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Summary:

In the spirit of reuse, I thought it would be nice to put all of my thoughts the pros, cons and things to think about when making the move between corporate web working and freelance web working, and vice versa.

cubicle

On March 1 I became a full-time employee, but I continue to spend most days as web worker telecommuting from my home office. Prior to taking this full-time position, I had been a freelance consultant for almost two years. Friends who are considering similar moves in either direction have recently asked me for advice. In the spirit of reuse, I thought it would be nice to put all of my thoughts the pros, cons and things to think about when making the move between corporate web working and freelance web working, and vice versa.

Advantages of Corporate Web Working

  • Regular paycheck. It is really nice to know exactly how much you are going to make and have it just magically appear without having to send invoices or nag to get it.
  • Taxes. These also magically come out of your paycheck with less hassle and no dealing with quarterly payments and more complicated taxes.
  • Insurance and retirement. Both of these are considerably easier and often better than what you would have as an independent worker when you look at things like company match in a 401k and the quality of many corporate insurance programs.
  • Less paperwork. Unless you happen to be a corporate accountant, corporate web workers can often avoid the piles of paperwork that are associated with running your own business.
  • Paid vacation. I like being forced to take a couple of weeks off a year and still get paid for it.

Advantages of Being an Independent Web Worker

  • Flexibility. When you are your own boss, you can be as flexible with your time as you want without worrying about your boss thinking you are a slacker.
  • Choice of projects. As an independent worker, you can pick and choose the projects that you want to work on (or not), and you can choose to work on something slightly outside of your normal work, either just for fun or to expand your skillset.
  • Tax advantages. Depending on how you organize your business and expenses, you can end up paying less in taxes because of all of the things you can write off as part of your business.
  • Balance. It can be easier to balance your work with other parts of your life when you have complete control and flexibility over your schedule.

Although I have listed five advantages for corporate web working and only four for independent web working, it’s not a question of numbers. The real question that you need to ask yourself is which of these advantages are most important for you and your current situation. In other words, you need to think about what you want, your expectations and your working style to decide what it right for you at this point in time. Here are a few questions that you might want to ask yourself:

  • Do I really want to own my own business? Is the increased flexibility worth all of the extra paperwork, or would I prefer to work in a more traditional corporate job?
  • Am I self-motivated and will I push myself hard enough to be successful on my own or do I rely on having a manager provide me with work and feedback?
  • Are my skills and talents better suited to freelancing or a corporate environment?
  • Can I market my skills to make the change to the corporate world or to become a freelancer?
  • How do I want to spend my time?
  • What do I enjoy doing and which path would allow me to more fully enjoy my work?
  • How well do I handle different types of stress? Keep in mind that financial, personal, project and other stresses may have a greater or lesser impact on you.
  • Are you comfortable with uncertainty, particularly financial uncertainty, or do you prefer to have stability?

For me, the decision to become a freelancer was the right one at the time. I had never been a freelancer and wanted the experience of having my own business. After the excitement wore off and the burnout from the long hours started to set in, I decided that going back to the corporate world was the right decision for me at this point in my life. I was lucky enough to maintain some of the flexibility to work from home most days while still having the advantages of a corporate job.

Have you moved from freelance to corporate web work or vice versa? What were the factors that persuaded you to make the move?

Related GigaOM Pro content (sub. req.): Enabling the Web Work Revolution

Cubicle photo by Mark Sebastian used under the Creative Commons Attribution-ShareAlike 2.0 Generic license, and bird photo by Flickr user Yogendra Yoshi used under the Creative Commons Attribution 2.0 Generic license.

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  1. I have the release of my new website scheduled for next week completely handled by freelancer – I enjoyed working with Lee . Second time trying to free lance a big project out. First time I was really sick of the freelancer begging me for a bonus..this time is all on track.

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  2. Great post Dawn, I’ve always has a full time job, which I sometimes work from home, but have always also been a freelance web worker in my spare time, I’m hoping to become a full time freelancer in the near future, but got a lot of planning and thought to go into it before I drop the security net.

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  3. Good balanced overview, and glad you’re able to retain much of the flexibility you had while getting some of the ‘corporate’ benefits :)

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