Oops, I Did It Again: My Last Rodeo with Dysfunction

Oops, I Did It Again

Yep, I stayed too long.
Eighteen months too long, to be exact.

I clung like a stage-five clinger to an organization that dangled promises of payment in front of me like a carrot.

“Michelle, we’re having financial issues,” the Director said (again).

Oh, I knew. I knew because the grant money I brought in was used to patch their financial dumpster fire—while my invoices sat unpaid for months.

Then came the new CFO—a former caterer who supposedly turned ledgers from red to black. He promised they had “a plan for me.” But that plan never materialized.

Every board meeting was the same: We’ll get to you.
Translation: You’re not a priority.

Finally, I snapped. I sent an email demanding payment. That forced a meeting with the Director and CFO. Instead of answers, the CFO hurled insults while the Director stayed silent.

And then the truth hit: there was never a plan. Just empty promises.

I realized that there hadn’t been a plan. They made promises: a partial payment, a job description, a seat at the table.

Guess what happened next?
More silence. More stalling. Then, on August 11th, I received an email from the executive board: All promises revoked.

This Wasn’t My First Rodeo

I’ve been here before.
The boss who took credit for my work.
The director I hired who later cut me out of my own projects.
Colleagues who ghosted me after pocketing my money.
A partner who accused me of being “insensitive and privileged.”

Different faces. Same dysfunction.

Why Did I Stay?

Fair question. Here’s the truth:

• I believed in the mission. Feeding hungry kids matters.
  
• I believed in the Director. I thought she had a heart.
• I believed my passion would protect me.

But the deeper truth?

I stayed because I’m the oldest daughter of an alcoholic father. I grew up fluent in survival skills that don’t serve me anymore:

• People-pleasing.
• Craving external validation. (Please like me. Please see that I’m good.)
• Avoiding conflict at all costs.
• Perfectionism and overachievement.
• Feeling responsible for everyone else’s happiness.
  
  

What I Did Wrong

Nothing—except to stay silent too long.

1. I tried to fix the unfixable.
   Perfectionism blinded me to the truth: I had no power here.
2. I wanted everyone to be okay.
   But my silence and self-betrayal only made things worse.
3. I avoided conflict.
   Meanwhile, the assholes thrived.

Shame, shame, shame. Fool me once…you know the rest.
But this time, I’m done playing that game.

How to Stop People-Pleasing (Without Becoming an Asshole Yourself)

Here’s what I’m practicing now—and what you can do, too:

1. Boundaries Are Non-Negotiable.
   If they don’t respect your time, work, or worth—leave. Don’t wait for “someday.”
2. Speak Up (Even When Your Voice Shakes).
   Silence is permission. Call it out. Use “I” statements. Write it if you have to. But say the thing.
3. Detach from Validation.
   Your worth doesn’t depend on applause or approval. Write down what’s true about you—even if no one else affirms it.
4. Stop Playing the Peacekeeper.
   Peacekeeping often means self-betrayal. Let things get uncomfortable. Conflict beats erasure.
5. Radical Self-Care.
   Not bubble baths. Real care: rest, therapy, joy, community, saying no. Build your life where assholes don’t get to call the shots.
   
   

Why People Sometimes Act Like Insensitive, Heartless, Arrogant Jerks (Even to Good People)

• Insecurity: They tear down others to focus on their inadequacies.
• Jealousy: Your success highlights what they lack.
• Scarcity Mindset: They hoard, sabotage, or exploit because they think there’s “not enough.”
• Unprocessed Trauma: Hurt people hurt people.
• Toxic Culture: If assholes get rewarded, they keep showing up as assholes.
  
  

Here’s the key

People aren’t assholes because you did something wrong. They are hurt people who are stuck in their own fear, ego, or need for control. You’re not responsible for fixing them.

Give yourself the self-compassion they didn’t, and maybe one day when you’ve done a lot of healing and filled your cup then you can give the jerks in your life compassion, too.

And if you’re ready to rewrite your story…

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