Painful Experiences: The Key to Your Future
The dark side of leading is being haunted by dark memories. Painful experiences shape you.
7 reasons painful experiences cling:
- Emotions don’t understand time. You feel fresh pain from old experiences.
- It could happen again.
- Others don’t get it. You don’t feel heard.
- Revenge motivates you.
- Blame is more fun than responsibility.
- Forgiveness eludes you.
- Your inner critic reminds you how disappointing you are.
Painful experiences are headwinds at first. When pain achieves its purpose, it propels you forward.
Release:
The three challenges of moving forward are learning, integrating, and letting go.
- Failures haunt.
- Offenses sting. Fear of pain blocks joy.
- Unmet expectations weigh down. A disappointing past grows heavier with time.
“Some of us think holding on makes us strong; but sometimes it is letting go.” Herman Hesse
5 principles for finding release:
- Press through. Don’t wait for pain to disappear.
- Grow tender, not hard. Let yourself feel pain.
- Stay vulnerable, not foolish.
- Listen to the darkness. What positive message comes to you from your dark experiences?
- Forget forgetting. Forgetting is a pipe dream. You always remember. Release requires habitual forgiveness.
4 forward-facing questions:
Build the future now. Behave your way into your preferred future.
You repeat the past when you wait for the future.
- What positive character traits are painful experiences calling you to develop?
- If things were better, what would they be like? Build “better” now.
- How might hardships expand your potential? For example, pain humbles the heart if you let it.
- Picture the future you would love to live. What forward-facing behaviors might you engage in today?
Support Others:
Your future includes people.
Turn others toward their future when they’re circling the black hole.
Come alongside:
- Accept, don’t reject or correct, their sadness.
- Ask questions.
- Listen.
- Reject the need to make it better.
How have painful experiences shaped you?
What advice do you have for someone experiencing dark emotions?
Still curious:
Painful Experiences: 5 Ways to Gain Advantage
Growth Hurts: Create Positive Discomfort
How Painful Experiences Changed the Trajectory of a Fortune 300 CEO





Timely. I’m in a position to counsel two households in the midst of painful experiences. In both situations my friends contributed to the pain. In one situation, the majority of the pain is self-inflicted – bad choices, unwise decisions, anger, frustration. My other friend was not treated well, so anger and grief are very much present. He was left out of discussions for too long, but it also highlights some lack of self-awareness. But hard to come to self-awareness unless someone says something to bring it to our attention. I’ll most definitely share this with them.
Challenging situations, Pete. All conversations begin in one of four places. You might find this post useful: https://leadershipfreak.blog/2024/06/25/the-4-trajectories-seizing-the-intentional-future/
I wish you and your friends well.
Becoming unstuck was a common theme in faith communities and industrial settings after the impact of COVID-19. Individuals also experience “stuck,” reshaping hardship as steps to growth is vital for restoring personal purpose and further development. Thanks for a fantastic Post.
Ken, I love this phrase, “reshaping hardship as steps to growth.” So clear and powerful. Thanks for adding your insight.
This is very timely today with some much needed great advice. Thank you!
My pleasure, Erin.
I am reminded that when “pushing through” forgiveness is for you not for them. In my experience forgiveness is not inclusive of repairing a relationship. These are two separate tasks and one can certainly forgive, but be unable to return to a place before the painful experience.
Thanks for sharing your insights, Joel. Forgiveness doesn’t necessarily mean we are going to be best friends.
It’s helpful to separate forgiveness from the work of building/restoring a relationship.