Leadership Struggles: How to Overcome Disappointment

Disappointment is inevitable. However, it’s our reaction to it that defines our character. You, as a leader, can react differently to disappointment than others.

Likewise, 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.

Conversely, true leaders do not blame their subordinates. Instead, leaders must overcome shortfalls and persevere to future success.

Understanding how to cope with disappointment is critical as a leader. So, here are three things leaders must do to deal with disappointment.

How to overcome disappointment

Photo by Moose Photos

Face It, Absorb It, And Let It Go

Brené Brown’s book Daring Greatly talks a lot about vulnerability when it matters most. Confronting the most delicate parts of your life, such as disappointment, can create a vulnerability you’re unwilling to expose.

However, if you do not face your defeats now, then you will learn difficult lessons later. Instead, recognize that you failed somewhere, with someone, or doing something that negatively affected your professional life. Recognition is a huge step toward recovery.

When facing your shortfalls, understand that disappointment IS NOT anger. You can be disappointed but not angry. Remember, when leaders get angry, they lose credibility.

If the leader does it right, 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 challenging failures to be successful.

After facing your disappointment, absorb it. Go into a room by yourself and assess what went wrong. David Goggins advocates for conducting an After Action Review (AAR) in his book Can’t Hurt Me.

An AAR reviews your positives and negatives of a given task/exercise; continue implementing the positive results while changing the negative outcomes. Repeating this exercise is how we get better.

When we conduct AARs with ourselves after a failure, we allow ourselves to absorb the lessons learned from that shortfall.

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. This is the part where you’ll be tempted to give up.

“Life is difficult.”- M. Scott Peck. The Road Less Traveled

Talk To Someone

Again, this could be easier said than done. But speaking with a peer or colleague could be an advantage.

Brené Brown also talked about how vulnerability is something we try to hide. Rather, we have to remember that we’re living the human experience, and that includes all the ups and downs associated with it.

Let’s apply this concept to leadership. Leaders must know how to overcome challenges to best support their subordinates who face their issues.

Confronting and conquering the failures in your life will assist your ability to assist those around you.

Additionally, for self-care, 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. The Arbinger Institute’s book Leadership and Self-Deception talk about how we must see the problem as it is without becoming self-deceived ourselves. Friends and families help us to accomplish this goal.

Sometimes, your employees want to know 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 not to fall into complaining. That gets awkward for the employees, and it degrades your ability to lead.

Forget Yourself, And Serve

Serving is part of leadership. Even while disappointed, you can create mental resilience in yourself by serving those around you. It may seem unconventional, but you find a greater appreciation for your co-workers and subordinates when you begin to serve others instead of turning inward after a failure.

For example, I remember playing baseball as a kid and getting upset after striking out or making an error. I lost my fair share of games, and it wasn’t pleasant.

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. We will love the team more when we serve them after suffering a setback.

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!

How to overcome disappointment

Photo by Gary Barnes


To requote F. Scott Fitzgerald, “Life is difficult.” It seems so simple to understand. However, when we’re in the middle of a complicated issue, we tend to wonder how it can end.

Leadership is no different. When we face crises, we must realize that life truly is difficult. However, we must also remain optimistic for a better future.

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

Books Mentioned

Daring Greatly by Brené Brown

Can’t Hurt Me by David Goggins. Read a book review here.

The Road Less Travelled by F. Scott Fitzgerald

Leadership and Self-Deception by the Arbinger Institute. Read a review here.

Photo Credit

Featured Image: Andrea Piacquadio

1: Moose Photos

2: Harvey Tan Villarino

3: Gary Barnes


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

  1. 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. Sami,

      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.


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