(1/3) You contain multitudes.

The cost of compartmentalization.

Do I contradict myself?
Very well then I contradict myself,
(I am large, I contain multitudes.)

— Walt Whitman, Song of Myself (1855)

What scared me most was that I’d stopped caring.

I didn’t care about the music business.
I didn’t care about developing new artists.
I didn’t care about becoming the next Rick Rubin.

And I especially didn’t care about endlessly repeating the same four or five conversations with artists and labels each day until my vocabulary had been whittled down to a set of responses so lifeless from overuse — sick, dope, crazy, etc. — that even my first grade English teacher would have been disappointed. Sorry, Mrs. Reynolds. You were dope.

After a decade of supporting the dreams of others as an artist manager, a light had gone out, a nihilism had crept in, and my relationship with the snooze button was getting more and more toxic with each passing morning.

8:00AM.
8:15AM.
9:30AM.
11:00AM.

I just didn’t care anymore.
Deep down, I think I knew why.

Dreams are a Jung man’s game.

The truth is I’d actually always envisioned myself as an artist more than anything else, but nobody in my professional life knew that, and nothing about my daily actions or interactions was reinforcing this identity I’d privately — but proudly — held since I was a teenager.

My artistic dreams had been my shadow since that one night when I was seventeen, studying for the college entry exams in the basement. And I did study, for about five minutes. The rest of the night was spent marveling at what I could only explain (then or now) as an act of magic, a gift from God, and a feeling I’ve been chasing ever since. I started spacing out, and then it happened:

The way I see it
Everybody is entitled to their own lives
People living dreams through their kids
Why try?

Let ‘em be who they wanna’
Let ‘em be who they gonna’

I can’t believe what half of these people are doin’
Spend their whole life pursuin’
Things that aren’t important to ‘em

Daniel Witcoff, The Way I See It (Excerpt)
Chicago, Illinois
Winter 2007

When I finally lifted the pen from the paper a few hours and twenty four bars later — about two full verses in your typical rap record — I felt like I’d just woken up from a dream, as confused as I was enamored. Where did those words come from? Who were they about? Why did my inner-narrator’s voice sound so much like Common’s?

Dazed, I looked down at my watch. Amazingly, it had only been five minutes. I couldn’t believe it.

A conflict of interest.

Right then and there, I understood that creativity comes from somewhere outside of ourselves, that even the most imaginative among us are more conduit than creator.

Something spiritual had been awakened in me that night and I’d found my first love.
But at seventeen, I didn’t understand what love meant, or what I was supposed to with it. And I think it scared me.

If it hadn’t, I probably wouldn’t have spent the next fifteen years battling with it, playing tug-of-war between believing that I was destined to be the next great artist…and trying to rationalize it away.

Valley of the shadow.

The hundreds of verses and hooks throughout college, the secret open mic performances in New York and Los Angeles during my early twenties, the impetus for getting into the music business in the first place.

All of it was demonstrative of this romanticized gap between believing this could be something special — that I could be something special — if I were to focus on it, and never believing enough to give myself permission to find out.

What do you end up with?

A music manager surrounded by folks who had trusted those instincts, who had given themselves that permission.

A partitioned person decently successful at helping others follow their dreams, decently unsuccessful at following his own.

An insecure adult torn apart by these internal opposing forces, ripped this way and that by the lack of connective tissue between the vibrant and varied and valid parts of himself that seemed to be in constant conflict, an orchestra waiting on its conductor.

Snap back to reality.

So here I was at 32 years old, needlessly suffering the consequences from this lack of consensus on who I was, what I was.

Something needed to change.
Something needed to bend.
Something needed to break.

Call to adventure.

And so, in May 2023, I decided to quit my job, walk away from my roster, and spend my 33rd trip around the sun doing something I’d always dreamt of — being a full-time artist.

🛎️ NEXT FRIDAY 🛎️
October 31st, 2025

(2/3) From managing artists to being one.*

*Just a temporary title.

Let’s figure this shit out together.

If you’re like me and have spent too much of your life raging at the world for not fully understanding you, while raging at yourself for not letting it, press subscribe and let’s figure this shit out together.

Thank you for reading,

Daniel