When Speaking Up Doesn’t Look Perfect

Growth rarely looks as graceful as we imagine it will.

A friend of mine, someone who openly identifies as a people pleaser, has been doing the hard work of changing that pattern. He’s been learning to stop defaulting to appeasing, peacekeeping, and smoothing everything over at his own expense. Ingrid Clayton, author of Fawning, describes this kind of healing as reconnecting with your true self and agency.

And that’s what this work really is. It’s learning to come back to yourself.

Recently, my friend found himself in a situation where changes were being proposed that deeply affected him. In the past, he likely would have gone along with it. Swallowed his feelings. Minimized his discomfort. Told himself it wasn’t worth making waves.

But this time, he spoke up.

He gave voice to what he actually thought and felt. He named that he had concerns, not only about the proposed change itself, but also about how it was being brought forward. He did something that can feel incredibly vulnerable for someone used to self-abandoning in the name of keeping the peace: he let himself be seen.

And it got messy.

The conversation became heated. Emotions escalated. He noticed himself getting dysregulated and not showing up in the way he wanted to. So he stepped away. 

Later, when we talked, he said something that stopped me in my tracks, “I feel both proud of myself and ashamed.”

What he shared is such a wise and human reflection.

The Messiness of Real Growth

We often talk about growth as if it should look clean. Composed. Inspiring. Neatly packaged.

But real growth often looks much messier than that.

When we challenge an old pattern, especially one rooted in keeping ourselves safe, we are pushing beyond what is familiar. That does not mean we will do it perfectly. It means we are trying something different. It means we are stretching beyond an old survival strategy and into a new way of being.

For someone who defaults to people pleasing, growth might mean saying, “Actually, I’m not okay with this.”

It might mean risking disapproval.

It might mean feeling the intensity of your own emotions while also dealing with someone else’s reaction to them.

And when you are already emotional, when the stakes feel high, and when your vulnerability is not warmly received, it becomes that much harder to stay grounded and composed.

That doesn’t excuse causing harm. It doesn’t mean anything goes because you were triggered. But it does mean we need a more honest understanding of what growth asks of us.

Pride and Shame Can Coexist

What I appreciated so much about my friend is that he didn’t use his pride to bypass responsibility.

Yes, he felt proud that he spoke up.Yes, he felt proud that he didn’t just collapse into old habits.And yes, he also recognized that some of how he showed up was hurtful.

He took responsibility for that. He acknowledged the impact of his words. And he moved toward repair.

That matters.

Because the real challenge here is not choosing between pride and shame. It’s learning how to hold both.

We can feel proud of ourselves for taking a risk, for using our voice, for interrupting an old pattern.

And we can feel ashamed that some parts of how we showed up were not aligned with who we want to be.

Both can be true.

In fact, both often are true.

Don’t Let Either Feeling Take Over

I think this is where so many of us get stuck.

Sometimes pride takes over, and we use it to avoid looking at the harm we caused. We tell ourselves, “I did what I had to do,” and we skip over the part where our delivery may have wounded someone else.

Other times shame takes over, especially for those of us with a loud inner critic. We fixate on every misstep. We make the fact that it wasn’t perfect mean we failed. And in doing so, we erase the courage it took to show up differently at all.

Neither response helps us grow.

If pride overrides shame, we lose accountability.

If shame overrides pride, we lose momentum.

Growth asks something more nuanced of us. It asks us to build the capacity to stay with the tension. To hold the yes, and. To recognize the courage and the imperfection. The progress and the repair. The breakthrough and the bruising.

The Real Work Is What Happens Next

To me, this is the deeper invitation of leadership and personal growth.

• Can we expand our capacity enough to stay present with competing truths?

• Can we let ourselves be proud without becoming defensive?

• Can we let ourselves feel shame without turning cruel?

• Can we notice the messiness of the moment and still ask, “What is the next right thing?”

  
  

That next right thing might be taking a pause before more damage is done. It might be circling back to acknowledge impact. It might be offering an apology. It might be giving yourself compassion instead of contempt. It might be asking for support so you do not have to hold the weight of it alone.

Because often, what helps us stay in that both/and space is safety.

Safety within ourselves.Safety with a trusted other.Safety in knowing we are not broken because we got messy while trying to grow, we are human.

I think that’s part of what my friend needed in that moment. Not someone to tell him he was completely right. Not someone to tell him he was terrible. Just someone who could sit with him in the complexity of it. Someone who could help him hold both the pride and the shame with compassion, honesty, and perspective.

That kind of space matters.

It’s often what allows us to move from self-protection into self-awareness. From self-condemnation into responsibility. From rupture into repair.

Do you Accept the Challenge?

If you find yourself in a messy situation where you’re feeling the pull of competing feelings, take a moment to pause and reflect.

• Where is growth asking you to break an old pattern right now?

• Where are you feeling the tension of two seemingly opposing truths at once?

• And what would help you hold both with a little more steadiness, compassion, and courage?

Because growth is rarely tidy.

But messy does not mean wrong.

Sometimes it means you are finally telling the truth.Sometimes it means you are learning how to use your voice.And sometimes it means the most honest thing you can say is, “I’m proud of myself. And I’m not done learning.”

If you’ve found value in what I wrote here and you want to support me in continuing to create, guide, write, and make space for deeper transformation, I invite you to buy me a tea.

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