We all know someone who has been there:

You graduate high school or decide to leave full-time kollel, and you want to start your own business. Should you go into your family’s industry? Should you be innovative and try something new? Do you have the necessary funding and skills to undertake a venture? Should you be ambitious and go for the gold, or first confine yourself to a meager-paying entry-level job?

You have been working in your first job for several years and have won accolades from your employer and colleagues. You work well with people, complete tasks responsibly, and have a grasp of your industry that surprises even those more experienced than you. You have been rewarded with meaningful promotions and raises, but you still see a clear ceiling for how much you can ever realistically earn — while your boss doesn’t stop upgrading his lifestyle due to his increasing success. Is it time to go on your own? Do you stand a chance in an industry saturated with established players?

You have accumulated some investment assets from your parents, parents-in-law, or savings. Perhaps you can use it to purchase an existing business with a track record, which seems to offer both reliability and growth potential. Can you trust what the current owner or broker is telling you? Which one of the various purchasing options best suits your talents?

Or perhaps, are you better off brushing away your ambition, being safe rather than sorry, and making do with a stable, respectable job or profession — where you can sleep at night without worrying about the newest competitor or market change?