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Always Be Ready to Leave (Even If You Never Do)

https://andreacanton.dev/posts/2025-11-08-always-ready-to-leave/
96•andreacanton•9h ago

Comments

BinaryIgor•8h ago
Very wise; have been following this approach since years and I highly recommend it. This one (from the article) is a gem:

"I’ll work like I might stay forever, and like I might leave tomorrow"

Besides practical benefits of this approach mentioned in the article, it's the attitude that brings you closer to stoicism that just makes your whole life, not only professional one, better.

OutOfHere•2h ago
Stoicism is probably one of the best candidates for a world religion, not that any philosophy or religion should be too limiting.
ta9000•1h ago
I learned of stoicism in the last year and it’s been transformational for me.
sfpotter•4h ago
Has a paragraph of the form "Talking to people who can actually change things? That’s professional problem-solving."? That's written by AI.
sph•4h ago
No em dashes, but there’s enough “it’s not X, it’s Y” give aways of LLM usage.
pstuart•2h ago
I've used double dashes for years and now they get automatically turned into em dashes, and I'm not an LLM (that I can tell so far).
readthenotes1•2h ago
I asked Perplexity to provide a witty reply--but none of the ones provided were amusing enough.
setopt•2h ago
I manually type en- and em-dashes, which on Mac is easily typed using the Option key and on Linux is easily typed with a Compose key, and even on iOS you just long-press the hyphen key.

I had to learn the difference between hyphen, en-dash, and em-dash when typesetting scientific papers and theses in LaTeX, and after that it just doesn’t feel right to not use them "properly".

MikeTheGreat•1h ago

    and I'm not an LLM (that I can tell so far).
Maybe ask your doctor to administer a Turing test?
novok•1h ago
There are em dashes: "I’d been talking openly about my struggles for over a year—lack of motivation, missing promotion, compensation not matching my contributions."
onraglanroad•3h ago
No, that's just the way some people write. Where do you think AI learnt to write like that?

@dang these complaints about AI are more tedious than any other complaints about the website. Might be time to add something to the "guidelines".

ptsneves•3h ago
I agree. The complaints about AI are about the form and not the substance, ergo the substance is fine.
jryle70•2h ago
This. Such complaints have become so cringe worthy, they drown out any comments with substance.
seabass•1h ago
Strongly disagree. If you read enough of it the patterns in ai text are so familiar. Take this paragraph for example:

> Here’s what surprised me: the practices that made my exit smooth weren’t “exit strategies.” They were professional habits I should have built years earlier—habits that made work better even when I was staying.

“It’s not x—it’s y.”, the dashes, the q&a style text from the parent comment, and overall cadence were too hard to look past.

So for a counterpoint about the complaints being tedious, I’d say they are nice to preempt the realization that I’m wasting time reading ai output.

neilv•1h ago
Regardless, people are going to start writing naturally like current LLM output, because that's a lot of what they are reading.

A tech doc writer once mentioned how she'd been reading Hunter S. Thompson, and that it was immediately bleeding into her technical writing.

So I tried reading some HST myself, and... some open source code documentation immediately got a little punchy.

> So for a counterpoint about the complaints being tedious, I’d say they are nice to preempt the realization that I’m wasting time reading ai output.

Good point. And if it's actually genuine original text from someone whose style was merely tainted by reading lots of "AI" slop, I guess that might be a reason to prefer reading someone who has a healthier intellectual diet.

radley•1h ago
Curious - is your concern that the post is 100% AI generated? Or do you object that AI may have been used to clean up the post?
novok•1h ago
AI writing often leads to word inflation, so getting the original more concise one is helpful IMO. Hiding it is the annoying part, marking that you use AI to help you and having a 'source code' version I think would go over much better. If a person is deceptive and dishonest about something so obvious, how can you trust other things they say?

It also leads to slop spam content. Writing it yourself is a form of anti-spam. I think tools like grammarly help strike a balance between 'AI slop machine' and 'help with my writing'.

And because they are so low effort, it feels like putting links to a google search essentially. Higher noise, lower signal.

radley•47m ago
> I think tools like grammarly help strike a balance between 'AI slop machine' and 'help with my writing'.

I found Grammerly to be often incorrect, but it's been years since I tried it. I use LanguageTool instead, simply to catch typos.

onraglanroad•4m ago
Ok, well this post seems very similar style from the same author. Why isn't this ai also? https://andreacanton.dev/posts/2020-02-19-git-mantras/
ta9000•1h ago
I agree.
OutOfHere•2h ago
Please cease and desist from labeling things as AI. If you want to criticize the material, assume good faith and criticize it as if it is written by a human.
seabass•1h ago
You can compare the writing style from the earlier articles like this from 2020, pre-GPT.

https://andreacanton.dev/posts/2020-02-19-git-mantras/

xdfgh1112•1h ago
I guess AI is the new catchall term for "cliched or bad writing"
greatgib•1h ago

   The best time to document isn’t two weeks before leaving. It’s right now.
Clearly AI written or virtue-signaling post, because this doesn't make any sense. If you are leaving it is that you are unhappy with the company, and you owe them nothing and they owe nothing to you, I don't see why you would stress yourself with documenting your work when you are leaving... Their loss if you go.

But even more, why a small employee in his right mind would make himself replaceable for the good of the company...

radley•1h ago
Good habits and reputation carry forward.
xdfgh1112•1h ago
Before AI people would still say things like this. "The best time to plant a tree is 10 years ago. The second best time is now". Among the set of such constructs, some are overused by LLM and have become a symbolic of it, but they will still show up in human writing with the same frequency as before.
Ecstatify•1h ago
Honestly, it sounds like the usual clichéd advice.

I was expecting something more practical, like doing an interview every six months or something along those lines.

Supervisors and HR just smile and nod.

Maybe if he had a better relationship with his manager, he would’ve realised sooner that he was just wasting his time.

Documentation is like an untested disaster recovery plan.

When a major issue happens, you’ll be the one called.

You should delegate or automate the task and remove it from your workload, especially if it carries high risk.

I’d actually love to read the dark arts equivalent of this article.

neilv•1h ago
> I was expecting [...] like doing an interview every six months

Incidentally, I hear advice like that (especially a variation, of "practice" interviews) on HN, but I really wish people wouldn't do that.

Actually, please don't do this resource burning with startups or other SMBs, unless it's clear they want to burn resources.

But feel free to burn the resources of FAANGs, who mostly created the idea that interviews should be a series of performance rituals that you have to practice and refresh on.

(Though the related phenomenon, of techbro frequent job-hopping, wasn't the fault of FAANGs. It seemed to start during the dotcom boom, pre-Google, especially in the Bay Area, AFAICT, where a lot of people were chasing the most promising rapid IPO. At the time, the rumors/grumbling I was hearing from the Bay Area made me want to do a startup in Cambridge/Boston instead, just to avoid that culture. After the dotcom IPO gold rush ended, it seemed that job-hopping for big pay boosts and promotions became a thing, and that job-hopping culture never went away. But I don't think we'll find much team loyalty anywhere anymore, not from companies nor from colleagues, so that's no longer a reason I'd avoid the Bay Area specifically.)

bdangubic•59m ago
I don’t think SWEs realize just how many companies out there will look at a resume of a job hopper (even if there is 10 years at FAANG, say 2 at each) and outright reject the candidate on those grounds.
fn-mote•53m ago
You’re hiring a job hopper because they have skills you need NOW.

They are job hopping because they want high level compensation and maybe a position on an high-impact team, instead of being sidelined and powerless against the disrespect of their manager.

Your company can make those work together.

I’m not saying every job hopper is the right hire. I am offering a reason they get hired anyway (availability!) and leave anyway (respect and $$).

bongodongobob•52m ago
Absolutely. I had a stretch of consulting gigs for a couple years and I recently was denied an interview because they "didn't like the short periods of employment" even though they were specifically indicated as short term contract jobs!
RealityVoid•14m ago
I understand ever having done consulting is seen as a red flag now, so that might be more to blame.
caminante•36m ago
Not true.

The talent view is that this candidate is in demand by peers, and it's the candidate's choice to put in a full 2y and leave early before vesting.

atherton94027•58m ago
> Actually, please don't do this resource burning with startups or other SMBs, unless it's clear they want to burn resources

Startups are fine scheduling candidates for 5-6 rounds of interviews, they should be fine with the occasional tire-kicker

jay_kyburz•43m ago
You can't know your market worth without putting yourself on the market.
neilv•22m ago
> Startups are fine scheduling candidates for 5-6 rounds of interviews,

Not all startups are like that, and you might not know in advance.

Though, incidentally, I did find one about a month ago, and I will take this moment of inspiration to complain about it, constructively.

I bowed out of an imminent offer, because I thought that the CTO's gauntlet of evaluation steps was a sign of the day-to-day I should expect: that I would only be valued like an untrusted junior commodity worker.

(I have a lot of experience, my detailed resume shows that, and I'd been patient and met more than halfway with the process.)

Meanwhile, the initial pitch about why I might want to work there had worn off, after 5+ calls and a takehome. I wasn't going to invest any more time+energy+soul, submitting to the final grilling/hazing step, of a job I no longer wanted.

ProTip: Unless you are a FAANG, or are paying FAANG-like money, don't act like one towards prospective hires/colleagues. Otherwise, you should expect to hire only people who are moderately good at interviewing (good enough to pass your nonsense, but not the nonsense of the people who pay more). And you should expect them to hop without loyalty, because you do FAANG arrogance and nonsense, without paying for the privilege.

ghaff•51m ago
There's probably some happy-ish medium of people toughing it out through a bad situation they don't feel they can change--and jumping at the first instance of itchy feet (which is admittedly harder at the moment).

Not sure when the job-hopping culture--especially on the west coast--really came in. I do associate it with post-dot com but I'd really have to look at the data. Certainly wasn't really true pre dot-com at large tech employers.

neofrommatrix•45m ago
Honestly, if companies cared enough about the interviewees time as well, people wouldn’t do this. I was looking for a few months, and companies put you through the wringer of 6-9 interviews these days. Two should tell you whether a candidate is a good fit or not. Then there’s the case interviews where candidates put in dozens of hours prepping decks and what not, and then get rejected without any feedback at all.

And this was exclusively at SMBs and startups. At least, the FAANG companies have structure and you know what to expect.

bayarearefugee•1h ago
Well written blog post, but its a bit too adjacent to LinkedIn slop-posting in actual message, for me.

I can't help but think the real take away is that you should trust your gut and quit a lot sooner and the poster basically wasted a year being jerked around.

If you are telling your employer you are unhappy for a whole year and they don't fix the conditions leading to your unhappiness, they are telling you they don't value you enough to make those changes (for the sake of simplicity, I'll just assume the employee's specific points of dissatisfaction were reasonable fixes and not ridiculous asks).

You don't owe them a year of soft landing when you quit, in the vast majority of cases they wouldn't have given you anywhere near that if they let you go.

bitwize•52m ago
Remember that immediately after Mao's Hundred Flowers Campaign, in which the CCP solicited "honest feedback" about how well they were doing, came the Anti-Rightist Campaign, in which the complainers were identified and punished, sometimes executed.

If the decision makers are welcoming honest feedback, chances are pretty good it's to put you on a potential troublemaker list so they'll know just who to hand pink slips to at the next round of needed layoffs (if not before).

Unless you're prepared to lose your job TODAY, treat your employer like the Roman Empire, and the CEO like Caesar.

dullcrisp•34m ago
I get the feeling that maybe Mao wasn’t always such a good guy.
te_chris•12m ago
Getting downvotes for this, but genuinely laughing over here
mathattack•42m ago
I’m amazed how many people leave on bad terms. Over any medium and long term time horizon it’s a terrible strategy. You never know who will do a quiet back channel reference, and many times we wind up working for the same people.

The other piece of advice about documentation is important beyond leaving for a new job. Many people lose promotions because “who could possibly backfill them?” Creating a high talent well documented organization is a great signal for promotion readiness, and takes a roadblock away from it too.

tschellenbach•40m ago
Yes it's crazy.

There's the founders podcast about Elon Musk. Apparently he stayed in good contact with the Paypal people, even though they fired him and later on that relationship saved Spacex.

alpineidyll3•40m ago
The author left out the most important detail:

- Before being ready to leave, make sure you either have, or will have, another opportunity or no need for an employer. VERY often (especially in tech!) employers/managers will have employees, not for their labor, but for vanity, to build a pyramid to themselves, or for image reasons. Such people will immediately send you packing for complaining about non-productivity. Your perception of your superior's alignment can easily be wrong.

Given that precondition... I agree with the premise.

weinzierl•38m ago
"Always be ready to leave"

Big yes

"For a year before leaving, I talked openly with my supervisor and HR about my dissatisfaction"

Big, big, big no. Might have worked for OP this time but in general this will backfire drastically. In many European countries this can even reduce the usually robust protections you have as an employee.

bartvk•27m ago
It completely depends on the management. Be sure to know them.
grumbelbart•21m ago
> In many European countries this can even reduce the usually robust protections you have as an employee.

Huh, where?

caminante•9m ago
Huh, why would openly complaining about your job to your boss/HR be protected in a "just cause" regime?
ahtihn•13m ago
> In many European countries this can even reduce the usually robust protections you have as an employee.

Which countries specifically?

outworlder•3m ago
Indeed. I _have_ been able to (mostly) talk about things that I was dissatisfied about, but out of dozen bosses I had, that was with only two. I wouldn't trust the others to start looking into a replacement the moment I gave even a hint of dissatisfaction. For some others, I could express disagreement about outcomes or company policies, but in some cases even pushing too much on those topics can get you fast tracked out. I have seen it happen.

To be able to have (again, mostly) honest conversations with a boss or HR is a privilege. In 99% of the cases, HR is there to protect the company, there were only a handful of HR employees that went above and beyond. And even then, you had to make sure not to use some triggering words. I mean this in the literal sense, there are a few things that, if you say, that triggers an automatic HR response, regardless of who you are talking to. Hinting of leaving, even with an unspecified timeframe, is one of them.

In general, don't do this.

Refreeze5224•35m ago
Absolutely. You employer is willing and able to fire you and eliminate your healthcare coverage at the drop of a hat with no remorse, and we should all never forget, and always be prepared for that fact.
rufus_foreman•17m ago
Except for gross misconduct, COBRA.

Yes, you will need to pay for the coverage that the employer was paying for, but that's not "eliminate your healthcare coverage at the drop of a hat with no remorse".

more_corn•16m ago
Some of the best work I’ve ever done has been in preparation for leaving. Documentation, automation, security, reliability. Theres nothing like the clarity of leaving to show the gaps.
iku•7m ago
When I read the title, I was curious: is it about a business setting, or, maybe, about a private relationship / marriage context? As someone, who has walked away from more than one relationship, I see this perfectly applicable and sensible advice in both contexts, really. Thanks.
idiotsecant•6m ago
Always being ready to leave a relationship sounds like personality flaw, not sensible advice.

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