Why I Wrote The Contemplative Leader

My First Leadership Experience

When I was fifteen, I found a way to get out of class for weeks on end. It wasn’t just to skip school that I organized a fundraising disco for charity. I’d had a fun experience at my first ever school disco when I was thirteen, and I wanted the younger boys to experience something similar. Plus, we’d recently completed our first state exams, so class wasn’t quite as focussed as it had been. I had a written permission slip from the headmaster which I produced any time a frustrated teacher questioned why I had missed yet another class. And my excuses were pretty good:

Fundraising phone calls with local businesses. Trips to collect the free snacks and beverages that companies had donated for our tuck shop. Meeting with the Jesuit priests, the trustees of our school, to accept their IR£200 to kickstart the charity fundraising. That same day we received their check, we decided to ‘invest’ it in the local bookmaker’s office - and promptly lost the lot, backing horses at the Cheltenham racing festival.

We visited seven girls’ schools to put up posters and make announcements in their school assemblies. We didn’t tell anyone that we weren’t planning on inviting any of the other boys’ schools in the area. When teachers later asked why there had been so many more girls than boys at the disco, we said ‘we wanted the odds to be good for the younger guys’.

Everything came together really well on the night. We had contacted the most famous DJ in Dublin, and he brought his CD collection, lights, a huge smoke machine, and megaphone. The tuck shop had almost £1,000 of free sponsored food for sale. The biggest rugby team players volunteered to be bouncers at the door. Teachers supervised the dancefloor – our gym hall. The police were only called once. The priests never found out that we gambled their money, and we made thousands of pounds, way more money than we had anticipated for our charity of choice. Aside from all the chewing gum on the herringbone wooden corridor floors, the whole event was a roaring success. For everyone else, that is. But not so much for me.

“You can’t control everything.”

Throughout the whole night, people were coming to me to ask questions – my teachers, the rugby players ‘bouncing’ at the door, the DJ. I had designed the evening that way, with me as a hub of information through which most other spokes had to pass. I had planned it to a tee. I’d thought of every detail, each sequence of actions that should happen on the night. But I was so invested in the specifics of the evening - from the tuck shop cash float to the supervision rota of teachers - that I was completely stressed out. I spent the evening running from one person to another, trying to avert some imaginary disaster.

I checked in with the bouncers, the teachers, with our team of organizers, the tuck shop, the DJ, then back to the front door. I wanted to be involved in everything and I wanted everyone to tell me what they were doing. Then I started finding ways to either do a ‘better’ job myself or tell the others what they needed to do differently.

At one point, the brother of a classmate, an eighteen year old bouncer at the front door, grabbed me by the shoulder and pulled me aside. “Hey, you gotta relax. Leave the door to us, that’s our job. Stop stressing.” He sent me back inside with a parting message, “You can’t control everything.”

His words rumbled around my head for the next few weeks. They returned to me four years later when I headed up a student society in college, and dearly wanted to be in control of all of the tasks that two of my “incompetent” committee members were not doing very well.

“You can’t control everything” came back to me again during the last few, frustrating weeks of a job that I ultimately resigned from in my mid-twenties. When a girlfriend broke up with me. When I couldn’t pursue my dream job. When I lost a job. When clients decided not to renew a contract for another year. When the quality of work that was done by team members fell short of my expectations and I became exhausted after doing their work myself.

“You can’t control everything.”

Overcoming Fear with Control

This simple, obvious statement was a revelation to me. And an early indicator of a pattern of life to come in the years ahead. The more I sought to control, the less things seemed to work out the way I wanted them to.

I tried my best, I worked really hard. I had a lot of wonderful, surprising, and sometimes rewarding experiences along the way. But my hyper-focused, outcome-oriented approach didn’t give me the safety, the certainty that I was seeking. In time, as I reflected on the roots of this desire for control, I realized that it was coming from a place of mistrust in others and fear within myself: fear of being left out, fear of not fulfilling my potential, fear of being led by people I didn’t respect, fear of failure, fear of being ‘found out’.

And as I started to look around, really listening to others and putting myself in their shoes, I realised that other people were afraid for similar reasons, and were also desperate to be in control.

Some displayed this in obvious ways, the ‘alpha’ leaders, the ‘captains’ with a plan, demanding that others follow them. But most did it in much more nuanced ways; manipulating others to their way of thinking; staying quiet and choosing not to participate in the initiatives of others so that these initiatives would fail; finding obvious and not-so-obvious ways of getting their way, often of not making changes and just keeping the status quo.

Without a doubt, we all need some certainties in our life. We cannot effectively live or lead if we wake up in a vortex of total uncertainty every day. But living and leading without being in control is something different altogether.

And the topic for next time.