Ask HN: What steps and preparations should I make before quitting my job?

Start by taking the rest of the day off. Go home sick if you have to and regroup. Don't quit while you are angry/upset. If you still feel like you want to leave write a resignation letter tonight and do it in the morning or after a few days when you have gathered your personal effects/data.

Quitting whiteout having something lined up OR not having enough cash in the bank is always a last resort but sometime if things are that unbearable it has to be done.

Also, this is not the last time you will be rejected for something you really really want start preparing yourself for that ahead of time.

Agree with andymoe. Don't let your current emotional state dictate your decision. Take time to think about it, talk it over with your wife, etc.

My best advice is to try and get something going while you currently have a job (you said you have time to learn right? why not use this time to build something?)

I once reached out to Seth Godin for advice on whether I should try and get a job in tech or just run with the startup idea I had on my own. He told me to quit and start immediately. In retrospect I'm really glad I didn't go with his advice since I would have felt completely lost and unprepared after the initial rush of doing my own thing. Instead, I've worked on side projects in my spare time, and eventually one idea clicked and the company is taking off (feel very fortunate).

Go with your gut, but also make sure you feel in control of your life and have options. Stick it out, save money, and if you do quit, you will be more comfortable supporting your decision as well as your family.

Wow. I've been there. 3 times actually. Unfortunately, your question is deceptively complex. There are several smaller questions/concerns contained within your dilemma.

Financial:

Can you afford to quit? You say you are married. If you don’t have kids, you’ll need 6 months living expenses. Better yet would be to have a years’ worth. I have heard conflicting reports on how easy it is to get unemployment if you quit. For now, I would assume that you cannot get unemployment.

Next, Quit or Don’t?:

If you decide to quit - here’s what you should do:

1. Give tons of notice. Since you don’t have anywhere to go, you can keep earning money and be openly looking for a new gig. The fact that it’s out in the open should alleviate some of the stress for you.

2. Figure out why you’re so unhappy. Write down two answers. First, an answer that is well rehearsed. This is the answer you can tell your boss and co-workers so you don’t blow up and tell them they are killing you. Second, an answer that is the real reason. If you’re this miserable at a job you’re going to have to do some serious soul searching to figure out why and you’ll need a plan of attack to deal with these issues so they don’t disrupt you in the future

3. Find the person who will be most upset about your quitting and manager your relationship with them. This will be huge on down the line.

4. Ultimately, be nice. You’re leaving and the way you leave will stay with you forever in the minds of your bosses and co-workers.

If you decide to stay - here’s what you should do:

Don’t phone it in. The anxiety of being at a job that you hate and continuing to do half-assed work will crush you. Better to take risks on projects that have the chance to excite you and do great work for the company. If you’re going to leave anyway, just find a way to politely decline the work you don’t want to do and pick a project that has a chance to be a game changer.

Next, look for another job. I know this is obvious, although in my opinion, you have 3 ways to go with this:

Option 1: Get another job, any job. Call recruiters. Call everyone you know. Shotgun resumes. Apply to jobs you know you can get and get a new one. Once within the new job give yourself 6 weeks to determine if you like it. If you like it, great, you have a job you like. If you don’t, move on to Option 2 or 3 and figure out how the fuck you’re going to explain why you have been job hopping so aggressively. Just be happy that you have a job that doesn’t make you cry. If it does, go to therapy.

Option 2: Figure out what your dream job is with extreme detail. I mean everything where is it? What do you do? Who do you work for? What your boss is like? How much you will get paid? Size of company, revenue, industry, etc. EVERYTHING. Write at least 3 pages on this and find companies and positions that match your target and go after them with everything you’ve got.

Option 3: Start freelancing. Be slightly less selective about the projects you take, but find a market that you are comfortable serving and do whatever it takes to give them what they want. Maybe even finding a few projects that pay $15 or $20 an hour will give you and your wife more confidence that you can quit. And if you do well you might be able to parlay those into an even more successful full-time side gig.

And when it’s all said and done and you have your dream job, do something nice for your wife. Dealing with this type of thing really sucks for women and I think taking a trip with her and showing her that you’re happy will do wonders for both of your psyches.

No specific advice but just wanted to say hang in there and try to keep positive. When you say: "I've been told I was in line for a raise but was just waiting for approval. That was six months ago, when I asked what was happening I was told 'still waiting'." - this means they are lying to you and they don't think you will have the guts to leave. Do your best to develop something on the side that you can show to potential employers, they usually are impressed by the initiative required for something like that. Visualize the day you have a solid offer on paper in your hand and you can tell your current job "Thanks for everything but it's time for me to go" - just focus on how good that will feel!

Thanks so much for the advice.

The second I read @andymoe's comment I knew it was exactly what I needed to do. I left, went home and must have sent out two dozen resumes.

I'm back at my desk today and I've 'confessed' my feelings to my office best friend. I was surprised to find that she feels just as crapped on.

It's honestly like a weight off my shoulders. I'm not alone here anymore. Don't get me wrong, I'm still following through with @Chrisclark1729's advice. I think it's really really solid - but it takes more time to accomplish.

I'm going to wait until Monday to see if there are any hits on those resumes - and spend the weekend trying to weigh the cost/benefit of getting out 'now-ish' vs. earning while I look for work.

Advice for the job search: make it known to your dev friends that you're searching for work. Networking will yield a higher success rate than just sending out resumes blindly. Same goes for attending meetups in a technology that interests you--sometimes the meetups are sponsored by companies that are hiring.

Otherwise, good luck bud--I remember this feeling too. It's terrible, but my friends and family really helped me through it. All the best for you.