A Letter to Penny

A few weeks ago, I ran a session for an amazing group of leaders where we discussed, among other things, our mindsets. Specifically, what we believe about ourselves as leaders and as people in general and how what we tell ourselves in these instances is so very important. 

I made the argument that if a friend told you their new diet consisted only of Pop-Tarts, Dr. Pepper, and M&Ms, that you’d question their sanity. If they asked you to join them, you’d pass. 

That’s because even if you think each of those items tastes great (I personally do), you know they’re bad for you, so eating only them would lead to bad results. 

In that session, I asserted that for many of us, we are essentially feeding our inner selves that exact kind of harmful diet. We’re telling ourselves we’re not good enough, that we’re not smart enough, that we’re fat or ugly or weird compared to everybody else. 

Then, hoping that we’ll perform optimally when it matters most. 

The audience agreed and we had a great time reversing so much of this inner monologue through an exercise called “Self-Belief Declarations” - check out my book to learn more. 

A few days after this, my wife walked into our bedroom and handed me a folded piece of paper. She was cleaning out my daughter’s room and found something she thought I’d find interesting. 

On the cover it read, just like this - typos and all. 


“to: older penny” 

“from: yunger penny” 


My eight-year old daughter, unprovoked, wrote a letter to her future self. 

I unfolded it and surrounding a multi-colored unicorn (she didn’t draw it but did color it in) was what she referred to as “These are some words I would use to describe you” with the sweetest adjectives sprinkled all about. 

Below that was a note to her future self. It was the most wonderful, inspiring thing I’ve ever read. Written by a child. A child probably too young to know yet that you’re simply not supposed to tell yourself great things about yourself. 

I read it and began crying. 

I asked Penny if it was okay to share that she wrote the letter with you all, and while I’m not totally sure she gets what this email list is or what I even do for work, she told me it was okay to share that she wrote it but asked if I could keep what she wrote, private. 

I agreed, with one exception. 

The very first line, after she wrote the greeting, “Dear older me” read, “I am so proud of you.” 

It took an eight-year old to remind me that we should tell ourselves things like this more often. So, if no one has told you in a while, not even yourself, I’m proud of you. 

And if you’re up for it, please follow Penny’s lead and tell yourself good things about yourself. I know I will. 

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First Impressions