X Factor and Britain's Got Talent mastermind Simon lost his mother Julie in 2015 when she died at the age of 89.
Described as the 'most beloved person' in Simon's life, her loss had a profound effect on the star. He cancelled X Factor auditions due to take place in the days after her death, and was visibility shaken and upset when he eventually returned to work in the public eye.
The loss of Simon's mother came 16 years after his father died of a heart attack at the age of 81 – a day that the talent show judge called 'the worst day of my life'.
Now the Daily Star has reported that Simon has revealed that he still struggles with being an orphan, and misses his parents dearly, admitting that he still turns to his parents for advice and for counsel.
'I still talk to my mum and my dad in my mind now if I am having a difficult decision or I am struggling with something,' Simon revealed.
'I have a mental conversation with the both of them and I absolutely know what the answer is - it is the weirdest thing.'
The 58-year-old now has a son of his own, Eric, who was just one when his grandmother passed away and is named after Simon's late father - Eric Cowell.
Born in 2014, Eric is now three-years-old and growing up to be more and more like his father every day, with Simon admitted he's already teaching Eric important life lessons – just as his father did for him.
'Because he was successful, my dad, when he ran his company - he said everybody around you has an invisible sign on their head which says "make me important",' Simon told Good Morning Britain host Piers Morgan in 2015.
'What I understood from that is that you've got to recognise that everyone around you wants to be recognised, wants to be appreciated.'