I’m often asked how I made the transition from introverted IT nerd to platform speaker. As with any sort of growth, it’s never the one thing. Yet, as I look back at my journey, certain paradigm shifting moments stand out. In particular, an encounter with a homeless man on the streets of San Diego. It was one of those sliding door moments that helped me overcome my fear of speaking with strangers. I hope you take heart from this story.

It was September 2005. Sue and I had just completed the Tony Robbins 6-day Leadership Academy in San Diego. It was during this bootcamp that I found my life’s calling and the seeds of EQ Strategist were sown. On the final day, a Sunday, we finished around noon, feeling incredibly uplifted.

Tony’s concluding messages and the closing tune of “Life will never… be… the… same…. again” were still ringing in my ears. He reminded us of key principles to hold to heart and gave each of us a challenge.

The three key messages:

  • If you’re serious about changing lives, treat coaching as a vocation, not a job. Serve with all your heart regardless of whether or not you’re paid for it.
  • Leaders are influencers. You lose the ability to influence the moment you judge someone.
  • Take MASSIVE action, get out of your comfort zone to make Growing to Serve a priority, to fulfill your highest potential in the course of living your purpose. Talk is cheap. Walk the talk.

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And the challenge: To apply the skills we’d learned to serve someone that very day. “Perfection is the lowest standard you can aspire to”, he’d said. “Don’t let the thought of needing to be perfect hold you back from taking action and creating that momentum. That’s how you grow. The first step is always the hardest!”

All of these resonated and yet, I knew it would be an incredible challenge for me to authentically bring alive not just on that day but for as consistently as I could every day from then on. My “Ready. Aim. Fire.” success recipe to that stage had been conditioned by a conservative upbringing and coloured by a quite significant fear of failure. So, in reality, it would’ve been much more like “Ready…. ready….. ready. Aim… aim… aim. Ready….. ready…. Aim………….Fire!” The comfort of procrastination had been a constant companion for much of my life leading up to that moment.

You never change things by fighting the existing reality. To change something, build a new model that makes the existing model obsolete. – Buckminster Fuller

And after all the sacrifices Sue and I had made to be at that bootcamp, I felt a gnawing pressure to apply my fledgling coaching skills that very afternoon itself. But with whom? After all, I was in a foreign city with no friends or family. I found my mind starting to make up “excuses”.

I left Sue at a spa so she could indulge in a massage. Such events, as inspiring as they are, are incredibly taxing – mentally and physically. She needed some time to decompress.

I on the other hand, felt the need to let that adrenalin continue to course through my veins at least until I’d scratched that itch to put into action what I’d promised myself when I left that bootcamp. To follow through on Tony’s challenge.

And so I sauntered towards a shopping mall in downtown San Diego looking to buy an electric adapter for my computer.  As I waited at a pedestrian crossing, I noticed a man seemingly asking for alms. He was well-dressed – denim jeans, jacket and cap – and every time someone would walk past, he’d bow and hold out his cap. Instinctively, I turned and started walking towards another direction. Having taken two steps forward, my self-awareness kicked in and caused for me to pause. “Hmm, interesting decision. Why am I walking away? What’s the thinking of this situation that’s bringing up this sense of anxiety that’s causing me to react like this?” I felt embarrassed at the judgmental thoughts I had – “ Lazy. Taking advantage of others.” And other less charitable ones.

Tony’s words rang in my ears – “You lose the ability to influence the moment you judge someone”. The next thought was scary “Maybe this is the person I’m meant to be coaching today”. Sliding door moment. Noticing my heart rate go up several notches, I took a deep breath and said to my ultra-protective ego “Thank you, not now”.  Turning around, I crossed the street and walked resolutely towards my unsuspecting coachee, or should I say, victim.

My heart beating out of my chest, I kept striding forward. “Fake it till you make it”. “If I can’t I must, and if I must I can!” Just like the proverbial “duck on the pond” – seemingly calm on the surface, yet paddling like crazy underneath.

I walked straight up to him, maintaining a steady and friendly gaze. As I got to within “social distance”, he bowed and held out his cap. I looked him in the eyes, smiled and said as calmly as I could “Sir, how are you doing today?”

[Prospective coachee, a little perplexed] “I’m doing fine, thanks”

[Internee coach] “Sir, I see you’re asking for help. I’d love to and before I do that, may I ask you a question?  Why are you doing this? You look fine. And you look most able. I’m just curious.”

He stared at me momentarily. “Is this guy for real??????” And then he bent over, pulled his shirt collar away from his back and said “Sir, do you see a scar?” I nodded. There was a lesion snaking all the way down from his crown to the middle of his spine. “Ten years ago, I was working with the US Navy. On the ship deck one day, this huge pallet comes crashing down. Shattered my spine. I was in hospital for six months. The doctors said I would never work again. I showed them! Six months later, I wheeled myself out of the hospital and here I am today. Never been back. The problem I have is that I’m an outdoors kinda guy. An office job would kill me. I have not been able to hold down a job because a side effect of that accident is that when I stand for more than an hour, dizziness overcomes me and I have to lie down for a good 30 minutes. No company has been willing to give me a job with a condition like this. So for the past ten years I’ve been on the government pension. I get a check every two Thursdays. My next check will get to me in four days.” He pulls out his jeans pocket. Nothing inside. “I’m clean outta cash. Just hoping to get a meal.”

I could feel his sincerity and had started to feel very different about him.

Me: “If you’re after a meal, let me buy you one. What would you like?”.

Him: “No, no, no, sir. I wouldn’t want to put you through that much trouble.”

I persisted and he finally relented. We turned around, took two steps and walked into a Pizza Hut Express restaurant. From the back of the queue, we peered at the board “Mini pizza, Coke and fries – $7”. He looks at me and says quietly, “A little expensive?” I said, “No, I can manage that. But don’t you want something healthier?”

Very frankly, when I’d asked him what he’d like, I really had to manage the judgmental self-talk that was going on inside my head. “Oh, be careful. You’re gonna get ripped off.” And so by saying “What would you like?”, I had literally and deliberately given him an open check. And here he was, trying to save me money. I felt even more embarrassed.

“Can I make a request? My favorite meal is two cheeseburgers, a Coke and fries. Only $2.50. There’s a McDonalds franchise just 50 yards up the street. Can we go there?” I said, “If that’s way you really want, absolutely! Let’s go.”

So my new found friend and I walk across the street. We make small talk. I used my fledgling rapport building and listening skills to learn more about him. As we chatted, I saw from the corner of my eyes this other person ambling towards us. He was disheveled and looked stoned. And yet, every time someone would walk past him, he’d reflexively hold up his hand, palm skywards. Just about everyone walked right past, seemingly in oblivion. As we walked past him, my new friend puts his hand in his jacket pocket. He pulls out what I think was the only financial possession he had – a quarter (25-cent piece).

I watched this in stunned silence. Here I was seeking to coach and yet, I’d just been coached. At the bootcamp, another of my profound learnings had been that one’s wealth is defined not by how much one has but by how much one can give. This man was certainly far wealthier than I was.

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We went to the Maccas and had a great meal. At the end of the meal, just before we said goodbye, he pulls a small plastic “ziplocked” envelope from another pocket. He poured its contents out onto the table. A variety of pills. Green ones. Yellow ones. Red ones. Multicolored ones. He holds one up and says it’s for his diabetes. Another for hypertension. Yet another for cholesterol. It seemed to me like he had every condition under the sun. He thanked me warmly and said that he’d been waiting all day to have a meal just so he could have his medication. And that if I hadn’t stopped and bought him that meal when I did, I would have found him an hour later sprawled on the pavement with some paramedics having to resuscitate him. “Thank you for giving me another day”, he said.

I walked out of that restaurant. It was one of the most surreal yet humbling experiences I’d had. My decision to pause and exercise my self-awareness and self-management in that micro-second had created for me this incredible opportunity to have a profound connection with this beautiful human being. I found myself rooting for him silently. And thanking him from the deepest part of my soul. That day, that man gave me one of the greatest gifts I needed – it helped me overcome my fear of talking to strangers.

It’s truly in the moments of your decisions that your destiny is shaped. Whenever you’re faced with uncertainty, instead of reacting, pause and reflect on this question – “what would Love do?” And act on whatever spontaneously pops up.

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To watch this story shared live during a virtual workshop on Coaching to Grow Leaders for a group of senior executives from Jakarta, Indonesia: