Engaging Culture

Why You Should Start Conversations in Unexpected Places

Traveling a great deal gives me remarkable opportunities to start conversations with all kinds of people, and you’d be amazed at how often those conversations lead to unexpected stories and insights. Listening to the media, it’s understandable that you’d think the world is a dangerous place, and the best thing we could do is to disengage – especially from strangers. But that’s an incredibly distorted view, and when we close ourselves off from conversations – even with odd or unusual people, we close ourselves off from vast learning opportunities. The things I’ve learned over the years engaging in these conversations has literally been life changing.

Just to give you an idea of what I mean, let me take shared rides. Here’s a list of the last handful of Uber and Lyft drivers I’ve met on the road and had extensive conversations with:

1. A 74 year old former Frank Sinatra impersonator who told me about performing all over the world – especially in Las Vegas and Japan. He had retired from the business six years ago, but was thinking about going back into training. When he found out what I did for a living, he wanted my advice on re-starting his former career as a Frank Sinatra impersonator.

2. A young hotel clerk at a swanky Hollywood hotel who drove for Uber on weekends. He had amazing stories of entitled rich hotel guests and their wacky demands. Plus, he revealed the most high maintenance celebrities (I’ll keep that a secret) and how high-end hotels deal with crazy customers, drugs, hookers, and what they do when a guest dies in their room. I urged him to write a book and his response was: “Don’t worry. I’m already keeping a journal that I’ll publish one of these days.

3. A retired executive that was driving to fill in his extra time. I discovered he had actually started his career in his 20’s as a Christian evangelist. He talked on and on about how much he loved preaching and loved seeing people come to Christ. The problem? It was back in the 60’s, and back then he couldn’t kick his smoking habit, and when pastors found out he smoked, they stopped inviting him to preach. This was back when there weren’t many good programs to stop smoking, and he struggled with it for years. He said that one night after preaching at a big revival meeting with great results, he stopped on the way home at a diner. He decided to have a cigarette, stepped outside, and at that moment the host pastor drove by.

He was never invited back.

As a result, he stopped preaching, and was so discouraged, he walked away from God. He changed jobs and spent the next four decades working in business. We had an incredible conversation about how smoking would have never kept him out of the kingdom, and why he may have given up on God, but God hasn’t given up on him. Needless to say, we had a little revival meeting of our own in the car.

4. I recently had a driver who thought he was an expert on Christianity, but after five minutes, I realized most of what he knew he’d learned from wacky videos on YouTube. What surprised me was his confidence. He rarely read the Bible, but was supremely sure of his “expertise.” My old Ph.D. in Theology kicked in, and I don’t know how much I changed his bad theology, but I certainly got him seeing things differently.

It reminded me that most Christians would have been confounded by this guy because based on the research for our latest book “The Way Back: How Christians Blew Our Credibility and How We Get it Back” most believers today are shockingly unequipped to defend why they believe.

5. The last driver I’ll mention was a shared ride driver in Dallas. Always looking for a way to bring up a chance to share my faith, I noticed pretty quickly that he was playing worship music on the radio. When he realized I was a Christian he told me that driving the car is his opportunity to share Christ with people. He said, “After all, I have them trapped for 30 minutes or an hour, so they can’t escape.” He was an incredibly gracious guy who had a genuine passion to reach people with the gospel. Arriving at my hotel, I stepped out of the car embarrassed that I’m not as intentional about evangelism.

That’s just my last five Lyft and Uber drivers. I also sat next to a gentleman on a flight recently who turned out to be an FBI profiler. He specializes in interviewing serial killers, and pulled out his iPad to show me a few recent interviews he recorded on video. We talked for the entire 3 hour flight about what he’s learned over the years about psychopaths.

The next time I conduct an interview with a potential client, I’ll have a new set of skills.

Try it out. Put the book, video game, or social media down, and start up a conversation with the passenger next to you, the person in the doctor’s waiting room, or your next cab driver.

You never know what you might learn….

What’s the best conversation you ever started with a stranger?

Photo by Dan Gold on Unsplash

Photo by Dan Gold

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  1. Phil, I love the stories in this post! I too am a fan of engaging with strangers. So many interesting people and the chance to see life through a different lens.

    One of my favorite personal conversations was actually taking a quick Uber to/from a drugstore during the NRB Convention in Orlando. In conversation with the driver I found out a most amazing story. She had been driving a couple to the airport who were returning to their home country of Japan. In conversation they learned that this Uber driver was a single mom with kids at home etc. They asked her to please stop at the grocery store on their way to the airport. They then proceeded to pile a bunch of bags of groceries into her car not for themselves, but for her as a gift. And then they were off on their airplane leaving behind an unconditional gift!

    She was so moved by this act of kindness that she shared it the next morning through an app to all of the Spanish-speaking Uber drivers in her area. (Maybe as many as 200!) and she shared about how God gives us an unconditional gift with his son, Jesus and eternal life!

    The other drivers started asking “When are you going to give us another story?” So, ever since then she’s been giving them a Gospel filled mini-message everyday that they can’t wait to hear! Just think of the life giving, eternal effect of that couple with their gift having no idea the ripple effect!

  2. One of the things I’ve loved about Uber in NYC is hearing the stories of the drivers most of which are immigrants and their journey to America. I’m also an airplane talker and typically start with: “Are you going home or away?” It’s amazing where that question often takes the conversation.

    1. Me too. That’s typically how I start a conversation as well on flights & have found the Uber stories to be similar. A recent Uber story was of a neurosurgeon who was driving while trying to reinstate his license here in the US.

  3. I felt like I was scooping up amazing stories all along the way on my most recent trip. The most remarkable was the conversation I had with a man who was groomed by the Mexican cartel here in the states. He found his way out but is now hoping his children can survive the neighborhood he lives in. I’m always looking for a way to connect people with God – if they are open – and we had a great conversation based on his hope for his kids. Living in LA, so many people are focused on “the industry” that most life stories are similar. Step outside this Hollywood bubble and you’ll find people are living extraordinary and interesting lives… you just have to listen for them and ask questions.

  4. I’m a little cynical on this one… I have a few actor friends who drive for Uber/Lyft here in Pittsburgh, and some also in Chicago, New York, and LA. All of them have confessed to making up elaborate back stories to tell people in their cars and they tend to change those up as an improv exercise. Their stories of what they’ve told people generally make me take all my ride-share drivers with a grain of salt haha. The flip side is I’ve actually walked away from flights with new business based on chats with people I was sitting near so that’s a good thing!

    1. That sounds like a friend of mine, who, when he attends weddings and sits at a table of people he doesn’t know, makes up an elaborate story about being something like “a driftwood artist.” He passionately tells them that “I don’t find the wood, the wood finds me and speaks to me about what it should become.” People still spellbound…. 🙂

  5. Sometimes the conversations are short but powerful. We were leading a team in Spain and went to get candy at a store to give out and hopefully open the door to share more about our faith. The owner was a Moroccan man of muslim faith. At the time we knew little spanish but he really wanted to communicate with us something, finally we realized, he was apologizing for 9/11 (we had said we were americans). It was such an incredibly holy moment we all teared up and he had to leave to the back because of the emotion. He then offered to show us around his town and be our guide. Such hospitality for us strangers it was inspiring and beautiful! So many amazing moments with strangers have happened when I am open and don’t have my phone or camera..Good post Phil.

  6. Traveling over the years I have had so many amazing and intriguing conversations… I have been able to share my faith with some and share interesting stories with others. My most recent Uber driver was a musician from Peru who drives Uber during the week and DJ’s on weekends. Before that my driver was ex-military who rebuilds and sells Tonka trucks (metal toy trucks) and drives Uber to help meet his budget. Amazingly, he make more from selling the rebuilt Tonka trucks than from Uber. Who knew? My most interesting conversation over the years was sitting next to a gentleman on a long flight who was both a microbiologist and music composer. During the flight, he shared some of his music with me and how he used music to help envision solutions to biological problems. At first I thought he was just a bit odd – but during the conversation I found out he was on his way to receive an award for a well-known medication he created. He and I have continued to remain in touch. The moral of the story is that God can use any conversation with anyone to impact the Kingdom. Remember – all of our friends were once strangers to us.

  7. As an addition to this conversation, The Wall Street Journal just published a story revealing that research studies have shown that people’s moods improve after they have a conversation with a Starbucks barista or a volunteer at a museum. They also found that people are happier on days when they have more interactions with acquaintances they don’t know well and that students enjoy class more when they interact with their classmates.

  8. I usually feel like I need to use travel time to catch up on work, read, make phone calls, grab much-needed sleep, or choose to engage with my driver or seatmate. I’m often weary, but the Spirit’s promptings to value people over those other choices has always been a game-changing choice. Sat by a business tycoon on one flight who couldn’t have been more opposite of me—swore like a sailor and drank like a fish the entire flight, shared how many marriages and divorces he’s been through, listed the number of women he’s slept with, extremely wealthy, yet totally unhappy and unfulfilled. Once he asked what I did…I went for it and was able to share how life could be better and we exchanged numbers and kept in touch. He’s actually become a OneHope partner and sent Bible App for Kids Story Book Bibles to all his grandkids! Usually make incredible connections with people who send me to my knees in prayer, force me to think outside my bubble, or end up becoming strategic partners. Never undervalue the power of human connection!

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