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There’s that moment, maybe you know it, when your kid clings to your leg, or maybe they run away, and you’re supposed to smile, wave, and walk away. The new school drop-off goodbye can feel like a gut punch.

It’s completely normal to question yourself during these moments. Am I doing this right? Should I stay longer? Should I leave faster? These are all valid concerns that many dads, including myself, have experienced.

When my son was 1 year old, he cried every single drop-off for weeks. It tore at him. But then the teacher sent a picture of him, and five minutes later, the same child was happily playing. What felt unbearable was just a transition, not a reflection of failure. I remember feeling so helpless and questioning my parenting. Seeing that he was happy and engaged so quickly after I left reassured my wife and me that we were doing the right thing.

Now, my son is preparing to start a new school as a preschooler next week.

Here are a few tips to help make that handoff smoother for both of us:

When you honor your child’s emotions and hold the boundary, you show them that it’s safe to feel and still move forward. You’re not abandoning them, you’re teaching them that they can do hard things, and that you’ll be there on the other side.

Those early goodbyes build the emotional muscles, which are the psychological skills and resilience that help our kids handle change, trust relationships, and grow into resilient humans. And for us dads, they’re a chance to practice empathy without rescue to stay steady when big feelings rise.

One of the most important things a dad can do for a family is take control of his finances. Tracking your income, spending, and investments provides peace of mind and relief, setting a strong foundation for your family’s future.

I use Monarch to stay on top of everything. It’s a game-changer for organizing finances, budgeting, and long-term planning. It’s empowered me to create a system that works for my family, and I highly recommend it.

💡 Special offer for my readers: Use my code HERE for 1 free month of Monarch.💡 (Note: I may receive a commission if you join through my link—thanks for supporting the newsletter!)

Reply directly to this email with your question, or use this quick form to submit anonymously. Whether it’s about family routines, connecting with your kids, or managing stress, I’m here to help!

Let’s tackle parenting together, one question at a time!

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