The Year That Broke Me Open

A letter to everyone in the arena right now.

I've been quiet lately. Not idle — quiet. Behind the scenes I've been building Reimagine Ranch and Serafina, our new platform for purpose-driven creators who want to discover their gifts, bring them to the world, and find the community that matches their purpose. I'm genuinely thrilled by what's possible now.

But that's not why I'm writing.

I'm writing from a place of deep pain, deep growth, and deep truth. Not to trauma-dump. Not to make my burdens yours. I'm writing because whatever we reject and judge in ourselves, we end up rejecting and judging in the world — and I'd rather meet you in honesty than perform for you in polish. If sharing the hard parts of my year helps you look at your own growth edges with a little more compassion, then the telling is worth it.

Into the arena

If you want to live your gifts — really live them, out loud, where people can see — you are going to go through initiations. There's no other way than to get in the mix and be the man or the woman in the arena. You reveal yourself for the world to see, and the world shows you your shadows.

This year showed me mine.

I made mistakes. After our last event in Austin, there were a lot of them. I was moving for all the right reasons, and I still went too fast and broke too much. I've been held to account for things. I've apologized for things. I've been through legal challenges I never saw coming — humbling, embarrassing, and close now, God willing, to resolution. There's no version of stepping into prominence that skips this part. As you rise, the margin for error shrinks — drastically — and mine got very, very tight. That's brutal. It's also a gift, because it calls you into a better way of being.

The fall

Let me be specific, because vague honesty isn't honesty.

The world changed a lot between our second event in Miami in the summer of 2023 and our last one in Austin this spring. Miami was a quarter-million-dollar event. Austin brought in $87,000. That's roughly $170,000 less than even my most conservative plan — and I had made real bets on the back of past success I was sure would hold. It didn't. That put me in a genuinely dangerous financial position, and it's taken a long time to recover, readjust, and rebuild.

Here's the part that's hard to say out loud. There were nights this year when I had nothing. I ate a jar of peanut butter for dinner and then didn't eat for four days. I called it a water fast. It wasn't a fast. Every card was maxed, every account was empty, and I was broke. I don't know if that makes people nervous about me as a leader. I'm telling you anyway — because it showed me how much I love this work, and because I think I agreed to something this hard on purpose. To find out who I really am under that kind of pressure. To meet myself in the shame, the doubt, and the self-loathing, and to clear what needed clearing.

The shadow work

The tests didn't stay in my bank account. They showed up in my relationships.

I entered into relationships I thought were right, with women I still treasure and respect. And underneath, for the last year or so, there's been a deep knowing that I'm not meant to be in a relationship right now. I've committed to a season of celibacy, and it feels honest. I couldn't give what the women I was with deserved, because there were still damaged parts of me seeking validation and vitality from the feminine instead of tending them myself.

I've had to admit, out loud, that there have been layers of codependency and layers of narcissism alive in me. That is painful to say. I've worked hard not to condemn myself for it, because I know my intentions and I know how I'm here to serve — and I also know I haven't always been able to serve at the level I want to. So the last many months have been deep, excruciating inner work: brutal initiations and ceremonies that crushed and polished me in ways I'm strangely grateful for. Savagely brutal. Savagely beautiful.

The part we don't talk about

I want to be careful and clear here, because this is the part that matters most.

Entrepreneurial mental health is real, and we do not talk about it enough. Recently a man in the Austin area — an entrepreneur, in a community a lot like mine — took his own life. I've lost one of my best friends on this planet to suicide. We have to make these conversations okay.

We have to make it okay to feel our pain. Okay to feel shame without being ashamed of feeling it. Okay to not be okay in the moment. Because that allowing — that willingness to let the feeling actually move — is what lets it move through you. When we block it, judge it, tighten around it, our authentic self can't come through. And authentic self-expression is medicine.

If you're in the pit right now: you are not weak, and you are not alone. Feel what you're feeling. Reach for someone. Say the true thing to a person who can hold it. That's not a detour from the mission. It is the mission.

What it's all for

Living your purpose is not just a business. It's a spiritual journey, and it will test every single thing in you — your relationships, your heart, your mind, your body, your faith. Everything in me got tested this year.

What held was this: love is honest, love is kind, love doesn't boast. That's the way of the Christ. That's the way of the warrior, too — let's not forget what kind of warrior Yeshua was, and what he walked through. Perfect love and perfect courage in the same body. I believe that's what we're here to remember: no victims, no villains, just powerful creators, divinely blessed, fully accountable, aligned to our truth.

That's what we're building at Reimagine Ranch — a place where that can be cultivated. Sacred community, regenerative pioneers, new thinkers building a parallel society: a real, living answer to a world of extraction and control. The solution isn't to rage at the dragon. It's to build the better thing.

Coming back

I've stayed quiet partly out of shame — about money, about the messes I've been cleaning up. That season is ending. We're coming back, and we're coming back with love.

If you're in the arena right now, bloodied and doubting: stay in it. Trust yourself. Trust the force that made you. The pressure is not punishment — it's the portal. I'll see you on the other side of it.

— Jackson