Assertiveness - How to develop it?

Q:  I tend to be a "people-pleaser."  This gets me into trouble sometimes.  I follow the crowd and it's not always where I want to go.  Do you have any tips to help me get over this?  I am a male in my early twenties.  F.S.

A:  First, acknowledge the skill that you have already developed.  You know how to please people and go along with the crowd.  This is not a bad thing in itself.  So I suggest you place value on this skill and keep it in your toolbox, because you might need it again someday.  It sounds like you over-use it, though.

Second, deepen your acquaintance with the person you live with 24-7, birth to death, guaranteed.  That is yourself.  Learn your feelings by tuning into them often.  Experiment with your likes and dislikes, in healthy, appropriate ways, so that you know them well.

Third, do you respect yourself?  Self-respect often suffers when we overly use people-pleasing.  Measure your current level of self-respect on a scale of 1-10.  Set a reasonable goal to improve that number, and check in every week or so.

Fourth, become familiar with the terms pro-active and re-active.  When you find yourself reacting (going along with the crowd), realize that you could be pro-acting instead and explore ways to do it.  Proaction gives you decision-making power over your own life.

Fifth, when you find yourself going along against your better judgment, refrain from judging yourself.  Resisting the status quo perpetuates it.  Instead, go "outside the box."  Instead of blaming yourself, say with great interest and curiosity, "Oh, there!  I just people-pleased again!  How interesting!"  That will break the cycle of people-pleasing > self-blame > more people-pleasing.