Optimistic Leadership: A Better Story

I’m sorry, optimism?! When you’ve been gifted with so much passion, it can get overwhelming to think of all systems you want to change and injustices you want to fight. Sometimes, the state of the world just gets us down and it’s hard to feel excited about the future. But in order for our leadership to be effective, we have to maintain optimism about the future. So what even is optimism?!

Optimism isn’t defined as being happy all the time. It isn’t being ignorant about any of the hard stuff happening in the world. It is choosing to believe that not only can YOU persevere through setbacks and challenges, but the entire story can be different, it can be better. It means that in your individual moments of chaos, you believe that the pain is not only temporary, but it can be fought through. Those who have an optimistic outlook will roll with the punches, will be more proactive and persistent and will not abandon hope. Similarly, you take that belief about yourself and apply it to the bigger picture; this human story that we are all participating in will one day be a little safer, a little more equal, a little more inclusive.

The future belongs to the optimists because they are passionate enough to believe in a more positive version of the narrative. As you discover all the layers of your leadership, we are hopeful that the next two weeks will solidify a sense of optimism for the future; a hope that will sustain you throughout the journey.


Activity #1 -- My Strengths

Research shows that focusing on celebrating your own strengths helps fuel the optimism for the future. The more often you celebrate what you are good at, the more excited you will be for what's to come. Because knowing what we're going into the future with is all we really need to stay upbeat! So let's discuss:

    • Individually, list out your top three strongest qualities

    • Now, for each strength, list out a recent example of when you displayed that.

    • Share what you discovered about your strengths. What are they? How have they been showing up in your life recently?

Sometimes it can be difficult to think through what our strengths are, because we just don't know! Here's a fun challenge to get you thinking about your most admirable qualities: What are your favorite characteristics that your best friends possess? Now, which of those characteristics do you also see in yourself? Feel free to think individually, or share out loud if you are comfortable!

Isn't it crazy how easy it is to brag on our besties, but it's so difficult to do the same with yourself?? Why oh why?! 

Activity #2: A Letter of Self-Compassion

Have you ever heard of self-compassion? Simply put, self-compassion means that you treat yourself with care and concern when confronted with your own mistakes, failures and shortcomings. SO EASY RIGHT?! Let's break it down:

  • Self-kindness: “… that we be gentle and understanding with ourselves rather than harshly critical and judgmental.”
  • Sense of common humanity: “… feeling connected with others in the experience of life rather than feeling isolated and alienated by our suffering.”
  • Mindfulness: “. . . that we hold our experience in balanced awareness, rather than ignoring our pain or exaggerating it.”

Source: Neff (2011, p. 44).


This specific exercise is called “A letter of self-compassion” and you’re gonna start with choosing an aspect of yourself that you dislike and criticize.

  1. Write in detail about how this insecurity makes you feel. What thoughts, images, or stories come up when you think about it?
  2. Next, imagine someone who is unconditionally loving, accepting, and supportive. This friend sees your strengths and opportunities for growth, including the negative aspects about you. The friend accepts and forgives, embracing you kindly just as you are.
  3. Now write a letter to yourself from the perspective of this kind friend. What does he or she say to you? How does this friend encourage and support you in taking steps to change? Let the words flow and don’t stress about structure or phrasing.

After writing the letter, put it aside for 15 minutes. Then return to the letter and reread it. Let the words sink in. Feel the encouragement, support, compassion, and acceptance.

Activity #3: Taking a Daily Vacation

Now before you grab your pen and paper, let’s go on a daily vacation, shall we? Are you living life at a crazy fast pace? Do you feel like you lack time to actively savor all the experiences in your life? Then this is for you.

Research has shown that, rather than their intensity, the frequency of positive emotions and feelings is a stronger predictor of our overall level of optimism. Meaning that it’s more effective to increase the number of positive experiences, than it is to intensify them.

So how do you “take a daily vacation”?! Glad you asked!

  1.  You’re gonna choose a different vacation every day. For example, going for a walk, chatting with a friend, taking a hot bath, watching the sunrise while sipping on some tea. The only limit is your imagination. Just choose something you enjoy!
  2.  Before you actually start, remember, your daily vacation is a time to relax. So set aside your worries for a while.
  3. During the daily vacation, try to be present and experience what is happening. Notice the sensations. How are you feeling? What positive emotions are you experiencing? Take a mental note of them.
  4. After your daily vacation remember to plan ahead for the next day; what will tomorrow’s daily vacation be? Look forward to it!

Everyday, before you go to bed, take at least five minutes to remember the positive emotions that you savored during the day, and on the weekend take 10 to 15 minutes to look at all the positive emotions of the past 7 days. How did you feel this week compared to other weeks? Are there any differences? How do you feel right now?


Journal Prompts

  • How has optimism played itself out in your life?

  • Optimism for the future does not negate the past, so it’s important to address what can keep us from feeling optimistic. What are some of the barriers you have, either about yourself or the world around you, that keep you from feeling optimistic?

  • Optimism is different than just being happy + positive all the time. Reflect on how this has looked in your life and write out those feelings.


Resources For You

Happiness 101





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