Are you thinking of quitting the nine to five?

It's likely that there are some things about your job that bug the tar out of you. We all have days like that, including me.

Work may bug you enough that you might start up a side business after hours. Once that side business gets rolling and you look at the numbers, you might begin to consider handing in your two weeks' notice.

The money you're bringing in might equal your salary at your day job, or you think that you might be able to get there quickly enough with an extra 40+ hours per week working at that side business.

If this describes you and you're working towards being able to work from home, that's great.

You've come to the realization that there is no such thing as free time, and you like having more than one basket to put your eggs in.  You may have come to realize that business sectors fall in and out of favor and experience rough times after the booms, and want another source of income as a hedge for those rough times.

I'm nowhere close to being able to quit my job with the side income I get from my ventures (including this blog) but I'll share some of the things I'll need to get in order before even considering this seriously:

• The money to replace my job would be way more than just replacing my salary.  The paycheck is just the start of my compensation for my job.  I also get paid holidays, paid sick leave, bereavement, paid jury time, group health insurance, group life insurance, and retirement plan matching.  I have the benefits of a payroll department taking care of most of the financial communication with the IRS, as well as other benefits of the division of labor so I don't have to do everything myself.  Most of these benefits go away along with the paycheck if I were to quit.
• Going to being my own boss might be a rough transition just in terms of getting things done.  I've heard both sides of the story from people who have gone from employee to self-employed.  The lack of an externally-imposed schedule staring me in the face would be scary since there's even more of a burden to work efficiently.  Sometimes the wheels of the workplace turn slowly, but that inefficiency can act to reduce the expectation of what results can be achieved in a regular workday.  Having more time to fill efficiently is great, but without a well-oiled workflow it won't be a benefit to have more time.
• I'd be in closer proximity with my family.  That's an absolutely wonderful thought but as hard as it is to tear myself away from my wife and daughter when I need to go to work, I'd need to do the same thing if I were at home, and that would mean either becoming The Bad Guy during working hours and turning my daughter away when she wants my attention.  That can create extra stress.
• The work may change if I'm depending on it for all of my income.  Blogging is fun now.  If I have a slow month and the commission checks aren't as high as they usually are, it's not going to give me an ulcer.  If my websites are down or if my internet connection goes down because of a storm, it's not that big of a deal.  But why?  Because right now I don't need every penny I get from my websites, because I have a more stable job.  I know I be way more stressed if I had nothing to fall back on.  Would that take the fun out of it?  Probably some of it.  Would it still be enough fun to justify the heartburn?  I don't know.
• It wouldn't be my decision alone.  My family and I are used to a certain standard of living now.  If I were to quit, our standard of living would drop for a time.  Even if I were making more at blogging than I was making at my day job, the loss of the day job's income would hit our standard of living.  The reward for doing this (hopefully) comes down the line a bit but until that happens the finances would be tight.  These decisions would be much easier to make if I were still single, but I'm not.  There's nothing wrong with this — I love being married and being a father — but it is a very important consideration that I ignore at my own peril.

I'll be the last person to discourage you from trying to work for yourself, but depending on where you are in life the transition may need a lot more planning than it would have at other times.  The route I'm taking now is just to keep my day job and build up the other stuff after hours.  This likely will limit what I might achieve at the other stuff, but quitting now would be too risky for my family's well-being and comfort.  These are decisions I make, and they're decisions that you'll have to make, too.