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How to Keep Going When Hope Turns to Disappointment

Throwing in the towel feels like relief when hope turns to disappointment. 

Sometimes the voice in your head says, “It’s not worth it.”


Meaningful achievement includes disappointment.

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

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

How to Keep Going When Hope Turns to Disappointment:


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.

7 questions for reflection:

Nagging disappointment shouts, “It’s not working.” 

  1. What are you doing that doesn’t serve you/others well? Remember that obvious answers aren’t the answer.
  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.
  3. What do you want others to stop doing?
  4. What personal values need fuller expression? Darkness and lethargy move in when you move away from personal values.
  5. What unmet expectations might you have for others? For yourself?
  6. How accurate is the accusing voice in your head? Inaccurate?
  7. 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 energizes you?

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

How might leaders keep going when hope turns to disappointment?


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