by Kat Silverglate ©2023

Some say when we pray for patience God allows challenges and tests. How else would one know the presence of patience if not by circumstances that require it? Most of us have been there, haven’t we? During a challenge, as our agitation builds, we look at the person getting on our last nerve, and we blame them for our disquietude. Tag them as the cause. Treat them as the enemy with whom we are sparring. But then that desperate prayer rises in our memory, and we wonder: “could this be You Lord?”

When Sky Woodward wrote a prayer in 2007 for:

“the possibility of being a deeply spiritual person who has a positive, rather than a negative impact on people I care about,”

God brought her people to impact and to care about. Lots of them. But to understand the desperation of that prayer, we’ll first need to introduce you to the little girl who became a take no prisoners, prize-winning fighter with the slogan “I’ve got this” emblazoned on her game-day heart.

Sky grew up the oldest of three children in a small Oklahoma town to a farming dad and a devoted homemaking mom. To understand just how small the town was, her high school 30-student graduation class included 20 kids who had been in every grade together since kindergarten. Her mother had two non-negotiables – church and college. Church was by far the easier of the two. Part of the atmosphere in that small town and the epicenter of countless wholesome activities and gatherings, she sang in the choir there, went to summer camp, and distributed food on a mission trip. And while at nine years old she felt the Lord’s call, embraced it and was baptized, she wasn’t moved to integrate faith and daily life.

As to college, Sky quotes her mother word for word with a preacher’s fervor. “I may be raising children in a small town, but I am not raising small town children.” The expectation to exceed her environment set the tone for just about everything Sky did.

 “It feels like I was born a hard charger. Ambitious. Driven to prove myself worthy of bigger things. I gravitated toward activities where I could peel away and set my own agenda. I had zero desire to follow the crowd. What could they teach me? Why did I need them? I was essentially un-mentorable because I always had this feeling inside like I’ve got this. I can see in the rearview mirror now how God was holding my arrogant young self by grace.”

As a middle schooler who loved debating, she knew she wanted to be a lawyer. She went to her state university on a leadership scholarship, completed college in 3.5 years, then landed an internship on Capitol Hill with a US Senator.

 “When I got into a top 25 law school, my ego absolutely exploded. I thought to myself, ‘I’ve got this!’ But I didn’t have any worldly perspective. No background in life. No context for what I was learning. I was clueless and my first-year grades showed it. I was ashamed, humbled to the point of humiliation. For the first time ever, my confidence was shaken to the core. I was ready to quit.”

And then God got in Sky’s way. An unexpected mentor showed up during a summer internship with a trade organization in DC. She listened to her crisis of confidence, watched her work and concluded:

 “You have the aptitude Sky. I’ve seen your work here. You’re smart. Just because you don’t have the background yet doesn’t mean you’re incapable. You need to approach learning differently.”

The self-declared un-mentorable one found herself listening to and taking outside advice. After law school graduation, she landed a clerkship on the Maryland Supreme Court. Unbeknownst to her though, this was only the first of many rounds in the humbling ring with the God who gifted her to lead.  

She married her law school sweetheart after passing the California bar exam. When the question of children came up during her premarital counseling through the Catholic Church, she responded bluntly: “we’ll get around to that at some point.” Her cradle Catholic fiancé tried to explain the significance of the question, but she was laser focused on one thing – proving herself. Partnership first. Then kids. As a five-year lawyer, she was already managing a huge asbestos trial docket in San Francisco.

“I’d been at this firm for all of two years and had strong opinions about what the firm was doing poorly, what they could do better, what was fair and unfair, and I wasn’t shy about expressing it. I was a punk.”   

And then God got in her way. Knowing her husband wanted to return to Baltimore where he grew up, she put her toe in the water by interviewing with a firm there.

 “I told the hiring partner my complaints about my firm. He didn’t pull any punches with me. ‘Why would I hire you when the gripes you have at your firm will become the gripes you’ll have with us?’ He rejected me on the spot.”

She knew humility had landed another punch. More, she knew she needed the arrogance knocked out of her, but she didn’t know how to do anything but put up her guard and deflect the blow. By the time she left the California firm a year or so later, she was billing 300 hours a month and was sick from exhaustion. Humbled by the grind and now certain the Baltimore move was going to happen; she saw an opening at the firm that rejected her and applied again. They gave her an offer, but not before cross-examining her extensively on her poor grades.

 “I already had a chip on my shoulder. Now I had something to prove. Those grades didn’t reflect what I could do.”

She hit it harder than ever. And she excelled. And then God got in her way.

 “I always gravitated toward defense work. Plaintiff’s work requires empathy. I embraced my sharp edges. Took no prisoners. And then my sister gave birth to my niece Maya the day after my 32nd birthday. When I held her for the first time, something came undone. I was head over heels in love. Holding that little life and feeling the way I did in that moment; I knew I didn’t want to be that selfish person anymore. I went home and told my husband, ‘I’m having a child.’”

She knew a child would give her more than her own achievement to think about. Force her out of self-absorption. Make her considerate of another life. Humble her. It did.

“Pregnancy was humbling in every way. I gained 60 pounds and was border line pre-eclamptic. They put me on bed rest. I decided not to have an epidural because, well, I’ve got this! But I didn’t. There were complications. I nearly bled to death. It was terrifying. I felt, for the first time, the fragility of my own life. Motherhood softened me.”

She went back to work keeping her soft mother-self isolated from her professional life. On the day she was going to be elevated to partner, God got in her way. She put her son in a bouncy seat while she jumped in the shower to get ready for the biggest day of her life. He had a blow-out poop. It was everywhere.

 “Standing there naked, I felt my humanity deeply. In that moment, all the bigness of the achievement faded into this thought. ‘You’re Finn’s mom. Right now, you have the privilege of cleaning his poop’ I felt small in a good way. It’s hard to describe how important that moment was. It was the first realization I had that my worlds needed to become integrated. I was painfully aware that the soft part of me was isolated from my professional life.”

But how would this happen? This integration? She had no idea. But God did.

After defending the hardest case of her career that required her to travel to Miami weekly for more than half a year, getting fired by her biggest client, and being promoted to equity partner, she got her answer. Three years into her equity partnership, several associates let her know that she was too hard charging for them. She knew her ambition made her difficult to work with, but she felt sucker punched by the complaint. A big case in Baltimore County gave her a reason to move to another office and to seek out professional coaching.

“I had deep moments of clarity and grace as a result of that coaching. I’d never acknowledged that my drivenness affected others. I could see that people were hurt. I took responsibility and made genuine apologies. It was humbling. A start. But I still had miles to go. And I knew it. That’s when I wrote that prayer.”

Another law firm came calling and she took the offer. When she butted heads with a lawyer there, God got in her way.

Her sister got pregnant again only to discover that the baby had a birth defect that would lead to death either in the womb or shortly after birth. When she decided to carry the baby as long as God allowed her to live, Sky began to question her own faith. Baby Isabella was born naturally and died the next day. Sky delivered the very public eulogy.

 “I’d prayed for a miracle. It didn’t come. I could easily have turned away from God. But delivering that eulogy and watching the impact this baby’s short life had on so many people drew me close to God. That was a miracle. I prayed like crazy that He would give me the strength to speak without falling apart. To do justice to this life. To honor the grief of others. He delivered. I kept my composure. God had me in His grip. And I knew it.”

She started to attend a mega-parish and decided to do a six-month intensive emotional bootcamp course to explore how she showed up to people. That’s when she did a deep dive on that humble prayer she had written – the prayer for the possibility of showing up with a positive impact on those she cares about. And that’s when God went beyond getting in her way. That’s when God got in the ring with her for the fight of her life.

The priest of her parish started to give messages that wrecked her notion of the interaction between faith and daily life. “We are a parish for others, not to self. We are a church for people who don’t like church. You need to get out of your seat or give up your seat. Don’t be a consumer.” It was a throw down. And God carried these words to a place in Sky’s heart where she couldn’t stop wresting with them.

“My primary thought in church before this point was ‘what’s in this for me?’ Church was all about me. I was a consumer. I started to serve as a greeter. At the information desk. Wherever the need was. I started serving on the Parish Council. It totally changed my view of my role in the body of Christ and in the world. But the major shift happened in my view of leadership. Whatever I’d led in my life up until this point, it wasn’t about service. It was about proving myself. I was still that girl from a small town proving she wasn’t a small-town girl. My focus shifted to three things: why am I here, who am I serving, and how do I stop feeding my ego?” 

With too many twists and turns to describe in this limited space – a divorce, yet another firm shift, suffering a 20 million dollar verdict against her best client in the biggest trial of her life and then having it reduced to $1, turning 50, becoming an empty nester,  interviews with the White House for a federal judicial appointment, being short listed but not selected to serve on the Maryland Supreme Court and then twice short-listed but not selected to serve on the Appellate Court of Maryland, COVID isolation, non-life threatening but chronic health problems, falling in love, getting remarried – Sky finally came to the end of herself. She was exhausted as a lawyer, tired of wrestling with ambition and desperately seeking God’s will for the rest of her professional life.

“There was one thing that consistently made my servant-leader heart beat hard and strong. I had been appointed to the Board of Directors of Helping Up Mission at the end of 2020, a Christian mission serving the addicted, homeless, and impoverished people of Baltimore. They had a 500+-bed urban campus for men and were about to open a 250-bed campus for women and children. It didn’t matter how exhausted I was, I’d go to a board meeting and I would come completely alive. I cared deeply for these people and I could see the impact of my work in changed lives. This was the answer to my prayer. This is where God wanted me.”

By God’s amazing grace, Sky now serves full time as Helping Up Mission’s General Counsel and Chief Administrative Officer.

 “I look back on my life in the law and I can see how every one of those trials, those challenges, those wins, those defeats prepared me for this. That body of work is why I’m capable of doing this job. God knocked me off my feet and then picked me up and put me exactly where I belong.”

WRESTLING WITH GOD:

Through Genesis 32, we see a bit of Jacob in Sky. Alone in the dark about to face his angry brother, a man comes from behind and starts to wrestle with him. They go at it. Hard. All night long. Jacob won’t give up. The man can’t stop the fight without destroying Jacob, so, the scripture says, he “touches” him. Touches him on his hip socket. The touch wrenches his joint leaving him with a limp. Still Jacob won’t give up.

We think we are wrestling with people. With impatience. With arrogance or pride. But we are all, like Jacob, ultimately wrestling for the blessing of God. A God whose touch makes it abundantly clear that His power is far greater than our resistance. Our rebellion. Our resolve. We are to fight the good fight of faith as Timothy says, but we can’t lose sight of the One we wrestle to hold on to. To know by name. To find peace with. Amen? Amen!

Our January Mission:

In your mission pack you have a pillow box that opens on both sides. The sticker on the outside says “in” on one end and “out” on the other. Shake out the contents. There are ten paper tags in your box. Here’s the basic concept. Each and every time we feel a poke, a prod, or an inkling that God is getting in our way or moving us toward His good purposes, we are going to write it on a slip of paper and put it in our box. We are going to start “boxing.” Each morning, consider pulling the slips of paper out of your box and praying over your responsiveness. If you respond, write a note on the back, fold it, and put it back in. The folded slips are what we pull out of our box to praise.

Some of the tags in you box have words. If you would like a PDF with a description of each tag and what you can do with them to grow in responsiveness to God, email us at [email protected]. We’ll get it to you right away.

Our goal is to do this activity for 31 days in January – writing down each prompt, nudge and poke, folding each one that we walk out in our daily life, and praising God each day for a life of responsiveness to HIM!

Happy New Year! May we all be filled with joy as we grow in responsiveness.