At the tender age of 52 I am giving it a go again.
I had a reasonable job and reasonable pay but a very mundane duty list. I found it not worth continuing in those circumstances. I always believe that if you are not happy what you are doing and you can't improve the environment you are in, get out, try something else. Of course that doesn't mean ignoring the fact that we all have responsibilities, namely our family, our commitments to others but still within reason in a calculated way I thought as an individual we are also responsible for our own wellbeing. Being happy with yourself reflects on your relationships, it is not always money that determines ones happiness.
How do I say these things in confidence, well since the age of 11 I am working. Out of 41 years in service I was only on anyone's payroll no more than 10 years and self-employed for the rest of 31 years. My happiest times were always the ones that I was self-employed, dictating what I did, how I did it because I always had the confidence in my ability and belief that I would succeed in whatever I got involved.
Aha, not all went according to plan. When I look back I can see lorry loads of mistakes, misused opportunities also shit loads of financial loss on some but I also accumulated some wealth in the process.
So my answer to my own question is as above, if you have the confidence, you feel it is the right time, go for it. What can happen? At worse you will fail, what if it works!
You kinda blocked potential answers to your post by first asking a question in the topic and then answering it with your post
Both being self-employed and someone else's employee have their benefits and what is best for who probably depends on what character does that 'who' have?
If he has zero self-discipline, he will drown on his own. If he struggles with financial pressure, making tough choices on which a lot depends, he will probably struggle too. If he's lazy, no way he can do it!
Being self-eployed awards talented people with strong characters, being an employee is much easier. Many people appreciate the comfort and the fact that once the shift is over, they bring no stress and responsibilities home. So I guess it depends on what someone looks for in life and how he feels with a certain lifestyle. Nothing wrong with either!