I’m deep into my great 60th birthday road trip adventure—a little sun-kissed, a little margarita-fueled, and a lot reflective. I’ve had a lot of windshield time with my thoughts. There’s something about a long drive that helps me peel back the noisy layers and get my head clear.

Last week, I gathered with my family and my New-Old friends to celebrate milestones - my sister’s 29th and my parent’s 62nd wedding anniversaries, and my 60th birthday - south of Bend, Oregon in Sunriver. There were handmade bud vases and napkin rings made by Kirly (who, by the way, found her love of clay at a Dare retreat and is now headed to Italy for a ten-day immersion—proof in action that learning never stops, and you never know what door a Detour might open!). There were hand-calligraphed place cards made by my friend Yvonne, flowers by my friend Kristin, and laughter and love from all who gathered.

During dinner, my nephew’s girlfriend, fresh into her twenties, asked me a tender question: “What advice would you give someone my age?” On the spot, I answered:

If you can stay true to yourself and know what your core values are, everything always works out. When I look back, even at the hardest moments—divorce included—trusting my gut was my lifeline.
Choose your partner with eyes wide open. And live with them first! We see red flags, but oh, how often we ignore them. How we are together in daily life tells you so much more than words or big gestures ever could.

On my drive the following day, my tires rolled north toward Sunriver, and that question kept echoing in my thoughts. What would I add, now, to my answer? What has the benefit of *almost* 60 years, a half-dozen pivots, and my fair share of heartbreaks given me perspective on? What do we owe our 20-something selves?

Here’s what crystallized:

You will be asked, quietly and constantly, to put others first. As women, especially, we often find ourselves automatically taking on the role of caregiver—the one holding it all together. So much of it is unspoken, but those roles can become concrete before we even realize what’s happening. In my own marriage, my path as primary caretaker wasn’t so much chosen as it just...unfolded. Babies, illnesses, life. Suddenly, what felt like “just helping” became a full-time job that I hadn’t consciously agreed to. Looking back, I wish my husband and I had had more honest, regular conversations about what we both wanted, what we both needed.

If you bury your needs, they grow underground. There’s an old truth: “What you bury grows.” If you don’t say the hard things, if you keep shoving yourself to the bottom of the list, those feelings don’t disappear—they wait. I learned, sometimes the hard way, that writing your concerns down, naming them kindly but clearly, can be magic. It creates air, a way forward, and the chance to be seen.

So, to the beautiful twenty-somethings (and to anyone, really):

Get fluent in your own values.
Learn what you’re truly hungry for, outside of anyone else’s expectations.
Keep asking yourself and your loved ones the hard questions, early and often.
Community, creativity, and courage are always worth cultivating.

And above all: Don’t fear the Detours. In my experience, this is where you find out what you’re made of. And where you discover the wild, surprising corners of your own heart.

Now, I turn the question back to you, my wonderful community: What advice would YOU give a 20-something-year-old? What do you wish you’d known sooner, or Dared to do without apology?

With all my love from the winding road,
Sheryl

P.S. If you haven’t watched “Women Holding Things” by Maira Kalman (shared by Maria Shriver HERE), please take a few moments. It’s a balm and a revolution in poem form. You’ll see what I mean.