So work for myself or contract?

Good Morning all,
Just recently came across this site and have to be honest, this has me PUMPED! I am a computer / Network Support guy and have been seems like forever. I have always wanted to own my own business and allow my hard work to count toward my own financial freedom, not someone elses. I have been studying and working on doing Java / Flash pages for many years and dabble a lot with it for friends and family and am wondering if there is a market for this to work on my own. My question is this-> "How do I turn what is basically a hobby into something I can make money at?" Am I going to better off looking for companies that will "contract" me to do a job and thereby remove the problems with looking for work or will I be better off just making my own little start up and offering my services to the public? I really do not mind the idea of starting slow and doing all the work in my "off time". Really like the vibe I get from all of the questions and answers I have seen here thus far and am really curious to hear your answers.

If you're the right temperament, launching on your own with contract work will make you focused and hungry... possibly literally. This is good. Working through the joys and travails of contract work will drive you to put you heart and soul into making your startup work or lead you back to the safety of employment.

Quite a few contract workers eventually work for someone they've contracted with. This is not a bad outcome if it answers the self employment question for you once and for all. If instead it drives you to succeed in your startup, you can learn invaluable lessons from your contract work along the way.

14 years ago I went from the safety of a job to doing contract work while working on time clock software that we had just begun marketing on the web. The Internet was just emerging as a legitimate place to publish business software. I learned a ton during those first few years. As a bonus, I still have valuable relationships with companies I worked with in those early years.

Starting with contract work is a gentle, relatively safe way to get a taste for a little more independence and autonomy in your working world. You could even start this while currently working as an employee, doing contract work during your off-hours to test the waters.

Freelancing services like elance and renta-a-coder might be able to get you started with some simple work.

Later, as you get a feel for what you're good at (business-wise) and start to see the problems that customers come to you with (ie. solving somebody's pain) you can evolve this into a startup.

Starting's easy, but stepping off into the unknown can be scary!

Depending on where you are will determine how hard it may be to just find work by just starting your own business.

For example, in Knoxville, TN, much of it is based on relationships, so I am currently doing two contracts that will hopefully turn into them leading me to other businesses, and as I expand my personal network here I will hopefully have more people coming to me.

You will need to be honest about what you can and cannot do, and a reasonable expectation of how long a task will take, otherwise your reputation will suffer, and for a start-up reputation is everything.

My personal preference is to start a startup vs doing contract work. If you do contract then you can get little more money compare to job but still your hard work won't pay off. If you are ready to work hard and want to be your own BOSS ( In reality customer will be your Boss but still better than managers ;) ) then startup is a way to go.