Awakening is not an end in itself , but means to an unknown end।This is the problem!Our conditioned minds see every pursuit in terms of reward and punishment, or gain and loss. We humans have lost the virtue of doing things for doing sake.There is always an incentive. The desire to grab that incentive turns a joyous journey to a painful and tense conflict.Existence doesn't work like this. Everything around us is happening without any reason. Life simply is! Howsoever hard we might try to rationalise it. So, firstly, awakening can not be a tense hammering on us, rather it is a smooth dawn of realisation of small pleasures and joys of day to day life।
And thank 'God' , there is no end to awakening। It wud have been so boring that every Buddha, every Krishna, every Muhammad, every Christ wud have immediately committed suicide on becoming realised souls।

For example, when Jesus is being crucified, he looks up the sky and utters"oh father you have deserted me". but, the next second, as his consciousness soars he realises his mistake, bows his head in surrender and utters"thy will be done". that is the moment he becums Christ. An awakened soul becums more awakened .
Same is a story in Ramkrishna Paramhansa's life. He was a realised soul ,in constant conversation with Maa Kaali. In the later years of his life he went into Vedantic sadhana and had to cut through that very same Kaali in his meditation.When he came out of his meditation , on being asked by his teacher Totapuri ,Paramhansa said "The last barrier has fallen".
Even he had barriers to overcome.so, I guess it is all about our evolutionary level.The spiritual world is a voyage to the unknown with very unpredicatble path and results.Since the quest is infinite, the journey can not have finite parameters too.