It’s a strange situation to have someone you don’t know in your personal car. And – as if that weren’t weird enough – I figure that, since I’ve given approximately 1,000 rides over the course of a year, and since the average passenger pick-up was 2.5 individuals, I have had about 2,500 strangers ride with me!

Living in Orange County – one of the most diverse counties in the United States – these 2,500 people represent a wide array of different ethnic, religious, and socioeconomic backgrounds. Within these various backgrounds, I have had conversations with millionaires, homeless, widows, newlyweds, business individuals and every other type of person under the sun.

At first I didn’t plan to drive for rideshare companies to meet these different kinds of people. Like most people who drive for rideshares, I started driving to make ends meet. My wife felt the Lord tell her to take a year off of work to be with our kids full-time, and I wanted to honor both her and the Lord, so we decided to make it work. One of the most accessible and immediate ways to bring in extra income was to drive strangers around town.

However, driving a full-time shift every Friday night for a year turned out to be more than just a path to extra income. My time invested behind the wheel became an opportunity to encounter, encourage, and entertain a world much bigger than the one in which I was used to living. Driving these strangers around brought me into the thick of a world of hurt people, and it opened my eyes to an expansive mission field of people who are all searching for something.

While each encounter was certainly unique, I want to offer three stories of my time driving for a rideshare that stand out in my mind. My goal in sharing these stories is that they will inspire you to think outside your box of influence—and to think bigger!

It’s True: Money Doesn’t Buy Happiness

Why do we envy people who do not have it all together? After all, no one has it all together—including the rich and famous. So, if even the rich and famous do not have it all together, why do we envy them? We tell ourselves, “If only I had this much money or that particular something, then I’d be happy.” Obviously there are people who do have it more together than others, but my first story happens to be about a rich passenger who was desperately searching for something.

One Friday night, I picked up a lawyer who happened to represent several top-name singers, and in order to prove to me that he was a major player in the music scene, he Googled his own name and showed me pictures of himself. Low and behold, there he was with one of the top pop music superstars of our day. This guy was the real deal.

We started to chat and immediately I knew he was inebriated, but our conversation was lighthearted and fun. After a few minutes, we were interrupted by a phone call. On the phone was a girl he’d dated for seven years, and he was telling her how great she was. In fact, he would periodically put the phone down and tell me how great she was! But I could also hear in his one-sided conversation that she was disappointed and hurt. It turned out that he was supposed to be home to her hours ago, and he kept telling her, “I’m coming home. I love you!”

His girlfriend may have been hurt, but she was also relieved that he was at least going to come home to her. We were driving in Orange County and she was waiting in Los Angeles, so she probably expected to see him in about an hour or so. But after he hung up, he called a childhood friend who lived right down the street from where we were. They made quick plans to meet up and have drinks ten minutes out.

After he hung up with his childhood friend, he told me, “Hey, I have a friend who lives down the street. She is a well-known news anchor. Drop me off at her house!” So, instead of this passenger going back to his girlfriend who was waiting on him and expecting him to be on his way, he totally blew her off to have drinks with a “friend.” 

Through the conversation I had with him during our drive, it was obvious to me that he was missing something. Between phone calls, he would make comments like, “Why is life like this?” Even without any context to his drunken ramblings, I could clearly sense that there was some deep pain in this passenger—pain that had been there for years.

Dropping this top-tier attorney off at his childhood friend’s house, I was reminded that our external circumstances really have nothing to do with our happiness. Rather, our happiness has everything to do with how we respond to our outward circumstances. Ideally, internal fulfillment comes from our Creator and not from our circumstances, which are always fleeting.

God-Filled Moments

One night, I picked up a girl from Laguna Beach. She was wearing her “Friday best,” so when I picked her up I assumed that she was just getting a ride to party somewhere and that she was one of those “rich girls.” I forgot to never judge a book by its cover because, as it turned out, there was so much more going on.

I asked her, as I did most passengers, “What do you have going on tonight?” She said in a soft voice, “Just going to my friend’s house, getting out for a bit.” I pressed her a bit, “Do you not get out much?” She replied, “It’s a long story.” I said something like, “We have time, if you want to share.” (I’ve learned asking open-ended questions gives people permission to share without obligating or pressuring them to share.)

She went on to share that she’d been married for a couple years and that her husband had been struggling with depression and other mental illnesses. She stood by his side, trying to get him help—help that he resisted. She talked a little about the internal battle he was fighting and how she was not able to help him. Then, one night when they were both in a room together, he pulled out a gun and shot himself. Her husband committed suicide in front of her!

The ride was only supposed to be 35 minutes but it ended up being closer to an hour because there was a major accident on the freeway. This gave us time, and she started talking about counseling, her healing process, and I was able to listen and ask questions along the way. This allowed her to continue to talk, if she wanted—and she kept sharing.

When we got to her destination she shook my hand and said, “Thank you!” The “thank you” was not just a casual courtesy but a sincere, heartfelt “thank you for taking the time to listen to me.”

I initially judged her by her appearance when I picked her up, but I learned very quickly how far off I was. There was something special – I would even say holy – in that moment. God used me to allow her to continue to work through her grief and pain and to encourage her in the Lord, and all because of a freeway delay.

A Divine Appointment

Tony was with his brothers and their spouses when they thought it would be fun to visit a tarot card reader who was “reading fortunes” on the street in downtown. They spent about an hour with this card reader, and they also passed some time getting to know one another in the process.

After the reading, his brothers, their spouses, and he and his wife decided to call it a night and started to get in their vehicles to go home. It was then that the tarot card reader told them that she had fallen on hard times and needed a ride home. There wasn’t any room in the vehicles, but Tony felt for her situation and told his family that he’d walk her home and get a ride back.

When they got to her apartment, she invited him in. Tony politely declined, but she kept insisting that he come in with her. He told her, “I used to be a bad guy, but I’m not anymore.” She persisted, but he reiterated his refusal and called for a ride to come pick him up.

Tony got in the car and was pretty distraught. We started chatting and, naturally, he asked me what I did for a living. I told him that when I wasn’t driving I worked as a campus minister at a Christian college, and he just couldn’t believe it. He excitedly exclaimed, “What? Man, I cannot believe God has put you in my life. Just when I think God isn’t there, this happens!”

A few years earlier, Tony had an employee who would occasionally go up to him and say, “Tony, you’re loved.” Tony used to think that he was weird and just to get back to work. After a number of these exchanges, Tony asked his employee, “Why do you say I am loved?” That, in turn, led to a conversation about faith. Shortly after that, Tony put his faith in Jesus.

Years had passed, life had hit, and Tony felt that God just wasn’t around. On our drive together, Tony kept saying, “I can’t believe this! I can’t believe this!” He was in awe that God would use someone like me, a rideshare driver, to remind him that he was, in fact, loved and not forgotten. 

A Worthwhile Conversation

Never in a million years would I have thought that I would meet these people, but driving strangers around has helped me remember that the world is much bigger than my customary sphere of influence. With all the different types of people I’ve encountered, I’ve learned that honest and open communication is an essential tool for inviting healthy dialogue on faith and other related issues.

So how do we have conversations with strangers that can potentially lead to faith discussions?

First and foremost, it’s crucial to find commonalities with people around you. They may not be believers; they may even say something you disagree with or find offensive; but find a common ground and a starting place for a healthy conversation.

Second, when you decide to drive for a rideshare, do so with purpose. I started to drive out of a basic financial need, but I quickly started to see that I had a much bigger purpose.

Most of the time when passengers get in the car they will say, “How long have you been doing this?” When I was asked that question (or something similar), I would generally respond by saying, “I am driving so my wife can be home full-time with our girls.” That statement led to other questions and on into all sorts of good conversations, conversations that many times led to faith discussions—because the follow up question was usually, “What do you do when you’re not driving?”

Here’s an engaging idea for driving with a purpose:

When you pick people up and the conversation naturally starts, imagine you mentioning to them that you are driving for this company and that 100% of what you make (tips included) goes to a credible non-profit that is reaching out to help those enslaved in sex trafficking, to poverty, or to an organization that brings resources and tools to the mentally ill. Even if they’re not believers, their interest will be piqued, possibly leading into a conversation about faith—and you’ll be able to raise funds for a credible organization.

This really accomplishes two things. One, it arouses their spiritual curiosity, and, two, it provides an opportunity for a healthy conversation about your faith in Jesus. But you must have integrity when you do this; I cannot emphasize this enough! There have been too many pastors who have robbed from others, giving Jesus a bad name.

Regardless of your reason for driving, drive with a purpose. Maybe your purpose is to raise awareness for an organization. Maybe your purpose is simply to listen and encourage people on the road of life. Whatever it is, find your purpose for driving and ask God to open up those hearts and minds by means of a rideshare conversation.

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