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

It worked great when I did it, though I'd put an asterisk on the "without anything planned". I decided I wanted to move to NYC, but on my terms, not anybody else's. So I quit my job and kind of treated planning on moving as a job, as well as doing a few other things with the extra free time.

But I also was pretty confident in my ability to find a new tech job in a good market. It worked well the last few times, and I changed my Linkedin location before I went just to see how many recruiters popped up. The traffic left me confident I'd be able to get a tech job there when I was ready.

I also had a rough idea of how long I planned to stay without a job and how much it would cost and had enough to cover that comfortably, with enough extra buffer to come up with a new plan if getting a new job turned out to be harder than I thought.

You don't necessarily need a "plan" like having a job, but you should do that sort of planning. Some people have enough rich family or friends that they'll never really end up on the streets somewhere if something goes wrong. If you don't, you'll just need to plan a little better, and beware of unknowns. There's a lot of ways things can go wrong, it'd be best to account for them. And to have the life experience to know what might go wrong and how.

I quit my job in 2018 without any other opportunity lined up.

I used all of my savings to go on an extended trip to Asia, the idea being that I'll travel around, work on my own projects, and do some freelancing to cover my expenses.

Things didn't go as planned though, I got robbed in the hostel I was staying at and lost my macbook. Eventually I decided to cut my trip short and go back home where I started freelancing (which I'm still doing currently) and I would say it was one of the best decisions I ever made.

Congrats to you, your child, and your employer who was remarkably amazing throughout the whole thing! You're a good dad

I'll add another cautionary tale....

At the start of my career, I worked as a SWE at one of the FAANGs. After 3 years, I couldn't take it anymore. I hated everything I worked on, nothing was meeting my lofty expectations, and I thought about quitting constantly.

Eventually I pulled the trigger to go and "do my own thing." I didn't have a backup job - instead I worked on my own projects with a cofounder and tried to turn them into a startup. We struggled mightily. We didn't raise money, and we couldn't find product market fit. Every month I was watching my bank account drain, and I wasn't drawing a salary from anywhere. The stock in my own startup was worthless.

This continued for 2.5 years. Eventually, I had had enough, and I knew something had to change. I went and tried to get my old FAANG job back, but couldn't - probably due to my entitled attitude when I was there. I struggled with interviews for a couple of months, and eventually landed at a company several steps down from my old position, making about half of what I had at FAANG.

About a year ago, I switched back to a different FAANG after having been at that other company for 6.5 years. Why I stayed for so many years is a long story.

So ironically I'm back to where I started, but wow did I cause myself a lot of trouble. I watched for years as my old friends went on to make double and triple what I did, for doing the exact same job. In the meantime, I was more stressed out, dealing with a worse bureaucracy at a company that didn't value engineering.

Leaving FAANG was something I had to do. I had to get the startup out of my system, and I couldn't continue at my original job the way that I was. You can't buy perspective, but I probably cost myself something like 1-2 million dollars in the process. Many times over the years I've questioned "Why couldn't I have just stayed at that cushy job like so many of the people that I knew?" I know there's no way that I could have given my emotional state at the time, but I can't help thinking about it.

So I could tell you a bunch of lessons from my experiences, but unfortunately they're probably best learned yourself. You have to follow whatever you think is right and hope that things will work out for you. Usually they will in the long run - but the short term might be painful.

He's just hopping around on a tourist visa