60 Days with the Homeless
A Heart Transformed
A little over two years ago, I was living for myself in a big way. I wasn’t just caught in selfishness—I was actively hurting the people closest to me. But then God softened my heart and began speaking loudly into my life. It was hard to ignore.
I had grown up hearing powerful stories of Moses parting the sea, Daniel in the lions’ den, and Shadrach, Meshach, and Abednego being saved by the Lord. But I never connected the dots that the same God who did wonders for them is the same big, bold, and powerful God we serve today.
In May of 2023, I was on my knees, weeping, asking Jesus not just to be my Savior, but to be the Lord of my life. From that moment on, I’ve been all in on Jesus. Stumbling here and there, sure—but laser-focused on meeting Him, seeing Him face-to-face, and longing to hear the words: “Well done, my good and faithful servant.”
Prayers Answered Through People
After our surrender to God, my wife Jennifer and I began praying big prayers—healing, wisdom, and support with the people in our lives and strangers. One prayer we deeply loved seeing answered was the simple request: Lord, give us opportunities to serve Your people in need. To live out our faith and not just talk about it.
When two of our adult kids moved out, we had two free bedrooms in the basement. So, we prayed for clarity: God, use these rooms for Your kingdom. Bring people into our lives if it’s your will. Let our love for You be shared with others.
And then came Tim.
Tim’s Story
Tim had grown up in foster care, surrounded by drug and gang violence in a rough part of Chicago. Most of his life was spent moving from place to place. He told us stories about his grandfather, who loved the Lord and took him to church. It didn’t fully sink in for Tim, but the seeds were there.
Fast forward—Jennifer was out Uber driving when Tim came up on her route. She struck up a conversation, prayed with him, and quickly gave him my number. (As a Side note - a rule in our married and surrendered life now is that if my wife encounters men in need, she gets them in touch with me. If I encounter a woman in need, I get them in touch with my wife. These safeguards have protected our marriage and established boundaries to help us avoid falling into sin. )Tim was leaving the men's shelter in Beaver Dam and was about to be on the streets again.
Before he left the shelter, we invited him to our Sunday night home church/Bible study/gathering. Tim was struck by how boldly we lived out our faith. He said he had been around people of faith before but hadn’t seen it lived out like this.
That Sunday, Tim came over—and he brought a friend with him: Thomas.
Meeting Thomas
When I met Thomas that Sunday night, I saw a man who had been through it. He was timid and insecure. But he joined us—he ate with us, worshiped with us, and studied Scripture with us.
Near the end of our study, as we began sharing prayer requests and praise reports, Thomas opened up: two days earlier, he had tried to take his own life. After 25+ years of homelessness, living in hotels and cars, he was hopeless. His story was heartbreaking.
The room fell silent. Eighteen of us sat in stunned compassion.
I’d worked at the Capitol in Madison, passed by and spoken to many homeless individuals. But I never imagined we had people right here in Beaver Dam suffering like this—people who had never heard an encouraging word, beaten and neglected as children, rejected by family.
Our “Why”
After meeting Tim and Thomas—only days after we had prayed for God to use those spare bedrooms—we prayed again. And in that prayer, we felt the Lord prompting us not just to talk about faith, but to act.
So, we offered them both a room in our home.
The questions came quickly from others:
What about their mental state? What if they steal from you? Aren’t you worried about safety? They’re on the streets for a reason…
All logical questions. But here’s the thing:
When God calls you to obey, you obey.
No conditions. No disclaimers. Just obedience.
Yes, we used wisdom and discernment. But ultimately—we prayed for opportunity. He brought us people. We obeyed.
Faith Over Fear
“But Jesse, be smart. Don’t risk your family. That’s not wise.”
Fake news, bro.
Jesus said to take up your cross daily. To surrender your life for Him. Your comfort. Your plans. If He calls me to house two guys, I trust He can protect my family—just like He parted seas and shut lions’ mouths.
We are called to be set apart.
If non-believers can show love, how much more should we, as followers of Christ?
60 Days: What Happened Next
Those first weeks, we learned a lot. Tim and Thomas saw our lives—prayer/studying with my wife in the morning, men’s group, Sunday studies, BDMC events, fundraisers. They became our brothers.
We even took Thomas and his son camping with us!
Two weeks in, Tim lined up housing. During that transition, a friend of his—“Jane”—was kicked out of a shelter in Madison with her two young boys. They were headed back to the sidewalk.
Tim told her about the Mission Center, and our emergency shelter efforts. One room had just opened.
“Jane” and Her Boys
Taking in a mom and two kids felt different. Jennifer and I were nervous—but we prayed.
God made it clear: Help them.
You may have seen our Facebook post asking for donations. The response was incredible—clothes, toys, essentials. Thank you.
Their stay was lively, to say the least! Toys were everywhere. Naps and early bedtimes became our rest windows. But we truly enjoyed them.
“Jane” immediately searched for housing support. She was resourceful—but her story was heartbreaking: she had been trafficked to pay off her father’s debt. She survived gang violence, drugs, abuse… and had her boys during that time.
We were shaken.
Support Beyond Us
We realized “Jane” needed more than we could provide. We connected her to organizations like Shelter From the Storm in Sun Prairie. But resources were slow.
When we learned her abusers might be looking for her, we worked fast. After about a week, she was placed elsewhere. We had the chance to show her Jesus. To pray with her. To bless her boys with essentials.
And then—Tim had moved out. “Jane” had moved on.
Only Thomas remained.
Living With Thomas
By this time, Thomas had settled in. We called it the “homeless fog”—a mental haze from years of instability. It started to lift.
We increased expectations: work, chores, consistency.
He’d slip back now and then—video games late, calling into work. But we pushed him to stay focused. Over two months, we were able to witness to him through Bible studies, serving, and living life, all while raising our two teenage kids, who are still at home. Our prayer is that Thomas, seeing us live an obedient and servent lifestyle, will fill the void in his heart. Breakthroughs did happen. Commitments were made. Rubber meets the road when you're on your own and have to make a choice.
When opportunities come your way as a believer, who do you choose? Do you choose to live in faith? That your trust in Jesus, your hope in salvation, and letting Jesus be lord of your life will hold you through what he has called?
As for me and my house, we will SERVE the lord. We choose to live FOR Jesus, not just add him to our life.
Lessons Learned
Eternal Impact > Earthly Results
We may never fully know what God did in these 60 days. But we trust Him.
Did we reflect Christ?
Did our faith inspire them to follow Jesus?
Were seeds of hope planted?
These are questions we ask, and it’s what makes our journey in faith bittersweet. We put in the work, but we don’t always see the results, and that’s okay! I sure can’t wait to get to heaven to see how God used these different moments behind the scenes!
We continue praying for Tim, Thomas, and “Jane.” Here are some personal lessons I’ve learned:
1. Structure Is Necessary—but Flexible
Each person was different.
Tim: independent and proactive
Thomas: needed reminders
“Jane”: had great days and off days
You have to adapt the structure to the person.
2. Pray About Everything
We weren’t therapists or life coaches. But we are prayer warriors.
We prayed constantly WITH them—for workdays, for healing, for salvation, for the next step in their journey.
3. Have an Exit Strategy
Be Spirit-led about timing.
Tim needed 2 weeks.
“Jane” needed trauma care beyond us.
Thomas needed more time and help managing benefits.
Clarity and communication are key.
4. Everyone Must Work
We’re not your parents!
Tim and Thomas had to keep full-time jobs. That expectation kept them grounded. It also kept them busy in a way that prevented idleness, which biblically is dangerous.
5. Encouragement Is Powerful
We underestimated how much words matter. Homelessness often leads to a sense of mistrust; these individuals need encouragement, love, and support.
Scripture talks about taming the tongue, but also about encouraging it. We used every opportunity to speak life and show love.
6. Live It, Don’t Just Say It
Our goal wasn’t to impress them.
It was to show them a life of peace and joy because we serve God.
By week 3, Thomas was accustomed to us stopping to pray with strangers, distributing kits, and offering rides. No doubt he thought we were crazy!
My life verse and our mission center's core scripture passage is 1 John 3:18 - “Let us not love with words but with actions and in truth.“
Final Thoughts
My dad told me:
“Listen to God and obey what He calls you to each day. Don’t let the Eeyores of life change your obedience to God.”
Tim, Thomas, and “Jane” will forever be in our hearts. We still keep in touch. Their time in our home may have ended, but our prayers continue.
Thomas is now gone, we have two rooms in our basement… empty… Is it time again to pray for opportunity?!
If this story encourages you and you want to see God work in a big way —pray a bold prayer:“God, give me an opportunity to serve Your people.” It’s simple. It’s scary. And it’s powerful.
Ephesians 3:20 says God can do immeasurably more than we think or ask in his mighty power.
Do not underestimate how God can bless people through you. Love you all!
