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When I started off in GTD, I didn't even use a computer program. I wanted to keep it as simple as possible. I stuck with pen and paper for about 6 months before I got comfortable with GTD.

I would envision your friend following the same route. It's tough enough to add GTD into your life while also trying to learn how to use OF.

Your friend (like many of the GTD adoptees including me) will fall off the bandwagon then get back on again. It's just gonna happen because he needs to make GTD a part of his daily habits. And any habit is hard to adopt. For example, I wanna get fit. But going to the gym is unnatural for me. So I have to learn to adopt the gym habit into my daily and weekly habits. Some days I'd look forward to going to the gym. Other days, I just wanna be a couch potato. It takes some effort to go to the gym until it just becomes a habit and I automatically head to the gym on Monday, Wednesday, and Friday.

GTD didn't finally click in for me until I read a blog article called Zen To Done: The Ultimate Simplicity Productivity System (also known as ZTD).

Here's a quote:

1) GTD is a series of habit changes. This is the main reason why people fall off the GTD system ó itís a bunch of habit changes that are attempted all at once. If youíve read Zen Habits long enough, you know that focusing on one habit at a time is best, and guarantees the most success. In addition, GTDers donít apply proven habit-change methods (the ones I talk about on this site) to change their habits.

Solution: ZTD focuses on one habit at a time. You donít have to try to adopt the entire system at once ó itís overwhelming and itís too hard to focus on your habit changes if you do too many at a time. Instead, focus on one at a time, and adopt the system in phases. Use proven habit-changing methods (30-day challenge, commitment, rewards, motivation hacks, etc.) to successfully adopt each new habit.
There are 10 habits in the ZTD system. I printed this out on a single sheet of paper and started adopting one habit at a time. I choose one of the habits to work on for a few weeks until it becomes auto-pilot. So far, I've gotten six out of the ten habits on auto-pilot. When I feel like I've adopted the habit I've been working on it, I check it off and then choose another habit to adopt.

It wasn't until I got to the ZTD habit of "reviewing your system and goals weekly" that I started using OF. OF has helped me with this aspect quite well.

The eBook (PDF format) can be found here:

It distills the 10 habits into book format making it easier to read. It's well worth the download.

The ZTD variation of GTD has helped me tremendously. Now it's not so hard to adopt into my daily and weekly habits.

I'd also recommend downloading all the OF video tutorials and the manual on the OF page so that he can get familiar with OF. That certainly helps a lot.