The Wilderness Period
Before this guide existed, before the Applied AI Society, before any of the work you’re reading right now, I spent years building things that looked successful from the outside.
Woke Folks was a movement that got real traction. Civics Unplugged brought young people into civic leadership and attracted serious institutional support. Edge City pushed the boundaries of what intentional community could look like. Alpha Schools (with Lael Alexander) explored what education could become. By the metrics the world cares about, these were wins. Press coverage. Funding. Growing communities. People using the word “visionary” in reference to what I was building.
And I was miserable.
Not miserable in the dramatic, visible sense. Miserable in the quiet way that only you and God know about. The kind where you’re performing at a high level and everyone is applauding, but when you sit alone at the end of the day, you feel a hollowness that no amount of external validation can touch. My diagnosis was simple once I was honest enough to name it: I was building movements that did not accrue back to me and did not point to God. Every ounce of energy I poured in was generating returns for other people’s visions, not the purpose God had for me. The return-on-energy was terrible, and I kept trying to fix it by working harder instead of working differently.
This is far more common than people admit. I talk to professionals all the time who have built impressive careers, impressive companies, impressive portfolios, and feel empty. The instinct is to blame themselves: maybe I’m not grateful enough, maybe I need to push harder, maybe success will feel real at the next milestone. But the problem is almost never effort. The problem is foundation. When you are building on the wrong foundation, more effort just gets you further from where you need to be.
After Alpha Schools, I entered what I now call my wilderness period. Post-Egypt, if you want the biblical frame. It was a season of stripping. God stripped the small thinking. The people-pleasing. The willingness to lend my gifts to whoever showed up with a compelling pitch. It was uncomfortable in every way. I didn’t have a clear next step. I didn’t have the safety net of someone else’s organization to operate within. What I had was a growing conviction that the next thing needed to be built differently, from the foundation up.
I believe God “cloaked” certain gifts during that time. Not removed them. Cloaked them. Hidden them from the exploiters and the extractors, the people who had a track record of recognizing talent and redirecting it toward their own ends. The gifts were still there, still developing. But they were being protected, reserved for deployment toward kingdom purposes at the right time.
That cloaking felt like failure in the moment. It looked like stalling. From the outside, people probably wondered what happened to me. The answer is: I was being prepared, and preparation does not always look like progress.
Here is the practical lesson for you. If your return on energy is consistently bad, if you keep pouring yourself into things that leave you drained and directionless despite real competence and real effort, that is almost always a signal of misalignment. Not a signal to work harder. The correction is not more effort. The correction is different direction. Sometimes the bravest and most strategic thing you can do is stop building, sit in the wilderness, and ask God (or whatever you call the deepest source of truth in your life) what you’re actually supposed to be building.
The wilderness is not wasted time. It is recalibration time. Everything I’m doing now, this guide, the Applied AI Society, the consulting work, the teaching, all of it grew from seeds that were planted in the wilderness. I would not trade that season for anything, even though I would not want to repeat it.
Key Takeaway
When your return on energy is consistently poor despite real competence, the problem is usually misalignment, not insufficient effort, and the correction often requires a wilderness period of honest recalibration.