating from what I had learned)
• trying to teach "How to program in OS/2" using C++, to a class of smart consultants who do not know C++ and have no programming experience on personal computers is not a recipe for success

Fortunately, that wrong turn gave me a bitter taste of my own limitations. I'm good at one-on-one mentoring, I'm not good at classroom teaching.

Alas, I regret having floundered in front of my co-workers, and burning a week of their time and two weeks of my time. The embarrassment still stings.

Probably trying to work on too many things at once.
I wanted to dish out a game and a few libraries, but it really got to be a lot.

Now I'm jammed and still working on my fabled game.

I was planning to get into tech right after I finish my mandatory army time. After finishing it, I thought of working as a call center agent to get passive income while learning. I got promoted to become aeam leader super fast and got completely distracted by my goal chasing other goals in management while coding was my main passion.

When I was in university, I hope to becomes a machine learning engineer after graduated. But it seems to difficult to get job from companies and I decided to do freelancing first. In these 3 years, I have been worked on several hand-on AI projects and successfully completed freelancing tasks. But I spent most time on non-AI projects (because there is only few AI freelancing tasks). Being I can't get general intuition and fundamental approach of implement AI technical from just freelancing tasks, until now I don't have confident to perform companies job. So I am going to apply to companies job since now.

I recommend to apply companies jobs rather than freelancing.
Thanks

I tried to spearhead a web design agency inside of an established consulting company that did not operate in that space…twice in the span of 6 years! Yeah, I know, what the heck was I thinking. Ended up going nowhere both times. But at least now I know how to run my own studio and it's gone so much better!

Not using þorn and eð sooner.

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A couple of times I've tried being freelance, but I just can't sell myself.

The first time, I wanted to pivot away from financial services and into a field I hate less, but I didn't know anyone outside financial services, so I had to find a regular job.

The second time I just couldn't take the struggle of finding clients while at the same time doing work.

At the precusor to my career, when I was in uni, I thought I wanted to do AI, I studied psychology and then interactive intelligent systems, but I couldn't get my head around the maths involved, so I changed course to being a regular developer.

After a re-org I was reporting to a boss that I did not get along with, and vice versa. I stuck it out for 6 months before I started looking, took 3 months to find another position within the company (internal lateral moves take far longer than being hired off the street), and 3 more months of transition time. In hindsight, I should have started looking right away.

Lesson learned.

A decade later I was in a similar situation, and put in my resignation right away. Did not have a new job in hand, just was not going be in that untenable unbearable soul-crushing position again. Not worth the emotional trauma and mental well-being. Felt like the best course of action, and everything turned out alright.

I think fear of the unknown and one's own comfort level (and optimistic hope that things in that bad situation will get better... but they won't and don't) may keep a person chained to a bad situation for much longer than warranted.

Addiction of bad habits 😔 which is a big reason of my all failures 🤞and I am still fighting with them.