A few things I wish someone had handed me, and what I am telling them now
There is a particular kind of pride that fills your whole chest. Not loud. Quiet, the way it settles in before you even know it is there. I will feel it twice this spring. My grandson crossing one threshold, my nephew crossing another. Both of them stepping into something new and slightly terrifying, an adventure and a growing, all at once. Both of them trying to look like they are not the least bit nervous. Boys. They are just like us in that way.
Eighth grade graduation and high school graduation are two different animals. One is leaving the small pond. The other is leaving the pond entirely. But what strikes me is how much of the advice I want to give them is the same advice I wish someone had handed me in a sealed envelope at their age. Not wisdom I would have listened to, probably. Let’s face it, at that age we knew everything. Or thought we did. But wisdom I would have unfolded later, when I actually needed it.
Here is the other thing I keep thinking. We talk about graduation like it only happens twice. High school, college, done. But that is not true. Life keeps handing us graduations. Leaving a job. Moving to a new city. The children leaving. Turning fifty. Midlife is its own graduation, new and unfamiliar territory, no map, no locker assignment. So this letter is for my boys. And honestly, it is for all of us.
Always Ask
This is the one that took me the longest to learn, and I am still working on it. We talk ourselves out of asking before we ever open our mouths. We decide the answer is no before anyone has had a chance to say yes. We assume the scholarship is for someone else, the internship is already filled, the seat at the table is taken.
Ask anyway. The only thing anyone can say is no, and no is not the end of the world. No is just a door closing, sending you down a different hallway to a new door to knock on. I have watched people get exactly what they wanted simply because they were the only one who asked. The rest of us were standing outside, certain it was not possible. I am guilty of this even at fifty-nine. Still learning. Getting better.
Ask for the opportunity. Ask for the explanation. Ask for the second chance. Ask the question in class that you are sure everyone else already knows the answer to, because I promise you, half the room is thinking the exact same thing. Be the one who is brave enough to say it out loud.
Seek Every Opportunity
When I left my small grade school and walked into St. Mary’s Academy, I was, to put it mildly, shocked. Nearly five hundred girls. Moving between classes. Finding my way around two buildings that felt enormous. I had been trying to fit in my entire life, but this was a different scale entirely. And yes, I was absolutely one of those girls who could not get her locker open.
Four years later I headed off to university and felt the exact same thing, minus the locker. Except now multiply the hallways, the faces, and the buildings by roughly twenty-five. Fifty-two buildings. I know because I counted, standing there on the first day wondering what on earth I had gotten myself into.
What I know now is that the people who look back without regret are almost never the ones who held back. They are the ones who tried the thing that sounded interesting, joined the club they were not sure about, raised their hand for the project nobody else wanted. Opportunity hides in the places that feel a little uncomfortable, and if we are being honest, usually the very uncomfortable ones. Nobody grew from staying comfortable. Nobody.
You will not love everything you try. Nobody does. That is fine. Even the things that do not work out will teach you something worth knowing.
Travel If You Possibly Can
I studied in France. I was not much older than my nephew is now, and I wandered into churches and down narrow streets and sat in cafes where I did not know a single person, and it changed everything. The way I understood the world. The way I understood myself. You do not know how big the world is, or how big you can be, until you have stood somewhere that has nothing to do with where you came from.
Travel does not have to mean Paris. It can mean the town two hours away, the college visit that feels completely foreign, the summer road trip to somewhere none of you have ever been. Travel changes you. It pushes your boundaries, opens your eyes and your palate, teaches you, embraces you.
Be Kind, Even When It Is Not Easy
Everyone you will ever meet is carrying something you cannot see. The kid who seems to have everything together is sometimes the one who is barely holding on. The person in the cafeteria sitting alone, that one matters. It costs you nothing to sit down.
Kindness is not weakness. It takes far more confidence to be kind than to be indifferent. I have never once regretted being kind to someone. I have absolutely regretted the times I was not.
Be kind to yourself, too. You are going to make mistakes in these new places. Embarrassing ones. The kind you will replay at two in the morning with remarkable clarity for the next six months. Give yourself the same grace you would give your best friend. Speak to yourself the way you would speak to someone you love, with kindness and the kind of encouragement that actually helps.
You Do Not Have to Figure Everything Out Today
There is enormous pressure on young people to already have the plan, the major, the five-year roadmap, the confident answer to what do you want to be when you grow up. Here is the truth: you are not grown up yet, and that is exactly as it should be. There is time. Take some of it to simply enjoy this stage of your life. You will grow up soon enough.
My answer at their age would have told you nothing about who I became. I thought I knew where I was going, what I would do, who I would be. I did not know then. I am still figuring it out now.
Life has a way of rearranging your plans and replacing them with something better, stranger, and more interesting than anything you mapped out at fifteen. The woman I am today, sitting in the Indigo Room with a French toile cup of drinking chocolate, writing about the things that matter to women over fifty, was not in any plan I made. She arrived through a thousand unexpected doors, and I am glad I walked through every one of them.
It is enough, today, to show up. To be curious. To be kind. To ask the question. That is more than enough.
A Letter I Will Keep Writing
What I want most for both of these boys, and for every woman navigating her own graduation this year, whatever it looks like, is this: do not let the size of the next chapter talk you into making yourself small. It will not be perfect. Nothing is. But it will be full of things you have not discovered yet, people you have not met yet, a version of yourself you have not had the chance to become yet.
I will be watching my grandson and nephew from a distance, my heart full and swelling with pride, with hope for their futures, with all the good things I wish for their adventures ahead. Hoping they carry some of this with them. And hoping too that when they need to talk, they call someone who loves them. We always pick up.
Do you have a graduate in your life this spring? Or does this season feel like its own kind of graduation for you? What is the one piece of wisdom you had to learn the hard way? I would love to know.
Have a wonderful day!
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