As you look back on your career and life to date, where do you wished you’d been a little braver, trusted in yourself more, and been less cautious in the chances you took? Anything come to mind? When speaking to people in their forties and beyond, many tell me that if they could do their career over again, they’d have taken more risks, settled less and spoken up more often. In short, they wished they’d been more courageous in the risks they’d taken. Perhaps you relate.