PHOTO: Jon Feingersh/Getty Images; Post-Its: UFUK ZIVANA/iStockphoto

Most of us dream of being our own boss, answering only to ourselves, choosing what we’ll do and when, and accomplishing great things on our own. Many of us have already accomplished this goal. Some of my former engineering students started their own consulting firms soon out of college. I started my own business eight years ago, after a 30-year career at a public agency. And we all know of the famous bosses of technology—the Steve Jobses of the world who go out on their own to develop the megaproducts of our age.

But, alas, most of us have to deal with the challenges of getting a steady income, putting food on the table, and gaining experience in our chosen field, supported by our employers, before we can consider breaking away. So how do you know when you’re ready to branch out on your own? Here are some things to consider on the “if” and the “when” of becoming your own boss.

Identify where you are already your own boss. In your current job, what activities are you responsible for, how many people do you supervise, what level of dollar responsibility do you have? These are all measures that show you are accountable for results, with some degree of independence. Don’t forget to include your membership in voluntary organizations, like professional societies. Being a chair of a professional committee or a scout leader gives you some measure of taking responsibility for running things.

Ask yourself what you like and dislike about having responsibility. Are you comfortable when other people depend on you to make decisions, or would you rather not have the added pressures? Are you willing to work harder and longer hours to get a job done, or do you place a higher value on being able to leave work at a regular time each day? These are tip-offs on whether or not you have the inner drive and motivation to be successful on your own.

If you’re looking for more opportunity and autonomy, here’s something you can do right away: try “managing your boss.” You can exert more control over your work than you think by helping your boss. Don’t wait to be told what to do all the time, take more initiative under your general guidelines, keep your boss at least as well informed as he or she would normally expect, and see whether you get more support. Treat your job as if it were your own “candy store”—as if you were running your own business. This attitude will probably make you more effective and give you a sense of how you would operate if you became the boss.