5 Connections, 5 Insights: 71-75 of 100

Project Horizon is a global conversation experiment by high-performance coach and advisor Dr. Tim Dutton. It aims to uncover diverse human perspectives by connecting with 100 remarkable people worldwide, linked through six referral-based chains.

ON THE GO? LISTEN TO THE INSIGHTS 🎧

71. Investment guru and modern-day philosopher

72. Social media influencer from Czechia

73. Art gallery director in Nigeria

74. Big wave surfer and ten-time world paddleboard champion

75. Former comedian and Comedy Central Roast regular

I’ve written plenty about the amazing experiences I’ve had with this project. It’s about time I wrote about a rubbish one.

And it was all my fault.

Connection 71 is a financial investment guru who was also highly spiritual. After a successful career in the investment world, he experienced somewhat of an epiphany and decided to pivot to a life of greater personal purpose. He now spends his time building and supporting a community of investors. From what I could tell, whilst providing bigger picture insights and trends, he also tries to encourage his community to stay connected to themselves and the world around them.

He’s also spoken on stage at Tony Robbins events alongside figures like Barack Obama. I could see why from the eloquent way he shared his perspective on life.

Alas, I fear neither of us got the most out of the experience.

I’d turned up to a co-working space to take the call. Something seemed ‘off’ as I walked through the suspiciously quiet office space. Nonetheless, I squeezed into a phone of the phone booths and got set up. this setting up process just seemed to lack the presence of Wi-Fi. ‘No problem’, I thought, ‘hot-spot will do’.

Shortly after exchanging “hello’s”, one of the workspace managers appeared in my periphery. Aware my weak mobile data was causing already causing a lag in conversation, I broke off the conversation to ask the manager where the Wi-Fi had gone.

“It’s off from 5pm this evening as there’s work being done.”

Slightly confused and embarrassed due to the poor start to the conversation with Connection 71, I quickly get out of the booth and move closer to the window where my mobile data should be stronger.

This causes a second disruption to the call, and I’m concerned I’m coming across like the call isn’t important to me. We get going again on my phone this time, in the hopes there’ll be less lag.

A few minutes go by, and another workspace staff member enters the room. It’s just the two of us (and my guest zooming in from Toronto, Canada). I sense the staff member waiting for an opportunity to say something. After hoping she’ll realise I’m busy for a couple of minutes, I give in to her presence and once again excuse myself from the conversation.

I’m now feeling entirely disrespectful of Connection 71.

He politely continues. He shares how he developed his various perspectives on spirituality, as well as how his love of journalling came from reading his late grandfather’s journals. He’s delivering gold, but I am struggling to become fully present again, and I notice my questioning becoming poorer. Not being present, and feeling the pressure, I throw together questions in a hurry. They feel incongruent with the conversation.

After roughly 50-minutes, as I’m fumbling my way through another shoddy question, my guest respectfully interrupts to tell me he must leave. He doesn’t tell me why and, quite frankly, I don’t blame him. I can’t say for sure how he experienced those 50 minutes. But I can glean a lot from the fact he was the only connection to explicitly say they won’t be referring anyone into the project.

As I write this, it’s been around 9 months since the conversation. Having reflected on it many times, I think the key takeaway is know when to abort mission. If conditions aren’t right, reschedule to preserve credibility.

Hope he didn’t tell Barack about it.

Connection 72’s father had passed away a few days before our call.

Whilst they had reconnected somewhat in his final few months, she felt their relationship had been strained. In fact, most of his relationships were strained. In her opinion, this was down to him valuing “truth” and “himself” more than his relationships.

“He was never really good at building them, and then he was there alone in his final days, months, years”. When I asked how what she took from observing her father’s situation, she said, “I think [I’ll] try to have more friends, or more people, there… not only your partner. To have an actual friend circle.”

Due to the strained relationship, it felt like she didn’t know much about her father. When the priest asked about him, she felt she didn’t know much about his journey through life.

She had found her father’s journal which he had been writing in since 1967. At the time of our speaking, she still hadn’t opened it. Whether it’s right to open it or not is up for debate, but I sensed her desire to understand what went on behind the scenes for him.

This wasn’t exactly the conversation I was expecting to have with a social media influencer from Czechia. We did explore other topics (like breaking into the English-speaking social media space, for example), but the conversation was marbled with the emotions of the recent passing.

I often forget, and then remember, that the people we interact with – strangers or not – are travelling through the story of their lives just as we are. When we meet them, they may just be in the shitty bit. That was a big takeaway for me.

I also wanted to highlight the importance Connection 72 placed on building relationships throughout life so that we’re surrounded by people who care about us at the end.

Connection 73 was a creative director at the Centre for Contemporary Art in Nigeria. The Centre is based in Lagos, but delivers art education across the African continent, which has recently included work in Cape Verde and Cairo, Egypt.

When I asked about her experience of both places, she said that they offered entirely different experiences. Cape Verde is an island off the coast of West Africa with a population just over half a million, whilst Egypt is the “junction between Africa and the Middle East”, with Cairo alone home to over 22 million people. Despite the differences, she tied the two experiences together by reflecting that they both taught her “what it’s like to be African”.

Naturally, this opened the door for me to ask: “So, what does it mean to be African?” (If you’re reading this project for the first time, I am a 30-year-old curious white man.)

As soon as I asked the question, I wondered if there was an element of absurdity to it. Was I over-generalising? Would it be like someone asking me, “What does it mean to be European?”

Connection 73 responded thoughtfully, “There’s being African by birth, being African by ancestry, and then there’s having an affinity with Africa”.

She was born to Nigerian parents but spent her first 20 years growing up the UK. At the University of Nottingham, she found a community of Nigerians who were born and raised in Africa and had come to study. I can only assume these cultural influences impacted her as, upon graduation, her friend told her that she had “arrived at university English but left Nigerian”.

Of her identity, she said “I feel very much like I’m diasporan… to be diasporan is to be African”. A google search told me diasporan meant someone of African descent, but living outside of the continent. I wonder what this means for her identity now she’s living in Nigeria.

What seemed interesting was that she became ‘more African’ through her relationships with Nigerians at university than it seemed she had since moved to live there.

What I’m taking away from this conversation is that identity formation is both complex and fluid. It cannot be pinned down based on where someone was born or grew up. And it’s heavily influenced by our social surroundings.

Connection 74 was one of those big wave surfers who you see on YouTube. When I started this project, he was the archetypical ‘cool dude’ I half-hoped would be recommended at some point. And here he was!

Not only was he a crazy big-wave surfer, but he had also won the Molokai to Oahu paddleboard world championships ten times. This is a 32-mile race across the Ka’iwi Channel, which is known as the ‘Bone Yard’ and is one of the deepest channels in the world.

I thought it was peculiar then that was the only person in the project so far to invite another person onto the call with them. His marketing consultant.

I can only assume I didn’t frame the conversation clearly enough. This lack of clarity may have led to him seeing the interaction as an opportunity for business networking, rather than as part of a storytelling and human connection mission.

Moving into his next career phase, he had recently begun holding corporate retreats on the North Shore of Hawaii, where he lives (not jealous at all…). The retreat puts clients through a series of water-based exercises, such as holding your breath whilst walking under water holding a big rock or sitting in freezing cold ice baths. The goal is to build resilience and enhance wellbeing.

His marketing consultant fired questions at me to see if I would recommend the retreat to my coaching clients. Whilst I was happy to explore the topic, I couldn’t help but wonder how much more interesting the conversation would have been without the business chat.

Throughout the project, I’ve made it a personal rule not to discuss my own business during the conversations. I feel it ‘contaminates’ the social connection and gets in the way of truly learning and connecting from the strangers I meet. Ultimately, I fear they’ll feel like they’re being ‘pitched’ to. This project is at its best when it’s done just for the sake of it.

So, if I manage to get hold of Connection 74 again, I’ll make it crystal clear I’m keen to hear his gnarly stories of falling from 100-foot waves.

“What do you reckon she’ll take the piss out of you for?”, my fiancée asked me.

I was just about to speak to an American lady with a reputation for being one of the most brutal ‘roast comedians’ ever. She’d sold out the most famous venues and been nominated for Grammys. Most excitingly for me, she had roasted the likes of Pamela Anderson, David Hasselhoff, and Donald Trump.

As someone who enjoys comedy – and really enjoys being taken the piss out of – I couldn’t wait to speak to her.

And it was awesome, but for a different reason.

After selling out Radio City Music Hall and Carnegie Hall – two of the most prestigious venues for comedians to perform in the US – the head of Live Nation said, “Next up, Madison Square Garden”. Alongside an understandable excitement, she described feeling a sense of “nothing ever being enough”. This seemed to plant a seed which grew into her official retirement from comedy in 2018.

I didn’t get the sense that she retired due to being ‘burnt out’ with comedy. It seemed more profound, like: ‘there’s more out there in the world that I can do if I release myself from this identity of being just ‘the famous comedian’’.

My favourite thing she said was, “I don’t need an identity other than human”.

Nowadays, seems to be highly aware of the need to tune out the external noise. As the host of a podcast, she refuses to look at the number of downloads she gets (she calls them “achievement numbers”) and has negotiated with her producer to disable to comments section.

Alongside the podcast, she has a growing interest in embodiment coaching and raising money for LGBTQ+ charities, as well as mentoring up-and-coming comedians. She’s left behind the sharp, one-liner, insult comedy and encourages comedians to “tell the story… to tell the truth”.

To me, the story she told felt like an evolution in finding purpose and a clear identity.

Note: Naturally, I always hope that people find the conversations as stimulating as I do. That said, I don’t normally receive much feedback. Connection 75 offered some by mistake when she Cc’d me into one of her emails to the next person by accident! Thankfully, she had some kind words: “He’s such a great guy. 29 years old but an old soul. Knows being a high achiever is just filling the hole and doesn’t really work. Nice deep convo.”

Phew.

The five conversations highlighted the need to build relationships long before we need them, that identity is never fixed or simple, and that what looks like extraordinary achievement from the outside might not always mean the person is feeling fulfilled. They also taught me a couple of project-related lessons around framing conversations clearly, and rearranging them when the conditions aren’t right!

Next time: connections 76-80.