One courageous quote

"Your job, throughout your entire life, is to disappoint as many people as it takes to avoid disappointing yourself."

Glennon Doyle

One personal story

Five months ago, I started posting on social media.

Not casually. Intentionally. As a creator. Putting my face, my thoughts, my work out there for people to judge, scroll past, or engage with.

And it's messed with my head in ways I didn't expect.

Not the algorithm. Not the analytics. The likes.

More specifically: the pressure to create for validation instead of truth.

To optimize for applause instead of authenticity.

I can see where this can end up if I’m not intentional and deliberate about reminding myself why I started creating content in the first place.

It's a trap I've fallen into before…

The Corporate Version of This

One of the reasons I left Apple (and corporate America in general) was because I realized how much energy I was spending managing perception.

Managing up. Reading the room. Calibrating what I said based on who was listening.

I wasn't leaning into my gifts. I was leaning into how my gifts were received.

And there's a ceiling on fulfillment when you're in people-pleaser mode. You can climb the ladder, hit the metrics, get the promotions; and still feel like you're living someone else's life.

Turns out, I'm not alone in that feeling.

The Data on People-Pleasing

Research suggests that nearly 50% of people identify as people-pleasers, and it's linked to higher rates of anxiety, burnout, and resentment. We say yes when we mean no. We shrink to make others comfortable. We abandon ourselves to be accepted.

Dr. Michael Gervais, a high-performance psychologist who's worked with Olympic athletes, Navy SEALs, and Fortune 100 leaders, calls this FOPO: the Fear of People's Opinions.

Not lack of talent. Not lack of opportunity. Fear of what people will think.

The #1 Regret of the Dying

The Top Five Regrets of the Dying, is a book written by a hospice nurse, Bronnie Ware. Everything is based on actual conversations she had with her dying patients.

The number one regret?

"I wish I'd had the courage to live a life true to myself, not the life others expected of me."

Not "I wish I'd worked harder." Not "I wish I'd made more money."

I wish I'd disappointed more people.

What I'm Learning

Five months into this creator journey, I'm learning that the cost of avoiding disappointment is self-abandonment.

Glennon Doyle is right. Disappointing people isn't a side effect of living authentically, it's a requirement.

The question isn't whether we'll disappoint people. We will.

The question is: will we disappoint them, or ourselves?

One question

Where in your life are you choosing someone else's comfort over your own?

One weekly challenge

The Disappointment Dare: This week say no to one thing you’d normally say yes to just to keep the peace. Practice standing up for yourself. Notice what happens; both internally and externally.

Start where you are. Use what you have. Do what you can.

With courage,

Jonathan

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