First, assess your assertiveness skills. Decide on a scale of one to ten how assertive you are.
What situations are you assertive in, and what situations do your skills need work. Document this on paper, since it is important that you know what you need to work on.
Who do you need to be more assertive with? Are there certain people in your life who you speak your mind to, and others who you are more fearful of? This is also important to figure out.
Try figuring out why you are not more assertive with those individuals and situations. What are you afraid of losing? Are you afraid of losing a relationship, a friend, a customer, or an employer.
Document these fears on paper in a notebook. Then, write down the worst case scenario if you were more assertive in these situation.
Decide on the situations that you want to be more assertive in, regardless of your fears. You may be taking some risk, and it is important to assess this risk. If it means losing a job, for example, you may not want to be more assertive with your boss.
When you start to become more assertive, promise yourself to let go of the guilt. You are not a bad person for standing up for yourself, your boundaries, and your rights as a human being.
If guilt starts creeping in, remember that you did something positive for yourself. If there are consequences for your assertive behavior, such as loss of a friend, remember that you gained your self-respect. It is up to you what is more important.
Remember that once you start becoming more assertive with others without feeling guilty, that it will be easier to practice this behavior more frequently and in many areas of your life.
Tips and Warnings
It is important, however, on many occassions to be more assertive with others. And the most important idea is that after you are assertive, that you do not feel guilty about this.
Being assertive is truly important in communication with others, in addition to having people respect your personal boundaries.