Thanks Greg, indeed much of these things is about the head.
To enjoy breathless diving you need confidence and the ability to forget about analysing.
To facilitate this you need to be weighted correctly, know your limits and abilities.
Do you have a buddy?
If you do you can safely go past some contractions, do a nice Co2 schedule etc.
If you're alone, it's is impossible to explore one's abilities and limits.
A thing you can do however is to limit your dive to your first contraction, without hyperventilation (!).
This is the easy comfort zone. Your challenge becomes, "how far can I get comfortably".
You'll need to learn to relax all your muscles, streamlining, breath and hr control, swim efficiency.
When I start my water session, I usually do some muscle warm up swims. Free stroke, back crawl are excellent to warm and loosen up all the body parts.
Now test your weighting in the pool, us a deepish exhale, followed by a slow (~7 counts is fine) belly and chest inhale, and gently push of at the shallow end of the pool and see weather you float up or sink. If you got extra weights correct your buoyancy to be neutral. If you do not have weights, then you need to reduce the amount of air in your lungs.
Once you've found this, lets' go for a swim.
I like to experiment, and often deliberately go extra fast / slow in order to learn the upper and lower limits of my technique and materials.
So just play with all the variables, propulsion, streamlining, stiff - loose etc.
After a short while you'll find something that works reasonably well.
You can see how far you get until you first contraction, when you do have that, slowly come up to side of pool (swim next to the wall).
Now some mental trick.
When you swim focus on feeling the water flowing over your skin. You can trust you subconscious to do the technique, you just focus on feeling the water and enjoying it. It helps to keep the eyes nearly closed (less distractions and input to consume your brain computing cycles). This trick works because it helps to stop judging and estimating where we are and where we may get. It helps to keep the mind in the moment, and enjoy that more.
Remember to limit your self to the first contraction, and do not hyperventilate (Breath more volume of air then you naturally do).