From Finish Line to Starting Line: What Graduation Reminds Us About Growth

This weekend, we celebrated a big milestone: Dylan’s high school graduation! As I looked on with pride, it got me thinking about growth, transitions, and the quiet courage it takes to step into what’s next. I’m sharing a few reflections in this week’s post.

Family picture at mass

Somehow, our baby is now a high school graduate!? Dylan graduated this weekend and it still feels a little surreal, to be honest. There were caps in the air, speeches that hit just the right note of inspiration, and a well-earned sense of accomplishment and pride all around.

But as I watched Dylan walk across the stage to accept his diploma, I couldn’t help but reflect on how transitions—whether from high school to college or one career chapter to the next—often stir the same emotions: pride, excitement and a bit of uncertainty about what’s next.

Overcoming Challenges

The last four years were full of incredible change for all the kids to navigate. Dylan’s school experience came with its fair share of challenges—from learning with dyslexia to adapting during COVID. But through it all, he kept showing up, learning more about what drives him and overcoming hurdles as they came. Over time, he’s come into his own—discovering a passion for triathlon racing and a love of travel that’s opened his eyes to the world beyond the classroom. Watching him grow into who he is today has been one of the greatest joys.

As someone who spends a lot of time thinking about career development and personal growth, I couldn’t help but notice the parallels. Whether we’re stepping into a new role, experiencing a job loss, or rethinking our purpose, transitions invite us to ask the same big questions: Who am I becoming? What am I ready to leave behind? What do I need to take with me?

Watching Dylan move forward reminded me that the qualities we value in young adults—grit, curiosity, resilience—don’t fade with age. They’re the same ones we call on again and again as we navigate the winding path of a meaningful career and life.

A Few Highlights

And, like any big milestone, this one deserved a little celebration. His sister Mia made a short highlight reel to mark the moment — a special way to honor the journey and recognize how far he’s come.

This fall, Dylan heads to the University of Oregon to begin his next chapter. We’re proud—not just of where he’s going, but of everything it took to get to this point.

Because the finish lines we cross are often just new starting lines—and sometimes, those are the ones that matter most.

Cheers to all the graduates!

Thanks for reading. xx

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Danielle Cullivan

Career Insight Studio

Danielle Cullivan is a seasoned leader in tech with over 20 years of experience in Fortune 500 companies. She is also the creator of Career Insight Studio, a career and lifestyle blog dedicated to providing insights and new perspectives for working women. Danielle lives in the Pacific Northwest with her husband and high-school-aged son, and visits her college-age daughter as often as possible! 

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Cheering for Dylan was the best way to start the day — even if it started waaaay too early. 😅 So proud of him for taking on the half marathon at Track Town USA with 15,000 runners today! 🏃‍♂️💚