Good luck. Unless you've got a lot of money to hold yourself up for a while, I would suggest not completely abandoning your day job. As you should know, even the geniuses of the web have failed in their business projects. The most important trait when it comes to a successful business is usually luck.

One of the problems with being self employed is qualifying for and affording health insurance, if you live in the U.S. It works out okay if you have a spouse with a day job for the benefits. Otherwise insurance can be a hurdle, especially if you have a family.

I agree with Stoutfiles about the money, but not about the luck. To a great extent, successful people make their own luck.

I've been self-employed for several years, doing something like you're envisioning. Here's a few thoughts:

You'll need a solid plan for how you'll keep the bills paid while you're getting your business vision off the ground. It would be wise to have enough money saved that you could live for a year from savings if you had to. Scale down your lifestyle and pay off debts. The fewer encumbrances you have on future income, the more freedom you'll have to pursue your vision.

Be very, very careful about whose advice you listen to. Many forums are populated with posers, and there's no shortage of self-appointed gurus who preach that it's easy to make buckets of money if you just buy their course. It can be productive to learn new things from someone who is truly an expert, but in many cases that I've checked out, what they offer is 10% useful content and 90% sales pitch. Be careful out there.

Be realistic about your own strengths and weaknesses. Being your own boss is a mixed blessing sometimes. Do you have the right kind of work habits and self-discipline to work independently and productively for extended periods? Do you have the business savvy to formulate a plan that will have a realistic chance to be earning income a year from now ... and the persistence to stay on course through the inevitable ups and downs?

This quote has been my guiding star for several years:

Great things are not done by impulse, but by a series of small things brought together. -- Vincent Van Gogh

@Stoutfiles - I would'nt say I have a lot of money but I could cover living expenses for more than 24 months if needed and I consider this to be a primary ingredient. Trust me. Thanks for your feedback.

@Jane_doe - Agreed. I do live in the US. I do have a family and fortunately a healthy one. I have very good health care now.

A couple of years back, I took extended leave from my job at which time I had no coverage. During that time I used health care from the NASE. It was very affordable and provided a lot of flexibility in its plans. Thanks for your feedback.

@buckworks - I agree that you must create your own luck. I didn't say before but Ive been brewing this idea for 2 years now, so considerable thought has gone into it.

We live a very conservative life style but we expect it to become more conservative as I move forward with this plan.

Ive been plugged into the net for a while and can usually smell the gurus that are really gurus at selling information. Your are so right about that.

Ive run an IT consultation business for the last 10 years in addition to my day job. However, my client list is small and manageable so Ive had the own boss experience for some time.

Self discipline, working independently and productively for extended periods of time. I strongly agree with your feedback on these work habits.

I would also answer yes to all of them in both my corporate and self employed roles, which is one of the supporting reasons why Im looking at pursuing my self employed venture full time.

I've found the pay off to be much more limited in my day job given the work I put in and I don't expect that to change over time. Id much rather be putting that time and effort into doing something I am passionate about while building something that belongs to me.

Also, these habits are the source of the earlier mention luck creation in my opinion. Its clear you are someone who understands why I posted. You have hit on some really good points and I am very appreciative of the feedback.

Ive been brewing this idea for 2 years now, so considerable thought has gone into it.

Thinking is good, but what have you actually DONE about it?

What concrete, practical steps have you taken to this point to start laying some groundwork?

I made the leap two years ago. My advice is don't leave your boring job until you're making the same amount from your web job. Otherwise you risk blowing through your savings and wind up back there. Don't quit your job until you're making the money.

wow kmb40., we are on the same boat.

I had a very nice job offer with pretty attractive pay that I quit on August 10th and have been working from home since then. What I make now? (psst..$2 a day)

But I think we have to take this risk someday. For me, I have no liabilities now - unmarried with decent savings, so right age to try. I have given myself one year to prove, or else go back to the corporate cubicles.

Regarding how to focus on sites, well if I were to tell you what I have been doing, my day consists of three things primarily - first, write a bit on one blog that I have had for the past two years and which is making me that lucrative $2 a day. Most of my time goes into me obsessively adding content for another new site of mine. I am not going to waste time on researching keywords, competition,etc. Just going to write content obsessively. And I already see something like 10 uniques a day from the search engines.

Then, I spend one hour in writing freelance for one another website. It doesn't feel good to be not earning anything at all..So, a bit of freelancing does not hurt.

I would advise you not to focus on too many sites. Just pick one and build it aggressively.

Good luck and keep us updated.

Just going to write content obsessively.

You need good content, yes, but on its own that is not enough. You must must MUST have a strategy for promotion.

It is true that good content will attract traffic and links over time, I have experienced that, BUT that only happens if enough people know about the site to begin with.

Once the basics of your site are in place, re-balance your work so you're investing a consistent portion of your time into intelligent ways to promote your site, not just build it.

I would advise you not to focus on too many sites. Just pick one and build it aggressively.

That works for some people, but it is like betting your money all on one stock. It could turn out to be a Google or an Enron. Sites fall in and out of favor in the rankings all of the time, sometimes due to factors outside your control, like search engine bugs or competitor dirty tricks. Personally, I think it is safer to have a variety of sites going after thousands of different search terms.

@buckworks - that 2 years has been spent, doing research, looking at ways to monetize, protoyping, and testing, testing, testing.

@swanny007 - agreed, issue is, I feel that the available time won't allow me to grow the venture without dedicating more to it.

@anand84 - so I'm not alone after all. Thanks for your feedback and good luck.

@jane_doe - I think a solid core site that has a relevant relationship to others is a good approach with a proven track record.

that 2 years has been spent, doing research, looking at ways to monetize, protoyping, and testing, testing, testing.

What about your marketing plan?

Like many here, I make a living with a content site, no ecommerce at all. It's an ad supported site.

Sounds simple, but it's not as easy as it sounds, and all the best content, even if it's backed by great tech won't earn much if you don't attract the right audience for the site.

2 years thinking about it?
You're approaching it the wrong way.
Just start something. This is not a business where a long perfectly written business plan will do you any good.
Just start something. Work at it hard.
Just start something. Measure its success carefully then try something else slightly different that includes the successful bits.
Just start something. Try different approaches on different sites to figure which things you are good at and also are happy to do day in and day out in a grinding way that will make you money.

My advice to anyone considering this biz is - don't leave your day job until you just don't have time for it anymore! Ideally this will overlap with the start of income.

Start off by simply going to the County Seat, get a DBA and a EIN. Then you can put your plan to work while still working your day job.
I did it for 10 years. You can't really be creative full time anyway. You will burn out before you know it.
Start of with just putting in an hour or two a day on your content. I found that early morning worked best for me.
I would get up around 4am and start writing and designing.
If I waited until I got home I was usually brain dead and could not produce anything worthwhile.

Don't quit the day job until you are earning at least your current salary from your content network. I waited until I was making double my day job salary before quitting. That was a great day. ;-)

I spent 6 years doing both a fulltime day job and a part time side business. Building up a new content site can take a few years. I know this may not be what you want to hear. But that is the reality.

DIY networks are pretty competitive. But as I always say, there is always room for one more. ;-)

Kmb40 - Do you have any sites making money at all now after two years of part time work on several sites? If so, what percent of your day job income have you replaced in those two years?

I've been running my business for almost 20 years now, and I have some credentials regarding small business, which I'm not prepared to share...

There's some good comments here...First, it's not luck. Trust all of us who have succeeded. It appears to be luck when one is often in the right place at the right time, but people don't see the thinking and work that gets one there, ready to take advantage of things that open up.

Second, here's my advice. Never ever start a business with the idea that it is an Internet business. Or that the primary function of your business is to run a website(s). The Internet is a tool to leverage your business. It shouldn't be where your business is located in its entirety.

That's really really bad.

Run your business that focuses on a function and creating results for you clients/customers that is independent of the medium.

For example, you talk about writing content for a blog. Don't think of yourself as a blogger, webmaster, etc. Think of yourself as a writer, and your universe of potential revenue expands almost infinitely. You are currently using the function of creating text. Everything you write can be repurposed, repackaged, republished, provided you are good.

Are you good?

Further example. Write for you blog with the thought in mind that you might peddle modified articles of the initial one to other places on and off line. If your stuff isn't good enough, then why are you putting it online? It's a major problem--people writing "content". You don't succeed writing content. You succeed by creating material that is helpful, entertaining, useful and valuable. Sadly most people who go out to creat content, create junk that has no value anywhere, except to maybe get a little traffic from search engines.

If you can only think of your possible business in terms of being a webmaster and ads paying the way, do NOT start your fulltime business. If you think LIKE a real business, not a virtual one, and think broadly, that's different.

And, plan on a minimum of two years of low income. Commit to no less than two years.

First, it's not luck. Trust all of us who have succeeded. It appears to be luck when one is often in the right place at the right time

That is the definition of luck. Luck isn't magic; it's being in the right place at the right time. Maybe a big site randomly stumbled upon your site one day and linked hundredss of thousands to it. Maybe you made a site about blue widgets and suddenly every celebrity suddenly loves blue widgets.

I've developed great sites that made next to nothing. I've developed crap sites that made tons of money, and most of those sites I lucked out on. I got in at the perfect time or got some links from sites that I probably didn't deserve.

There IS a lot of luck involved when it comes to hitting it big on the internet. If you go in to your idea thinking just because it's flawless you can't fail...well, you'd be wrong.

You need good content, yes, but on its own that is not enough. You must must MUST have a strategy for promotion.

Thanks for the advice Buckworks. Apart from legitimate PPC, I find almost all kinds of promotional means on the internet pretty shady. Be it adding valuable answers on Yahoo Answers with a small link to my site or Ezine articles (again with my links inserted), or social media marketing (aka spamming), I am yet to stumble upon some promotional methods that is 'Colgate' White. It'a all gray somewhere.

Besides, don't you think search engine is the best word-of-mouth tool? My other tech blog now gets mentioned frequently on Twitter, and those who tweeted were those who came across my site via search.

It could turn out to be a Google or an Enron. Sites fall in and out of favor in the rankings all of the time, sometimes due to factors outside your control, like search engine bugs or competitor dirty tricks.

That is definitely critical that we don't rely on 'bluish green widget' keyword for our bread and butter. My site is going to have thousands of different keywords targeted. But by building them all in a single website, I am building a mammoth site, Google will know that this is pretty huge; instead of having different websites for different minorly different topics.

Also, when you are starting out, don't you think it would be better to focus on one, and move on to another as the first one stabilizes. Otherwise it would be like chasing more than one hare and catching none.

But by building them all in a single website, I am building a mammoth site, Google will know that this is pretty huge; instead of having different websites for different minorly different topics.

I didn't mean to start ten all at one time, and some people might want to take their chances with one site and many will do fine with that. But personally I sleep a little better having my income spread around a bit, and there have been many times that has worked out for me.

Agree with Jane Doe.
You start one then you think of something extra that is related and you extend the site. Then you think of a concept is unrelated and you start another site.
Eventually you have a quantity of work & sites that mean when you think of a new idea, you don't have time for it and you have to decide whether to not try the new idea, or sell one of the older sites because this idea has more potential.
You don't just try to start 10, you work with the ideas you have.

And, I hate to say it, but while you think of 'telling other people about your site' as spammy, you are unlikely to do well. I am proud of my sites. I stand up tall and tell people what they are and what they offer them. 'Spammy' isn't promoting your site, its only in making bad choices in how to do it.

When I first launched my site 10 years ago, I had t-shirts made and gave them out to all my friends and coworkers. Many probably thought I was foolish, but many of them still have their shirts to this day! I get comments all the time how someone just wore my shirt to the gym or somewhere and people would ask them about the site. 10 years later and I'm still getting a return on those shirts.

Plus people like free stuff. ;-)

One of the common factors you're going to see with respect to people who've been successful on the internet, one that I've seen a lot anyway, is that they were largely already in place years ago. They already had a site, or sites, online and were getting some fairly decent organic traffic and this was all long before the idea of monetizing that traffic ever really kicked in. It certainly wasn't the focus back then. Not with me it wasn't. We, and I'm using the term loosely here, didn't build websites with the idea of making a buck in mind. We built sites because we had information to share and the net was the biggest soapbox we could find to stand on. Monetization only came later.

We built sites because we had information to share and the net was the biggest soapbox we could find to stand on.

Interesting observation wyweb. That is exactly how I started out 10 years ago... I wanted to share some information with the largest audience I could, and help people along the way... It wasn't until 2003 (4 years later) that I found out I could monetize what I had built.

One of the common factors you're going to see with respect to people who've been successful on the internet, one that I've seen a lot anyway, is that they were largely already in place years ago.

I do not think it can be generalized that way. But what can be said is that people who were the firsts in the niche they were in, do have an amazing advantage over the rest.

For example, if iPhone was to launch just today, and I am going to write comprehensively about it, over time, I become authoratitive. I needn't have started it when Tim Berners Lee pronounced 'Internet'.

You make a good point anand84 and I really wasn't trying to generalize that broadly. I was basically speaking about my own experience with internet marketing and how it came to be and the fact that I have repeatedly seen longevity as a key metric in snagging search traffic. I've never bought traffic. I am wholly dependent on search and if it ever dries up I'm going to have to find a real job.

Getting started today would be impossible for me. StoutFiles wrote about luck. Luck has been huge in what little success I've managed to obtain. I got some .edu links way back when. I had PR7 on a junk site that was poorly coded and probably an eyesore to most people yet consistently knocked back 25 - 30K page views a day. It wasn't because I knew what I was doing. It was because I was already in place in a niche that would later become extremely competetive. I was rewarded because I was one of the first, not because I was particularly good at what I was doing. I just happened to get there before most of the others did.

And that was it. There was nothing else. I'm not a good coder, my graphic skills are weak and I didn't even know what SEO meant until 4 or 5 years ago. Nothing I have intentionally done has earned me this position.

My site is older than yours and some idiots years ago felt it was worth linking to, and yes, it is that simple.

I couldn't do it today. It would be absolutely impossible for me to break into this niche without an enormous advertising budget. I'd need the slickest design, the most user-friendly interface, the fastest, friendliest checkout. I'd need SEO skills that I don't have and would probably have to pay for. I'd need a host that was faster than the one I've got now. I'd need a friggin' miracle if I was just starting today. Or two.

With me that's all it was. Luck. My web education started after the traffic started rolling in. The money only came later.

In summary, if I had a day job right now I'd dang sure hang onto it.

Never ever start a business with the idea that it is an Internet business. Or that the primary function of your business is to run a website(s). The Internet is a tool to leverage your business. It shouldn't be where your business is located in its entirety.

Why not? I think with diversified sites, income and traffic sources, Web income can be a lot less risky then having a single employer who can fire you on a moment's notice.

Jane_Doe, what Coachm probably means is that you are limiting yourself and your website's potential if you are only going to think of it as a mere website. If you think of all things you can possibly do had it been a brick and mortar store, then you will end up finding a lot more revenue streams.

I think it's true, but cannot be applicable all the time.

Never ever start a business with the idea that it is an Internet business. Or that the primary function of your business is to run a website(s). The Internet is a tool to leverage your business. It shouldn't be where your business is located in its entirety.

It has nothing to do with whether it is an internet business or brick and mortar shop... it is about the concept/product you are offering... a website or brick/mortar shop are just mediums to offer your concept/product. And in many cases it does not make sense to use one or the other...

So technically the same could be said of brick and mortar shops... it is just a tool to leverage your business...

This thread caught fire.

@ken_b

What about your marketing plan?

Thats been covered and is a living subject.

@leadegroot

2 years thinking about it? You're approaching it the wrong way.

Its too late to change the approach and I understand your point about "just starting" but I don't do anything without planning on some level. as stated earlier I have working prototypes in production, so it would be more of a dedication to it at this point and not really a start from scratch.

@coachm

Never ever start a business with the idea that it is an Internet business.

I see the Internet as a medium. For the purposes of monetization, I have looked beyond it.

I really appreciate the discussion from all of you. This is very valuable feedback.