"Ten years back, I was dreaming to being where I am today, " Shahid told in an interview as he sat back to recall his journey.
His career as an actor started with him playing the cute lover boy in "Ishq Vishk" in 2003.
"Mausam", which marks the directorial debut of his father, veteran actor Pankaj Kapoor, features Shahid as Harinder Singh - a young, fun-loving boy who grows up to be an aware, mature and confident individual.
It's almost as if "Mausam" showcases Shahid's transition in Bollywood.
"I'm glad this reflects! I remember when I sat down with dad, he said 'Beta, I want to show you not just in one shade, I want to show different aspects of you as an actor'. So that was the effort with 'Mausam', " he said.
Shahid admits he was confused initially, but knows what he wants now.
"A decade back, I was running around trying to get myself any kind of a role, going to different places, and auditioning and being rejected. I was trying to make my body and just trying to get a break anyhow. Then 'Ishq Vishk' happened.
"When I started off, I didn't really know anything. I just had a lot of love and passion for acting. I knew acting was what I loved the most in the world. But I got confused. The first four or five years of my career, I was very confused - I didn't know what was right, what was wrong. There was no one to guide, nobody to tell me.
"Although my father is an actor, he wasn't the hero in films. Besides, he always told me that I need to make my own mistakes and learn from what I am doing. So I went through this whole phase of trying to understand what the right thing to do is, " Shahid said, and heaved a sigh.
And then?
"Then one day, I came up with a very simple solution - do what you want to do, do what you love doing! Forget about what would work, what wouldn't work, and what is supposed to work. I started doing films that excited me, films I believed in, and that's when my career started taking some kind of shape.
"I started this process about four or five years back, and now I am very happy and fortunate to be where I am today. I'm very satisfied with the kind of work I am doing. But I have a long way to go, " said the actor, who went on to feature in films like "Vivah", "Jab We Met", "Kaminey" and "Badmaash Company".
Like each of his films, "Mausam" has been a learning experience for him.
"I completely let myself go as an actor for 'Mausam'. I just blindly followed whatever my father said and that itself was a new experience for me. I'll do that a lot more often because I think it brings out new things in you as an actor.
"I've learnt that the father is always right - as much as you discuss and argue, he is the boss! And because I was closely associated with the film as dad was directing it, my understanding of what happens behind the camera has gone up a lot more because my exposure to it was so much more, " he said.
So is direction ever going to be on Shahid's agenda?
"No, no, no! Not at all. I've seen my father go through too much stress making this film. I have no interest in direction. So not at all!" he said, flashing his million-dollar smile which could make any girl skip a heartbeat.