Understand his strengths & weaknesses.
Having a good sense of self worth involves knowing your own strengths while working on your weaknesses. Just because a person is confident in his strengths and talents doesn't mean he has to be arrogant. Teach your teenage son to be proud of his abilities and gifts without being condescending to others. A strong self image can help him perform at school, excel in sports and relate with friends.
Set him up for success.
Every person is good at something. It may take some trial and error, but you need to help your teen find his niche. Once you have identified his talents, you can put your son in the position to succeed. If he's a gifted athlete, allow him to play sports. The healthy competition and camaraderie of team sports and organized athletics can boost self esteem and strengthen skills. If he's a talented musician, invest in lessons or instruments if possible. Even if his strengths and loves aren't the same as yours, nurture his abilities and support his choices. Praise his progress and celebrate his achievements, whether they're big or small.
Check out his friends.
Friendships are important to teenagers. The teen years are also a time when many kids make mistakes regarding friendships. Though you can't pick and choose your child's friends, you can encourage him to surround himself with people who have the same values and character. Make your home a place where your teen can bring his friends to hang out. This will allow you to check out and monitor his relationships without being overbearing. Teach your teen that friendships should be built on honesty, respect and common interest... not based on what's cool or popular.
Improve your own self confidence.
Break bad habits so you don't pass them on to your children. Don't always put yourself down or be fearful of trying new activities. Raising confident children can be therapeutic and can help you deal with your own self esteem issues. Do what you can to strengthen your own self image and boost self confidence, while passing on positive messages to your teenage son.
Encourage him to open up.
Communicating with teenagers can be difficult, and teen boys have a more difficult time talking to their parents about doubts or problems than girls do. Encourage your teen son to express his emotions, and don't discourage him with old stereotypes about masculinity ("boys don't cry"). You'll often find boys are more willing to open up when taking part in a task or activity, rather than just sitting down for a talk.
Try to engage your teenage boy in conversation during an activity such as doing yardwork, drawing or even playing video games. The lack of eye contact may encourage him to communicate. Once he starts talking with you about his problems or concerns, you'll be able to work with him to find solutions and help build his self esteem.
Give him more responsibility.
Help boost your teen's self confidence by showing your confidence in him. By giving your son more responsibility, you'll enhance his self worth. Make it his responsibility to do the weekly yardwork, go grocery shopping or pick up younger siblings from school. He can get his first job and pay his own cell phone bill or car insurance. Volunteering is another excellent method to help your teen boy feel good about himself. Giving back to others or working with a team to reach a goal will help him achieve a sense of accomplishment and pride.
More tips for parents of teens
How to help teens adjust to a new school
What to do when a teen loses a friend
Helping teens form real friendships