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How Leaders Deal With the Dark Side of Disappointment

We’ve all had them: DISAPPOINTMENTS.
  • Someone we’ve trusted leaves.
  • We lose a big business opportunity.
  • We’ve made a mistake or a misstep.
  • We fail. Get up. Just to fail again.
  • We patiently wait for our turn to be passed over again.
  • A loved one shares a heartbreak or a loss.
Most people who know me describe me as: positive, energetic, and optimistic.

Most people who really know me well knows:

  • I’ve been broken at times.
  • I’ve been disappointed and let down.
  • I’ve dealt with the dark side of disappointment.
How do you recover from the dark side of disappointment?
1. Commit to getting back up.
One of my favorite Proverbs that provided me strength is Proverbs 24:16: “For though a man or woman fall seven times, they rise again.”
2. Look at heroes of resilience.
I have three different close friends who have nearly died recently– two of cancer, one of Covid, right at death’s door. They wouldn’t let go somehow. Some way, they rallied through faith, courage, and resilience.
Note: They provide me perspective and courage to rise my seventh time.

3. Grieve and then come back.
I have an amazing sister, Becky. She has had an extraordinary career in marketing for over four decades. A leader. A picture of resilient adaptability and a comeback spirit! Her secret? “I grieve 24 hours over a business loss and then I’m determined to come back!”
I clearly remember her telling me of a time when her team lost a big business deal. It was theirs; they earned it only to have it taken away at the 11th hour. Heartbreaking. The team was devastated and disappointed to pour blood, sweat, and tears into their efforts, only to lose it at the very end.
My sister gave them the next day off to grieve and then the following day, she set her alarm for 5am. She got to the office really early to start over, rebuild, and find the next success for her and her team. And they did!

Today, commit to getting back up, looking to heroes, and grieving but getting back up.

Here’s to your strength to rise again!
–Steve

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“The purpose of Leadership Quest is to help professionals develop their personal leadership, vision and emotional intelligence. Everyday I strive to help leaders and teams achieve their desired goals in sales productivity, leadership, time maximization, and life-balance. ”

About the Author

Steve Gutzler is the President of Leadership Quest, a Seattle-based leadership development company. Steve is a dynamic, highly-sought-after speaker who has delivered more than 2,500 presentations to a list of clients including Microsoft, Starbucks, the Seattle Seahawks, Pandora Radio, Boeing, Cisco, Starwood Corporation, the Ritz Carlton group, and the U.S. Social Security Administration. He recently was voted #1 by the readership of Huffington Post as the Most Inspirational Leader on Social Media.

A published author on leadership and emotional intelligence, Steve resides near Seattle with his wife Julie where they enjoy time with their three adult children and six grandchildren.

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    • L.O.S.S. Learning Opportunity Stay Strong 2025September 10, 2025 - 3:06 pm
    • Why Most Journals Fail (And What Actually Works)July 22, 2025 - 1:24 pm
    • Leadership Lessons: How to Avoid the Traps That Derail SuccessMarch 11, 2025 - 4:19 pm
    • From Conflict to Connection: 15 Ways to Elevate ANY RelationshipMarch 4, 2025 - 11:54 am

    About Steve Gutzler

    Steve Gutzler is the President of Leadership Quest, a premier leadership development company based in Scottsdale. As a dynamic and highly sought-after speaker, Steve has delivered over 2,500 impactful presentations to renowned organizations such as Microsoft, Starbucks, the Seattle Seahawks, Spotify, Boeing, Cisco, Starwood Hotels, Ritz-Carlton, and the U.S. Department of Commerce.

    A published author and thought leader on leadership and emotional intelligence, Steve lives near Scottsdale with his wife, Julie. Together, they cherish time spent with their three adult children and six grandchildren.

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