The Rebel and the Leader

Updated: Feb 18, 2019

Some of the best leaders are drawn from the ranks of rebels – and also some of the worst.

When you find yourself at the bottom of a pyramid and want to climb it, you have a limited set of options. The base of the pyramid is the largest part. You’re in the crowd.

It is certainly important to be competent, but to advance you also have to be noticed. It is not enough to be good. You also have to be noteworthy.

One option is to passionately serve those above you, make them look good and help them achieve their objectives; hoping that you will be rewarded with more responsibility, influence and prestige. This is the path of least resistance. It’s not easy, but it is well traveled. Odds are good that you will grow in your ability to lead and earn more trust from those around you.

This path is more predictable because on each step of the way you are actively imitating and reflecting the behavior of those leading you; whose favor and approval you seek.

But there’s another option. This path is narrow, steep, strewn with rocks and fraught with danger. Like a high-stakes investment, the potential payoff is high but so is the risk. This is the path of the rebel.

The rebel is not imitating or primarily seeking approval from other existing leaders. In fact, the rebel is often actively positioning themselves in contrast and counterpoint to existing leadership and practice.

Instead of currying favor, the rebel is speaking truth-to-power, opposing the past and seeking transformation. Rebels make great heroes. They also make powerful cautionary tales.

Most people who take the path of the rebel fail, not because the critique is wrong or the vision is faulty, but because they do not make the transition from being the opposition to being in charge.

Some of our greatest leaders started, and in many ways remained, rebels throughout their lives. However, the skills that make an effective rebel are not entirely sufficient to make a transformational leader.

Here’s an example. As a very young man, I was involved in a campaign to unionize restaurant workers in a small city in the southern US. I was an excellent rebel.

I agitated, organized, built a campaign and gathered a small army of supporters over the course of a year. At one particular establishment, I had personally taken a job there as part of the overall organizing strategy. I and some collaborators had successfully convinced most of the other staff that they were being treated so unfairly by the owners, that they should consider unionizing.

Our plan was to organize a confrontational meeting between staff and the owners. After a year of groundwork, this was to be the formal launch of the unionization campaign. The assumption was that the staff would make their demands and the bosses would resist; showing just how much they didn’t care about their workers and providing angsty emotional fuel for the fight ahead.

The problem was, that’s not what happened.

We did indeed get the owners to the meeting. The staff, egged on by rebels like me, laid out their concerns about several unfair and unsafe workplace practices. People were upset and ready for a struggle.

But then… something remarkable happened.

The owners didn’t argue. They didn’t even seem angry. Instead, they thanked everyone for coming to them directly with their concerns. They admitted that much of what was shared was indeed a problem and needed