Ask HN: If I quit my job, will I ever work again?

You won't make a lot of money, but at least.. you will make money when you need it.. and you will make enough money to survive!

The work will be waiting for you when you get back. If you're in an area with active tech gatherings you can show for those and keep up your connections. Nobody worth your time would hassle you over a short break that produces some noteworthy portfolio items(like open source work or a degree).

No matter how many times this gets asked on HN, the answer will always be 'it depends' and what it depends on is 100% you.

How is anyone else besides yourself supposed to answer this? Only you have true insight into your motivations, skills, desire, and ability to succeed.

There is no cap or limit to what you are able to do (okay, let's set aside physical limitations - not everyone is meant to be a football player or pole vaulter) - there is a soft cap set only by your desire to work hard.

It shows you care about personal development, it gives you accomplishments to mention at an interview and demonstrates that you're self motivated.

So without knowing all other determining factors i'd say go for it. But like others are saying, only you know your own situation.

Ergo, your problem is motivation. Allow me: I'm going to keep calling you a pussy over and over again until you quit your job. Of course, you won't be able to hear me because I'm in my basement and you're not[1], but trust me, I'll be saying it. Pussypussypussy.

[1]Unless you're my black lab, in which case one of us needs to get the other to the hospital.

And now I'm working as a contractor on a web app for some company called Apple. And am contacted by recruiters virtually every day, even without Apple on my resume.

From the description of your current situation I'd say it's worth it to go for it (go do your thing). But I think you already know that :)

Don't you think it's worth it to risk a little, put your neck on the line a little, maybe even put yourself in a bad spot for awhile, for a chance to live like you want to? Life is living, live it and make it.

You're asking if you're going to have problems finding a technical job after quitting so that you can spend time improving your skills. Are you kidding? I can't even imagine this hurting you career, and I wouldn't be surprised if you end up with unsolicited interviews if you write up what you're doing in some way (whether it's on a blog or via something like github or bitbucket). Sure, there are companies that won't hire you after a sabbatical, but do you really want to work for those sorts of places?

P.S. Good luck (not that you'll need it)!

As long as your skills are valuable to someone you will be able to get a job.

I'm sure you will be just fine after 6 months.

Midway through, an idea that began as a learner project turned into a startup, 3-6 months turned into 9+, and I'm learning more than I ever have, and about more than just the programming topics I'd planned on.

Meanwhile, I've gone to meetups and startup events (like the Work at a Startup Day), and my personal projects -and my commitment to developing the skills to build them on my own- have been the starting points of lots of conversations with cool people from cool companies, opening doors to opportunities I'd have never had if I'd still been working at a full time gig that my heart wasn't into.

The most important thing for me has been making sure to use my time well. It's easy to squander the time, so it's paramount to have a plan and stick to it. That said, the plan can be pretty flexible since you set the schedule (assuming you don't have dependents limiting that).

My biggest concern is whether I'll be able to go back to a "regular job" after the freedom of working on my own projects on my own schedule. But I'm hoping that I won't have to find out.

Do it!

Instead, we came up with a compromise, I quit my job and start working as a contractor while she continue doing awesome at her job.

The compromise should give me the time and mental energy to find awesomeness.

To really answer your question, my path is easier, I could just find a "safe" job later when things get tough.

To answer the last paragraph, I just love programming so much. After a stressful day at work, I need my Python as bad as I need a cigarette. I don't need a break to seek that mythical awesomeness (My definition of awesome is to finally launch a useful service for real people). I need a break to ran away from those pesky Employee Agreement contract, crappy boss, and mental drain caused by him/her.

My life at home is not different at all nowadays. Just a lot less stress.

PS: Future boss might ask, why there's a gap in your resume? I know my old one would.

I spent the last 3 years working at a firm where luckily, the concept of "sabbatical" was accepted and almost encouraged in your third year. I've seen a number of different things that people have done, and given your goals, here are a few ideas that you might find relevant:

- Take a job that you absolutely would never take for the money, but want to do for the experience. Former colleagues of mine have taken eye-opening jobs working for various non-profits all over the world, had the chance to travel, and reboot. The benefit here is you get a chance to think about your career and what you might actually want to do. Take a job at another company that you're interested in, if permitted - If you're going to spend time doing stuff you can do remotely, do it in a foreign country where you can ride the currency exchange and do really cool stuff when you're not working (e.g. buenos aires, china, etc.). Mobility is priceless

A TED speaker Stefan Sagmeister makes it part of his career to take a year off every 7 years. I recommend watching this video before making any decisions.

A month after I returned the CTO at my old job contacted me and gave me an offer I couldn't refuse. How about that.

I like a lot of things about the job/company/people. I think I just needed to get that out of my system. Although, I would like to do more trips in the future.

My life has returned to normal in some ways, but I'm much wiser and more mature than before, and also making more (and saving more).

I can't think of any negatives about the experience. Although, yeah, quitting was tough--including all the stuff you need to wrap up (i.e. moving out, into storage, canceling subscriptions, selling car or other stuff you won't need, breaking the news to your parents, etc).

I kept a travel blog, if you want to get inspired: http://bp321.com/travels

And my top 100 photos from the trip (in random order): http://billpaetzke.smugmug.com/Travel/Best-of-Southeast-Asia...

Do it.

I noticed a few weeks ago that I am always kind of tired after work, and can't do anything really useful. So I decided I'd go to bed early, and then get up at 4am to work on stuff I wanted to work on. Fresh coffee, fresh from sleeping, and not tired from work.

Then around 9, I go to work and have a normal day. I might be a little tired at work, but I'd rather have the awake-and-creative me for myself. I don't get paid enough to give them that.

  We rest here while we can, but we hear the ocean calling in our dreams
  and we know by the morning, the wind will fill our sails to test the seams
  The calm is on the water and part of us would linger by the shore
  For ships are safe in harbour, but that's not what ships are for

You're not always going to be able to work with people with the exact same culture or skill levels. That is going to happen anytime you work at any place, including your own, where the number of people > 5 (it's my _magic_ number)

So why do people leave companies ? better money and better promotions. If you believe your master's degree will help .. do it (and get the paper) (sometimes they just do it to spend six months in Phuket)

I see you have not really mentioned about being an entrepreneur - maybe I'm reading too much Freud, but you need to think what you want out of the six months you wont be earning.

Eventually I got bored and got back in the game.

But it was such a good time. Really recharged my batteries and left me in a position to do much more interesting work than when I began.

Just do what seems fun and challenging and see what happens. Good luck!

These days most tropical beaches have wifi, so you can still do all that boring stuff you listed above. You'll just do it from a laptop while living in a grass hut and eating Thai food every meal. Trust me, it's way better that way, and it's also a lot cheaper than sitting out your sabbatical in your expensive apartment.

Step one is to head down to the bookstore and park yourself in the Travel section. See if you can make it 20 minutes into Lonely Planet's Southeast Asia on a Shoestring before you head over to the coffee shop to boot up and book a flight.

Don't worry about your career. It'll still be here when you get back. As others have said, taking six months off often just gives your friends time to find you awesome contract jobs at their companies. Chances are you'll have something lined up before you even leave the beach.

Good luck!