I totally agree with your sentiment here:

Why are we still stuck in the industrial age, where working during the day hours, being at a certain location, and hammering away for 8 hrs was equivalent to producing a certain amount of output?

If you haven't seen the Ted talk below, it's a must watch:

http://www.ted.com/talks/dan_pink_on_motivation.html

What a great talk..

Now, to forward to boss or not to forward....

I feel the same way.

It's funny you mentioned working-from-home companies, because that's exactly how I deal with this problem. :) And it's something everyone should ask about at an interview; these days, a company had better cough up a VPN to hire me.

It's simple: I know that I'll think of something at midnight on a Wednesday, and want to log in to flush it out (or sometimes, when I wake up on Sunday). So I work at home at least half the time; and if I'm feeling even slightly lacking in energy, I don't even bother logging in. I know that eventually the drive will return (probably later that afternoon or evening). I have a cell phone, I check E-mail and office voice mail now and then. And I've been finishing at least as much every week as I did years ago when I was in the office all day long, except I'm a lot happier.

I do have VPN access, its just for after hours work though :-\

Does your company have a policy to let people work from home as long as they are productive, or did you have some convincing to do?

The VPN has always been available, but I have only used it extensively in recent years. It probably helps that teams are now spread further around the world, because it has forced people to restructure their work to deal with large gaps in communication. We'd already been sending messages and waiting hours for a reply, so people no longer expect to be in constant contact. So I didn't really have to convince anyone, I just reminded key people that I do work at home a lot, and to call me by cell when necessary.

Though, I've seen certain managers have a real problem with people working at home, and they even managed to fire people based apparently on that. Fortunately, those managers are no longer here, because that same intolerance made them ineffective managers.

"I don't see myself taking the YC plunge because I am married and have a kid, so taking a risk is kinda hard at this point." ... "I'm leaning towards saving up and then taking 3-4 months off my job to work on my own product."

Couldn't you do both? Seems like you could save up and go for YC while working on your product. Either way you'll have a similar amount of risk. One could even argue that with YC's network you'll have less risk since you'll be around like minded people and more opportunities will open up for you if your original idea fails.

Whatever you decide, go for it!

This resonates with my recent experience. I got bored of the 9 to 5. My job was alright, sometimes fun even. But last Wednesday I woke up and just couldn't do it. So I quit and started working on my own project.

When it's repeated a thousand times, it starts sounding like a cliche, but it is true - life is short. Do something which fulfills you.

So no, there's nothing particularly grand about making money. That's not what makes startups worth the trouble. What's important about startups is the speed. By compressing the dull but necessary task of making a living into the smallest possible time, you show respect for life, and there is something grand about that.

- http://paulgraham.com/startuplessons.html

Good on you. I hope it works out for you. Please do post updates here (to motivate yourself, and others :)) of your experience.

Thanks hackoder. I'm looking forward to writing a nice long 'Thanks HN' post. But not before I have something to show. I am scared announcing my plans might make me less likely to accomplish them.

I've found that taking steps to get people involved with my plans makes me more likely to achieve them. I'll definitely be sharing initial versions of my app with the community here.

Do you want to relocate to NYC and work on exciting product at the already profitable startup? We offer great salary, meaningful equity and I guarantee you the product will get you excited. See my profile.

"Do you want to relocate to NYC and work on exciting product at the already profitable startup?"

I think one of the things he's looking for is the ability to work from home.he mentions it very clearly.

If you're looking for a company to work for, you might enjoy:

http://www.codesourcery.com/

...depending on your interests.

Thanks. I feel a little under-qualified for what they are developing, but this strikes home with me:

CodeSourcery has no central office. We work when we want in an environment in which we are comfortable. We can work wherever we want: from a coffeeshop, a library, or anywhere else on the planet with an internet connection. We see our friends and families throughout the day; not just early in the morning and late at night.

Good to see that there are companies which are interested more in what you can do and less in forcing their way of working on you. Are you working for them?

Why can't you build a great product working by your schedule? Working on a team doesn't mean being with the team at all times. You need both time alone and time together.

That was exactly my point. I want to be able to work by my own schedule (with reasonable overlap with the team) and still build a great product. What I feel is that companies (or atleast mine) aren't structured this way.

You're right very few companies are structured that way, but you can start your own.

What kind of product do you want to work on that you would feel passionate about?

I've been considering that myself quite a bit, and I find that its a combination of things:

- Something where I can interact directly with the client/consumer. I dislike having to program by specs, when I know that they are written by someone who doesn't understand end users. Simple, effective touches are usually missing, and the feedback loop is so long that apps take years to evolve.

- Something challenging. I want to stay up at night visualizing possible solutions. That kind of excitement makes the time spent worth every second. And with the opportunity to think and implement a solution that works really well for the problem.

- Something that makes a difference. Doesn't have to be something ground-breaking, but it shouldn't be a CRUD front-end either.

This is harder to quantify than I thought. I guess it depends on the novelty of the idea, the silken smooth end-user experience (think iPhone- I own a G1 myself, but man does the iPhone provide a great experience), and the quality/succinctness/simplicity of the code.

I'm doing freelance contracting and trying to build a development/consulting shop partly for the same reasons you gave: I like the freedom and I think it's more efficient and modern, and frankly more adult & unpatronizing. Lets me work when, where, how I want, and unlocks enough extra free time & energy that I can spend more of it on other things like hobbies, friends, family or other enterprises or personal investments. A net-win overall. Not perfect, has downsides. You have to spend more time selling yourself, and there's more uncertainty about your future paycheck stream. And can be more isolating. And this giant spider hunts you wherever...oh wait. Nevermind that last thing.

But seriously, back to your post, if you do take time off to work on your own product, I suggest you don't burn any bridges employment-wise, and maybe set it up as an unpaid sabbatical with your existing employer, with an agreed upon return date. That way, you have the option of returning to them and that steady paycheck if your experiment doesn't get traction. This is more important because you have wife and kid. Also, use tools/tech that are good for rapid development and experimentation (Python, Ruby, etc.), make a Minimum Viable Product, launch/feedback/tweak/repeat, and don't underestimate the importance of marketing & advertising.

Another option for striking out on your own is to ease into it gradually by first becoming a contractor/consultant. The work you do is similar to salary/staff in that you're writing software for other folks, fixing bugs, etc. except you have more freedom/time/control to work on other stuff, like a product/service startup. And you can blur the line by developing a product/service whose design was informed by, driven by common demands from, or was a by-product of, your contracting work. That was the 37Signals route I think, and lots of similar stories out there.

Thank you. That is exactly what I'm thinking of doing. Take unpaid time off. Launch my product early (2 months into the leave, hopefully), interact directly with consumers, implement, improve, and hopefully have something that I can work full time on at the end of 4 months.

Re: your point about isolation, this is why I like the WFH approach. You give people freedom, but you still work as a team. It seems more win-win to me overall, than striking out on my own.