Am I Cut Out for This?

Every leader experiences insecurity at some point, though no one wants to admit it. Insecurity, put simply, is a deep feeling of uncertainty about yourself. It’s an acute lack of confidence that makes you easily suspicious, overprotective, self-conscious and offended.

If you’ve ever led anything, it’s not a question of if you’ve felt it, but when. It’s the feeling that you don’t deserve to be in the room. You’re the wrong age. You’re not smart enough. You haven’t done enough. You don’t know the right people. You’re the wrong person.

Insecurity secretly erodes the leadership capacity of scores of leaders. It makes leadership hard, but if you pretend you never feel insecure, leadership gets even harder. Fortunately, I have worked with incredible leaders who’ve learned how to battle insecurity by cultivating a deep sense of inner legitimacy.

Underprepared for Insecurity 

Years ago, I ran my first half-marathon. I was confident I was going to do well. It’s only a little over 13 miles. How hard can it be? You might say I was overconfident and underprepared. With only weeks to race day, I created a quick plan and got started. I ran a mile on the first day, then added a mile each day after that. The plan was foolproof—as far as I knew.

But when race day came, my plan didn’t go according to plan. It turned out I had taken too many rest days. But amazingly when I lined up with thousands of other runners, I still felt confident. When the starting gun went off, I started fast and strong, passing people right away.

At Mile 6, the pain hit me gradually at first, then all at once. It started in my lungs, then pushed down toward my legs, and finally exploded out of my toes. By Mile 12, I was a limping, sweating, groaning mess, barely putting one foot in front of the other. 

With less than a mile to the finish, I just didn’t care. I only cared about stopping the pain. I was underprepared and unbelievably tired. The worst part was, that tired had snuck up on me. I was both shocked and overwhelmed by the feeling of exhaustion.

I ultimately finished the race. And while it was an unnecessarily hard experience, I learned a valuable lesson. Leadership is like running a marathon. Most people plan for the day-to-day work of leadership, but are surprised by the feelings of insecurity that hit them out of nowhere. All leaders feel insecure like all distance runners feel tired. It’s not a question of if runners will feel tired, but when. Runners know the tired is coming—and when exhaustion hits, they have a plan for it.

The best leaders are no different. They know insecurity is in their future, and they’re always prepared for it. How do they prepare for it? They prepare by cultivating internal legitimacy.

Internal and External Legitimacy

Legitimacy, at its core, is simply having permission to lead; however, internal and external legitimacy are easily confused. Internal legitimacy is when you believe in yourself. It’s about getting permission to lead from your relationship with God. You believe in yourself because God believes in you. God has called you, and that’s all the permission you need.

Alternatively, external legitimacy is when other people believe in you. It’s about gaining permission to lead from your relationship with others. When people say, “Yeah, I trust her,” or you can tell they catch your vision, you’ve got external legitimacy.

External and internal legitimacy are both important, but you can only combat insecurity with a strong sense of internal legitimacy. You have to believe in yourself long before others believe in you.

Here’s the critical element: When you feel insecure (and we all feel it from time to time), you instinctively turn to external legitimacy to try to gain confidence from others. You look for reassurance from your colleagues, clients, family and friends. You try to become whatever people want you to be, so you inflate your résumé, drop names, hide parts of your past, or claim to know more than you do, all to earn external legitimacy from the positive opinions of others.

A Tale of Two Kings

King Saul battled insecurity like no other leader in Scripture. When he faced extreme pressure in his leadership, his character caved in, and he grasped for external legitimacy. Then, when confronted, Saul defended himself by naming the source of his insecurity, saying, “I was afraid of the men and so I gave in to them” (1 Sam. 15:24).

When we feel the pressure of insecurity, we too fearfully look to those around us for permission to lead. It’s like we’re wearing a sandwich board saying, “Please tell me I’m good enough.”

But when leaders build internal legitimacy, their leadership doesn’t rest on people’s opinions, but on their sense of calling from God. They can leave the crowd, lead the crowd or follow the crowd. The crowd, in this sense, doesn’t matter. They are following God.

In contrast to Saul, David had a strong sense of internal legitimacy. Long before he was king, his family, his peers and even his leaders doubted his legitimacy to lead. To them, he was the wrong person. But the future king grabbed a few stones and ran toward Goliath. With his internal legitimacy on full display, he said, “You come against me with sword and spear and javelin, but I come against you in the name of the Lord Almighty. … This day the Lord will deliver you into my hands” (1 Sam. 17:45–46).

David believed he deserved to be on the battlefield simply because he was called by God to be there. He wasn’t fighting for respect or power. He was just trying to please God, and that gave him the internal legitimacy he needed to fight, and eventually powered his rise to the throne.

Internal Legitimacy

All leaders operate from two stages, the frontstage and the backstage. The frontstage represents public leadership. This is where you make decisions that directly affect others. It’s where you carefully watch the effect you have on people and the example you set. When you’re on the frontstage, you’re more polished, and that’s fine. But internal legitimacy is forged backstage.

Backstage represents private leadership. It’s when you’re not leading anyone but yourself. This is where you dedicate and rededicate yourself to God. It’s where your character is shaped. When you’re backstage, you confront fears, sort out your thoughts, talk to God, and confirm your calling. It means spending more time alone, wrestling with God, and finding comfort in his unconditional love.

Every leader feels insecurity, but extraordinary leaders prepare for it. They prepare for frontstage leadership by doubling their focus on backstage leadership. They cultivate inner legitimacy and refuse to grasp for external validation. And they acknowledge occasional feelings of insecurity, but refuse to let those feelings cripple their calling and derail their leadership.

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Dan Owolabi
Dan Owolabi

Dan Owolabi is co-founder of Owolabi Leadership, executive director of Branches Worldwide, and is the author of Authentic Leadership.