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  • Julius de Jong

How to Talk to Strangers (Episode 10-39)

Open up, connect, and possibly change your life

This morning I was reflecting on my friends and the people closest to me. I realized that more than a few of them where people that I had no connection with before I met them. Zero! We didn’t go to the same school. We didn’t share common friendships. Nor did we grow up in the same region, city, or even continent in some cases. They were strangers when I first encountered them. Today, they’re close friends who are dear to my heart. We shared amazing experiences, built businesses together from scratch. Travelled together. Cried together. Overcame hardship together. Laughed together until our bellies ached. These people literally helped change the course of my life. Through meeting them, it enabled me to meet a whole string of other people which I would otherwise have never met. And I don’t mean through introductions by them. That obviously happened too, but it’s more profound. Because of meeting some of the people that I did, I shifted my focus in life, or even moved to another country or continent. That in turn resulted in new opportunities, which then led to new connections again.

Thinking of it now, through meeting a stranger and connecting with him, I’ve moved to Switzerland, developed a whole new side of my business, and ended up teaching in two Swiss universities. Furthermore, as this one stranger awakened my love and appreciation for Switzerland, there I then met a whole range of new people, completely unconnected to my first friend who triggered me to move there to start a business with him. Years later, I decided to move to Myanmar with the goal to start a business there. In order to meet new people, I started organizing a Meetup, connecting foreign and local entrepreneurs. I still remember the first event. There was me, one person who showed up through the Meetup website, and one stranger from Japan who I had met the evening before in a restaurant while having dinner. I had told her about my event, and she showed up. I just checked, and the Yangon Business Network now has 978 members. The Japanese lady who was the second attendee to my first Meetup told me about the then launch of the European Chamber for Commerce in Myanmar, and suggested I attend.

On the day of the launch event, I asked at my hotel for a taxi. A driver showed up who could speak English, and we ended up talking the entire ride. As I had told him I was doing market research, he offered to be my driver and to help me where he could. That was the start of a cherished friendship, and later also business relationship. Together with him, and later others too, I started two companies in Myanmar, where he is a director in both. Because of my activities in Myanmar, I ended up meeting someone in the Netherlands who is an expert in organic waste valorization, my focus for the activities in Myanmar. We started working together, and have now been in business since 2015, and founded four companies jointly. More importantly than the business connections though, are the friendships that have developed between me and these wonderful individuals. It has been an amazing journey, and I know we’re just getting started. Think about it! All of this because of connecting with strangers! Because of getting over that awkward moment and starting a conversation. I simply could not imagine how my life would look without all these amazing people who’ve come on my path to share the journey with me. If there is anything you take from the above, I hope it’s the courage to say ‘hello!’ when you feel drawn to someone, somewhere, sometime.

Benefits of connecting with strangers

As I hope I’ve illustrated through my personal experiences, great things can happen when we reach out and connect with strangers. We get to learn new things, learn about new people, and get to have new experiences, or even entire new chapters to our lives. This is extremely valuable, and enjoyable. There really are no words to describe the impact a stranger can have on our lives. It’s simply amazing. When you talk to strangers you’re making beautiful interruptions to the expected narrative of your daily lives, and theirs. You’ll make unexpected connections [and find amazing opportunities to learn, expand your awareness, and gain new perspectives]. When you don’t talk to strangers, you’re missing out on all of that’ (Stark, 2016). Another great benefit of connecting with strangers is that we get feedback on ourselves, our thoughts, and our assumptions. If we’re lucky, we’ll get our assumptions challenged. It’s so easy to get stuck in our own mind with our static thinking and assumptions. Strangers, and people outside of our regular circles can be invaluable in helping us break free from the rut and discover new perspectives. Connecting with strangers also dispels fear says Kerrie Phipps in our interview on talking to strangers. As human beings, we are conditioned to fear the unknown. We fear people groups we don’t know or are not familiar with, or a certain demographic of people we’re uncomfortable with (Phipps, 2021). However, when we approach these people with curiosity, gratitude, and awareness, we’ll discover the human being behind our categorization. What happens next is the beauty of life.

Listening to our intuition

Many times, I’ve seen someone somewhere, and I was just pulled to them. My intuition told me to reach out and connect. There was something there. However, not always have a had the courage to act on this feeling. But the times I did, have always been amazing. We need to learn to get over our inhibitions and the awkwardness we might feel by just reaching out to a stranger, and do it! As Kerrie explained, the nervousness is temporary. All we need to do is start the conversation. Just say ‘good morning’, or simply ‘hi!’. It can be incredibly rewarding when we do make that first step (Phipps, 2021).

The opposite of our attraction is also fascinating. When at first glance we feel we’re not interested in someone, we can actually challenge that, and ask ourselves; ‘what’s there to discover about this person?’, ‘what can I learn from him/her?’ Brené Brown said it beautifully; ‘people are hard to hate close up’ (Brown, 2019). Everyone deserves a closer look, and we all benefit from looking closer at people and discovering who they really are.

Strangers are dangerous

‘In many parts of the world we’re raised to believe that strangers are dangerous and cannot be trusted’ (Stark, 2016). We’re uneasy around strangers because we’re missing context. We don’t know what their intentions are. However, that doesn’t have to mean their intentions are all bad. ‘Believe in others, that is the absolute best strategy if we want to live a meaningful life’ (Gladwell, 2019). If we do so, it comes with a price. It means we will sometimes get deceived and disappointed. However, as Malcolm Gladwell states, that’s not a sign of us doing it wrong, it actually is a sign of what we’re doing right, as most people are good at heart and deserve our trust. So, let’s step over our initial reservations and fears about other people. Instead, let’s seek them out and connect with them for who they truly are; human beings, just like us.

Our mistakes when connecting with other people

A big preventer from us connecting to other people are the assumptions we have about them and ourselves in relation to them. As Kerrie explained, the biggest mistake is making the assumption that people don’t want to talk to us. This is rarely the case, as people tend to be very happy to connect once we’ve made that first step. She also mentions the assumption that other people are better than us, or that we think they think they’re better than us. ‘We can assume the worst of people, while we want them to think the best of us’ (Phipps, 2021). For this, we must be aware of the conversation in our heads, and how much we’re expecting other people to be friendly and take the initiative. Actually, if you think about it, it’s very empowering to realize that we are in control, and that we can take the first step. We don’t have to bother with our assumptions. Instead, we should just make that first move and find out in practice about that other person. Ask ourselves, ‘what am I expecting of others, and what am I giving?’ How am I making it easier for other people to connect with me, rather than putting all the responsibility on them? (Phipps, 2021).

Fear of rejection

I love what Kerrie said when I asked her about fear of rejection, and how to overcome this when talking to strangers. Our brain automatically alerts us to potential dangers, and potentially harmful situations. As she so rightfully suggests, ‘we need to challenge the fears that come up’ (Phipps, 2021). In many cases, it’s not the people we encounter that are threatening, but our past experiences we have unconsciously attached to this new and unfamiliar person. Our brain holds on to these negative experiences because it wants to keep us safe. We need to consciously examine our fears and check in with ourselves if these are relevant and related to the person we encounter, or merely triggers from our past experiences. It’s also important to not take things personal, when someone is unavailable to have a talk, or simply too occupied to notice our attempt at connecting. When we give into our curiosity, we can overcome our fears and discover something and someone new and worthwhile. Try it! We should use our senses, instead of our fears, and our perceptions instead of our categories. Judging people based on categories and fears results in bias, and we all know we are better without it.

Make a great first impression

‘People learn everything they need to know about you within the first few seconds of meeting you’ (Lowndes, 2003). Without saying a word, you’re sending clear signals about how you’re feeling about yourself and the person(s) you’re interacting with. Therefore, when wanting to connect with someone, make sure our body tells that message too. Pivot your heart towards them, smile, don’t cross your arms, and make sure you thoughts about that person are positive and uplifting. When you send out a ‘negative vibe’, expect the same in return (Boothman, 2003). ‘First impressions are the most lasting. "The way you look and the way you move" provide 80 percent of the information people use to form their initial impressions of you’ (Lowndes, 2003). Therefore, make sure your first impression is a positive one. We don’t get a second chance to a first impression, so make sure to be nice and positive towards the people you encounter!

Asking permission

People are occupied. Our minds are occupied. Our brains can only focus on so much at the same time. Therefore, when we want to connect with someone new, let’s say in the train, or down the street somewhere, it’s useful to help them switch their focus. When we ask someone for permission to engage with them, we help them do just that. We give them a moment to switch gears, and move their focus from where it was, towards us. This doesn’t always have to be verbal. Also, eye contact and a smile help people refocus their attention towards you. Verbally it could be as simple as, ‘excuse me, do you mind me asking you about what you’re doing here?’, or ‘do you have five minutes, can I talk to you about XYZ?’ Asking permission not only helps others shift focus, but it also helps us. When we pause for a moment and ask so that the other person can shift gears, we at the same time can tune into them ourselves. From there, we can give that other person our full attention, making it easier for them to feel seen and return the favor.

Do talk to strangers

In her book, ‘Do Talk to Strangers’, Kerrie Phipps has laid out a teachable framework for connecting with strangers, the ASKING model, comprised of the first letters of Awareness, Start Small, Keep Going, Interest in Others, Natural Confidence, and Gratitude. I highly recommend reading the book for yourself and practicing what you learn. However, I’ll attempt to provide you with a short summary to help you get an idea of the practice below.


We don’t make significant progress with any goal without a good awareness of the situation (Phipps, 2014). When talking to strangers, we need to tune our awareness towards them. Therefore, when wanting to connect with others, we first need awareness. Both of ourselves and the person we’re trying to connect with. We need to be aware of our body language, our posture, and our expressions. As Kerrie explained during our talk, even a neutral expression can be interpreted as threatening (Phipps, 2021). It’s therefore very important to smile. This shows other people we are easy to connect with and that we are non-threatening. We need to take responsibility for the possible impact we might have on others. We also need to cultivate awareness towards the other person(s). How would they perceive us? What would help them feel secure about connecting with us? What’s going on for them? Of course, we cannot be fully aware of all that is going on in the world, but we can shift our focus towards being more empathetic towards the person we’re engaging with. It makes a difference.

Start Small

In her book ‘Do Talk to Strangers’, Kerrie lists three simple steps to connect. We can all do these, without exception. And it’s simple: 1. Make eye contact, 2. Smile, and 3. Say ‘hello!’. That’s often all we need to get a conversation going. The smile in this regard works miracles. Other simple ways of connecting are making a compliment or commenting on something that you and that other person have in common or share. Such as a delayed train, or rain that just started. Anything, really. This is what Kio Stark calls triangulation. Finding a social conduit is another way to start a conversation (Stark, 2016). This could be a dog you engage with, or a baby. From there, you can connect with the dog owner, or the baby’s parent. How you start the conversation doesn’t really matter. The important thing is to start. Just have a go and get over the possible slightly awkward moment at the start. I know from experience, it’s very much worth it. ‘You make a bigger difference than you know’ (Phipps, 2021).

Keep Going

To keep a conversation going, it’s important we’re making things fun, comfortable, and easy for the other person. Quality questions help with that. A quality question is easy to answer, fitting with the context, and non-intrusive. Ideally, they bring a smile to your face (Phipps, 2021). For instance, ‘what do you love to do?’, or ‘are you from around here?’, ‘what book have you recently really enjoyed?’ are good examples of quality questions. ‘What’s the best book you’ve ever read?’, is a much more difficult question that can make people feel uncomfortable and put them under pressure. ‘What else?’ on the other hand is a great question that helps unlock more creativity and many more ideas to keep a conversation going. To read more about asking questions, also have a look at my previous post, ‘How to Ask Better Questions’, and my interview with Steve Hobbs on this topic, as he has got a lot of great things to share about this. Being vulnerable and disclosing something about yourself is also a great way to connect with others and to keep a conversation going. Tell something true and personal about yourself that makes you vulnerable in a way. The interesting thing with vulnerability is, that it always invites people to do the same, and they open up too. (Stark, 2016).

Interest in others

We can’t have an interest in others without awareness, and we can’t have awareness without attention. So, our attention needs to be with the other person. We need to be curious about them, and what makes them tick. Asking ourselves, ‘what is there to discover and learn with this person?’ is very helpful in my opinion. Because there is always something to learn, and something to discover with other people. That’s a fact! We can choose to be interested, and we should. You won’t know it until you try, but it can literally change your life. ‘To make people feel great about you, focus your conversation on them’ (Lowndes, 2003).

Natural confidence

When feeling nervous to connect with someone new, we can tap into our natural confidence, as suggested by Kerrie in her book and during our interview. Our natural confidence comes from when we’re being ourselves authentically, instead of playing a role or hiding behind a façade (Phipps, 2021). The things you do without thinking are the things you do with natural confidence. In those instances, we’re just being ourselves, instead of acting from behind a mask. Realizing this can help us shift away from feeling awkward, and back into our body, naturally confident. It’s okay not to be perfect, and it’s okay to just show up as we are. Then, when we stop trying, we find that we just are, naturally confident.


Showing gratitude is a great way to connect with people. It’s when we’re giving something, instead of asking. Everyone loves to receive. And to give gratitude, is as good to give, as it is to receive. I personally believe that being grateful has a huge effect on our wellbeing and happiness. Therefore, when expressing gratitude for others in our interactions with them, it’s not only benefitting them, but also us. It also shows we’re seeing people and acknowledging them specifically. Kerrie mentioned an example of thanking the bus driver for a safe ride, during our talk. This creates recognition for the other person, and builds a connection, even if it’s just momentary. In any case, it always lifts our spirits (Phipps, 2021). Lastly, practicing and expressing gratitude is also a great way to shift away from any anxiety we might experience when connecting with a stranger, as it simply benefits our wellbeing tremendously. Writing this, at 11PM on Sunday night, I’m just feeling grateful for having connected with Kerrie and the amazing conversation we’ve had on the topic of talking to strangers. I’m sure it won’t be the last conversation, and most certainly has renewed my inspiration for talking to strangers, and making them my friends. And for that too, I’m grateful.

Conversational competence

We’re getting to the point that in many cases we’d rather text someone than actually to speaking with them in person (Headlee, 2016). We need to (re)learn to have a conversation. Conversational competence might be the single most overlooked skill we need to teach and learn again. Celeste Headlee identified 10 rules for having coherent and confident conversations which I really appreciate. Find them listed below, or watch her TED talk here:

1. Don’t multitask. Do one thing only; focus on the conversation. Be present, be in that moment of conversation with that other person;

2. Don’t pontificate. Don’t preach and state your opinion without any room for response, discussion, pushback or growth. Instead, enter every communication assuming you have something to learn.

3. Use open ended questions. Start questions with: who, what, where, when, and why. What was that like? How did that feel?

4. Go with the flow. Thoughts will come into your mind, and you’ll need to let them go. Because if we follow them, we stop listening.

5. If you don’t know, say that you don’t know. Talk should not be cheap.

6. Don’t equate your experiences with theirs. If they’re talking about a loss, don’t start talking about a time where you experienced loss. Experiences are unique for everyone. It’s never the same. All experiences are individual. And more importantly, it’s not about us. When listening, we don’t need to prove how amazing we are or how much we suffered. All we need to do is listen.

7. Try not to repeat yourself. It’s condescending and its boring. We shouldn’t keep rephrasing our points and raising them over and over.

8. Limit the details. People generally don’t care about the years, the names, the dates and the other details we’re struggling to come up with.

9. Listen. This is the most important part of having coherent and confident conversations. When our mouth is open, we’re not learning.

10. Be brief. Keep things short and concise. A good conversation is like a miniskirt; short enough to retain interest, but long enough to cover the subject.

Photo by Lashonda Delivuk.



As the 39 Ideas For Life project might have you suspect, I am a very curious person. I love learning about (and from) other people, and about what makes them tick, and what makes them unique. Although I find it a bit scary at first sometimes, I really enjoy connecting with strangers. Because of this, I’ve talked to Kerrie Phipps from Australia, to learn about talking to strangers. Kerrie has written five books, of which three have been about connecting with strangers, titled and ‘Do talk to strangers’, ‘Do Talk to Strangers: Travel Toolkit’ and her latest ‘How to talk to strangers’.

Apart from being an author, Kerrie is also a public speaker on connecting confidently and a coach who helps leaders hear themselves think, asking questions no-one else will ask. Above all, I think Kerrie is an amazing human connector who is exceptionally interested in people and their wellbeing, and helping them progress and create a better, more human, and connected world.

Our recorded interview lasted almost 1 hour and 20 minutes, but we actually talked for double that time. It was such a pleasure to speak and connect with Kerrie. I know this has just been the start. From my first encounter with her via WhatsApp, approaching her for this talk, I’ve felt welcome and appreciated and simply really enjoyed our connection. I’m sure we can all benefit from some of the lessons Kerrie has shared. Please enjoy the recording, and if this is useful for you, don’t forget to reach out and connect!

Website of Kerrie Phipps:



Boothman, Nicholas, 2008, How to Make People Like You in 90 Seconds or Less.

Brown, Brené, 2019, Braving the Wilderness.

Gladwell, Malcolm, 2019, Talking to Strangers.

Headlee, Celeste, 2016, 10 ways to have a better conversation. TED talk., accessed on 12 September 2021.

Lowndes, Leil, 2003, How to Talk to Anyone.

Phipps, Kerrie, 2021, How to Talk to Strangers.

Phipps, Kerrie, 2014, Do Talk to Strangers.

Stark, Kio, 2016, Why You Should Talk to Strangers. TED talk., accessed on 12 September 2021.

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