The Greatest Investment You’ll Ever Make: Time With Those You Love

Every morning, I open Ryan Holiday’s Daily Dad newsletter. His Stoic wisdom has become my compass, the reminder that in our chaotic entrepreneurial lives, our most significant legacy isn’t what we build, but who we become for those we love.

Today, I’m channeling some Holiday wisdom to share what truly matters.

This past Mother’s Day weekend taught me something no business book ever could.

Saturday was Mexican Mother’s Day. Eight years after a stroke that nearly took her from us, five years of which we spent as her full-time caretakers—my mother now thrives in assisted living. I took her to the nail spa, where we laughed like we used to. As Holiday might say: this wasn’t an obligation, but a privilege.

This morning..

My wife and I stood at Coast Guard Station San Diego, not as visitors this time, but as witnesses. Our daughter—18 now—took flight in a Coast Guard helicopter along the Southern California coast.

The same waters where I grew up and played as a child now stretched beneath her as she soared above the skyline.

I watched my wife’s face as our daughter ascended. This moment embodied what Holiday constantly reminds us in Daily Dad: We raise our children to leave us. This is the beautiful paradox of parenthood, success means letting go.

These moments with my mother and daughter represent what Holiday calls “the obstacle is the way.”

The stroke that nearly took my mother gave us years of deeper connection. The daughter leaving our nest is fulfilling the very purpose of our parenting.

Our nest will soon be empty.

My wife is launching a new newsletter called “Two Empty Nesters” to document this journey (we’ll keep you posted).

Like Holiday teaches, we’re not running from this new chapter but leaning into it.

When I read Daily Dad each morning, these principles resonate most: presence over productivity, love over legacy, and time over money. Holiday helped me see that the entrepreneur’s true wealth isn’t measured in revenue but in moments, moments that, once gone, no business success can reclaim.