Live From the Messy Middle

Dre Manning — Thu, 22 Jan 2026 20:14:42 GMT

I’m Dre Manning. A founder, father, and husband who grew up in the Bronx (Highbridge to be exact) and now lives in Dacula, GA.

This is a safe space, right?

Fuck it…

I’ve wasted a lot of time wrestling with the need to appear like I had it all together.

I didn’t.

And I still don’t, but I’m finally at ease with this. I’m learning to embrace the “messy middle”*, but it's a constant battle, and sometimes fear, ego, and pride are the victors.

As far as I can think back, I’ve always wrestled with this idea of the perfect appearance. I think about when my mom bought me the bootleg Air Max ‘95’s, and I asked my friend to draw a Nike check on them.

Now, I am a first-time founder who struggles with burnout. Operator fatigue and personal frustrations, but shows up every day to the office with a smile, a heart full of love, and a brain full of

Fuck this shit.

I mean, let’s be honest.

Social media sure loves the results, so why post about the struggle to get bookings at my content studio, or the headaches of launching a new service, or the complication of transitioning from working in the business to working on it while still running the business?

The fuck. This is GHETTO!

Since 2012, we have been conditioned to show our refrigerator door highlights. For the young ones in the back, back in my day, when you got good grades, awards, and took nice pictures. Your parents would hang them on the refrigerator door using magnets. Not post them.

But for me, it didn’t start there. I didn’t have a name for it.

I avoided showing the messy middle because I thought if people saw me struggling, they wouldn’t believe in me. They think I was incapable of doing what I set out to do and that I wouldn’t be seen as this trusted source.

They’d see the real me. A guy who grew up on Section 8. Single-parent home with a mother who suffered from undiagnosed/untreated mental health issues, which caused him and his brothers to go in and out of foster care.

Instead, I hid behind stage names and performative identities.

Man, I used to pee the bed (too personal? My bad)

Anyways…

I appeared buttoned up to hide the fact that I’m a multi-time college dropout. Who used to shoot dice outside bodegas. Drink obscene amounts of Henny in building lobbies. While emotionally abusing the women in my life, if they didn’t want to come to my mom’s house to have sex with me on my twin bed.

Terrible.

At 15, I was a Crip. By 16, I sold weed to my classmates (I even employed a few).

I changed my stage name from Dre Murda to Dremur and convinced everyone it was pronounced dreamer. I started wearing fitted jeans and cardigans to hide that I was a wolf in SB dunks. I said peace and love. Peace Queen, Peace King. When I really wanted to say

‘ sup nigga!

You’re probably wondering. Dre, how and what is the messy middle of this story? What were you working on that you didn’t want to showcase to the world? Simple.

I grew up in a household where I constantly heard, “What happens in this house stays in this house.” Those became the scripture I lived by. So, as a young father, I hid from my sons my financial struggles because that’s what “good parents do,” but to them, I became the parent who always said no. Once my finances shifted, I became an open book about everything.

On one end, you don’t want to trauma dump on a 9-year-old. On the other hand, you want to treat them like a whole person and provide them with insight into why you can’t do things. I know this now, but then, nah.

I’mma hold on to this mess. But what does this teach them?

I’m not sure.

What I do know. Many of us are still figuring this shit out. The evolution of adulthood has shifted from generation to generation. But everyone believes they know the right way of doing it. There are millions of written, recorded, and filmed think pieces of what we should or shouldn’t be doing with our lives at X age.

But let’s be honest, many of us are still faking it until we make it (even after we make it). Searching for a north star to help guide us through the trenches of adulthood. Today is not our parents’ and grandparents’ yesterday. It’s not as simple as getting a state job, finding a partner, getting married, buying a house, having some kids, retiring, and dying.

At 38, I’m still figuring this shit out, and that’s fine.

The promise I’ve made myself is to embrace the messy middle with open arms. This is where the great shit happens. This is where I can work to get better every day. It’s not about my triumphs, but about my preparations. It’s not about being or appearing buttoned up. It’s acknowledging that I don’t have the answers, but I’m willing to work and find out.

Embrace the messy, don’t avoid it.

Every year, I create a theme or framework as my single source of truth. This year, it’s a little long but simple.

Lead with curiosity. Walk with fear, while embracing love.

Simple.

I’m starting this Substack because I wanted a space that’s less about algorithms and more about real connections. I’m taking a year-long hiatus from Meta platforms (my wife and kids send me TikTok recipes to cook). I needed a place where I could share not just business updates but also the personal journey of being a founder, a father, a husband, and a Black man navigating it all. Something that feels like a public journal, not a highlight reel.

I’ll be mixing it up: some weeks you’ll get a written post, other weeks an audio drop. I’m still figuring out the exact rhythm, and that’s part of the fun. There are no off-limits topics here. I want to keep it real and let this space evolve naturally.

If you’re reading this and it resonates, I’d love to hear about your messy middle. What’s that thing you’re working through right now? Feel free to reply and share if you’re comfortable. And if you want to stick around and see where this goes, hit subscribe.

Let’s lead with curiosity, walk with fear, and embrace with love.

I appreciate you,

from dre.

*Messy middle: the often difficult, uncertain, and lengthy period between a project’s exciting start (conception) and its successful conclusion (finish), characterized by volatility, overwhelm, and a lack of clear progress, common in innovation, personal life (midlife), and consumer purchasing journeys where shoppers explore options

- Scott Belsky (The Messy Middle: Finding Your Way Through the Hardest and Most Crucial Part of Any Bold Venture)