Ask HN: Those who quit their jobs without anything planned. How did it go?

I will say that a cash reserve is definitely key. The second time I left a job without a plan, I underestimated how much cash I would need to sustain myself for a long period of time. I ended up moving in with a friend and did a combination of contract work and GrubHub for around 6 months. In that time I also wrote and shipped a mobile app that I ultimately abandoned because I didn't have a good model for monetization.

The closest thing I had to a "plan" for if things really went south was to live out of my car. I spent some time to retrofit the trunk of my car into covert sleeping quarters and practiced sleeping in it. LOL

When I started applying for jobs again, I simply explained that I took the time off from traditional employment because I had a few apps I wanted to write and needed to dedicate my time to, which was 100% true. Employers seemed to have no problem with this at all; I actually got more interviews that year than I did in the past.

The last time I left I had quite a bit of cash saved up and had less rent to pay, thus it was much easier to simply leave without another job lined up. I had a few business and engineering projects to work on, so my plan was to work on those.

IMO, having more than a simple financial plan is overrated. It's industry dependent, no doubt, but as a developer it can be scary to leave a job without another one lined up, and everyone will tell you to never quit without already having another job. If you are single or at least don't have kids, it's not that hard to recover from mistakes, especially if you have a support system.

The one other thing I would say is that I think it's best to have a purpose when quitting. Definitely quit if you are miserable, but quitting and then not having something to do can also be bad.

And I also believe if you do not have a dream now, it also won't come magically to you while doing nothing.

- I was at an abusive job and was underpaid

- I had interviewed with Flickr and got the role, but didn't realize I'd have to move out west and so said no. I now understood I was marketable

- I quit the job with the plan to take a month+ to decide on my next move

- I shopped around a bit and had 2 roles lined up, and took the one that sounded the most fun to work at and most sustainable (the one I turned down had a 45+hour a week MINIMUM)

THEN

that company got acquired and I was once again without a job. A few of us thought about starting a company, and I seriously focused on leveling up my Ruby on Rails skills. Within 6 weeks I had a role at a new incubator which was one of the most fun jobs i ever had.

THEN

That incubator got shut down, and a few of us thought about spinning out one of the companies or raising money. In the end, 2 of us decided to start our own development shop. That was 10 years ago and it's been hard work but awesomely rewarding.

I would NEVER have achieved all of that if I didn't take the leap to leave the abusive job. I highly value the time I took between jobs to test things out and make the right decision at each turn.

I didn't have to take the time off to do it, but if it's financially viable for you to take a few weeks and see the playing field in front of you, my personal experience is that it pays off well in the medium to long term.

I've been working as a contractor for several years now, and for about 2 years now I am also working on my own start up together with a partner but it's earning 0 because reasons. After having worked A LOT over the past few years, I had a big financial buffer that allowed me complete freedom in my decision to quit, which was a very important factor.

For a long time I felt like I might be close to burning out due to working too much, getting bored of work, being unable to get anything changed at the company I was working for (as a software architect), and dealing with relationship issues. I took all of March off to see if that would help, but within 1-2 weeks after getting back I realized I wasn't really ready yet but I kept going because it was a very convenient job. Second last week of April something small happened that pissed me off more than it should, revealing to me that I wasn't in a good state of mind to keep working there. The next day I informed the company I would quit as soon as possible (which ended up end of April).

I decided I was going to be working on my own startup for the foreseeable future while taking it easy to get my head straight again. I ended up just coding endlessly on the project as a means of being distracted while never really dealing with real issues because I did not have the energy to confront them. Meanwhile I keep going in circles dealing with the end of my relationship and I seem to be unable to move on. I've come to realize spending so much time on my own with little distraction has been an issue.

I ended up deciding to try to find a new job again and work for my start up only 2 days a week, but it has been hard finding something for 3 days a week. I obviously want to work on location 1-2 days, which is also not ideal with Covid.

The lesson I learned from this is not to quit when you're not happy about your personal situation, even if you can afford to financially and professionally. The distraction is probably healthy, and if your current job isn't, find another one that is instead of quitting altogether.