6 Questions That Will Help You Boost Your Self-Awareness and Navigate Midlife Successfully 

I recently had someone ask me what I do. Rather than answering the question like I typically do, I said, “I’m tired of hearing about leaders in midlife struggling just getting by. Even worse, I hate that some of them derail their families, careers, and, at some level, their lives. I decided to do something about it. I help leaders navigate the ups and downs of midlife.”  

This started a lively exchange that found us discussing the causes and what could help avert the problem in the first place. I kept pointing out that self-awareness is a critical life skill to help navigate midlife well.  

So, what is self-awareness, and why is it essential in midlife?

Self-awareness is the ability to understand our values, emotions, and motivations. When we’re self-aware, we can identify the things that trigger us, the things that stress us out, and the various coping strategies we use regularly.  

Self-awareness helps us know our strengths and weaknesses and how we relate to the world around us. It also helps us understand how we’re perceived by others so that we can interact with them in healthy ways.

Some leaders I work with pride themselves on being self-aware. However, when push comes to shove, they lack the ability to make sense of their internal drivers, frustrations, and feelings. Without a clear understanding of what drives them or an appreciation for the unchecked emotions that could high-jack their best thinking, relationships and interactions, they remain vulnerable to forces that could easily derail their lives.  

The good news is that self-awareness can be developed.  

If you want to boost your self-awareness, work through the following questions. I encourage you to slow down and reflect. Why not take two hours this week or next to write down your answers on a yellow business pad or journal so that you can refer back to them?   

1. What situations tend to disrupt me or produce negative thoughts or some emotion? What do they have in common? 

2. When am I at my best? When am I at my worst? 

3. How do I react to people when my goals are blocked? 

4. When negative thoughts arise, how do I deal with them? 

5. In three months from now, what will my life look like if I don’t change anything? How does this make me feel?

6. What motivates me to make progress? 

To get an even deeper understanding, ask some trusted friends to give you feedback on these questions or consider working with a coach who can help you explore your inner world in greater depth. 

Living a self-aware life doesn’t mean that we won’t experience challenges or setbacks. But it does mean that we are more likely to encounter them with a sense of purpose and direction. When we’re self-aware, we are better equipped to navigate midlife with confidence and grace. This one life skill can set us up to thrive in the years ahead and emerge triumphant on the other side.


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