Steve,
Don't worry, you will have no problems transcending in the future.
It is the very nature of the mind to generate thoughts. It happens all the time, whether we are aware of the process or not.
This process is effortless. For example, if we are sitting at home the thought may come, "I need to get some orange juice." No effort was needed; an inner desire for orange juice grew subconsciously until it matured as a thought.
Just as sleep is natural when we are tired and allow our mind to become dull, transcending is natural when we close our eyes and return to the syllable as effortlessly as we are already thinking other thoughts. The mind, in fact, longs for that restful, enjoyable experience even more than it longs for sleep at night.
Research has verified that transcendental consciousness is a fourth major state of consciousness, along with waking, dreaming, and deep sleep, with its own physiological markers.
If we are walking along a street and hear our favorite music, our mind instantly enjoys it. No effort is needed. This is the natural way to live, effortlessly and without problems. Anyway, what this shows is that the mind is naturally drawn to fields of greater enjoyment. Since reducing the level of activity of the mind is more enjoyable, the mind is spontaneously drawn to quieter levels of thinking, and transcending is therefore effortless.
In NSR, transcending is inevitable in every meditation session. All that is needed is to follow the easy instructions in the NSR manual: pick up the syllable effortlessly and take it as it comes.
Sometimes the mind is gripped by other thoughts. This happens during the release of a particular stress or group of stresses. At such a time it is not possible to think the syllable effortlessly. The instruction is simple: don't try to think the syllable. Just allow the attention continue to be on whatever is happening. Later, when it is once again possible to think the syllable effortlessly (because the stress release has completed), return to the syllable as a faint idea, with whatever pronunciation is comfortable and natural at that time.
The whole process of NSR, diving within using the syllable and coming out on a thought, is natural and effortless, and repeats many times in each session. The resulting deep rest, freedom from stress, and mental alertness is at the heart of all the many benefits we start to enjoy in our daily life.
Read this answer again anytime you feel the need.
David Spector
Natural Stress Relief/USA
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