Success is personal, its subjective with some proof of your achievement. Everyone has their own goals and once you reach or exceed your own goal its what you consider a success. If you feel that you're getting older and you never tasted the success that you really are expecting, perhaps you need to stop, smell the coffee before you drink it and reassess the situation, because maybe there are a few details or a few things that you've missed that is why you never experienced the success that you’re looking for.
The fact is that success is something that one needs to achieve at some point in their life because if you don't, then you will be less fulfilled. Sigmund Freud with his Psychoanalysis theory has to say about that. Success is necessary since it fulfills the void in one's life, without success everything is dull because there is nothing that people would work for, and if success is not met there is also a feeling of despair, misery and depression.
Assess your goals and be realistic: Assess your goals if your goals is indeed realistic or not, because sometimes if goals are very unrealistic, even if you spend a whole lifetime you still won't reach your goals. Even if you can't achieve your very audacious goals, you can still aim for other things. If you can't aim for the stars you can still aim for the sky and that can still be called a success. So if you want to be successful and achieve your bucket list like Ryan Kavanaugh, reassess it if it can really be achieved.
Have smaller goals leading to bigger goals: If your goal is really big, there are ways to achieve it and if you want to get it on time, there are a few notable roads that you have to take leading to that goal. In order to have a clear direction its best to break your very big goal into smaller parts. This is to give you a sense of achievement leading to a bigger goal.
Hev a clear plan: Dreaming and hoping that some crazy turn off events will lead you to your ultimate goal won't just do. If you really want to achieve your goals you need to have a clear plan like how many years it would take, what are the things that you need to do, who are the people that you need, how much money you need, do you need to buy certain tools or equipments to achieve it, do you need to learn some skills and many more. You need to have a career plan and this is by knowing the things that you will need to achieve.
If you think about the audacious goals there are some people that only dreamed it, not realizing that dreaming won't get you anywhere. If you want to be successful you need to assess your goals and be realistic, have smaller goals leading to bigger goals and have a clear plan on your goals. If you want to find good inspiration for that, Ryan Kavanaugh is one of those people.