This isn't at all a rebuttal of the post, more a different perspective. I started a new job while basically deeply depressed. It colored all my opinions of the company and my coworkers. As I'm coming out of that through a combination of medication and intensive CBT I'm realizing that a lot of the negativity I felt towards my job was the result of the depression. As things improve I'm realizing that the job is mostly neutral but my impression of it was colored by my mental health struggles. This isn't at all to say not to take the authors advice, just take care of yourself and be aware of the possibility that you may be distorting reality if there's any chance you're depressed
I find that I pick companies to work with when my goals and their goals align.
I visualize this alignment like two boats travelling on the ocean together, with a rope that runs between them, connecting them.
When the alignment is strong, the tension on the rope is low, and it's a great place to work at.
But over time, the direction of either party can change, and it results in a better alignment, or a drift from each other that starts to put the rope under increasing tension.
It's possible that the tension on the rope is good, and your trajectory will adjust. But due to the size of the company it's unlikely your small boat can adjust the heading of the company, but you might succeed, if you try.
The key is to know when the rope is about to break, and then disconnect from that company and start the process again with another company, aligned in your direction.
A couple of rules I have that have worked for me so far is:
Colleagues, tasks, compensation - if at least two of the three are good, it's fine to stay. If not it's time to look for something new.
The first year is a learning year, the second is a productive year, and the third is a "what else can I get out of this place" year. If nothing changes in the third year, then there's not much more to learn from the company and it's maybe time to move on.
> That job turned out to be shoddy, ancient, flaky tech all the way down, with comfortable, long-tenured staff who didn’t know (and did NOT want to hear) how out of date their tech had become.
Every time.
I don't care about your stack; obviously I have taste and preferences but I'm a professional, I'll work with whatever, as long as it isn't Rails. (Because there is no good work in that world.) But it will not take me a full day with access to your repos before I know whether there's anything you can do for me past signing the checks.
> It’s only been six months, but it’s starting to feel like it might not work out. How much longer should I give it?”
It takes a lot longer to tell if the job is right than if it's wrong. Six months is orders of magnitude longer than you need to give a bad job. Don't rage quit, but if it feels wrong it probably is, so start looking.
Had one job with a guy I had worked with for years elsewhere, and within my first couple weeks we sat down for a coffee and I said "so this isn't it a 5 year gig is it?" and he shook his head in agreement. Unfortunately COVID & life caused us to both overstay a bit.
You early don't owe anyone anything to stick with a bad gig.
I think most jobs you can tell from a combination of the recruiting process and then onboarding and your first week. I have felt the "I hope this isn't how it is every day" that the author mentions at a few of my jobs and they've all been stinkers.
Recruiting gives me an idea of how much the company generally cares about their processes. I like when am I given a timeline of the process and steps and now when I get a random call from the recruiter in the middle of a meeting at my current job because the new co didn't ask when I'm free.
Onboarding tells me how much the team is haphazardly shipping vs actually owning their product. The teams that have sucked are the ones where the onboarding doc is heavily out of date (like all covering a now-unused access request system) or I can't even get help from the team within my first week to have someone send me access requests to copy for the things that are missing. The good teams are where my manager already provisioned my access before I joined and immediately addresses any misses when I flag them. Or if they have good enough docs for me to quickly handle it myself.
Career development is another one that takes a little longer to suss out, but if I can have a good first-week chat with my manager where they will explain what my baseline performance expectations are and what I need to do to overachieve and get on promotion/raise track, that's a good flag. The teams I haven't been able to get that early from are the ones where manager usually doesn't care not only about your career but also about app maintainability or anything past their next meeting with their own manager.
My first job was the only job I just went home from and just cried because of how useless thah job felt. We were building a SaaS that took weeks for a simple update with 8 devs (of which 2 were actually good).
This was purely because of the legacy stack and poor management. The boss wanted to scale but did not care about tech, so we just never made real improvements. Sure, a feature got implement at least a week. We saw revenue grow a ton. We never saw time to improve our stack.
Safe to say I felt like I was adding nothing to that company. They just didn't want to grow despite saying the opposite. I get that the shiniest framework will not improve the project, but there were some serious bottlenecks that just got shoved under the rug
I do not agree with the "you know within a week"-take. I'm now 14 years working in IT-Security. 9 of those years for the same company.
I got my next job through a headhunter. The first weeks I had a really good feeling of the company I liked it there after a few months it got worse and worse like they couldn't hide all the bad things anymore. I quit, next job was more or less the same. I quit. My current job? The first month I thought to my self "oh my god, where do I got here?", but now a six months in I really like it.
Maybe also other factors have some plays here like my move from consulting into an internal role, colleagues, the overall freedom, but imho it's hard to generalize something like that.
My last job had some giant red flags right up front. “Who would I report to?” “We don’t know.” “Who would I work with?” “We’re not sure yet.” And then there was a high profile legal issue after I accepted but before I started, and it rendered the position I was hired for irrelevant.
I worked there for four years anyway. Every one of those red flags was a sign of a real problem. Three of those years were very good, but eventually the chickens came home to roost.
Huge yes to this one -- especially on the part about how important this is for managers to get right. I spent two years white-knuckling the wrong job for the wrong reasons. Pretty much every day I am reminded in some way of how thankful I am for having left and found a job with a culture I'm a better fit for.
I think the depth of relationship with a job is more complex than comments and the article talk about.
What is you reaction to the kind-of-shitty company that gives you an opportunity for great personal growth and creativity?
Great colleagues but a real monoculture?
///
I liked most of TFA but the end where the author claims that management is more committed than IC's seems really strange to me. Is that something people look for? It seems like it would come across as totally fake cheerleading. Anyway, outside my experience.
Of course some places I've known sooner, but those are the exception.
If it wasn't for the quality of life my current jobs is providing, I'd probably find something else. I just can't find anything right now that is intriguing enough and pays enough for me to make the jump without losing benefits.
Shortest I've been at a job was 3 months. I knew around the end of the first month that I needed to get out for two simple reasons - I didn't match with the company culture and the company was a sinking ship. I ended up completely leaving my time at that company off my resume because I realized it's not worth going into details.
Ironically, the skills (devops / cloudsec) I picked up in those three months have helped me double my salary.
Takes me X months to discover where X is when I realise I don't like it. X is usually between 6 and 48. When X is nearer 6 it was a bad move. When X is closer to 48 it is because sands shifted. I never had a visceral reaction that I have been in a perfect job. But I know good from shit. Usually shit coincides with company is struggling to find PMF to fund growth through revenue. Also can mean company is sold to another company.
It takes me about a month to know for sure. If the job isn't right for me, it takes me a few more months before I consciously decide that there is no way to make the job right for me.
I like companies that do tryouts. In the last 15 years I worked for 3 employers. Two of them did tryouts - a day or two literally working in their environment. One did not.
The two that did it both were great, the one that did not turned out to not be for me.
I'm with the last employer for the last 9 years, and not looking to quit :))
A long time ago, I had a chat with a nurse executive who rose up the ranks. Her advice was to stick to a position until the butterflies settle (or approximately q 5 years).
Nursing is known for lifers on single units, and personal growth doesn’t happen unless you are cognizant and strive for it.
I agree with the article, except for the last section, because many times the reason for me to quit was a manager who did not give himself, but was playing the game of pleasing upper management and not giving a shit about the hard working team. Also thr suggestion that you as a software engineer does not bring yourself to the table, is wrong, otherwise there would not be any developers suffering from burn-outs.
Good article. Very grounded. Sometimes a job sucks, but not enough to justify immediately job hopping and you just check out and take the payslip each month. Agreed it takes about a week for my gut intuition to work itself out, then if it's bad you just need to decide whether it's something you can stick out for awhile or if you need to leave ASAP.
If the real job doesn't match the interview, then it's the wrong job.
Simple as that.
I once took a position at a company that I had known because they were a customer of my then current employer. We'd always gotten along, they were nice folks, had a good interview.
In a very short time, I wondered what the heck was going on. There was so much drama, infighting, and backbiting, and it was the complete opposite of the company's external persona. People were constantly being moved to different desks with no rhyme or reason- as in, a whole department rearranged 4x in the 8 months I was there. I had 3 or 4 different desks in that time.
People were regularly worried about their jobs and whether the company would even be around after family fights. And when they no longer needed me they started playing games with me, writing me up for things I hadn't done etc. Anything to avoid having to pay unemployment.
I knew in the first couple of weeks. But a bit of me died at that job. Eventually they fired me. In retrospect, I wish I hadn't given them the opportunity and fired them instead. But I had mouths to feed besides my own.
Well, i guess it also depends on how much your coworkers are helpful to you as well. Because there are times some people are kinda introvert and they require a bit of more time to settle down. In certain situations you end up looking for work from home jobs as well. But that's just my perspective.
This is the same advice I now dispense to anyone I'm mentoring in software. I didn't for a long time because I had to learn this lesson the hard way a few times.
For my past several jobs, I've put together a job satisfaction matrix that I fill out once a month. If it scores below a threshold three months in a row, that triggers a job search.
It helps me because I have a habit of fixating on the team’s mission and ignoring my own happiness, so the monthly check-in keeps me from staying somewhere longer than I should.
I quit a job via a consultancy to a bank at about lunchtime on my first day.
I'm just not at the stage in my life where I'm willing to onboard to a transformation that starts with a half a day call authenticating so you can login to a remote VM to do your development.
Similarly I had a 2 week gig where they send me some shitheap of a windows laptop that takes 20 minutes to login, where they wanted future engagements.
Nope. Nada. No way.
You can see the value of your productivity straight out the gate. It's not valued and you will never be able to change it from your vantage point of IC or middle manager.
It doesn't really matter that they say otherwise, the evidence tells the story.
Got hired for a contract to "integrate this crypto[0] protocol sdk" but it turned out that they actually meant "implement this crypto protocol from scratch in an async manner" and by day four I was out[1].
Shortest perm job was about 5 months. Tiny office, 4 other people on the phone all day, impossible project (writing software for unreliable hardware), not a difficult choice.
[0] actual crypto, not currency.
[1] not just because of the bait-and-switch but because crypto is miles out of my wheelhouse.
The first few weeks at a new job always feel fresh and exciting. It usually takes a few months before I start to really get a sense of whether the job is a good fit.
Over time, I begin to see how I feel about the work itself, how I get along with coworkers, and how the daily pace and expectations fit me.
Curious if others have their own rule of thumb for figuring this out.
Way back in the 80s, I had started a new job, and they held a meeting to discuss the results of a recent employee opinion survey. The results were overwhelmingly negative. It made me realize I had made a serious mistake. I quit before a year had passed.
For me it generally takes six months, because as a reflection on my own headspace, it takes that long for me to trust that my intuition isn't just imposter syndrome/anxiety.
i worry that i've job hopped a bit too much and have a series of 2-3yr gigs on my resume.
part of my problem is that I get unhappy (or bored) with a job but sit in denial for too long. so by the time I start looking for a new position, I'll desperately jump headfirst into a new gig instead of lining up the perfect gig.
Or maybe not. maybe it's impossible to tell if a place is a good fit from the interview.
maybe we need better tools for assessing the dynamics of orgs from the outside. it's not just personalities, it's incentives.
I have opinions about it based on funding stages, but what it really comes down to is that culture is a function of growth. as an employee with a career success comes from hunting growth. the only real growth is from market fit, and even if you have market fit, if you aren't growing non-linearly you're going to get into a negative sum attrition game in the org culture (e.g. linear long term private equity returns).
questions to find answers for on the way in are:
- does anyone actually use their product and like it?
- how is that number growing? (non-linear, linear,
attritive)
- what was their last funding round or change in equity ownership? (e.g. who runs it and what do you have to do to satisfy their investment)
- what's their staff turnover and where do they go?
Sometimes it is experience that comes with finding out a job is right for you. The job itself can be great, the projects fun, but if the companies structure is anti-growth and headed for some idiotic goals (like "we want to start making the software that our most expensive supplier makes" aka want to go up in the food-chain in a already well-established market) instead of working with the chances they got- you will go nowhere. And you will know it.
If all the ambitious people leave- or go into inner exile, while the work stays the same but the company goes nowhere, the job has quit on you and its time to walk.
Will it help me get my n+1 job? Will the technology I’m using look good on my resume? Will I just be a code monkey who pulls well defined stories off the board?
Does it pay me market rates?
Is the bullshit/pay ratio worth it?
Post 2020 the rules have changed for me.
Is it remote and is it a remote first culture?
Does it pay “enough” to take care of my short and long term goals?
And funny enough, I would rather get a daily anal probe with a cactus than ever work for any large company or BigTech (again).
These days, I don’t care if the company is a shit show. I do 40 hours a week and money appears in my account - that’s the deal. I don’t work for “passion”, “alignment” or the “mission”. I work for the paycheck.
I do like the company I work for now. It’s the best job I’ve had in 29 years across 10 jobs.
>> How long does it take to form an impression of a new job?
>> Zero. You should give it 0 time. You already know, and you’ve known for a long time;
Oh boy, how developers are clinging to the illusion this is still 2021.
How long till they interiorize that they are now immigrants crowding at a day laborer site, hoping some farmer with a truck will pick 10-20 of them for a round of picking strawberries.
So when you're penniless with no perspectives and the countryman picks you out of a crowd of hundreds hungry and desperate, you arrive at the strawberry farm and realize instantly: nah, this is not for me!
How long it takes to know if a job is right for you or not
(charity.wtf)272 points by zdw 9 June 2025 | 201 comments
Comments
I visualize this alignment like two boats travelling on the ocean together, with a rope that runs between them, connecting them.
When the alignment is strong, the tension on the rope is low, and it's a great place to work at.
But over time, the direction of either party can change, and it results in a better alignment, or a drift from each other that starts to put the rope under increasing tension.
It's possible that the tension on the rope is good, and your trajectory will adjust. But due to the size of the company it's unlikely your small boat can adjust the heading of the company, but you might succeed, if you try.
The key is to know when the rope is about to break, and then disconnect from that company and start the process again with another company, aligned in your direction.
Colleagues, tasks, compensation - if at least two of the three are good, it's fine to stay. If not it's time to look for something new.
The first year is a learning year, the second is a productive year, and the third is a "what else can I get out of this place" year. If nothing changes in the third year, then there's not much more to learn from the company and it's maybe time to move on.
Every time.
I don't care about your stack; obviously I have taste and preferences but I'm a professional, I'll work with whatever, as long as it isn't Rails. (Because there is no good work in that world.) But it will not take me a full day with access to your repos before I know whether there's anything you can do for me past signing the checks.
It takes a lot longer to tell if the job is right than if it's wrong. Six months is orders of magnitude longer than you need to give a bad job. Don't rage quit, but if it feels wrong it probably is, so start looking.
Had one job with a guy I had worked with for years elsewhere, and within my first couple weeks we sat down for a coffee and I said "so this isn't it a 5 year gig is it?" and he shook his head in agreement. Unfortunately COVID & life caused us to both overstay a bit.
You early don't owe anyone anything to stick with a bad gig.
Recruiting gives me an idea of how much the company generally cares about their processes. I like when am I given a timeline of the process and steps and now when I get a random call from the recruiter in the middle of a meeting at my current job because the new co didn't ask when I'm free.
Onboarding tells me how much the team is haphazardly shipping vs actually owning their product. The teams that have sucked are the ones where the onboarding doc is heavily out of date (like all covering a now-unused access request system) or I can't even get help from the team within my first week to have someone send me access requests to copy for the things that are missing. The good teams are where my manager already provisioned my access before I joined and immediately addresses any misses when I flag them. Or if they have good enough docs for me to quickly handle it myself.
Career development is another one that takes a little longer to suss out, but if I can have a good first-week chat with my manager where they will explain what my baseline performance expectations are and what I need to do to overachieve and get on promotion/raise track, that's a good flag. The teams I haven't been able to get that early from are the ones where manager usually doesn't care not only about your career but also about app maintainability or anything past their next meeting with their own manager.
This was purely because of the legacy stack and poor management. The boss wanted to scale but did not care about tech, so we just never made real improvements. Sure, a feature got implement at least a week. We saw revenue grow a ton. We never saw time to improve our stack.
Safe to say I felt like I was adding nothing to that company. They just didn't want to grow despite saying the opposite. I get that the shiniest framework will not improve the project, but there were some serious bottlenecks that just got shoved under the rug
You might never know for sure if a job is right for you though.
I got my next job through a headhunter. The first weeks I had a really good feeling of the company I liked it there after a few months it got worse and worse like they couldn't hide all the bad things anymore. I quit, next job was more or less the same. I quit. My current job? The first month I thought to my self "oh my god, where do I got here?", but now a six months in I really like it.
Maybe also other factors have some plays here like my move from consulting into an internal role, colleagues, the overall freedom, but imho it's hard to generalize something like that.
I worked there for four years anyway. Every one of those red flags was a sign of a real problem. Three of those years were very good, but eventually the chickens came home to roost.
What is you reaction to the kind-of-shitty company that gives you an opportunity for great personal growth and creativity?
Great colleagues but a real monoculture?
///
I liked most of TFA but the end where the author claims that management is more committed than IC's seems really strange to me. Is that something people look for? It seems like it would come across as totally fake cheerleading. Anyway, outside my experience.
Of course some places I've known sooner, but those are the exception.
If it wasn't for the quality of life my current jobs is providing, I'd probably find something else. I just can't find anything right now that is intriguing enough and pays enough for me to make the jump without losing benefits.
Ironically, the skills (devops / cloudsec) I picked up in those three months have helped me double my salary.
It doesn’t take long to figure out.
The two that did it both were great, the one that did not turned out to not be for me.
I'm with the last employer for the last 9 years, and not looking to quit :))
Nursing is known for lifers on single units, and personal growth doesn’t happen unless you are cognizant and strive for it.
Simple as that.
I once took a position at a company that I had known because they were a customer of my then current employer. We'd always gotten along, they were nice folks, had a good interview.
In a very short time, I wondered what the heck was going on. There was so much drama, infighting, and backbiting, and it was the complete opposite of the company's external persona. People were constantly being moved to different desks with no rhyme or reason- as in, a whole department rearranged 4x in the 8 months I was there. I had 3 or 4 different desks in that time.
People were regularly worried about their jobs and whether the company would even be around after family fights. And when they no longer needed me they started playing games with me, writing me up for things I hadn't done etc. Anything to avoid having to pay unemployment.
I knew in the first couple of weeks. But a bit of me died at that job. Eventually they fired me. In retrospect, I wish I hadn't given them the opportunity and fired them instead. But I had mouths to feed besides my own.
This is the same advice I now dispense to anyone I'm mentoring in software. I didn't for a long time because I had to learn this lesson the hard way a few times.
It helps me because I have a habit of fixating on the team’s mission and ignoring my own happiness, so the monthly check-in keeps me from staying somewhere longer than I should.
I'm just not at the stage in my life where I'm willing to onboard to a transformation that starts with a half a day call authenticating so you can login to a remote VM to do your development.
Similarly I had a 2 week gig where they send me some shitheap of a windows laptop that takes 20 minutes to login, where they wanted future engagements.
Nope. Nada. No way.
You can see the value of your productivity straight out the gate. It's not valued and you will never be able to change it from your vantage point of IC or middle manager.
It doesn't really matter that they say otherwise, the evidence tells the story.
Shortest perm job was about 5 months. Tiny office, 4 other people on the phone all day, impossible project (writing software for unreliable hardware), not a difficult choice.
[0] actual crypto, not currency.
[1] not just because of the bait-and-switch but because crypto is miles out of my wheelhouse.
Over time, I begin to see how I feel about the work itself, how I get along with coworkers, and how the daily pace and expectations fit me.
Curious if others have their own rule of thumb for figuring this out.
Question is what is the value of suffering these fools? New skill? New perspective? What's the result of this transaction?
That to me is what defines staying power. If there's just no value, or a bad imbalance of toil to value, it's time to go.
part of my problem is that I get unhappy (or bored) with a job but sit in denial for too long. so by the time I start looking for a new position, I'll desperately jump headfirst into a new gig instead of lining up the perfect gig.
Or maybe not. maybe it's impossible to tell if a place is a good fit from the interview.
I have opinions about it based on funding stages, but what it really comes down to is that culture is a function of growth. as an employee with a career success comes from hunting growth. the only real growth is from market fit, and even if you have market fit, if you aren't growing non-linearly you're going to get into a negative sum attrition game in the org culture (e.g. linear long term private equity returns).
questions to find answers for on the way in are:
- does anyone actually use their product and like it?
- how is that number growing? (non-linear, linear, attritive)
- what was their last funding round or change in equity ownership? (e.g. who runs it and what do you have to do to satisfy their investment)
- what's their staff turnover and where do they go?
If all the ambitious people leave- or go into inner exile, while the work stays the same but the company goes nowhere, the job has quit on you and its time to walk.
Will it help me get my n+1 job? Will the technology I’m using look good on my resume? Will I just be a code monkey who pulls well defined stories off the board?
Does it pay me market rates?
Is the bullshit/pay ratio worth it?
Post 2020 the rules have changed for me.
Is it remote and is it a remote first culture?
Does it pay “enough” to take care of my short and long term goals?
And funny enough, I would rather get a daily anal probe with a cactus than ever work for any large company or BigTech (again).
These days, I don’t care if the company is a shit show. I do 40 hours a week and money appears in my account - that’s the deal. I don’t work for “passion”, “alignment” or the “mission”. I work for the paycheck.
I do like the company I work for now. It’s the best job I’ve had in 29 years across 10 jobs.
>> Zero. You should give it 0 time. You already know, and you’ve known for a long time;
Oh boy, how developers are clinging to the illusion this is still 2021.
How long till they interiorize that they are now immigrants crowding at a day laborer site, hoping some farmer with a truck will pick 10-20 of them for a round of picking strawberries.
So when you're penniless with no perspectives and the countryman picks you out of a crowd of hundreds hungry and desperate, you arrive at the strawberry farm and realize instantly: nah, this is not for me!