I don't mean to make this a sad thread.
I present two case briefly:
Consider two people. One all life has lived a luxury and comfortable life. Enjoyed food, had many boyfriend / girlfriend and saw all places on earth he/she wanted, did not have a difficult life and had lots of fun. Another person, lived a difficult life, with little money, no luxury.. was not even good looking.
Now, suppose both are just on the deathbed, living their last days, suffering dying, and waiting for the last breath.
1. Which of them is the winner in life, and is happier on the deathbed?
2. Does the person who lived a comfortable and luxurious life, thinks with himself "I lived my life fully. I did whatever I wanted. I don't want anymore, and I am ready to die". Would he/she gets comfort by such thinking while on the deathbed? Would he/she even thinks of past memories?
3. Does the person who had a difficult life, is suffering more on the deathbed, thinking, I had a bad life, I was poor, did not get what I want...and now I'm dying?
First of all, I reject the idea of "winning at life" as if it is something that you can package up in a neat generalized box.
It all depends on the person and what that person finds important in life. Some won't be happy until they have tremendous business success. Others won't be happy until they have children in whatever circumstances. Even others won't be happy until they save a tribe of gorilla's from extinction. There are so many different people with so many different interests, goals and ambitions... What you present here is simply a false dichotomy.
Having said that, I say that it is impossible to tell. Either could feel like they had a good and full life and either could feel the opposite. It all depends on what kind of persons they were.
The poor guy might be poor by choice for example. Having no interest in carreer success and instead all about being with family and enjoying the simple things in life.
The only thing I'm relatively sure off, is that both will still have some unchecked items on their bucket list.
While I like the idea that you are in charge of your own destiny, I also think it is kind of delusional in a sense. Or upto a certain extent.
When you are born, dice are thrown and you'll have to live with the outcome. There will be certain things that will simply not have a place in your future while there will be other things that you won't be able to avoid no matter what. The best you can do, is navigate life by steering in the direction you want, but in the end, there will be boundaries that you won't be able to cross.
For example.... I used to play high level tennis when I was young. At 15 years old, I played top 8 in Belgium in my age category. I sparred and trained with people like Kim Clijsters, Xavier Malisse, Christophe Rochus, etc. What became immediately apparant during those trainings and matches, was how those people were like aliens. No matter how good the rest of us were, no matter how hard we trained... these people were simply physically out of our league. I remember feeling a sense of accomplishment when I didn't lose 6-0 / 6-0 to Malisse, and instead managed to grab a game or 2-3. As it turns out, while MANY people can achieve the
skill level required for pro tennis - only very few have the body that can actually withstand such stress.
I have known many players, really really good players, that went absolutely nowhere. And really not because they weren't good enough. Rather... age 17 and the elbow gives problems.
Age 16 and suffering from chronic lower backpains.
Age 18 and the right ankle gives up.
Age 17 and the knees are destroyed.
Each of these are real examples. All of them resulted in permanent damage. Slight damage. But "slight" is already too much to be able to keep going at the highest level.
Just to illustrate.... when you are born, life throws some stuff at you and that's the toolset with which you have to manage. Some have a better toolset then others. Some toolsets are just different. Even the environment you find yourself in, is part of that toolset. Some people simply "never had a chance" to outgrow their environment. Others have to work
extremely and exceptionally hard to achieve even only half of what some other guy inherited while sitting on his bum.
That's just how it is. Life isn't fair. But you only have one, so one can only try to make the best of it, no matter what hand the universe has dealt you. You got your cards and those just happen to be the hand you're going to have to play life with.
If there is such a thing as "winning at life", then I'ld say that the winners are those people who accept and live with their toolset and make the best of it.