Yes… no… maybe… I don’t know…
There are so many different answers we can get. I think it all depends on what matters? How we measure success or happiness? How we measure proudness? What do you want to achieve to be proud of yourself? List things to own? Milestones you have reached that you set for yourself by the age of 25? 30? 40…? Do you consider happiness as something to be proud of?
Usually, when there is a class reunion, everybody is asking each other about relationships, houses, cars, kids to have. You can have everything you ever wanted, but you are still not happy. Nobody really asks if you are happy where you are and what you have achieved even it is the smallest thing in the world, but a huge step for you.
We have to set up our own measures and decide how we managed to reach it. Have we done everything we could to succeed? Were/Are we able to do more with a bit more effort?
Everybody has their own pace to go forward, and their own goal to reach it. My goal might seem silly for you and the other way around is also true.
I would say, it doesn’t matter where you are at the moment, but if you are working on your dreams you definitely should be proud of yourself. You might hit so many walls until you find your way, but hey, time passes even you just sit and wait!