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The Courage to Become | Amy Wolff

The Courage to Become | Amy Wolff

My Courage of Becoming Grey || Essay by: Amy Wolff

My whole life I've craved security, comfort, safety, and predictability.

When I was young, my parents gave me an allowance with the clear expectation that I would give 10% to charity and put 10% into savings. The rest I could spend on whatever my heart desired (probably Polly Pockets). But every month I gave 10% away and hoarded the rest into savings. That's right, as a kid I opted out of 'fun' spending. I chose security.

Which also explains why I see things as black-and-white. Clear right and wrong. Neat and predictable. In my teens years this kept me out of a lot of trouble (you’re welcome, Mom and Dad!). As a rule-follower with an active Christian faith, boundaries were comforting, not restricting. I learned to easily navigate life within the walls of my morality.

But unfortunately walls that keep you safe also keep you isolated.


Over the last few years I’ve felt overwhelmingly defensive and misunderstood (particularly while scrolling through my social media feeds). I’ve been easily offended, often irritated, and if I were being honest, quick to judge. I’m surprised I don’t have permanent damage from all the eye-rolling I’ve done at articles, comments, or at headlines from particular news sources.

That’s what happens when you build walls; everyone on the outside becomes the unrelatable unreasonable other.

Surely this wasn’t loving my neighbors well - picking sides, shouting from soap boxes, and devaluing perspectives and opinions when they didn’t align with my own. It was exhausting and felt rotten. Something had to change, and it wasn’t the others. It was me.

This is my story of becoming grey.

I remember the moment the transformation started. Several years ago I was sitting on my bed scrolling through Facebook when I saw a friend share a video of two men, both gay, speaking at a Christian university. One was arguing that gay marriage is not in violation of God’s will. The other was arguing that acting on his sexual desires was in violation.

What amazed me was the respect these men had for each other. They were on opposing ends of a divisive and deeply personal issue and yet they still honored one another. Their talk included practical ideas of engaging in difficult conversations with people who disagree with you.

When the video ended, I sat there bewildered. Courage stirred.

That’s the day I started my journey of empathy - to understand and sincerely care about the others.

Shortly after committing to the journey, I met Lindsey, Missy and Patrick.

Lindsey: When the Black Lives Matter movement began, I decided that having an informed opinion on the issue required me, a white woman, to ask a person of color about their experiences and feelings. I looked around my friend group: there was none. I looked around my church: none. My community: none. So when I got into an Uber downtown Seattle on a work trip and noticed my driver was black, I asked if he’d be willing to share his perspective with me. It was brief but meaningful.

Eventually a more thorough, and to be honest more difficult, conversation happened with my new beautiful black friend, Lindsey, over dinner. I’m deeply grateful for her patience as she walked me through every hot-topic of racial tension (oh yes, hello white privilege). Because of this conversation over 6 months ago, I am slower to form opinions reading the news, more aware of my words and unconscious biases, and I’m less defensive.

Lindsey is not other.


Missy: Hard conversations continue, just yesterday in fact. I met a new friend Missy downtown Portland for lunch where much of our conversation was about abortion. She is pro-choice. I am pro-life. What does courage and empathy look like for us? We sat and listened to one another, even when it was hard. We asked questions out of sincere concern and curiosity.

When she chose empathy, she saw that I’m not a crazy conservative devaluing the heavy emotions and decisions of a woman with an unplanned pregnancy. I’m trying to protect a child’s right to live, as if it was outside the womb. When I chose empathy, I saw that Missy was not a crazy child-killer but a woman who deeply empathizes with the anguish of others – including women who are often denied critical medical care at pro-life institutions. In the end, she still protests and I still mourn lost babies but we will not villainize each other.

Missy is not other.


Patrick: All these conversations wouldn’t have happened if I hadn’t met Patrick in October of 2016. I was referred to Patrick after I had an uncomfortable experience with a client (I didn’t know what pronoun to use because I couldn’t identify their gender). Patrick was highly educated on the topics of sexuality and gender so we met for a quick meeting in a quaint coffee shop (it’s Portland, after all). Thirty minutes into our conversation, Patrick told me he was gender queer. I didn’t know what that meant so awkwardly, yet sincerely, I asked him. He was specific. He was patient. He was honest. Then he sought to understand me.

While the conversation was insightful, it was something Patrick said right before we left that struck me.

We have solidarity.

He explained, my challenge to be an authentic Bible-believing Christ-follower in liberal Portland was similar to his challenge to be authentically gender queer in a world that didn’t hold space for him. We’ve both felt misunderstood. We’ve both felt judged. But more importantly, we both share humanity and the deep desire to be loved and heard.


We are more similar than we are different.

Patrick is not other.


This has been my anthem as I wade into new uncomfortable conversations. When I’m tempted to feel flustered or get defensive, I’m reminded that deep down, we want the same things. We want to be loved. We want to be safe. We want to be understood. We want to belong.

I confess, I still prefer things cut and dry. There are still non-negotiable black-and-white areas in my life, like my belief in God. Honoring Him is still my life-pursuit. But on specific issues, I was afraid that loving well meant compromising my beliefs. Or vice-versa, that being devoted to beliefs meant that I couldn’t generously love people who believed and lived differently. But I was wrong.

I have found that there are very few things that are black-and-white.

Most of life exists in the messy undefined middle, where there are diverse experiences, different perspectives, and deep emotions. This journey of becoming grey has been incredibly insightful and liberating for me. I’m not mad every time I open Facebook (it’s a modern-day miracle!).

It’s not comfortable. It’s not safe. It’s not predictable.  It requires courage to engage when it would be so much easier to stay within our familiar walls with agreeable people. But we can do hard things.

Instead of judging others, we can choose solidarity.  

We can lean into the grey together.


Essay by: Amy Wolff

Connect with Amy on her blog and at her passion project - Don't Give Up Signs Movement.


Hi friend!

I'm Catia, a woman, wife, mama, sister, sister friend, you know -- I wear a million hats just like you.

One of my biggest whys is that I want people to feel good about ALL of who they are. Including you.

The threads running through all my work (I’m an author - The Courage to Become, I’m a motivational speaker - TEDx, Choose Joy or Die , I am a private coach ) are hope, joy and empowerment.

If I could choose ten words that best describe me I would say: honest, welcoming, giving, curious, loving, earnest, empathetic, spiritual, playful, and sassy. Let's add: adventurous. That's 11.

Nice to meet you!


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