It's good to challenge ourselves with paths that are uncomfortable, as discomfort often makes us wiser, stronger, and more successful in all that we wish to do.
It's also good to travel paths of support and ease--those paths strengthen you too and help you to ally yourself to comrades, colleagues, and friends who will be your good companions and sources of support over time.
The comfort-discomfort balance is important to consider. You don't want to challenge yourself too much, and you don't want to choose for comfort too often either.