My Commencement Remarks: “Be wrong as often as you are right and pivot often.”

Holly May
7 min readJul 11, 2019

I was honored to be invited to deliver the 2019 Commencement remarks at the school I attended for 6th to 12th grade, Cary Academy, in Cary, NC. These are the remarks I shared on May 24, 2019.

2019 Commencement remarks at Cary Academy, NC, May 2019

Good afternoon.

To the Board of Directors and head of school, Mike, thank you for entrusting me with this opportunity, and for making Cary Academy a school that changes & improves lives.

To the community of educators and coaches who challenge students to pursue that tricky intersection of excellence, their passions, and integrity; thank you. Thank you for teaching us, some of the lessons I remember:

  • to embrace the discomfort of acting through 8th grade simulations of Watergate and elections (Teacher Name).
  • for teaching us to learn that team work and community matter more than winning matches (many coaches)
  • for teaching us to write critically with the power of “Although” (Teacher Name),
  • for teaching us to push our limits by memorizing every animal vocabulary word in Spanish (Teacher Name)
  • for teaching us to aim high and widen our horizons more than we initially planned (Teacher Name)

Thank you for the investment you made in me between 14 and 20 years ago (wow!), and thank you on behalf of the class of 2019 for the care and dedication you have invested in them. Whether they know it now or not, you have shaped them and they’ll appreciate it in time.

To the parents and loved ones who challenged and encouraged your kids to reach this point, congratulations on the accomplishment: you deserve as many kudos as the graduates themselves.

And finally, to the Cary Academy graduating class of 2019,congratulations, on this, your final day of high school and the first day of the independence and responsibility that accompanies this milestone. You did it. You’ve learned to connect across your differences as a class and to celebrate & lift up one another. From philosophy club to Bob Ross in the senior corner, to cultivating school spirit, the class of 2019 has brought a light-hearted earnestness to all its endeavors, and you’ve surely left a mark on the school community (even if not on the walls…)

— -

Delivering a commencement address is a big responsibility, or so I thought. I searched the archives of my own memory of my commencement on this very campus 14 years ago. Reflecting on the distinguished guest’s speech helped me enormously in writing these remarks….

It turns out I cannot remember a single word from that address, nor even who the speaker was!

This was a liberating discovery and helps me show up here today without the fear I might permanently influence or mis-guide you!

— —

Today, I want to encourage you to be wrong, and my wish is for each of you to pivot from the path that you envision for yourself today. Expect and embrace twists and turns in the journey ahead.

I’m visiting you today from Silicon Valley in California, where I am an executive at a startup startup. One of the fascinating things about Silicon Valley is how quickly companies evolve. Almost every successful business failed at its initial business idea or product. The word “Pivot” has entered startup jargon as a word that means to adapt in response to failure. This journey of failing often, and pivoting and adapting, creates the ingredients for business success.

I’m here today to encourage you that embracing failure and pivoting is part of personal success as well. I will tell you a few stories of my personal pivots.

— —

When I sat in your seats — 18 years old, ambitious, anxious, headed to college at Harvard — I had a plan.

I’m a planner, and I suspect many of you are as well — planning and goal-orientation are part of the foundations of your success.

When I sat in your seats, my plan was to:

  • major in biology at college
  • become a science teacher in a challenging middle school or high school — inspired by the teachers I had here.
  • return to North Carolina and perhaps get involved in local government like mayor or school board

So, I went off to college, and moved in to my dorm the same week Hurricane Katrina devastated New Orleans. I chose biology and took the required first year courses. I soon realized that 400 people in a lecture hall with professors who conflated teaching and monologing was not for me. I wanted a community and I wanted to matter to my instructors — it took me being wrong about my choice of major to discover those things mattered to me. So I fled the large major of biology for a much smaller and interdisciplinary major called History of Science.

It was a perfect fit for me.

But I had never even heard of the field when I was sitting in your seats.

Keep your heart and mind open to discovering new paths you may not know about today. Be open to pivoting on what you study.

— -

Another element of my plan back then — that was ultimately wrong — was to become a teacher, so I committed to try it:

1) I coached rec league soccer in Cambridge in my first year at college where I taught the fundamentals of soccer to 12 year olds and enjoyed sliced oranges out of plastic bags at halftime

2) And I spent a summer internship mid-way through college as a middle school science teacher in a summer enrichment program for talented students.

Although, these were rewarding endeavors, they were more challenging than anticipated and did not energize me in the ways I expected and hoped. In short, I discovered I was wrong about wanting to teach.

Approaching the end of my time in university, I was untethered to a path. I pivoted away from teaching science, and I didn’t know what I wanted to be when I grew up. For me, that ambiguity was an uncomfortable feeling.

— —

Another dimension that was an unexpected pivot off my plan, was getting quite sick in college, taking a semester off, and delaying my graduation by a semester, from June to December.

As a result, I gained an “extra” summer internship. I could never have planned on that “extra inning”.

Serendipitously, that final summer, I earned an internship at Quintiles, a large local company that runs clinical trials for drug companies (now it’s called IQVIA). It opened my eyes to the healthcare industry.

That internship experience kickstarted a future career at the intersection of business and healthcare. Of course, I didn’t know that at the time.

To paraphrase Steve Jobs:

  • you can’t connect the dots looking forward.
  • Whatever path you have in mind for yourself now — real talk — very likely it’s wrong. Let me underscore that. You will very likely pivot away from the path you envision for yourself today.

And being wrong on that stuff is great — embrace it, or better yet: give yourself permission to pivot — to be open to serendipity and discovery and the unknown.

You can only connect the dots looking backwards. You have to trust that the dots will somehow connect in your future. They will.

— —

Jumping to present day, my company makes software to connect the world’s health data to improve patient outcomes and medical research. At work, we have a cultural value for the organization that encourages innovation and risk-taking. We expect team members to be wrong as often as they are right. That may sound counter intuitive: “don’t you want employees to be right a lot?” is a prevailing logic.

If you’re right all the time, it means you’re not pushing your limits. It means you’re not setting ambitious enough goals, you’re not testing yourself truly.

You learn the most when you do things 15% outside your comfort zone. Sure, you’ll make mistakes and feel awkward and fumble some things, but you’ll learn which assumptions and plans you hold for your future are sound, and which are wrong. uncover new insights about what energizes you and what superpowers you possess, which in turn enable you to pivot to something that suits you better.

So — take the more difficult class; choose the harder hiking trail; plan the more challenging trip.

A successful life does not require perfection or success in all things. In fact, pursuing perfection on its own will crowd out serendipity and opportunities to be wrong, learn, and pivot.

Being wrong is OK — and your parents are hearing me say that!

To borrow from JK Rowling, beloved author of Harry Potter:

“It is impossible to live without failing at something, unless you live so cautiously that you might as well not have lived at all — in which case, you fail by default.”

— —

Having a plan is good and committing enough to give something a shot is key.

But let me make a distinction: tethering yourself to a plan with blind certainty is a form of close-mindedness that amounts to imprisonment — I hope for each of you to be free from the confines of a pursuing an un-changeable path for your future.

  • Set yourself free from the expectations you have for yourself.
  • Release the expectations your parents have for you — today is the expiration date on blaming your parents.
  • Reject the expectations society or your friends have for what you ought to do, who you ought to become.

The moment you are old enough to take the wheel in your life — and that is today — responsibility lies with you. You — and you alone — pick your path through university and beyond. You decide:

  • what you study
  • who you befriend
  • how you spend your time
  • how you treat other people…and yourself

You have agency. You have ownership — and importantly, this includes owning consequences — You’re the captain of your ship.

But that does not mean you must have a locked-in path. Ship captains, just like technology startups, pivot to new or smoother waters, adjusting to new circumstances.

So, I’ll wrap with these wishes for each of you as you commence on your next chapter:

Whether you stick to a defined path or embrace the pivoting, you will have ups and downs, no doubt.

1.) I wish you humility on your mountaintops — humbly savor the accomplishment

2.) I wish you resilience in your valleys — mine that experience for lessons; persevere

3.) And I wish you to be wrong as often as you are right, and seize the opportunity to pivot and recalibrate your plan.

Thank you, and congratulations.



Holly May

Head of People & Operations @ Datavant - rebooting what it means to be a People person