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Ben Halpern
Ben Halpern

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What is a wrong turn you took your career?

What is a direction you took in your career that turned out to be the wrong direction, and you had to pivot or reverse course?

Perhaps you took the wrong promotion, or pursued the wrong focus? What is yours?

Top comments (54)

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kspeakman profile image
Kasey Speakman • Edited

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.

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mistval profile image
Randall

I had not heard of Gall's law, but it strikes me as very true. Thanks for that tidbit!

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luiz0x29a profile image
Real AI

That's basically a rite of passage for a programmer. Everyone tastes it in their career at least once.

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besworks profile image
Besworks

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.

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mistval profile image
Randall

(Have never used Upwork so am curious) Why did one bad review cause so much damage? Wouldn't a lot of good reviews outweigh the one bad one?

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besworks profile image
Besworks

Well they don't fully disclose their algorithm but essentially extra weight is given to larger and more recent contracts. Since I generally do smaller fixed price jobs, this longer term one trumps everything else.

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mistval profile image
Randall

I see, that sucks, hope you can turn it around again!

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eugenee profile image
Eugene

FYI: "As a Top Rated or Top Rated Plus freelancer, your hard work has earned you the benefit of more control over your profile. This means that you can occasionally request the removal of client feedback." This passage if from Upwork support page titled 'Feedback Removal'

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frulow profile image
Frulow

Don't worry, everything will be fine soon. Keep it up

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besworks profile image
Besworks • Edited

Thanks for the encouragement. I know I'll bounce back eventually. Perseverance is definitely one of my more well-exercised traits.

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katafrakt profile image
Paweł Świątkowski • Edited

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, now 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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janmpeterka profile image
Jan Peterka

Wait, I thought both DataMapper and ActiveRecord approaches for ORMs are alive. I'm I wrong?

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katafrakt profile image
Paweł Świątkowski

Yeah, approaches are alive. I was talking about specific Ruby libraries that were creatively named like that ;) And DataMapper is dead for years. Sorry, I should have been more specific.

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janmpeterka profile image
Jan Peterka

Thanks for clarification :)

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suchintan profile image
SUCHINTAN DAS

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 .

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genevievemasioni profile image
Geneviève Masioni

What made you ignore those opportunities though? There must have been red flags. How can we know if the offer is also good enough? It’s important to not be arrogant but also to make sure we are valued correctly. Where’s the balance?

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suchintan profile image
SUCHINTAN DAS

Geneviève, I am currently a student and that time when those opportunities came in the university, I had my curriculum ongoing and thus my thinking at that moment was to focus on my studies and wait for the right time with the right skills to apply for the opportunities ( just thinking I am not skilled enough to apply for the role ).

But YES that only landed me in a bad situation because during that time very few fellows used to apply for those opportunities so competition was marginally less, and just like me other's were also preparing themselves with better skills and knowledge.

That's why when I started applying for the opportunities , the competition got high and tough . I regret my decision and learned this lesson as life is irreversible so those opportunities with such less competition would hardly come back.

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genevievemasioni profile image
Geneviève Masioni

I understand. I would argue that you’re better equipped now; both in terms of skill set and life experience. So you should be able to compete with others on the tech market. We tend to forget that even if there are a lot of candidates for a job offer, most of them are not qualified. So the people we genuinely compete with for a role are a few dozens or even less. And to win against those people, prioritizing your skill set is not a bad strategy. It pays off very well in the long term. It leads to higher quality roles. If you only recently started your career, you will have a lot more opportunities coming your way! Good luck. 😁

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genevievemasioni profile image
Geneviève Masioni

Also, interviewing is a skill in itself. Unfortunately there’s no better way to get good at it than to practice on the field.

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suchintan profile image
SUCHINTAN DAS • Edited

Thanks, Geneviève, yes you are right of course I am now a better version of myself and have acquired much more skills and knowledge. But I would like to point out that ignoring those opportunities was really not a good take in my life. And got to learn that you should always keep yourself open to opportunities and don't wait for the right moment. There will always be this thing in every exam of life that we feel, we could have done better no matter how much effort we put into it.

At least from college, I understood one major lesson The earlier you are the better you will achieve. Just a small example, Google Meet today date is mostly used for all meeting calls, but it would not have been into this market if they wouldn't release it during the pandemic. Just like Zoom and other services did, so time matters a lot, even in business if you release the right product at the right time it would succeed.

The same product was not successful pre-pandemic and will not be able to capture much in this post-pandemic.

So, yes with the same quality many things only work when the right time comes and if you miss that opportunity then no matter how better the quality is, it doesn't matter. You will not get the same opportunity again.

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eljayadobe profile image
Eljay-Adobe

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.

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rdrahuldhiman profile image
Rahul Dhiman

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.

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dinerdas profile image
Diner Das

Tried management — really wasn't for me.

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eljayadobe profile image
Eljay-Adobe

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.

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genevievemasioni profile image
Geneviève Masioni • Edited

Please don’t be too hard on yourself. Teaching is a job in itself. One-on-one tutoring and classroom teaching are almost polar opposites. It baffles me how companies think they can use one employee to teach others without providing any (teaching) materials or support (prior training in teaching for example) and think that everything will go smoothly.

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a_mujthaba profile image
Ali Mujthaba

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.

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genevievemasioni profile image
Geneviève Masioni

Wow it’s the first time I hear people think IT is a bad career choice. Where I’m from, people think you’ll never run out of a job and will crawl under job opportunities. (Which not entirely false.)

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yuridevat profile image
Julia 👩🏻‍💻 GDE

I really like this question because I think I would answer it differently depending on the situation.

If I were unhappy with my current situation, I might say, "If I had done this or that differently, then maybe..." .

Since I am very happy with how my life has turned out in the last 2 years, I can say that everything had to happen exactly the way it did to get to where I am now.

At the end of the day, we never know if things would be better or worse, just different (but maybe just as shitty), that's for sure.

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theaccordance profile image
Joe Mainwaring

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.

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mellen profile image
Matt Ellen

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.

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baenencalin profile image
Calin Baenen

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.

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steinbring profile image
Joe Steinbring

The biggest regret of my career is taking a job out of desperation.

I was working for a small agency (~75% of its income came from two clients) and the boss pulled me into his office on a Friday and said that he had to let me go because we weren't getting enough business in. I freaked out a little and ended up getting a job at a shop that paid less pretty much just because their stack matched what I was familiar with. Since then, I both started putting money into an emergency fund (three months of expenses) and started diversifying my skills. Not everyone is lucky enough to be able to do the first thing but the second is pretty universally doable.

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moose_said profile image
Mostafa Said

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.