Ride‑or‑Die: On Friendship, Mentorship, and the People Who Hold the Shape of Our Lives - Newsletter #52

Earlier this week, I taught a class to a group of young people about mentorship.

And as I do with every group I stand in front of, I shared something I believe with my whole heart:

"One of the most important things you can do in this life is intentionally curate and develop deep relationships with other people."

Not contacts. Not networks. Not followers.

People.

I told them that yes, mentors matter. Sponsors matter. Teachers, guides, and elders matter. We all need people who can see farther down the road and help us understand what’s possible.

But just as essential are the relationships that don’t come with titles.

We need our BFFs. Our ride‑or‑die people. The ones who know us outside of outcomes.

These are the relationships that steady us as we grow. They remind us who we are when the world gets loud, when seasons shift, when plans unravel or expand faster than we expected. They hold the parts of us that don’t show up on résumés or stages.

Mentorship can open doors. Friendship helps us walk through them.

Not long after that class, I watched a short Instagram clip of Sir Ian McKellen reciting a 400‑year‑old monologue by William Shakespeare from a lesser-known work portraying the character of Sir Thomas More, a piece about strangers, belonging, and the moral responsibility we hold toward one another.

The words were old. The message felt painfully current.

It moved me to tears.

I went to comment, still a little undone, and that’s when I noticed how many people I know were already there, liking the clip, responding to it, sharing their own reflections. Friends from the theatre. From college. From work. From chapters of life that feel both far away and right beside me.

So many names.

I couldn’t believe how many.

I just sat there and cried, not from sadness, but from a sudden, overwhelming sense of connection. Each name carried a memory with it: a rehearsal, a late night, a creative risk, a moment of support, a shared laugh. Some I talk with daily. Some I haven’t spoken to in a long time, but who remain part of my interior landscape. 

Like those who are no longer with us, we love them still, because grief is not a straight line but a messy, winding road, and when we keep telling their stories, we keep their memory alive.

It reminded me that relationships don’t disappear just because seasons change.

They stretch. They pause. They wait. And some do end.

And sometimes, they reappear quietly, in a comment thread, in shared reverence for language, in the recognition that values can bind us long after proximity fades.

In that moment, I felt so very lucky.

Lucky to have known so many wonderful people. Lucky to have been shaped by them. Lucky to still be held, however loosely, inside a web of connection that spans time, geography, and identity.

This is what I wish we talked about more when we talk about success, mentorship, and leadership.

Not just who helped us climb, but who stood beside us when we were deciding who we wanted to become.

"Our ride‑or‑die people. Our fellow witnesses. The friends who see us clearly and let us be whole. These relationships are not incidental to a meaningful life. They are the quiet architecture of it."

They regulate our nervous systems when everything feels uncertain. They remind us that we are not projects to be optimized, but humans allowed to change, soften, rebuild, and rest. They make our lives larger, not louder, but deeper.

So if, this week, a name crosses your screen and stops you. If a memory rises unexpectedly. If you feel that familiar swell of gratitude and recognition...

Let it stay for a moment.

That feeling is a connection remembering itself.

And it is worth tending to.

Empathy makes us human; actions make us warriors.

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