Don't go overboard choosing the latest and greatest frameworks, language, tools, etc. You need to be productive, try and stick with what you are productive with. Find a good balance.
If you have a family, in the most kind way you can think of, learn to say no. While you are at home trying hard to work, everyone will think you have lots of free time.
Find a place where you can work quietly when you really need it. Preferably not at home, not at a coffee shop, not anywhere you could be interrupted.
Find a mentor/buddy. Someone who knows more than you do. When some server configuration bullshit gets in your way, when some framework bug stops you, when some Ruby version 1.8.7 patch 154 won't work with Delayed Job (a made up example) you'll need someone with the experience to help you.
Wake up at the same time everyday. Got to sleep at the same time every day. Eat breakfast. Exercise. Throw out your television, don't visit HackerNews or reddit except once a day.
Use a managed hosting service avoid VPS unless you are already a good sys admin.
MOST IMPORTANT: Validate that there is a market for your idea before you build your product.
"Start Small Stay Small" has good advice here. Don't be put off by the title if you want to grow big with VC money etc. It's still a great book. http://www.startupbook.net/
It really helps to have a partner to stay motivated and keep from missing deadlines. Once you are completely on your own it is so easy to get distracted.
Agree about the validation. You can try to sell it before you have much of anything. A screen is all you need to try to sell it to people. Talk to as many people as possible. It is so easy to just sit in a corner and code - that is really dangerous.
I've done something similar, though gave myself many more months. I also pre-paid a number of expected expenses to get them out of the way. I still ran through the cash quicker than I thought I would. Thankfully, I've been doing consulting projects and that extended my run time.
I also gave myself a one month window at the end of the time frame to find a job. So, in your case, I'd only give you one month to work on your startup before needing to go look for a job.
I have enough for a couple of months. Thought on doing some freelance work when the money starts to run out. Any thoughts on doing freelance work while working on a bootstrapped startup?
Everyone's different about this, but only having 2 months would scare the hell out of me personally.
Given that you've already quit, you may want to reconsider getting more cash in the bank. Your living expenses are one thing, but depending on what you're doing you may need to pay for other skills (design, devel, etc), and cash is king.
What would be your plan after the money ends in 2 months? Go get another job? 2 months doesn't seem long enough to develop and test your ideas, nor to make something that would bring in a livable wage, let alone profit for growth.
If you've already got a product/service, and the 2 months is just to get sales in the door, that might be a different story, but cashflow can take a while to establish even then.
You can do some freelance work while working on the business, but they often interfere. Focus on doing one or the other for a while. Again, everyone's different, but if it was me, I'd focus on getting some billable freelance work in first, getting more cash piled up, then focusing on your idea.
Ahh - much better. OK - sorry if I was reading that too literally. 5 is much closer to workable. In that case, I'd focus at least one month just on the project and see how close you are to bringing in revenue. If you're close (within a month or two), keep plugging away. If you get down to 2-3 months, I'd focus on freelance work to get your runway back up to 5-6 months at least.
Others may work differently, and only you can really tell what's comfortable for you. But I've learned that it's much easier to think clearly when there's several months of cash in the bank at minimum.
If you have a family, in the most kind way you can think of, learn to say no. While you are at home trying hard to work, everyone will think you have lots of free time.
Find a place where you can work quietly when you really need it. Preferably not at home, not at a coffee shop, not anywhere you could be interrupted.
Find a mentor/buddy. Someone who knows more than you do. When some server configuration bullshit gets in your way, when some framework bug stops you, when some Ruby version 1.8.7 patch 154 won't work with Delayed Job (a made up example) you'll need someone with the experience to help you.
Wake up at the same time everyday. Got to sleep at the same time every day. Eat breakfast. Exercise. Throw out your television, don't visit HackerNews or reddit except once a day.
Use a managed hosting service avoid VPS unless you are already a good sys admin.