We might look at this particular aspect of the jiva issue from a different angle, so to speak.  Maybe you can feel comfortable, and have a better understanding of how and when that choice is made, by churning the following in your noodle.  While certain aspects of this particular issue are inconceivable, they are certainly not incomprehensible.

I started to contemplate the different possibilities of when the jiva is here in this material world, and when it first exercises its will and makes a choice to serve Krishna or to serve Maya.  

When does the jiva have a choice and when does the jiva not have a choice? 

The following are the possibilities that I could think of.

One:  A jiva is a resident of Vaikuntha, and it is here in this material world because it is participating in some lila of the Lord.  The question I have, did this jiva have a choice or for that matter not have a choice?

The only reference that I know of is that of Jaya and Vijaya.  Jaya and Vijaya did not really fall into the material world although cursed by the Kumaras.  They came to participate in the Lord’s pastimes.  Therefore, Prabhupada writes in Purport to Srimad-Bhagavatam 3.16.27,

“‘The inhabitants of Vaikuntha never return to the material world, but the incident of Jaya and Vijaya was a different case.  They came to the material world for some time, and then they returned to Vaikuntha’.

Srila Jiva Goswami writes that the feeling of enmity which Jaya and Vijaya acquired for the Lord is not because of the Kumaras” curse; rather it was by the will of the Lord.  By His sweet will, He wanted to enjoy fighting with them.  Moreover, the Lord does not consider anyone as His enemy because He is free from all dualities.  One should not think that Jaya and Vijaya chose to become enemies so that they could finish the curse quickly, because great devotees like them do not desire even salokya mukti without bhakti.  Moreover, with bhakti they are willing to go to even hell.  One should not think they chose to become enemies so that they could give the Lord the pleasure of fighting.  Such a desire is against the definition of bhakti.  Srila Jiva Goswami also explains that even the inimical feelings of Jaya and Vijaya were not real but only a shadow.  They entered into demoniac bodies but remained untouched within.  They descend to the material world with the Lord and return to His abode with Him”. 

Therefore, the conclusion is that the conditioned jivas are not here in this material world, like Jaya and Vijaya.  Moreover, if anyone from the spiritual world does come to the material world, then it is not by their choice.  They came from there to here because of the Lords sweet will.

Two:  If you are a jiva who at one point in time, in the past, was awakened from deep sleep (susupti), which is anadi, a state that had no prior condition.  My question is, where and when did this jiva have a choice or for that matter not have a choice?

Did this jiva wake up himself up?  

The answer is no.  Just like in our current life, when we are in an unconscious deep sleep, the Paramatma wakes us up.  It is also understood that Mahavishnu, or the Paramatma wakes the jiva who is in susupti.  This is stated by Srila Jiva Goswami in the Bhagavat-sandarbha.  I am not sure who does the waking up of the jiva in deep sleep; it is irrelevant, because they are the same person more or less.  When that happened, only He knows.  It is possible that if the Paramatma wanted you to know, then He could tell you how many exhales ago; Mahavishnu woke you up from susupti.  In that case, you could with some accuracy calculate how many earth years have passed since you were awakened.  However, acquiring this information is highly improbable, but technically, it is possible.

In addition, it can be concluded that you had no say or choice in that regard.  When you were awakened, you only had a subtle body.  You had no previous karma, you had been in deep sleep eternally, and you had no facility to choose to serve Krishna or Maya for that matter.  If the first gross material body Mahavishnu put you in was the lowest form of life, then it can also be concluded that you did not have a choice in that regard too.  If, however, Mahavishnu gave you any other gross material body for the first time, then the same is true.  You did not have a choice.  Before you were given a material body for the first time, you were in deep sleep; you had no choice to serve Maya or to serve Krishna.  You had no body to engage in karma or perform bhakti.  The only reason to place you in the body of the lowest form of life, is by default.  It is Mahavishnu’s choice not yours.  It gets worse before it gets better.  In that lowest form of life, you do not even have, the facility to choose to serve Krishna or Maya.  Ironically, this would be your situation as you progress up through all the other non-human forms of life of which there are 7,999,999 more