10 Scary Questions

In the spirit of Halloween, here are 10 scary questions to ask yourself and then answer to get the most out of life.

A version of today’s post first appeared 10 years ago. I’ve since updated my selection of 10 scary questions and I’ve also updated my book, which now contains new material about the importance of questions, what makes a good question and what makes a bad question and more than 1,000 provocative questions in my book That’s A Great Question.

Do we have the courage to ask ourselves the tough question? The obvious question? The scary question?

The majority of questions in my book are framed from a business perspective because that’s where most of the people I work with are focused. But the reality is I’m hired by business executives and then human beings show up. So you’ll also find plenty of questions about personal matters that inform and influence business decisions.

It’s often those questions that are the scariest. Here are 10 questions to ask yourself:

1. What am I most passionate about today? What specifically is at the heart of my passion? If I knew I couldn’t fail, what would I do?
2. If our company did not exist, who would miss us? For how long?
3. Are our organization’s values cheap words, or do they reflect our real behavior?
4. Are people moving toward our organization or away from it?
5. If I exerted just 5 percent more effort, what result would I achieve?
6. On a scale of 1 – 10 (with 10 the best), how would those closest to me rate their level of trust in me?
7. Would I agree to have dinner with myself? If so, would I enjoy it?
8. I’ve lived a rich, full life. It’s over and friends and relatives have gathered to celebrate my life. What’s being said about me in the eulogy?
9. What is my life’s purpose?
10. What three behaviors of mine do I want to change?

Self-discovery doesn’t happen overnight or even over a weekend.

It’s my wish for you that this process will prompt you to think long and hard about issues you’ve never considered in a meaningful way to help you come to grips with what’s really important to you. Second, that you’ll use your newfound conclusions to take action in order to get results and enhance your life.

The only thing scarier than answering the questions is not answering them.