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

Danielle Cullivan Signature

 

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, cheers on her son in college, and supports her daughter as she launches her career.

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2 thoughts on “From Finish Line to Starting Line: What Graduation Reminds Us About Growth

  1. Congratulations Dylan and thankful that he has been surrounded by such incredible parents and a SUPER BIG SISTER.

doses of inspiration

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Sometimes the best thing you can do for your work (and yourself) is to step away from it.
Whether it’s a long weekend or a long-awaited adventure, giving yourself space to rest and recharge can bring fresh perspective and energy you can actually feel.
In this week’s post, I’m sharing:
+ Highlights from my Croatia trip (Dubrovnik, Trogir, and a few hidden gems)
+ My “dream bucket” savings strategy: how small, consistent deposits made it possible, plus an investment app to help you save up (with referral link for a discount) thanks to @erikagentry for sharing! 
+ What I’d do differently next time, including travel timing and carry-on essentials
If you’ve been craving a reset or need a little nudge to plan your next “someday” trip, this one’s worth a read.
Link to all the travel details in my bio 👆
Thank you to @sarahcentrella for planning this amazing retreat, @estoveststyle for outfit recommendations and @timezonelesstravels for helping with travel accommodations. You all made this experience extra special 🥰
#workingmom #croatia #over50
We are officially in college countdown mode 💚