May is the season of graduations.

From preschool to PhD programs, caps and gowns seem to pop up everywhere. Families gather for ceremonies, photos, celebrations, and new beginnings. Perhaps someone you know is graduating, or maybe you are celebrating a milestone of your own.

Graduation season often brings reflection.

Have you ever looked back and thought:

“I wish I knew then what I know now.”

Two questions I wish someone had asked me decades ago are two of the questions I share in many keynotes, workshops, coaching calls, and everyday conversations are two that people have asked me. However, I change the endings depending on the conversation in order to make the question as relevant as possible. 

Two Questions That Matter and Have Made a Different to Me Are:

1. What do you want to see more of…?

  • …in the world

  • …in your workplace

  • …on your team

  • …in your friendships

  • …in your family

  • …in your life

2. What do you want to be known for?

  • …as a leader

  • …as a parent

  • …as a teammate

  • …as a friend

  • …as a spouse

  • …as a mentor

  • …as a human

At the end of the day, people may not remember titles or accomplishments but like the old saying goes, they will remember how we made them feel, how we treated others, and what we stood for.

Graduation may celebrate education, but life continues to teach us long after the diploma is framed.

Five Things I Wish I Knew at 13

  • Being popular is a state of mind and many times more about finding confidence than acceptance. 

  • Every single person has challenges, even when life looks perfect on the outside. 

  • Everyone has gifts — discovering them takes time. 

  • Kindness matters more than fitting in. 

  • You don’t need to have your entire future figured out. College isn’t for everyone. Some type of post High School education will serve you well

Five Things I Wish I Knew at 18

  • Comparison can steal both joy and confidence. Run your own race. 

  • What looks and feels like failure is often a learning opportunity in disguise. 

  • It is okay to change your mind about your career path. Most people do. Some people know exactly what they want to do early in life — many do not and both are okay. 

  • Failure is not the opposite of success; it’s usually a major part of it. 

  • Every person brings value to a team, even if their contribution looks different. 

Five Things I Wish I Knew at 22

  • Learning is lifelong. Real learning begins and continues after graduation. 

  • The little moments in life often become the biggest memories. 

  • You can make an impact no matter what your title or position. 

  • Money is not the root of all evil: greed is. It’s not how much you make it’s how you use it.  

  • Relationships matter more than resumes. 

A Leadership Reminder for Every Age

Graduation is not only about finishing something. It is also about becoming someone.

No matter what our age, we are all still learning:

  • how to lead 

  • how to grow 

  • how to adapt 

  • how to serve 

  • how to become better versions of ourselves and 

Perhaps that is the real lesson of graduation season: Learning never truly ends.

So, this month, whether you are celebrating a graduate, mentoring someone younger, or reflecting on your own journey, consider these two questions again:

  • What do you want to see more of? 

  • What do you want to be known for? 

The answers may shape more than a career.
They may shape a life, and it could be yours.

You Got This. And I have your Back.

Supporting you in creating the life and career you deserve,    

- Ann

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Motherhood and Leadership