I think the best way to build the confidence to ride a big, tall and heavy adventure motorcycle is to take off-road alone. Yes, alone. If you are always riding with friends, you can rely on them to take you out of a sticky situation. Pretty soon that reliance turns into dependence and you will always want someone around you. Now you may say that you always ride off-road in a group. But as you know, people can sometimes be left behind the group or they may take a wrong turn and end up in the wrong place. In that situation when they find themselves alone, they often panic and start doing things they shouldn’t be doing.
I ride my Triumph Tiger 800 XRx off-road alone all the time. It’s a glorious motorcycle to ride on tarmac. But its 220+ kg weight can be a handful to manage off-road. While on my morning and evening rides, I’m always searching for trails and tracks branching out from the village roads. They often lead to a beautiful place or sometimes a dead end. I make it a point not to wander too far away from civilization since I may need to walk back to seek help. So far that hasn’t happenned. But I have got stuck many times and have had to turn the motorcycle around on my own.
Here is a nice video by Brett Tkacs explaining the most common technique I use. Brett’s Mototrek YouTube channel contains a wealth of information, specially tailored for large capacity adventure motorcycle riders.
I always prefer taking my lighter and more manageable Hero Impulse dual sport motorcycle off-road. But since I do ride my Tiger across India, sometimes alone, it’s important that I gain the confidence to manage it on my own as well.