3 Reasons Why Leadership is Depressing and How to Overcome

Jesse Carbo
City to City Miami
Published in
3 min readApr 25, 2018

There you are at the end of a long work week and you’re wondering, “Is anything I’m doing making a difference?”; at least that’s how I feel sometimes. As a leader I think about leadership a lot. To be honest, I don’t read many books on leadership but I’ve read my fair share and so many ideas and thoughts exist on the subject. I do know, from personal experience that leadership can be depressing, here’s my thoughts on why:

1. FAILURE IS INEVITABLE

You are going to fail as a leader. That’s a fact. If you never fail, you’re probably not leading. There is so much risk in leadership that eventually failure becomes a part of the job. This can be depressing because no leader sets out to fail. Failure often happens because of circumstances out of our control or capacity we have yet to develop within ourselves or our teams. No matter what though, failure is inevitable. Get used to it.

2. YOUR REPUTATION WILL BE QUESTIONED

We have all stood around the “proverbial” water cooler and questioned people’s leadership. I’m sure that I was the subject of people’s conversations at one point or another. If it’s not your leadership that others will question it’s your character or integrity. Either way, you will be questioned and that can be depressing. It’s a terrible feeling to sense that others don’t believe in you.

3. LOYALTY IS LOST

The first church I planted as the lead guy (senior pastor) was exciting especially because 10 of our closest friends joined us. What an amazing journey to have been a part of. These families quit their jobs, sold their homes and moved to a new city with me during the 2008 housing crisis and we worked together to plant a church. Slowly over the period of 3 years, circumstances changed and many of our friends moved away or back home. To be honest, I was hurt by some of their decisions to leave. I felt as if their loyalty to me and the mission had faded for less then good reasons. Over the years I have seen loyalty lost in the form of staff leaving a church, marriages ending in divorce, employees quitting jobs over negative situations, and my own loyalty towards leaders that I followed lost on principle. As a leader you will lose the loyalty of others for better or for worse, it will happen.

So how can we avoid being depressed in the midst of these challenges? Humility.

The alternative would be to deny failure by redefining our “truth”. To become defensive when our reputation is on the line and find ways to discredit those who are questioning us and to have an imbalanced views of loyalty that demand people follow without question. This kind of leadership is poisonous and ultimately destroys communities and organizations.

Humility leads us to a posture of learning and serving. Humility is the key to great leadership. Humility is what allows us to learn when we fail. Humility is what helps us serve others when are reputation is questioned. Humility is what keeps us steady when others loyalty to us is lost. We cannot survive as leaders without the strength of humility. Humility is the antidote to leadership that is depressing.

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Jesse Carbo
City to City Miami

My thoughts in under 500 words, read in under 5 minutes.