And probably the biggest one of all; what have I done with my life?
Some call it "taking stock of one's life" while others see it as a delayed existential crisis.
Reflection can be a bitch at the best of times and when she comes, she doesn't go away easily, making us wonder whether all we have in life is as good as it's going to get.
We're so easily entangled within the confines of comfort that we eventually stop dreaming and start settling for what we have instead of what we could have. Like some big red door, we are closed to the idea of greatness which is actually a lot closer than we think - if only we had the balls to start taking more risks.
No matter how much sunshine or prozac you have running through your veins, the truth is that most of us are pessimists.
We're constantly questioning ourselves and our own ability to achieve the impossible, too afraid to take the necessary chances that might actually lead us to success.
Instead of seeing the risk as an opportunity, we see it as catastrophic, over-estimating the likelihood of things going South and under-estimating our ability to overcome the challenge.
How often do we dwell in self-doubt or fear instead of just believing in our own potential? While the fear of the unknown and fear of failure are understandably paralyzing, it really can't compare to the greatest fear of all...regret.
As I found myself going through my very long list of regrets, wondering about my own courageous thoughts, I found myself reading an email from a dear friend who had just announced her separation from her fiance.
This shocker of a press release was sent to a number of family members and close friends, outlining the seemingly mutual reasons for the relationship's dissolution.
There was nothing mean or sordid about the declaration, and even though it read optimistically, I couldn't help but wonder about the consequences of taking such a huge risk at this stage in their relationship.
Surely after nearly sixteen years of being together and knowing each other inside out, people would find a way of making things work.
Were they just another example of your typical "times are tough, time to give up" kind of couple or had their relationship become nothing more than a relationship of convenience?
Properties, memories, two and fur-legged children. Surely the admin of breaking up with someone after such a long period was enough to frighten them back into conciliation not to mention the rigmarole of dating again which now seemed so foreign to both parties.
Was taking a risk the right choice and if it was, what about the guarantee?
"Choice and risk is like gambling. Sometimes you hit the jackpot and sometimes you lose it all. Either way you have to play your best hand but also know when to quit."
Some DMC and a bottle of wine later, we found ourselves talking about the road less travelled and the hardships that come with letting go of the familiar.
"There's definitely something in the water at the moment. Everyone seems to be breaking up."
While their decision was definitely not the latest trend in relationship couture, I could tell that through her questions and doubts, she had resolved in taking the risk of being happy.
"It's surreal to think that the life you had grown so accustomed to is no longer there, in fact, it's heart wrenching. I'm busy trying to keep my mind motivated by other things and through that process I am slowly but surely getting clarity.
I guess when you've exhausted all your options, and you're still not happy or even remotely content, it's time to see the relationship as another lesson learned.
No matter how hard the decision, you need to break through the barriers of the unknown and fear and starting living instead of existing."
It takes a lot of guts and courage to walk away from a comfort zone, whether it's a troubled relationship or a job that causes you mild to severe panic attacks.
We can never really know what's best for us until we put ourselves out there and jump into the line of fire.
Even then, there's no guarantee that we won't get burnt.
Failure is a part of the journey to success, which is why we should face and embrace it instead of cowering beneath it.
Look out towards that new open door instead of looking back at the one that should have closed a long time ago.
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