Going barefoot is something we have to learn. Maybe we don't have to relearn it every time, but as adults suddenly realising we're allowed to kick off our shoes and noone will tell us off - we usually do. Do you honestly feel that you still know what it was like to squish mud through your toes? Conversely, when did you last actually feel the thorns in your feet that you fear? Learning to go barefoot is about retraining yourself for safety rather than the myth of safety that shoes provide.
Let me illustrate with an example. Suppose one day a friend convinced you to become a vegetarian. He used all kinds of reasoning until you felt that your heavy-meat three-pieces-of-steak-a-day diet was too guilt-ridden to continue with. So, you threw out all the meat in your freezer and swore never to be tempted by the pink-plastic-wrapped stuff again. You didn't know much about nutrition though - it didn't really cross your mind - and you didn't change anything else in your diet. Soon you were craving meat incessantly, feeling like there was this missing something in your life. You felt more tired, which less socially-aware friends deemed as due to the lack of a good chunk of beef. You craved chocolate. Your social life suffered because you only ate chips when you went with friends to junk food stores. Cooking became a real chore, and all the meals seemed to taste the same. There was no excitement in any of it. You discovered that tofu was straight out of your worst nightmare. Very shortly, you were seen out at a well-known steakhouse, grilling your own selection of their finest and grinning the whole way through with your ideals trailing behind, lost on the floor somewhere under all that pink wrap. What went wrong?
Very simply, you didn't know what you were doing. Eating is one of the most natural things we can do, so natural we rarely think about it. By not bringing any good sources of absorbable iron into your diet you felt more tired. Nor did you ensure that you were getting sufficient protein. Eating meat had gotten you into some bad dietary habits, like a too strong dependence on fats and oils and a careless attitude towards the other components of a balanced diet. Removing the meat that protected you from the consequences of your habits brought everything to bear on you at once. So, what could you have done better?
The first obvious thing would be to learn enough nutrition to know that you could keep yourself healthy, to bring certain foods into your diet and be willing to cut down your intake of others. You'd be finding out just what your habits were, and seeing if they needed changing. The second thing you could have done was to explore the new possibilities available to you. You didn't lose meat, you gained a new way of cooking and hundreds of new potential ingredients. Many vegetarian restaurants can provide you with at least a couple of pleasant ways of cooking something, even tofu! There are always new things to put on your plate, as your vegetarian friend would have told you if you'd asked.
So, applying this to going barefoot: Even though it seems a perfectly natural thing to do, there are going to be pitfalls. You probably have bad habits ingrained in you from wearing shoes, as they tend to restrict the movement of many of the tiny and not-so-tiny muscles in the foot. These will need looking at and possibly (though not always) changing. You will need to actually look at the ground where you plan to walk as you go, a habit most people get out of when in shoes for too long. And, like tofu, there are some things you may have to introduce yourself to cautiously before you're really sure you're going to enjoy it. Poorly surfaced roads and sharp gravel comes in this category, and so does picking wild blackberries.
And, always but especially in these sort of cases, don't be afraid to lean on friends for moral support or suggestions, be it for your feet or your stomach. Being open to new ideas and experiences can bring whole new dimensions and delights to anything that you're doing.