Disqualify the myth. The first step that needs to happen when working with teen boys is to clearly explain that journal writing is not the girlie activity of keeping a pink diary under the pillow. Show him examples of journal books from distressed leather to simple spiral notebooks to online sites such as livejournal.com (see Resources). Read samples of journal entries written by famous males.
Interview the teen. Teen boys probably do not know what to write about. Many see writing as poetry or flowery prose. Ask him to tell you about his interests. Keep a list of what he says. Prod him to elaborate on sports, cars, hunting, or other interests he may have. You have developed a list of ideas for him to write about. Engage him in the activity. Ask him to list three words that best describes himself or three words to describe his favorite sports figure. He will soon discover he has a lot to write about.
Practice with sentence starters. Give him a list of three to five sentence starters and he fills in the rest. Then ask him to write freely for five minutes on one of the sentences or anything derived from the sentences. Remind him not to worry about spelling or grammar. Tell him to write naturally. Don't go beyond five minutes for the first exercise. Normal free writing is a ten minute activity, but for a reluctant writer, this may be too long. Judge what he can handle for a time limit. After the time is up, ask him to underline any key words or phrases that interest him. Try the free writing again. This time have him focus on the words he picked out. This is focused free writing. It helps writers to narrow their thoughts.
Read the opening to the book, "Catcher in the Rye" by J.D. Salinger. The style of writing is Stream of Conscious which is the basic idea of journal writing. You write what comes into your mind. Besides, he may want to read the book after hearing the first page. The main character is a teen, so it allows him to get into the mind of a teen character who is not stereotyped by the times he lived in. The main character is a boy struggling with all the conflicts most teens contend with such as independence, loss of a loved one, and relationships with girls.
Introduce him to the world of online journals. Livejournal.com has a great tool for designing your own journal layout. You decide if the journal is private or shared with a few friends. Wordpress.com is a free blog service that gives you the tools to customize your own blog. Explain the difference between blogging and true journal writing. Blogging is more public, whereas the journal is more for private thoughts. He may wish to do both, but the blog will open up a world of creativity that may lead to the private journal. Besides the online journal or blog, he can create his own journal in a word processing program.
Practice writing in a regular journal. Even with the world of computers, sometimes the regular journal gives you the freedom to express yourself any time and any place. There's something gratifying about a nice leather bound journal that you can watch fill and then go back and see what thoughts developed over time. Explain that it's his decision to use the tool he likes best, computers or notebooks. He may decide to use both. This is great for him and great for you because you just unleashed a new thinker of ideas, thoughts and discoveries.