There is at least one really good reason for not giving up a day job in order to do something you love. The things you love to do may not be exchangeable for enough income to live on.
This scenario of dull remunerative day job vs low-paying ideal job may be the most common situation of all. Many of us enjoy doing cool things that are a lot of fun and have found that very few people want to pay us to do them.
Photographers are keenly aware of this. Shooting beautiful photographs of exotic locales has enabled them to earn respectable incomes in the past. Today, digital cameras put professional technology into the hands of anyone with an American Express card. It is a lot easier to capture a hummingbird in mid flight or a boxer at the moment of impact than it was in the past. Digital cameras and minicams allow everyday citizens to capture events in high resolution color and sound that were the sole province of professionals just a few years ago.
Singers and musicians often find local venues which they love and where they are thoroughly admired. These venues often cannot afford to pay them very much, but they do offer them an audience and time on the stage. A weekly gig in front of people who love you does a lot for your soul and for your skills. The rewards are so great that it is worth keeping the day job.
Abandoning a friendly local venue for larger and possibly indifferent audiences in order to make your art a paying proposition calls for a drastic change in your attitude to your art. It is no longer a labor of love, you have to make decisions that will maximize your income. You have to play what the listeners want, not what you consider important. It has become a job. And then some drunk in the back yells, "Play Freebird!" and you wonder why you ever gave up your day job...
Programmers run into the same kind of trap. They start out writing games or cool applications at night and they find out that no one wants to pay for them. They haven't done their marketing or they would have found that people readily pay only for dull things like maintaining legacy software or utilities that run on Windows machines. Innovative software applications take an incredible amount of creative effort and require endless amounts of support, which startups rarely plan for and almost never deliver.
Freeware is the programming equivalent of a musician playing for the joy of it. Shareware is the equivalent of playing for tips. Both have their place in the world and are best supported by a solid day job that does not take over your life.
There are exceptions to every rule, of course, and I know when someone works very, very hard doing what they love and pushes themselves to achieve greatness, that their creations DO eventually command prices that free them from their day jobs forever. This may take years of struggle and personal deprivation, but it can be done. Furthermore, these people may still love what they are doing, even when it has become a livelihood instead of a labor of love.
Jeannette Caruth has made that transformation, and is reaping the rewards of years of learning to paint while supporting herself with a day job. I know of several others who have mastered a skill while supporting themselves with a day job.
The acid test is how good do you want to be? Good enough to be applauded, or so outstanding that people bid for your services? In either case, keeping your day job allows you to flex your wings before you have to fly for a living. In many cases, you may decide that a balance of a secure job and a non-paying but rewarding career is the optimum path to follow.
How many find that this describes your situation?
What would happen if you could keep this going for years?