Are You Cut Out For Contracting?

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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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?

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?

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

"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?

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?

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.

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?

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?

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?

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?

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?

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?

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.

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."

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

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