Know your work habits.
In any online writing, you need to be able to work independently. But if you are working for clients or content sites, you may need to pair that with teamwork. If you don't work well with others, you may want to go solo and write for your own blog or domain. But even then, you might still need to deal with people in one way or the other. If you like to be the only one to correct the work and will accept no changes to your material, you're better off writing for yourself. But keep in mind that even if you don't have to bend for editors, you still need to consider what your readers want.
Pay attention to your writing style.
What style and voice is present in your work? Can you change it up some to fit what clients want? If not, you may be better off either finding clients or content sites that align with your style or writing for your own venue. Check out contributor communities and content sites to see what the top writers are doing. Does it look like something you'd be interested in doing? If not, move on to the next or create your own venue that matches your style. When writing for private clients, I learned that analyzing their needs based on their audience and existing content helped me provide the best content for them. If you'd rather write freestyle without analyzing things, your own website may be the best option, providing you will still cater to the audience.
Consider your schedule.
Managing time and deadlines will be of more importance when writing for content sites and private clients. You'll need some sort of schedule when writing for yourself. But it will likely be more flexible that way. Some private clients may prefer to speak with you about projects during certain hours. Usually it will be normal business hours. If you cannot commit to that or are unavailable during the day, content sites, contributor communities, and your own domains may be the better option. Most contributor communities do not require you to be available during specific times. There can be deadlines if you claim certain assignments, but it is up to you at what time you write the material.
Think about your goals.
Are you looking to get your byline featured across multiple sites? Would you rather keep your name to its own venue? Do you not want your name out there at all? What are your revenue goals? Writing for private clients can sometimes involve a great deal of ghostwriting, which means your byline will not be featured with the content. Content sites generally feature your byline with the content. Some also offer opportunities to be featured on high quality web properties. It could take more time to build up a reputation on your own venue. But if that is what you prefer, the hard work can pay off, if done right.
The best fit for you is the closest to covering your main desires.
Consider all of the above, as well as any other factors that are important to you. Then, decide which option most fits that mold. You could be like me and choose a combination of two methods, choose just one, or go for something else together. Regardless of which choice you make, be sure it is one that aligns with your individual goals and dreams for the future. Remember that not everyone will have the same needs. Just because one plan works for your friends does not mean it will do the same for you. Align your writing career with your unique plans for the best results.
*I originally published a version of this via Yahoo Contributor Network