College Drop-Off Tips: 3 Ways to Make the Transition Easier for Parents & Students

In a world that never stops changing, few transitions compare to sending your firstborn off to college. My oldest, now heading into his third year at his university, has grown in ways I never could have imagined—but so have I. As I prepare to send my younger son off this fall, I feel a bit more ready. Still, as every parent knows, each child and situation is different.

Along the way, I’ve learned valuable lessons—some I wish I could do over and others I’m grateful for. In this four-part series, I’ll be sharing insights from my experience, starting with three key takeaways that either helped tremendously or, in hindsight, I wish I had done differently.

Include Siblings or Other Close Family Members on Drop-Off Day

As Cher famously sang, If I could turn back time, I would! In all the planning and preparation for my oldest son’s college send-off, I didn’t fully grasp how deeply his absence would affect my younger son. The two had been inseparable since they were little—sharing a room, playing on the same sports teams, riding to school side by side. They were the first faces they saw in the morning and the last before falling asleep.

Looking back, I regret not bringing my younger son to drop-off day. I assumed he’d want to stay behind—after all, he was starting his junior year of high school, serving as captain of the cross-country team, and had commitments to uphold. It never even occurred to me to ask if he wanted to be there.

The day itself was a mix of emotions—heart-wrenching, exciting, overwhelming—and in the weeks that followed, I saw my younger son struggle to adjust. It took a couple months, but he did eventually find his way. I realized that being at drop-off in person might have helped him process the transition, offering both closure and a tangible way to navigate the space his brother left behind.
If I could do it again, I would have invited him. Maybe he would have chosen to come, maybe not—but at least he would have had the choice.

Create a Sense of Home in Their College Living Space

My oldest has a strong sense of independence and was sure he didn’t need much to make his dorm feel like home. But when we finished setting up his room, it looked so bare and impersonal that I made an executive decision—I had my husband run me to the store and I scooped up an area rug and some throw pillows for him and his roommate.

In the grand scheme of life, it was a small gesture. But as I drove away that day, with my heart cracked in two, those plaid pillows peeking back at me as I closed his dorm room door behind me brought unexpected comfort. I couldn’t be there with him, but I could make sure his space held small reminders of home and how much he’s loved.

By his second year, I ignored his protests and added even more homey touches—perhaps because I had grown, too. Leaving him still stung, but knowing his space felt warm and familiar made the transition just a little easier for both of us.

Make Plans Before You Leave For The Next Visit