When you hear that an entrepreneur should not be afraid of failure, I think you are misunderstanding it. It doesn't mean that failure is unlikely, it means that failure is not a big deal.
Corollary: whatever bold move you want to try, make sure that failing is not going to be a problem, especially a financial one. Note that in this context it is assumed that embarrassing yourself is most definitely not a big deal, which is way easier to say than to act upon.
In the story linked, what was the worst thing that could happen to this lady? The CEO taking the remark the wrong way and being pissed? Or laughing at her, maybe? Who cares?
You quit your job and start a company? Depending on the kind of company, your chance of success will vary considerably. After you failed, you just get a new job/go back to your previous job and that's it. You lost a couple months of incomes, some savings, and you can laugh at your epic failure with your friends.
The dirty secret is that your friends will probably love you more after you failed, because truth being told, they are unlikely to want you to be more successful than themselves...
Corollary: whatever bold move you want to try, make sure that failing is not going to be a problem, especially a financial one. Note that in this context it is assumed that embarrassing yourself is most definitely not a big deal, which is way easier to say than to act upon.
In the story linked, what was the worst thing that could happen to this lady? The CEO taking the remark the wrong way and being pissed? Or laughing at her, maybe? Who cares?
You quit your job and start a company? Depending on the kind of company, your chance of success will vary considerably. After you failed, you just get a new job/go back to your previous job and that's it. You lost a couple months of incomes, some savings, and you can laugh at your epic failure with your friends.
The dirty secret is that your friends will probably love you more after you failed, because truth being told, they are unlikely to want you to be more successful than themselves...