To succeed as a contractor, it's critical to go beyond examining your technical strengths and weaknesses. You have to understand what makes you tick.

By Ingrid Goldbloom Bloch | August 2008

Whether by choice or because of shifting market forces, at some point you may face the question, "Do I want to work for myself?" Being a contract worker can be your ticket to freedom from office politics, flexibility and larger earnings. But if you don't have the right temperament, contracting can present a host of problems.

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To succeed as a contractor, it's critical to go beyond examining your technical strengths and weaknesses. You have to understand what makes you tick. According to Alice Ain Rich, a career counselor and human resources advisor based in Boston, "You have to become CEO of yourself. You have to be in charge of your own destiny. You are, in essence, your own product."

To help determine whether you'd be happy - and successful - as a contractor, ask yourself these questions.

What is my marketability?

Often, people both under- and overestimate their abilities. In today's marketplace, it's important to have a realistic view, to understand what technology is hot and which companies are using it. Ain Rich suggests forming your own "board of directors," people who will give you honest feedback about the compatibility of your skills and work style with the current state of the industry.

How good are my marketing and communication skills?

For many, this is the toughest area. You simply must be able to promote yourself, to communicate to others what you've accomplished and get them to understand your value. "When it comes to self-promotion, most of us stink because it brings on a whole new psychological component than when we are promoting someone or something else," explains Ain Rich.

"Marketing yourself is completely different than performing that function within a company," adds Rich Cohen, a former independent consultant who's returned to corporate life as vice president of product management at a UK-based telecommunications company. "When I became a contractor, I had to use the same skills to market myself that I used for my company's products and services. I became the entire company and had to perform all the marketing functions from soup to nuts."

Do I take initiative?

Contractors need a certain mindset of initiative, perseverance and determination. Richard Rosenlev is a software engineering contractor for 23 years who is currently on a long-term contract with the semiconductor tests division of Teradyne in Boston. "You need to be in constant job search mode," he says. "I used to go to networking groups ¿ Then I got lazy. I worked for one company for eight years, and when I got out, there were no jobs and no networks.¿ Rosenlev started over by scanning newspapers and Web pages to find jobs he could do and problems he could solve, and worked hard to convince companies to hire him.  Now he networks on an ongoing basis.

You also must be in charge of your own learning and development. "People are expected to be independent, self-motivated and work through things on their own," says Ain Rich. "Companies don't want you to learn on their time."

What motivates me to do good work?

If you command a high enough wage to cover your benefits and account for time spent looking for work, you can make a good living as a consultant. However, factors besides money motivate people: Not having to deal with crazy bosses and office politics, for example. Or, time flexibility, or the excitement that comes from working for different organizations. "What I love about my work is that I've been exposed to many different environments, industries, technologies and people. It's been very intellectually stimulating," says Cohen.

Since you won't have performance reviews, validation for a job well done has to come from your own personal satisfaction that you're doing good work and making the right trade-offs. 

Do I have decent time management skills?

You need to balance your time working with time off. You need to build in time to network for future jobs as well as make time for ongoing training and development. Some may have difficulty working at home: "They say to themselves, 'What's in the refrigerator? What's on TV?' If you can't buckle down and do the work you are going to be in trouble," cautions Rosenlev.

How important is it to me to have Colleagues?

You aren't truly part of the company or part of an ongoing team. Dr. Bruce Katcher, president of Discovery Surveys in Sharon, Mass., and former president of the Society for Professional Consultants, notes contracting can be lonely, especially if you are someone who needs connection with others. "If you have an ID it will be a different color, and if there are bagels, you can probably have some, but they weren't meant for you," he says. However, Ain Rich adds, if your self-esteem comes from getting the technical aspect of the job done - as opposed to being social and connecting with others - you're actually better off. Ultimately, you need a thick skin, and you can't worry if people like you or not.

How do I view my contributions?

Do you need to see projects through to completion or is it enough to know your individual contribution was enough? "When working on term projects, you won't see a project through to fulfillment," observes Katcher. "If you want to have a say in the development and see the people use the code you wrote, you won't as a contractor¿"

Can I tolerate ambiguity and risk?

Are you the kind of person who's willing to live with a level of uncertainty? If you have a family, are they capable of supporting you through the ups and downs of contract work? Can you ride out the slow times with a degree of calm and certainty? "It takes a degree of courage," says Cohen. "You rely solely on yourself. When you are an employee, there is a larger entity that supplies support and some degree of predictability."

What environment do I do my best work in?

Are you energized by the kind of risk, change and undefined rules you would find working for a start-up - or do you prefer stability and structure? Do you want to work as part of a problem-solving team, or do you want to be independent? Do you need the buzz of an office environment or the ease of working from home? By identifying the work structures that support or stifle you, you'll be able to seek out opportunities that allow you to be most productive and happy.

Do I have good negotiating skills?

Negotiating is often difficult for people. It's one thing to know what you want, but it's another thing to ask for it. From childhood, people have been conditioned not to be greedy or pushy. You may fear that if you ask for too much, a company won't want you.  
If you've done your homework, know your value and the going rate for the type of work you do, negotiating will be much easier.

"Don't sell yourself short," Katcher advises. "Provide them with several options for what you can do for them and how much it will cost for each option. That way you will not be negotiating whether you will work with them, but how you will work with them. Clearly define the deliverables so that if there is scope-creep you can tell them that it will cost them more for you to do this additional work."

"Contracting is a complex work commitment with its own joys and pitfalls," says Cohen.  By taking an inventory of yourself beforehand, you will be going in with your eyes open and you will have a better chance of success.

Ingrid Goldbloom Bloch is a career counselor and career development trainer based in Newton, Mass.