Leadership Struggles: How to Overcome Disappointment

“Life is difficult.”

M. Scott Peck. The Road Less Traveled

It happens from time to time. Disappointment is inevitable. However, it’s our reaction to it that defines our character. How your boss reacts to lousy news says a lot about how they handle small defeats. When the significant losses come, some employees want to head for the hills to avoid their boss’s reactions.

True leaders do not blame their subordinates. Instead, leaders who take responsibility for their actions are more likely to succeed in life. Understanding this point will also help to overcome disappointments in life, too. Keep that in mind. Here are things leaders must do to deal with disappointment.

Face it, absorb it, and let it go

Brene Brown’s book Daring Greatly talks a lot about vulnerability when it matters most. Disappointment is no different. Leaders need to express their frustration with a situation, person, or event to identify the problem accurately.

It’s important to understand that disappointment IS NOT anger. When leaders get angry, they lose credibility. If you’re disappointed, then face the fact. The worst thing to handle disappointment is to numb it with something else. I would even argue that it’s acceptable to show frustration in front of subordinates. If the leader does it right, then their subordinates will do everything they can to support their leader. It might not be comfortable, but leadership isn’t about feeling comfortable. Leadership is about navigating the dirty waters to be successful.

After facing it, absorb it. Go into a room by yourself and assess what went wrong. Do not make this a self-deprecating exercise. It’s a review of yourself. What could have gone better? Why did this item, project, performance fail? If it’s personal, what did I do that went wrong? Absorbing disappointment IS NOT placing blame. If leaders place blame on the systems around them, then they are contributing to self-entitlement and pity. I’ll admit, there are occasions where the system is wrong, and some teams/individuals get the brunt of that malfunction. I would argue that the performer is mostly responsible for their performance.

The last part is to let it go. Find something that will help you to cope with your disappointment. Avoid unhealthy coping mechanisms, but find something that can help you release the frustration. Now that you have faced it, absorbed it, it’s time to allow it to dissipate. Be patient with yourself. Letting go is easier said than done.

Talk to someone

Again, this could be easier said than done. But it could be to your advantage. Brené Brown continues talking about vulnerability as something we try to hide. We have to remember that we’re living the human experience, and that includes all the ups and downs associated with it.

Applying this to leadership, find a close colleague or a friend to help you through the issue. Everyone has their struggles, so we need to acknowledge that someone else may have a piece to the solution. Similarly, friends and family can help illuminate an otherwise complex problem.

Arguably, it’s essential to address your employees about your struggles, too. Open up to your employees about what you’re struggling with and ask them for help. Being honest creates mutual trust and confidence within the team because the employees are interested in your success. However, I caution you to not fall into complaining. That gets awkward for the employees, and it degrades your ability to lead.

Forget yourself, and serve

Being a leader means that you serve. When something bothers you, it’s good to face it, as I said earlier. But it’s more important to continue to serve. I remember playing baseball as a kid and getting upset after striking out or making an error. After such games, my dad would tell me that it’s more important to go back to work for the team than to sulk in the dugout. Similarly, we leaders cannot host a pity party when there’s work to be done.

We cannot afford to stop serving. Our companies, employees, and livelihoods depend on the attitudes that we have towards failure. When we realize that we can continue service after suffering a blow is when we have grown to love the team. Service comes out of a strong desire to see the team do well, not by our own efforts. Instead, through the efforts of the group is where a leader realizes the fruit of their labor. Don’t forget to give credit where credit is due, though!


Did you read the quote at the beginning? Life is difficult. It seems so simple. But it’s not. When leaders suffer disappointment or defeat, their loss should not be someone else’s gain. Instead, it should be your lesson learned. Leaders must understand how to overcome their disappointments for the betterment of the team they lead.

What have you done to overcome disappointments? Let me know in the comment section down below. Thanks for reading!

2 thoughts on “Leadership Struggles: How to Overcome Disappointment”

  1. Sami says:

    Life is difficult, and in leadership, life is often lonely.  Disappointment and loneliness can result is difficulty coming to a good conclusion for the disappointment.  You can’t talk to your team, because you as a leader are expected to get on with things. Not sit and rehash what happened.  When I was the leader or boss, I was fortunate to be commuting a bit to have time to work through disappointing results.  With no distractions, this gave me reflection time to think and consider.  

    I do think that in the active workplace, to wait till the end of the day, and have all the facts before doing your analysis is also helpful.  When possible I liked to have some sort of list as a start of the analysis, even while commuting home.  Often I found that the disappointment pointed to a weakness that I had not considered.  While building a team you sometimes overlook obvious issues and only realize the issue in reflection.    Understanding that disappointment goes hand in hand with success was a major milestone for me.  Interesting information.

    1. Robert says:


      Leadership is lonely. You captured that idea so well. In your experiences, do you think that many leaders cope well or not to their disappointment? Success does come with disappointment, and that’s a difficult lesson to learn. I appreciate your comment. It is one of the most profound comments I have received on one of my articles. Thank you.


Leave a Reply

Your email address will not be published. Required fields are marked *

Related Post