Contracting Pros and Cons 1

General Issues

Ask yourself the following questions and answer them honestly:
  • Does the contract position hold out the promise of being a temp-to-permanent position? If so, how committed is the employer to living up to that specific promise?
  • Does the contract position pay an equivalent salary that is more than your current salary?
  • If you're hired, how does taking on this contract enhance your skills set?
  • If you get the interview, what is your gut feeling about the people you'll be working with – and for?
  • What is it about this specific contract position that appeals to you, both from a technology standpoint and from a skills set enhancement standpoint?
  • Many times, a firm hires a contract tech writer because they have a skill set that's equal, if not superior, to those of the staff writers, making management's expectations of the contractor that much higher. Are you up to that kind of challenge?
About pros and cons of being your own boss: the advantages and disadvantages tend to be the same. For example:
  • You can determine your own schedule - that can be an advantage or a disadvantage, depending on you.
  • You don't have co-workers - that can free you up to be more productive, but you miss out on all of the things that co-workers bring.
  • You don't have to deal with a boss who doesn't understand what you do in the first place; on the other hand, you don't have anyone but yourself (and the customer) to drive you and make sure you meet deadlines. Remember that some people seem to need a boss.
  • You have to handle a lot of fees, taxes and paperwork that may have been taken care of by payroll deductions before. But you may get to keep a greater share of the value you are generating. That depends on a lot of different factors, such as your ability to get as much work as you can handle (or handle as much work as you get) and the tax structure that you will be dealing with. You may work longer hours, but the compensation goes to you and not some middleman.

Other Comments

  • For many, satisfaction comes from a job well down, some extra spending money (after paying taxes), and knowing that when you're done with a job you'll never, ever see it again!! Except when the client writes a new scope of work, which brings a fresh schedule and a fresh bag of money. Freelancing is great for people who are goal-oriented, but not so great for those who like the comfort of doing the same things regularly.
  • There is the attraction of a 40-hour week and lack of an overwhelming work load. Yet some people missed owning some things, being a “regular” employee (contractors can be very important but that doesn't mean they're treated with the same respect), being able to make a long-term contribution, having sick days or vacation time. They felt that nothing was ever “theirs” and people never forgot they were a contractor. It was hard on their egos and work ethic.
  • Don't be afraid of w-2 contracting.
  • This is the best kept secret. I still say…this is the best kept secret.

Lifestyle Issues


  • What many love is the flexibility. Some are parents, and being able to put in the hours at the time of day they want/need to, is worth all kinds of other trade-offs.
  • Others like being able to take a day off when they please.
  • Some prefer freelancing and doing most of their work at home….working onsite if and when they feel like it. For others, if they couldn’t freelance, they wouldn’t be able to work at all.
  • Some stated that they loved the autonomy.


  • There is reputed to be a high rate of depression among people working at home. You can easily get house-bound, so you need to find reasons to get out and get fresh air and human contact regularly. Perhaps get out for regular bike rides and other sporting activity. Whatever you like to do in leisure time, remember that you need that to keep in good mental health.
  • Some people find it lonely; others miss the collegiality that they had with others in an office. It’s friends that you can pal around with that make all the difference at work.
  • It can be difficult to set limits. Because you rarely leave home to work, it’s not easy to leave work at the office.
  • It can be difficult getting family, friends, and neighbors to understand that just because you’re home all day doesn’t mean that you’re available to kaffeklatsch every afternoon, pinch-hit when someone’s babysitter calls in sick, or gab on the phone.
  • If you have older children, and don’t have separate lines for family and business, set some clear rules about phone use during business hours. And think carefully about call waiting. The same service that lets your business calls beep in on your teenager’s 2-hour chat with her boyfriend also will let said boyfriend beep in on your business calls.

Office Politics


  • Many contractors find themselves much more focused - the issues are more clear-cut; tasks have a beginning, a middle, and an end. Office politics and other internal corporate idiosyncrasies aren’t a factor for contractors.


  • While the pluses of staying out of office politics are obvious, consider what you miss out on. Some factors include: who is the most supportive of certain job functions or departments (i.e., who’s a friend of documentation or usability - and who isn’t), who are the obstacles, who can you go to first when you’re trying to rally the troops for a new proposal?
  • You’re usually the last one to know anything - which can work against you.