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Both times I have quit my job with nothing else lined up have been stress-filled disasters with a dreadful financial countdown timer. I would never do it again. The second time, our savings left us about 1 month away from my wife and I living in our car.

This thread has been unreal! I don't know who these people are who can just leave their jobs and go off to windsurf in Ibiza, but congratulations on how fortunate you are! I think the rest of us have bills to pay that can't be deferred, a need for health insurance, a family that likes food and shelter, and maybe a few months of an emergency fund. I would certainly not use an emergency fund to go "find myself" in Bali.

I think there's probably the assumption that a lot of these people have some money saved up outside of just emergency funds.

I know quite a few close friends, for instance, who are saving up "F You" money to be able to quit their job and do what they want (even short of full FIRE movement folks).

A friend of mine went to live on a beach on the other side of the world for 2 years. He would just follow the tourist party every day. I don't have what it takes to do that. It's really all about the mind set. He did have an exit strategy: Ask his mum for a ticket. Which he eventually did. Hearing about it afterwards I was somewhat angry with him that he never called to ask for money. A few hundred euro goes a long way compared to nothing?

When it was my time to leave I didn't even have a car to live in. I maintain a complex agenda where I would invite myself a week in advance to sleep on vaguely familiar peoples sofa for 1 night never more than 1x every 14 days per household. The bargain was this: I clean your kitchen, I cook an elaborate meal, I clean the kitchen again, I sleep on your sofa and leave after coffee in the morning. If I had money I would spend it on the meal but usually I had the host pay for it. Some people I barely knew would compensate for it by turning their kitchen into something like a war zone. I joked how welcoming it looked. Others never bothered to cook anything elaborate and welcomed the formula. It was a surprisingly interesting period that lasted something like 8 months. I think I've actually helped a good number of burned out people who just gave up cleaning the house and/or cooking and badly needed a break from it.

To add to the other side. I cannot imagine not having a capability to just gather my things and leave. All it takes is savings that can keep you running in modesty for 6 months. In my country, including health insurance, without mortgage/debt/kids its about 10k usd ("central" europe).

Its not much honestly. Peace of mind and poker plays you can swing towards shity employer are worth it. 6 months to find new SWE job, when I constantly pinged by HR and have generally good relations with previous employers(they would take me if i ping them), is plenty of time

How does the number change when you kids?

> It also looks like you should have a strong plan to do something (hobby, hike, or work in another capacity). If you don’t, you may just stagnate and waste some of your prime years for growth and development.

Having been on this journey too, I provide this reassurance for those on the edge of quitting: trust in your superego. Your superego is always there, always watching, always asking: "is this what you should be doing?". When you are working on someone else's project, doing something you don't want to, it is easy to ignore this inner voice, because in a way it is not your own. Procrastination, and stagnation, are natural when your job isn't your dream. But when you're on your own dime, things feel very different.

It is a mistake to extrapolate your tendency to procrastinate from the world of work to that of a free agent: with no immediate constraints it is much easier to recognize and slip out of those peculiar knots of irrational behavior that tend to trap smart people with unsatisfying jobs. But on the other hand, you will be forced to confront the terrifying choice of what to actually want! This is terrifying because, in a way, it is the most important choice you'll ever make.

Being in a situation where you only have yourself to blame, when you can't say "oh if only I didn't have these coworkers and that boss and my family and everything else holding me back (holding you up, really)," it's a different kind of fear. It's probably healthy, but surprisingly intense.

You're totally exposed and get to see exactly what you're capable of accomplishing. It's like that machine in The Hitchhiker's Guide to the Galaxy that shows you exactly how insignificant you are in the universe.

The total perspective vortex (the machine in hhg)

Very well put!

My 2c is that it can also be reverse. I have generally had a reputation of being very productive at work, even though I don't even really like or care about most of my projects that much, and my productivity doesn't increase very much when I do like a project. On my own projects where I can do whatever I want, I have a track record of being able to procrastinate for unlimited amounts of time.

OP is also asking people their experiences, but those experiences are informed by their local set of pros and cons.

What I've encountered: 1. I've never had bigger improvements in my financial outcomes than when I said 'f-it' and pulled the ripcord 2. Doing so dropped my into a stresspit that was grinding me into a red paste, resulting eventually in being Riffed 3. Which let me find a job that, while not great, has good work/life balance and is good for me, at this time, in my walk down my path.

Go into it informed and mindfully and you'll probably be fine, assuming you're in a market that needs you (A french chef in Washington, KS...population 1100, is probably not going to have a sustainable skillset in Washington, KS)

Dad told me 'Never quit on a Friday', but he was also a fan of trusting your skills to support you.

what's the reasoning to never quit on a Friday?

It gives you time to slow down and reflect if this is something you really want, or just a reaction to a long and difficult week.

It's similar to the "count to ten" principle, before yelling at someone.

Because you've been working all week so you're at peak tiredness

Good points mentioned by others at this level of the thread.

I'd also assume that it may be that having the weekend could put one in the mindset of relaxation and cause procrastination at the start of what could be an intense process that requires drive (depending on individual's circumstances).

Or maybe it's kinda the opposite where if one were to quit on say a Monday instead, there's a good chance that the work week mindset holds, kicks the individual into being productive (maybe more productive than usual out of necessity), and then that weekend would be very much needed to wind down/refresh and reflect on the progress that was made.

Again, just my assumptions, but seem like likely scenarios that could play out

Edit: spelling

Changing a job should be the result of measured, long term, reflection. Any one given Friday at the end of a bad week is not the best time to make a snap judgement.

If you still want to quit on Monday? Go right ahead...but a lot of times the stuff that seemed insurmountable on Friday, don't look quite so bad with a bit of reflection. Unless they still suck.

Personally on big decisions I set a date 2-4 weeks out to make a decision and let it gestate in my brain. I think I've only "pulled the ripcord" once in my life on a particularly malodorous company that I worked at after I was talked down to over my decision to refuse. to sign off on something. I felt it was a safety concern until I had taken the time to fix it and check it well. It caused some friction with a big client over a delay (a few weeks), but I didn't care because above all I'm going to do what is right and what I feel pride in. Never let anyone gaslight you ever; if they don't respect you then speak up and let them know that shit is not allowed. Sure you may get fired but I guarantee you will regret not doing it for forever. Probably I got thrown off a few athletic teams in high school :)

> All in all, if you are financially stable or have a supportive safety net, it seems like a potentially good risk to take.

This is probably the biggest factor.

How long could you go without a regular paycheck? Personally, I could probably make my savings last a year, but that's only because I have a wife that makes enough to pay most of the bills herself if it came down to that.

But I imagine most people outside the HN bubble don't have that. The majority of Americans can't afford a sudden $1,000 expense. They can't just quit their job out of the blue.

>Quitting to do your own thing, as long as you show employers why you did it in a year or two, shouldn’t be a detriment for getting rehired. That said, hiring managers may question if you’d quit again in a year (depending on your past employment tenure)…

It shouldn't be a detriment for getting rehired, period. If you are qualified for a role and pass an interview bar, there is no reason a potential employer should care about a break you took from working. I treated being asked about this as a yellow flag, as it may indicate the employer thinks you should be living to work.

My breaks have mattered “occasionally” with a few companies but by and large what you say is correct and it barely made people scratch their chin more than a few seconds, and I've had breaks (intentionally) of anywhere between 2-4 months every couple of years.

Hiring manager here.

Knowledge has a half life. If you have taken 6 months off, and have an interesting story, this is not a big deal. (For example, I took 8 months off to live in Istanbul. I had two interviews and two offers when coming back, one of which was completely outside my network.)

However, I had also just taken a month to do a functional course, and had worked half-heartedly on a startup that went nowhere. I had a story.

The longer you take off, the more of a story you will need, even if that's "in the last 3 months, I built a small toy to get myself reacquainted with React and Python" even if this is a Rails omakase shop.

Or, that story may be something completely different. All I care about is "can you hit the ground running?"

So what is the half life constant? Does it also apply to skill or only to knowledge? Are you hiring knowledge or skill?

It's impossible to answer the question for someone else, you have to address things like, what are my real values and priorities in life, not just work.

But some lessons learned. Manage your money carefully so you're not always in a inflexible spot, and manage your stress levels carefully. Pay attention to what is affecting you and why, and be good/take care of yourself emotionally so you're not always in stress/reactive mode.