How to Keep Going When Hope Turns to Disappointment

Dec 15, 2017 1 Min Read


Throwing in the towel feels like relief when hope turns to disappointment. Sometimes the voice in your head says: “It’s not worth it.” But, meaningful achievement includes disappointment.

Hard-fought battles taste sweet but include frustrations, setbacks, and disenchantment.

  • People disappoint. Good people leave. Bad people stay.
  • Results disappoint. You pour in more than you get out.
  • Circumstances disappoint. You expected advantage but received discomfort.
  • You disappoint. Failure isn’t intentional, but it happens. The cruellest disappointment is disappointment with yourself.

Winston Churchill said: “If you’re going through hell, keep going.

Reflection: Successful leaders reflect on disagreeable realities. Buried disappointments swell like boils until they can’t be ignored.

Nothing improves through neglect. You repeat what you ignore. Nagging disappointment shouts: “It’s not working.”

Here are seven questions for reflection:

  1. What are you doing that doesn’t serve you/others well? Remember that obvious answers aren’t always the right ones.
  2. What do you want to stop doing? Disappointment is motivation to stop doing things that aren’t working. There comes a point when stopping something feels like relief.
  1. What do you want others to stop doing?
  2. What personal values need fuller expression? Darkness and lethargy move in when you move away from personal values.
  3. What unmet expectations might you have for others? For yourself?
  4. How accurate is the accusatory voice in your head? Or inaccurate?
  5. Hold your disappointment in your mind. Now ask yourself four questions:
  •   What are you doing that makes you proud?
  •   What are you doing that makes you disappointed in yourself?
  •   What are you doing that drains you?
  •   What are you doing that energises you?

Tip: Record your disappointments on paper. Read them every day for a few days. What do you notice?

Dan Rockwell is a coach, speaker and is freakishly interested in leadership. He is the author of a world-renowned, socially shared leadership blog, Leadership Freak. To engage with him, email

Reposted with permission


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