Blog #698: Playing the Pleasing Game

Playing the Pleasing Game: You Can’t Win Everyone—But You Can Win Yourself.
In Playing the Pleasing Game, Shawn Anderson shares a deeply human insight: trying to win everyone’s approval is not just exhausting—it’s impossible. Inspired by feedback from a previous blog about kindness, the post shows how even heartfelt messages can receive criticism. Playing the Pleasing Game is a reminder that authenticity is far more rewarding than molding ourselves to please others. True peace comes when we accept rejection and still stand in kindness.
Living to please others is an impossible win.
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Two weeks ago…
I wrote a blog about my dog, a 5th grader…and kindness.
As expected, whenever I mention my dogs in a blog…
The number of responses I receive blows up.
I still haven’t answered all of them.
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90% of the responses to my blog are consistently positive.
In a world where there is seemingly so much unkindness and negativity wrapped in the news and with events around the globe, I can confidently attest that the world is still rich with kind souls who want to pass positivity forward.
Here are four excerpts I received in response to last week’s blog:
1. “I love these two stories! They remind me of what is most important.”
2. “You surprise me every week with something new. This one was my favorite.”
3. “Thank you, Shawn. I needed this today. We all need more of this.”
4. “If people remember me as a kind person, I’ll die knowing I lived life right.”
Feeling the positivity of others naturally feeds my best self.
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But most every week…
I also receive a wildcard reminder that we can’t please everyone. Here’s a far less positive response I received to that same blog:
“I signed up for your email thinking I was going to learn things about how to be successful. Instead, I got some bullshit about your dog licking your hand and your kid neighbor moving. I’m not into it. Take me off your mail list!”
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The Pleasing Game is not a game worth playing.
Of course…
Who among us wouldn’t love it if everyone liked us, loved us, hired us, praised us, rooted for us, and cheered for us?
But that’s not remotely close to being reality.
We will be rejected.
We will not get hired.
We will be ghosted.
We will be turned down.
We will not be liked.
If we fail to accept life’s reality…
We will either live in a consistently unhappy state of mind…or try to mold ourselves into an A.I. version others want us to be.
And you know what?
I think that would stand forever as our most brutal rejection.
Us rejecting ourselves.
S.
PS: To the emailer above who was not a fan, I responded:
Dear Friend…
Thank you so much for giving me a try.
I wish you giant success in reaching your goals.
Your fire for achieving success is admired.
Go get it!
With kindness and gratitude…
S.
EXTRA Thoughts…
Not everything fits into the overhead bins.
And rarely will our most authentic self.
✨
Miss last week’s blog?
Same day. Same time. Same person. BUT…two very different conversations were dueling.
Curious?
✨
This week…
May we find the inspiration to shine our best selves into the world.
Thank you for reading.
With humble gratitude…
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