Confessions of a Leader

by | Dec 13, 2021 | Leadership

Leadership is diverse. There is no “one size fits all” leader. I have observed individuals with various backgrounds, personality traits, and strengths who all have led phenomenally. 

These highly talented achievers may share some similarity in their skills, but what really connects them are their struggles. 

From my own leadership journey and also from the hundreds of leaders I’ve had the privilege to work with, I have recognized that there is a common burden or pressure that most leaders experience. 

Unfortunately, most of these individuals struggle to open up with others about these challenges. So today, I’m sharing three confessions that I wish the people around me knew.


Confession #1: I don’t always know the answer

It is a myth that leaders have all the answers. Even though this makes sense cognitively, for some reason people still have an expectation that once someone puts on the “leadership hat” they magically have it all figured out. 

Questions get more complex sitting in the leadership seat. The stakes are higher. A leader’s decisions affect not only the organization but also their people’s livelihoods. 

As a small business owner and leadership coach, I can tell you that there are many days when I’m not sure of the direction I need to take or how to help one of my clients solve their problem. 

If you feel this way, take comfort that you are not alone. It’s okay not to know all of the answers. But one of the responsibilities of a leader is to find the answer. Here’s my prescription for this confession:

Become consciously competent.


Fill in your knowledge gaps through reading, online courses, and surrounding yourself with people smarter than you. 


Confession #2: I am more insecure than I let on

Some of the most talented people I know are also the most insecure. A lot of this has to do with Confession #1. It’s easy for leaders to struggle with imposter syndrome, which is “loosely defined as doubting your abilities and feeling like a fraud.” 

Even though leaders are high-achieving individuals, sometimes they have a hard time knowing what success looks like in their role. Is it their company or team’s financial benchmarks, overall organizational growth, employee satisfaction scores, brand awareness, or even some combination of all the above? 

Not to mention that leaders have a target on their back. They reap the benefits and rewards of their role, but also have to navigate through the constant criticism and pressure that comes with being in leadership. 

If you feel like an imposter, again, it’s okay. You are in good company. Many exceptional leaders have had to work through this struggle. Here’s my prescription for this confession:

Make self-awareness a priority.


Self-awareness is not a destination. It’s a journey. Refine your strengths, compensate for your weaknesses, and minimize your blindspots. Also, recognize that self-awareness + skill development + receiving feedback = confidence. 


Confession #3: I am lonely

In one of my first leadership roles, I had a mentor and friend who told me, “It is lonely at the top.” That might seem odd since leaders are always around others. But loneliness is not the absence of people; it’s the disconnect from them.

Part of this is an occupational hazard. It’s hard to connect with others when there are some things you can’t share with them or you have to make hard decisions that at times are not popular. 

However, many leaders, including myself at times, aid to this disconnect by putting up walls. A lot of this has to do with Confessions #1 & #2. It’s hard to entrust yourself to others, if you are not content with who you are. Insecurity breeds anonymity. 

By now, I think you know what I am going to say. It’s okay if you have experienced (or are experiencing) loneliness. But we don’t have to live in it. Here’s my prescription: 

Cultivate community.


Build relationships with people you trust. Bring others into your inner circle who care more about your personhood, not your performance.


Final Thoughts

First off, this blog is not a “woe is me” for being a leader. I love being a leader! I wouldn’t trade the experiences or the opportunities that leadership has provided me. There are a lot of privileges that come with being in leadership roles and the struggles are part of the price you pay.

Second, as Peter Parker’s grandfather said, “with great privilege comes great responsibility.” I’ve said repeatedly throughout this post that it’s okay if you feel incompetent, insecure, or lonely. Those are very real feelings, especially for leaders. But it’s not okay to rest in those feelings and become complacent. It is our responsibility as leaders to wrestle with these struggles and use these challenges as opportunities for learning and growth. 

Be gracious with yourself, but not satisfied. 


Game Plan

Which confession resonates with you the most? 

If it is Confession #1, what knowledge area are you lacking in? Who do you know that is an expert in that area? Seek them out and make time to learn from them.

If it is Confession #2, what are your strengths? Ask people you trust to share what they see as your strength areas. Take time to reflect upon those areas and then create a game plan to leverage them. 

If it is Confession #3, do you have an inner circle? If so, do you spend regular time with them? If not, who do you trust with the most intimate details of your life? Make it a priority to meet with these people regularly.


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