Do You Know Where You're Going To?

There’s a song that has followed me for most of my adult life.
The Theme from Mahogany.
You probably know it as Do You Know Where You’re Going To?
Whenever it shows up, something in my life changes. Almost always it has to do with work.
I’m not exaggerating. Every major pivot in my life seems to arrive with Diana Ross quietly asking existential questions in the background. A grocery store aisle. A pharmacy checkout line. Random, ordinary places where life isn’t supposed to hand you revelation between paper towels and cough drops.
And every time I hear it, I’ve learned to pay attention. Because it usually means a new opportunity is coming. A new job. A new direction. Something I didn’t see five minutes earlier.
This week, though, the universe got a little theatrical.
I was at the dungeon where I work, folding towels and doing social media posts, when suddenly I heard it drifting through the walls. Not inside. Outside. Someone had parked nearby and was absolutely blasting The Theme from Mahogany like it was a personal announcement.
There I was, standing inside a dungeon, while Diana Ross asked me if I knew where I was going.
Subtle, the universe is not.
And for the first time, instead of thinking, Okay, what job is coming next? I had a different thought:
What if I stopped waiting for the opportunity… and created it myself?
Because there’s an idea that has been quietly simmering in the back of my mind for twelve years. Not urgent. Not demanding. Just patiently waiting for me to catch up to it.
Which brings me to this newsletter.
Right now, you hear from me three times a week: Sunday, Wednesday, and Friday. Three times a week where we share info and build our community.
But lately, I’ve felt a shift in the current.
Not burnout. Not dissatisfaction. More like growth asking for a little more room.
So I’m considering a change.
The newsletter would move to Wednesdays and Fridays, keeping our usual conversations alive and well. And Sundays… Sundays would give me space to create something new.
A project devoted to gentlemen over fifty. Not as a label, and certainly not as a limitation, but as a stage of life that deserves deeper conversation.
A space about cultivating a positive outlook without pretending life has been easy. About remembering where we’ve been and deciding what parts of that story we want to carry forward. About helping both past and future generations by finally making peace with ourselves in the present.
Letting go of guilt. Releasing shame. Laughing at the things that once terrified us. Making real-life connections instead of collecting digital applause.
Sex would still exist there, because desire doesn’t vanish with age. But it wouldn’t be the centerpiece. It would simply be one thread in a much larger tapestry that includes friendship, purpose, legacy, curiosity, and joy.
If GoNaked has been about freedom in the body, this new space feels like freedom in perspective.
Think distinguished gentlemen. Jackets on. Wisdom earned. Wearing a red jockstrap underneath because a little wildness never really leaves us.
I think this calling has been waiting for me longer than I realized. Twelve years of quiet nudges. Twelve years of “not yet.”
And maybe hearing Diana Ross outside a dungeon was the universe’s way of saying: now.
Growth doesn’t always mean leaving something behind. Sometimes it means expanding the house so another room can exist.
So here’s where I’m at.
In about a month, GoNaked will be published on Wednesdays and Fridays. That will stay exactly as they are. Our ongoing conversation continues. The community remains the heartbeat.
And Sundays? Sundays would make room for the Brotherhood of the Red Jock - A Society of Nearly Distinguished Gentlemen.
I don’t have the final shape yet. That’s part of the adventure.
But I do have a question for you:
When life starts asking where you’re going… do you wait for an invitation?
Or do you finally decide to write one yourself?