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What I wish I could tell my 21-year-old self.

A few thoughts 20 years later.

The future is bright.

It’s graduation season. I love this time of year. I remember that feeling of pride in what’s been accomplished and excitement for what’s next. I had many teachers along the way, but here are a few things I wish I could tell my 21-year-old self.

“Yes, and…” are powerful words. These two words build connective tissue between people. It illustrates alliance, openness and a willingness to play. Whether it be in comedy, business or personal relationships, yes and is an invitation to keep going.

Serena Williams was quoted saying “If you don’t do it, someone else will,” which speaks to my misguided tendency to wait until i’m perfect. Meanwhile, many others will try far before they’re perfect. I remind myself to throw my hat in the ring even if it means risking embarrassment. That step may not lead to the result I initially expected, but it will likely lead to something good.

A mentor at Microsoft once told me that “The answer is always no, until you ask.” I love how empowering this statement is. For me, it is a reminder that many things are not black or white. Life is full of moments that are negotiable.

“Power is the ability to change the rules.” This one runs deep. We all interpret power in different ways but this notion that crafting the life you want, that authoring the playbook is actually where you feel most powerful is a clarifying filter through which to see success.

“Medium produces mediocrity.” In Angela Duckworth’s book Grit, she hones in on a concept called deliberate practice. The idea that it isn’t enough to put in thousands of hours. This will produce a pretty good result, but not great. The Olympic athletes and celebrity CEOs who are at the top of their game focus specifically on identifying and addressing gaps in their craft and showing up day in and day out. I love this notion of getting out what I put in and being really thoughtful about always improving.

“Seek first to understand, then to be understood.” We’ve all heard this gem from Dr. Stephen Covey, but it didn’t hit home for me until recently. I’ve discovered it takes patience and discipline to listen first. It seems so obvious but many of us, me included, rush in to provide our perspective. Waiting a bit, observing the context and then contributing in a manner that furthers the conversation is a skill I wish I’d learned earlier in my career.

Congratulations to all of those entering this next chapter. But, for those of us well out of school, it’s never too late. There is so much potential and promise out there. 

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