The answer to this question depends mostly on what you’re good at and what you enjoy.

Focus on What You Know

The key to launching a successful freelancing career is to start with what you know and then build from there. When a company hires an employee, there’s a certain amount of training that the company expects to have to deliver to the employee in order to get them up to speed. The company is willing to make that investment because they anticipate a long-term relationship with that person and hope that the investment will pay dividends many times over while the individual is employed there.

This is generally not the case with a freelancer for hire. Unless the work is very proprietary or customized, companies expect a freelancer to hit the ground running and be productive from day one. This means that you have to know what you’re doing and be able to deliver without a lot of hand-holding. The best way to do this is to start with something you know well so that you can develop the confidence to deliver a quality result.

Conduct a Self Assessment

Many of the career guides out there have methodologies that you can explore to discover things about yourself. What Color Is Your Parachute? by Richard Bolles is particularly good in this respect, offering many exercises that will provide you with some food for thought.

You can start by asking yourself questions like:

• What am I good at? (…and also terrible at?)
• Do I have any special talents? (such as a way with words, musical ability, an analytical mind, public speaking, a math whiz, artistic flair, etc.)
• Am I a problem solver? (…or enjoy the challenge?)
• Am I creative?
• Do I prefer to work alone or as part of a team?
• What do I enjoy doing? (…so much so that I’d do it for free)
• What activities give you a sense of accomplishment?
• What kinds of goals and aspirations do I have?
• Do I have the right attributes?

The Steps for Self Assessment page of the University of New South Wales Careers and Employment web site offers a good introspective into these questions. Depending upon the results of your self-directed search, the site offers possible occupations at which you could become proficient. Assessments are based upon personality types identified by John Holland, a career choice and development theorist.

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Survey the Market

Before starting any business, it’s smart to first survey the market to determine the potential demand for your services. The first question to ask is: “Who is my ideal customer?” “Ideal” needs to be looked at from several perspectives: profitability, ease of servicing, need for your services, pleasant to deal with, sufficient quantity, etc. Once you identify your ideal customer, start compiling a prospect list with contact information and make a few exploratory phone calls to find out who you should talk to about the hiring of freelancers. Take the pressure off yourself at this point. You’re not looking for a freelance gig just yet, just trolling for information (although one might just fall into your lap, and then how could you refuse?).

You can often gauge the local demand for a particular job by the number and frequency of employment ads for that job, both in newspapers and on the Internet. Also check out sites like Craigslist and freelance job boards like Elance, Guru, and iFreelance for insights into the areas that seem to be in demand.

Test the Waters First

Once you have decided what area of expertise you are going to offer to the world, start small, and see if you can get work that you can do part-time without dramatically impacting the other areas of your life. You might even sign up with a temp agency and request assignments in your preferred area to gain some confidence. Your objective is to get a feel for what the freelance life is like and to use this time to gather ideas about how you would like to run your show.

Try to experience a variety of assignments in small companies, large companies, in different industries, and telecommuting situations where you can work from home part of the time. This will allow you to test out your home office environment to see if it will accommodate you and your family’s needs.

After you’ve done this for awhile, sit down and assess whether things are turning out like you planned. Does it look like there will be steady work? Are the benefits you hoped to gain by freelancing materializing? Discuss with your family how you feel about your new workstyle and check to see if it is having a positive effect on them.

Don’t Quit Your Day Job Yet

Once you’ve done all your due dilligence, followed all the steps, found your niche, and determined that freelancing is the life you want to lead, our cautionary advice would be to conduct one final exercise before cutting the cord with your employer. That advice is to sit down with a financial planner and determine if you can really afford to do this.

Freelancing assignments can be very hit or miss, vary in length considerably, and employers can be notoriously slow at paying you. Needless to say, a steady and predictable income stream it’s not, so you will need to learn how to budget wisely to pay bills that still come in even when your income does not. A general rule of thumb is that you should have 3 to 4 months of living expenses saved up and then you’ll also need another $1,000 to $2,000 put aside for start up costs.

Related Articles

• Types of Freelancing
• Establishing the Value of Your Services
• Successful Freeelancing Glossary
• Maintaining Life Balance