Dont listen to that kind of frivolous advise. He is 53 and is not likely to get employed to his old position / salary level again. He may think that he has no more ego, but in actual case, circumstances have forced him to swallow his pride and to settle for what he is doing now. Even to the extent of downgrading from his condo.

Everyone dreams of being their own boss, but not everyone can be one. While we cant be our own boss, we can work hard, save, invest and grow our wealth to feel like a boss.

A person can follow 4 career paths:

1. Be an employee
2. Be a sole proprietor eg dentist, GP, accountant, consultant, tuition teacher etc.
3. Be an investor
4 Be a businness owner

If you are good at something and really passionate about it, you can and probably do well as a sole proprietor. Being a business owner is out for most of us ordinary folks especially when starting out.

Being an employee is what most of us will start off as and likely to end our working life as one as well. But it is not all gloom and doom being an employee. When gainfully employed, we must strive to save and invest as much as we can. You will be pleasantly surprised what time can do to constant, and persistent savings and investments.

For my case, I have stocks of 30 companies and each financial year closing, I get annual reports from these 30 companies that gave me a sense of being a "boss". I am not craving to be a boss, but I can imagine what this can do for those who want to be bosses. Besides the annual reports, I get to attend AGMs and question the management teams of the companies. Why be a boss? The best part, is the dividends that rolled in !

It is important to do a bit of soul searching and see which category you are suited for. For most of us, it is to be an employee.