5 Tough Questions for Every Successful Man to Ask Himself Every Day

It’s a daunting time to be a man. Culture, politics, religion, money, women—all are more difficult to understand and navigate in a world that changes and moves faster and faster by the day. It’s easier now to get lost in ruthless cycles, false truths, and meaningless pursuits.

But success, personal happiness, and a fulfilling life are shaped by more durable things, and the important questions about them still hold. To deal with the anxieties of our generation, it’s important for a man to stop and take time to face himself with these tough questions every day. Shut out the distractions and stay on course.

1. Am I on the right track?

It’s always important to situate yourself; to be aware of where you are in life, and how you arrived there. This is a fundamental, everyday question that will help you shape your life goals and keep track of them. It’s also a question that asks you to look forward to the future and back at your past. Considering this question on a regular basis also opens you up to other crucial, sometimes cathartic questions: Is this still where I want to be? What is my purpose? Am I of significant importance to the people around me? To the world?

2. Is it OK to be unsure, fearful?

Fear is as essential to success as courage. You can only realize your full potential if you are acutely aware of the stakes: the possibility of failure and the consequences. A successful man would turn this uncomfortable question into a factor for motivation: How can I overcome my fears? How can I rise above them? Courage, after all, is not the absence of fear, but the decision to act in spite of fear. And one cannot act without first acknowledging that fear in the first place.

3. Am I making the right decisions?

Everyone wants success, happiness, and fulfillment. But different people define these things in different ways. How do you define success? Happiness? Fulfillment? Concretely, what do these things mean to you as an individual? It’s a question that demands a lot of serious reflection, but the answer will set your life direction. If you don’t know what you want, or if you can’t define it concretely, it’s easier to get lost. And even if you’ve answered this question already, it’s important to ask again and remind yourself. This will either motivate you more to achieve those goals, or wake you up to the fact that you already have.

4. What should I do with the things I have?

That leads us to another important series of questions that should help to situate you: What do you have? What tools and resources are available to you? What talents and skills are at your disposal? Once you’ve established your goals, these questions will help you build the path to those goals. After all, you’d need to be aware of what you have before you can begin to consider what to do with them. Also, asking yourself this on a regular basis will keep you aware of—and thankful for—your accomplishments, which is essential to happiness.

5. What can I still work on?

But at the risk of stagnation and unproductive contentment, a successful man who is aware of his current situation must also ask himself about the path ahead. Once you’ve established where you are, who you are, and what you have, keep asking: Is there more that I can do to improve? It certainly requires humility to answer this question honestly, because no matter where you are, the answer to this should always start with a yes.