It seems that one of the key decisions most web developers, designers, and other web professionals face when moving from one position to the next is whether to freelance or become a fixture in an organization. Web professions seem to have a natural affinity to the “1099 economy.” For several reasons:

• Skill sets can be as individual as the particular path a web professional has chosen. Though many developers can probably work across a range of tools, platforms, and systems, every developer has his or her preferences and experiences. This uniqueness tends to favor a better match of web professional to project, but not favor matching developers to full-time positions.
• Most web developers and other professionals have the ability to work remotely. Few rely heavily on the tools, accounts, and facilities provided by an employer. The lack of that dependency tends to create more independence.
• There are many local and online communities where a web developer can find mentoring, support, and social connections with peers. In fact these communities are often more robust than any that can be found within a single place of employment. Employees of larger development companies still often participate in these other communities.

However, in some cases a web professional might still benefit from taking a full-time position for some or all of his or her career. Not everyone has the instincts, confidence, or personality mix to get the most out of freelancing or consulting. Some reasons a web developer or other professional might benefit from working in an organization include:

• The process of finding clients, negotiating contracts, and maintaining positive client relationships can be trying for many people. Some people like to code, and hate anything to do with marketing or sales.
• Managing details such as invoicing, accounting, taxes, or even project progress can also be far more of a burden on some people than it’s worth.
• Larger projects can be great places to learn new skills, and receive mentoring on overall career growth. These are easier to get into as part of an organization.
• Connections made through a common work experience can be very valuable throughout someone’s career.

Some of these elements are changing as the information economy continues to evolve. It is getting easier for an individual to manage many of the details it once made sense for an employer to manage. But there will always be some kind of tradeoff. For some people, the employer can take away a lot of the distractions and let you do what you do best. Others will want to take more control over everything the make.