It used to be that having a job meant security and that freelancing or starting a business was the riskier choice. Given the last two years, though, you might be wondering if it isn't safer to be your own boss. After all, if you don't have an employer you can't be laid off, downsized, terminated, made redundant, or whatever cheerful euphemism the corporate world is calling it today.

As someone who threw off the yoke of employment almost twelve years ago, I can tell you that freelancing/entrepreneurship is not for everyone. What separates the happy freelancer or consultant from the unemployed nervous wreck is mainly confidence. The decision to go it alone must be made with the confidence that you'll be better off and happier that way. You have to trust that the work will come, as long as you put in the time and effort to find it. It's okay to have a backup plan (mine was electrician), but don't use it as a hedge. Unless you commit fully to the solo life, you'll never be confident you've really chosen it.

To help guide your decision, here are some of the pros and cons I've experienced:

PRO: Your time is your own

When I was employed, I used to resent the hell out of needing time off to stand in line at the post office or go to a doctor's appointment. I felt like I spent every weekend doing household chores that couldn't be accomplished during the week. Having someone else in control of my time was oppressive. As a freelancer, your time is your own. The laundry is always happily running. No one has to stress about staying home all day to wait for the repairman. Best friend needs a lift to the airport? You'd be delighted!

CON: You wear all the hats

Remember how much you used to fume at the IT guy crawling under your desk while your email was down for two hours? In the world of freelancing, you are the IT guy. If you can't figure out how to get your email working, nobody will. You're also the marketing director, the cleaning staff, the saleswoman, the bookkeeper, the accountant, the tax preparer, and the collections agent. Unless you're willing to become at least competent at these tasks, you might as well forget about freelancing. When your business is thriving you can pay someone else to do the dirty work—until then you're on your own. Get used to the idea now that you'll be spending only half your time doing the work you love.

PRO: Every day is casual Friday

The classic stereotype of freelancing is that you can work in your pajamas all day. Personally, I hate working in pajamas. I also hate high heels, nylons, hair spray, and uncomfortable clothes. If you're one of those people for whom a tie is as restrictive as a noose, the freedom to wear what you like is not trivial. You probably ought to brush your hair for client meetings but when you're freelancing it feels like a choice, not a loathsome obligation.

CON: Health insurance

If you are unable to get health insurance through a spouse or partner, this issue may be a deal breaker. Premiums for individual health insurance plans are ruinously expensive. And forget about qualifying if you have any pre-existing conditions—although if healthcare reform is passed, this situation ought to improve. Do I need to say it? You'd be crazy to forgo health insurance in this country. Please don't.

PRO: Get more respect

It's true. As a freelancer or consultant, you automatically get more respect than you do working for someone else. There's something about hanging out your shingle that makes people behave. Suddenly it's okay to say, "I don't work weekends," or "I can't start your project until I finish this other deadline." Suddenly you have the ability to set boundaries. And that's a beautiful thing.

CON: Isolation

When I quit my last job, I knew I'd rather work alone than with people I disliked or was indifferent to. However, not everyone is cut out for solitude. If you cherish water cooler conversations, smoke breaks with the girls, and office happy hour—be aware that freelancing offers none of that. Perhaps more important, you'll be losing the opportunity to brainstorm ideas and get feedback from colleagues. If you've ever worked from home, you know the Internet is often a poor substitute for a face-to-face meeting. While you will by necessity become more self-reliant, there's always the danger of becoming isolated, hidebound, and out of touch with your industry.

PRO: Work on the projects you like with clients you like

A corollary to getting more respect is the fact that the client-consultant relationship is a mutual one. Clients won't hire you if they don't like you. Similarly, you are under no obligation to work with clients you don't like. What tends to happen is you'll get along well with all your clients and extremely well with some of them. Clients will become friends and friends clients.

CON: Income fluctuation

Say goodbye to the steady paycheck. While you might make more money as a freelancer, don't expect it to arrive in nice, $5,000 increments every two weeks. Since cash flow is the lifeblood of any enterprise, you'll want to make sure you've always got a pretty big reserve to tide you over when things get lean. One delinquent client can suddenly have you scrambling to cover expenses. If this kind of uncertainty gives you stomach cramps, might want to hold on to that paycheck.

PRO: Success is what you make it

This is a subtle point, but an important one. The standard career path really can become a rat race where you lose sight of the things that truly make you happy. For most of us that means spending time with family and friends and engaging in meaningful hobbies and activities. Your income may go down as a freelancer. You might spend a lot of time worrying about how to generate business. But you'll also have the space to examine your life and what you're doing on this earth. The conscious act of choosing every day to freelance or run a business—and acceptance of the compromises required to follow that dream—can be a powerful model for other life decisions.

CON: The never-ending job search

Some people are natural self-promoters, god bless 'em. And some of us would rather chew our arms off than get up in front of a crowd and say, "Look at me! Aren't I great?" I truly think marketing has been the single hardest aspect of running a business. Unfortunately, unless you subscribe to the cross-your-fingers-and-hope-for-the-best business model, you're going to have to get out there and promote yourself. Regularly, if not constantly.

[ Kim Bieler wrote this article and she welcomes your comments. ]