This is the first of ten blog posts sharing lessons I wish I had known when starting out as a leader.

Lesson 1: Embrace Self-Encouragement

Henry had just arrived home from his leadership development seminar. He was feeling flush with excitement. Over the past week, he bonded with his fellow participants over shared values, goals, and new skill sets. This experience inspired Henry to dream big in his new leadership role. The only thing bigger than his dreams was his heart. He felt ready for the challenges ahead, fueled by a burning desire to prove himself in a world that often seemed stacked against him. But along the way, Henry faced a formidable adversary: his own inner critic.

Henry’s emotional high was short-lived. His first three months as a new director were marked by frequent moments of self-doubt and criticism. Whenever others identified a mistake he made, or he encountered a setback, his mind would echo with harsh words and self-condemnation:

“See? You’re not good enough.”
“Did you really think a week would be sufficient preparation?”
“What a fraud. Quit now, before you make everything worse.”

One day, Henry sat alone in his office, replaying the events of a particularly challenging day. While mulling over what he should’ve done better, he received an unexpected visitor - his mentor, Sarah. With a gentle smile, Sarah pulled up a chair beside Henry and asked him what was troubling him.

Reluctantly, Henry dripped out his frustrations, recounting every misstep and failure in painful detail. But instead of offering sympathy or reassurance. Sarah listened intently without interruption. Then she ask a simple, yet profound question.

"How does criticizing yourself improve your situation, Henry?" she asked softly.

Henry let Sarah’s question sink in.

“It doesn’t,” he admitted. “But it feels like the appropriate thing to do after I make a mistake.”

“And how’s that working for you?” she asked.

Henry paused, then conceded, “It hasn’t been. But what can I do instead?”

She replied, "Next time you feel your critic about to lash out, try asking yourself, ‘What would I tell my best friend if he were dealing with the same situation?’”

Sarah’s words caught Henry by surprise. He had never considered that kindness and encouragement could be directed inward, towards himself.

“But does that really work? Being kind to myself feels like a cheap trick, and a bit fake.”

Sarah pushed back. “I can understand your skepticism. But what makes the negative voice in your head any truer than a positive one?”

This question made Henry uncomfortable. He didn’t want to admit that his internal mind games were getting the better of him. But as he reflected on her question, he got excited about applying this truth laid before him.

From that day forward, Henry made a conscious effort to silence his inner critic and replace its voice with one of self-compassion and encouragement. Whenever he faced a challenge or made a mistake, he would pause and ask himself, "What would I say to my best friend in this situation?" And then, he would turn those words of wisdom inward, offering himself the same kindness and support.

Over time, Henry noticed a remarkable change in himself. He no longer dwelled on his failures or berated himself for his shortcomings. Instead, he approached each obstacle with a newfound sense of resilience and optimism, knowing that he had the power to lift himself up, even in the toughest of moments.

As Henry's confidence grew, so did his effectiveness as a leader. He replaced time beating himself up with distilling lessons and what next actions to take. His team rallied around him, inspired by his change in thinking and attitude. And as he looked back on his journey, Henry realized that the greatest lesson he had learned was not about strategy or tactics, but about the power of self-encouragement.

If you find yourself struggling with self-criticism and doubt, please take Henry's lesson to heart. Stop punishing yourself for your mistakes and shortcomings. Instead, practice self-compassion and encouragement, just as you would for a friend in need.

Big takeaway: Owning up to your mistakes shows maturity, but it becomes unhelpful if it turns into beating yourself up over things you can’t undo. Evaluating your experiences to identify and apply valuable lessons is helpful – until the mistakes show up repeatedly in your head.

You are capable of greatness. Every setback is an opportunity for growth. So be kind to yourself, believe in your abilities, and never underestimate the power of self-encouragement.

If you're ready to take the next step in your leadership journey, you are welcome to schedule a complimentary call with me. Together, we can explore how to cultivate a mindset of self-encouragement and unlock your full potential as a leader.