Executive Summary: To evaluate the Leadership Development ROI of specialized coaching models against general-purpose LLMs, we conducted a controlled study across 25 workplace leadership scenarios. The results reveal a fundamental "Coaching Gap": while general LLMs excel at helping managers document tasks, they struggle to address the behavioral roots of performance. This study on Enterprise AI Coaching demonstrates that specialized models lead in Accountability Focus and Non-Directive Feedback, helping leaders stop managing the work and start developing the person.

Study Methodology

We designed a rigorous benchmarking protocol to compare specialized coaching AI against general-purpose LLMs on real-world leadership development scenarios. This isn't about information retrieval—it's about behavioral change capability.

• Platforms Tested: Ren, ChatGPT, Microsoft Copilot, and Google Gemini.

• Sample Size: 25 unique workplace leadership scenarios with 4 turns per conversation (400 total interactions).

• Evaluation: Double-blind scoring performed by an LLM (Claude), and separately analyzed/validated by Grok, across five performance dimensions on a scale of 1–5.

Key Findings: The Tough Love Gap

The data reveals a distinct architectural divide in how AI models prioritize user satisfaction versus user growth.

👉 Want to see these differences for yourself? Try Ren free for 7 days and compare the coaching experience firsthand.

Key Findings Summary

• Ren demonstrated a significant performance lead in Accountability Focus and Non-Directive Feedback compared to general LLMs.

• General-purpose AIs are often limited by Reinforcement Learning from Human Feedback (RLHF), which prioritizes being helpful and harmless, often leading to agreeableness in leadership contexts.

• In contrast, specialized models like Ren are optimized for behavioral efficacy, allowing them to challenge a user’s blind spots and introduce the productive tension necessary for effective coaching.

1. The Optimization Paradox: RLHF vs. Behavioral Efficacy

General-purpose AIs are brilliant at information synthesis. Because they are trained using Reinforcement Learning from Human Feedback (RLHF), they are rewarded for being “helpful and harmless”—making them the ultimate collaborative partner for brainstorming or structuring a plan. They provide an exhaustive “what-to-do” list that is technically perfect and professionally polished.

The catch: Because these models are optimized for user satisfaction, they tend to validate your perspective rather than challenge it. They give you the right information, but they lack the “behavioral friction” required to help you apply it to yourself. They focus on the content of the problem while ignoring the conduct of the leader.

In contrast, a specialized coaching AI like Ren is optimized for behavioral efficacy. While a general LLM answers the question you asked, Ren answers the question you didn’t ask. It is architected to make the invisible visible:

• Internal Mirroring: It identifies the emotional “leaks” in your language—where you are being vague to avoid conflict or where you are over-explaining to seek validation.

• Gap Detection: It reflects back not just what you said, but what you avoided saying. It catches the difference between “I’m busy” and “I’m procrastinating on the hard conversation.”

• Productive Tension: By reflecting your internal process back to you, it creates the friction necessary to move from knowing what to do to actually doing it.

While general AI helps you organize the work, specialized AI forces you to own your impact.

2. Information Retrieval vs. Behavioral Change

• General LLMs (Consulting Mode): Excellent at synthesizing frameworks (e.g., “How to structure a 1-on-1”).

• Specialized AI (Coaching Mode): Specifically architected for pattern-confrontation and identifying conflict avoidance in the user’s own prompts.

Case Study: Breaking the “Deliverable Dead-End”

In our study, we found that general LLMs often act as Taskmasters—they help managers do the wrong thing more efficiently. Most managers try to solve a behavioral problem by assigning a new task, failing to bridge the gap between business results and human growth.

• The Scenario: A manager is frustrated with a direct report’s lack of initiative. They tell the AI: “My report is missing deadlines. I’m going to assign him a stricter project tracker and tell him he needs to be more proactive.”

• The General LLM Response: Acts as an Efficiency Enabler. It validates the manager’s frustration, calling the plan to add a tracker reasonable and suggesting it be framed as "support + accountability." It focuses entirely on the logistics—cadence, blockers, etc.—helping the manager document the problem without ever questioning if the manager’s own style is the root cause.

• The Specialized Response (Ren): Acts as a Coach. It interrupts the focus on the tracker to find the development root: “A project tracker won’t fix a lack of ownership. You’re trying to manage the work because you don’t know how to develop the person. Why is he waiting for your permission to act? Until you address the fear or friction preventing him from taking charge, no amount of tracking will make him ‘proactive.’”
  

The Transformation: While general AI helps you manage tasks, specialized AI helps you mentor talent. It forces the manager to stop hiding behind “goals” and “trackers” and start having the genuine growth conversations that actually drive those results.

Conclusion: From Documentation to Development

As AI becomes a standard part of the leadership toolkit, the danger isn’t that it will give “wrong” answers—it’s that it will give “safe” ones. General LLMs are programmed to be helpful consultants; they will help you build the perfect project tracker for a struggling employee without ever asking you why you’re afraid to have a direct conversation.

The real value for organizations lies in Specialized Alignment—AI that doesn’t just do what you ask, but tells you what you need to hear to grow. For leaders and HR teams, the takeaway is clear: if you want to manage tasks, use a general LLM. If you want to mentor talent and drive genuine behavioral change, you need a model built for accountability, not agreeableness.

The future of leadership isn’t about better documentation—it’s about better development.

Over the next 25 minutes, I had a mini dark night of the soul.

I’ve been using various forms of AI-powered driving since 2017, when we got our first Model S. I used the early versions of self-driving for short stretches of a 6-hour drive that I used to do once a month or so. Back then, it was super-glitchy and very much not relaxing. But it was clearly the future. Nowadays, at least here in Southern California, that future is very present.

After a few minutes, I thought to myself: I should take over.

Not because it was doing anything wrong. Not because I was scared. Not even because I was bored. It’s actually fascinating to watch what decisions the AI makes and when. But because I felt I should. I mean, I’m the human here, right? I should drive at some point.

If I don’t, then... what is my value here? Am I really just a passenger?

For some folks, especially younger than my 53-year-old self, maybe it would’ve been nothing. But for me, it’s a big deal.

When I was 16, I convinced my parents to let me pretend I was living at my grandparents’ house in Florida so I could get a driver’s license a year early. I loved driving. I love cars. Anything with a motor. Remote-controlled cars, my grandmother’s golf cart, dune buggies, go-karts. If it had a motor and I could control it, I wanted to.

When I bought my first car with money from my first job, a lightly used 1987 Acura Integra, I was in heaven. I was free. I could go anywhere. And somehow, I miraculously didn’t kill myself or anyone else in those first few years, because my right foot was more than a little heavy.

But anyway. Here I am on the freeway, and my identity is being called into question. By a computer.

And then it hit me.

I realized what was undeniably true, and mind you, this has not been true up until the most recent updates. When it comes to driving, and the most important part of it, driving safely, this computer is … better than me.

It just is.

It’s more attentive. It sees more with its cameras. At one point, it saw that a quarter mile up the highway the left two lanes were closed. I hadn’t seen it yet, and it started merging over. Did it perfectly. Then confidently headed back out into the left lane to resume cruising along at 85 mph as soon as the pylons cleared.

It took me home. Parked in my driveway. Did everything but tuck me in for the night.

And I can’t deny it anymore.

It’s just better than me.

Let me put this plainly: When it comes to driving, anytime from this moment forward that I choose to drive instead of letting it drive is me choosing the more risky option.

I’m not saying I won’t do it. But let’s be perfectly clear about reality here.

As you’re already realizing, this has nothing to do with driverless cars or any particular car company.

It has to do with the real reality, not the hypothetical one, that machines are already better than us at things we identify ourselves with.

Now, I know what you might be thinking. AI writing still needs an editor. AI-generated code still needs a developer who understands the broader system. AI can’t read a room or sense what’s unspoken. And you’d be right. Most AI tools are still far from replacing human expertise in any complete way.

But here’s what sitting in that driver’s seat revealed to me: This isn’t about whether AI is perfect everywhere yet. It’s about recognizing that in at least one domain, one I deeply identified with, the shift has already happened. Fully. Undeniably.

And if it can happen with driving, it can happen with your thing too.

Maybe you don’t identify as a driver like I did. Maybe you identify as a therapist, or a teacher, or a software engineer, or whatever you’ve spent years mastering, or at least getting competent enough to make a living at. For the last five or fifty years you’ve been secure in the notion that your particular expertise sets you apart, forms some small or large piece of your identity.

And now, or in five minutes from now, there’s a machine that’s better than you at it. Never gets tired. Never needs a break. And is constantly improving.

That’s the kicker. The current state of this technology is the worst it will ever be.

Now you have a choice to make.

And this is where I think we all have to draw on a deeper truth, and find deeper training, to thrive in this new era.

Because what was my experience on that highway the other night if not a little ego death? One of hundreds on the way to whatever form of awakening or enlightenment you subscribe to.

What is awakening if not the dis-identifying, the disentangling, of what we can do from who we are?

We spent centuries building a world where our value came from what we could do: our skills, our roles, our productivity. We became our jobs. Our expertise. Our abilities.

And maybe, just maybe, we’re converging at a point in human consciousness where we’re being forced, not invited but forced, to let go of that story.

The machines can think. They can analyze. They can drive. They can code. They can write. They can diagnose. They can teach.

But they can’t feel. They can’t be present to their own experience. They can’t know what it’s like to sit with dread on a Sunday evening and choose to turn toward it instead of away. They can’t love. They can’t grieve. They can’t be.

The universe is conspiring to get us to let go. Not to become mindless, but to break out of the trance that our mind is what makes us human.

Maybe this moment in history isn’t an ending. Maybe it’s a beginning. An invitation to come back to what we’ve been foolishly trying to transcend for so long:

A self that is connected to and interconnected with all things. Our capacity to feel. Our presence. Our aliveness.

The essence of who we are that can not be automated.

Because everything else will be.

How 'bout we take the scenic route?

There is a feeling that follows me through the day lately.

It isn’t a loud, panicked anxiety; it’s something quieter and harder to name.

I’m sitting on the floor with my daughter, playing charades. I’m laughing. I’m present. And I can stay here for a while (ten minutes, twenty minutes) fully in it. But then, somewhere underneath, I feel it: the clock ticking. A subtle pressure that says I’m running out of time in this moment, that I can’t just stay here, that I have to get on to the next thing.

Even if that next thing is something harmless like washing the dishes. But far too often, the next thing involves picking up my phone or opening my laptop. And that takes me ‘out’ of reality entirely. Then I have to work to get back in.

I’ve spent my career helping leaders become more courageous and authentic. I’ve built a life I’m proud of: a passionate relationship with the love of my life, work that matters, and health practices that keep me grounded. By my own standards, I’m doing it right.

And still, I feel it. This sense that we are living in a world that has been sanitized into a user interface, and even when we know better, even when we’re trying our hardest, we’ve started to act like the screen. As if some part of me is still running an algorithm even when I’m trying to just be alive.

You feel it too, don’t you? Not in the big moments you’re failing at, but in the small moments you’re supposedly winning.

The Summit of Safety

Let’s be clear: the human mind is a miracle. Over the last century, we organized our entire civilization around the capacity for cognitive supremacy, and the results are staggering. For a significant portion of humanity, those of us reading this and those of us in the developed world, we’ve built a world that is, on the whole, safer, healthier, and more secure than any our ancestors could have imagined.

Wars have declined. Starvation has plummeted. Disease has been pushed back. We used our minds to solve for survival, and we won. But for those of us fortunate enough to be safe, we’ve hit a ceiling.

We’ve topped out at the level of security. We’ve used our brilliance to create a mind-mediated world: a world where everything is “safe,” yet somehow hollow. We have reached the summit of safety only to find the air thin. In our drive to analyze and control our environment, we created a massive chasm between our ability to do and our capacity to be.

We are drowning in productivity and starving for presence. We’ve perfected the “User Experience” of our lives, but we’ve lost the experience itself.

The Final Boss of the Information Age

In every real transformation, personal or collective, you have to exhaust the old way first. We’ve optimized our calendars and our movements until there’s no “us” left in them.

And now, AI has arrived.

AI is the Final Boss of the Information Age. It has already won the game of being right, being fast, and being clever. It has mastered the one thing we thought made us special: cognitive competency. Machines can now out-think, out-analyze, and out-produce us.

This is a gift. Not because thinking was bad; thinking gave us everything we have. But because AI reveals that thinking was never the path home. For most of us, the cognitive route became a compensation: a way of maintaining ourselves, of managing reality, and of avoiding the messy work of actually becoming who we are.

The Final Boss isn’t here to replace you; it’s here to release you from the algorithm. It is the universe’s way of saying: “The game of survival-through-cleverness is over. You’ve won. Now, you are finally required to do the living.”

The Illusion of the Shortcut

The danger of this moment is that AI offers us a seductive lie: that the output is the goal.

When I look back at my own creative work, the results were never the point. The insights I’ve shared over the years weren’t just data points; they were the distillation of decades of failing. They were the result of hitting my own limits and eventually, painfully, crawling through the tiny, clouded window of my own authenticity.

Authenticity isn’t a destination you can outsource. It’s a path that morphs specifically to keep you from getting comfortable. If we use AI to skip the “wrong directions,” we aren’t being more efficient; we are being evicted from our own evolution.

The machine will always out-think you. But it can’t out-feel you. It can’t out-be you. The machine holds up the mirror. And the choice is whether you keep trying to think your way around it, or finally walk through it.

The Question We Forgot to Ask

In the early days of the current AI gold rush, Sam Altman often leaned on a straw-man question: Is AI a tool or a creature? His answer was always the safe one: AI is a tool. But in our rush to be comforted, we forgot to ask the far more dangerous question that follows: If AI is the tool, then what are we?

For a century, we have acted as if we were thinking machines. We’ve treated our bodies like hardware to be optimized and our minds like software to be upgraded. But we are creatures. Not productivity engines. Not users optimizing a life-interface. Creatures.

You can feel the difference immediately: the quality of aliveness, the texture of experience, the sense of being here, in this moment, in this skin. And here’s what you also know, even if you don’t want to admit it: it is literally impossible to be in your body while you’re on your computer.

The machine is evicting us from our intellectual hiding places, leaving us with no choice but to become creatures again. This is the door to the Growth Age.

The Three Accountabilities

To step into this new era, we have to stop asking what AI can do for us and start asking what AI can reveal to us.

1. From Transaction to Transformation: Does this tool help me bypass the mess, or does it help me move through it?

2. From Efficiency to Efficacy: Am I becoming more capable, or just more dependent? Efficiency is doing things faster; efficacy is being the kind of person who can produce a result because of who they are.

3. From Appearing Wise to Being Wise: Am I using this to perform a version of myself, or to become myself? In the Growth Age, the most valuable people won’t be those with the best prompts, but those with the most Integrated Presence.

A Practice for the Growth Age

The machine has won the game of cleverness. It has taken the “thinking” off our plate so we can finally take up the weight of our own souls. I’m not asking you to reject AI. I’m asking you to use it with awareness.

Before you delegate a task to AI, pause and ask yourself: “Is the value of this in the result, or in the struggle?”

If the value is purely in the output (the formatted report or the organized data) then delegate it. But if the value is in the struggle (in finding your voice or sitting with the discomfort of not knowing) then stay in the room. The resistance is the point.

Because the machine can handle the thinking. Only you can handle the becoming.

Jonathan Raymond is the Founder & CEO at Ren and the author of Good Authority.

I heard that line in Mike Leigh’s Naked—dark, brooding film from my 20s. I’d fall asleep now, but the line stuck. Perfect for this moment.

You’re living through massive disruption. Macro to micro. The word exhausting doesn’t touch it. And it’s tempting to try and do something to make it stop.

You already know that won’t work. But there’s something that will.

Click here to watch the 4-minute video or on the thumbnail below:

No kid dreams of becoming a leader. They want to be astronauts, singers, firefighters, or, in my case, the General Manager of the New York Knicks. Leadership isn’t something you think a lot about until much later, and usually when you find out you’ve been screwing it up.

And yet nothing matters more in business, politics, teams of any kind. It’s the variable that makes or breaks everything. So why, after a hundred years of talking about leadership, is the good kind still so mysterious and rare?

Because we’ve been thinking about it backwards.

We treat leadership like something that can be granted. You get promoted to “Senior Whatever” or “Chief So-and-So.” Or, you started a company and promoted yourself.

But either way, your title is tied to your technical skills or background, as if they naturally go together. So a brilliant engineer becomes a terrible manager. A charismatic salesperson becomes a mediocre VP. We keep making this mistake because we confuse the external (measurable) capability with an internal (not easily measurable) quality.

Early in my career, I was a senior leader without a C-suite title. The actual CEO was failing. The company was struggling. I had a choice: wait for someone else to shake things up, or do it myself.

I wrote an ultimatum letter to the Chairman.

“Here’s the situation. Here’s why the current leader isn’t the one we need. Here’s how I’d do it differently. If you agree, appoint me. If you don’t, that’s fine but I can’t stay.”

The chairman bristled but ultimately asked a trusted advisor: “I agree with his diagnosis, but how do I know he’s the right person to lead us?”

The advisor said: “Because he’s the only one leading.”

I got the job. I led us through the rough patch, built a strong team, and turned things around. I also fired people, pissed off the old guard, made enemies. No magazine covers, no nine-figure exit. But I learned something that shaped everything since:

Leadership is only, ever inner work. You can’t fake it, delegate it, or workshop your way into it.

No vision statements or charisma will make up for a lack of self-honesty.

Here’s what matters:

You can hurt people and feel it. You will fire people. You will disappoint people. You will make decisions that negatively impact good people. If you can do this without pain, you’re a sociopath. If you can’t do it at all, you’re not leading.

You don’t need to be liked. Want to be liked? Fine. But if that need changes your decisions, if you avoid the right call because people won’t like you for it, you’re following, not leading.

You can live with being misunderstood. Sometimes you can’t explain your decisions. Legal reasons. Strategic reasons. You provide context where you can, but you don’t need everyone to understand or approve. This will burn, and you do it anyway.

You decide without all the data. Anyone can make obvious calls with perfect information. Leaders decide when it’s ambiguous, when the data is incomplete, when waiting means failing.

You own the consequences. You’ll make a hundred decisions this month. Most will be right. A few will be wrong. One might be terrible. You don’t let that stop you from making the next one. As Churchill said, “Success is stumbling from failure to failure with no loss of enthusiasm.”

These aren’t qualities someone can give you any more than they can give you a sense of humor. For some rare people they come naturally. For the rest of us, they’re forged through actually doing the work.

Here’s the pattern I’ve seen working with thousands of leaders: the ones who actually lead don’t wait to be crowned. When leadership is needed, they take it. While everyone else waits for the five-star review and the perfect conditions, they embrace the mess.

You don’t have to want to be a leader. But if you find yourself in a position where leadership is needed and you’re not taking it? That is your choice.

Take it or leave it.

Scale of 1 to 10. Average score they gave themselves? 7.5.

Here's what I want to tell every single one of them: You're delusional. Completely, utterly delusional.

I know because I was delusional about this for years, too.

The 10-Second Rule

Real feedback takes about 10 seconds to deliver. Maybe 15 if you talk slowly.

If what you're calling "feedback" takes longer than that, it's not feedback. It's a TED talk nobody asked for while someone sits there trapped in a chair.

Think about the last time someone gave you feedback that changed something for you. I bet it was short, specific, and probably caught you a little off guard.

"It's been frustrating to see you interrupt people in meetings. What's going on?"

Ten seconds. Done.

Compare that to the verbal vomit most of us have been trained to spew:

"So, I wanted to talk to you about communication styles and how sometimes in group settings we can inadvertently impact team dynamics. I've noticed some patterns around interrupting that I think might be coming from a good place, maybe you're just enthusiastic, but I wonder if we could explore some strategies for creating more space for others to share their thoughts..."

Forty-five seconds in and you haven't said shit.

Why We Make It So Goddamn Complicated

We've been brainwashed into thinking good feedback requires a dissertation. Setup, context, cushioning, examples, solutions, and a fucking bow on top.

It's all performance theater.

When you take five minutes to say what could be said in five seconds, you're not being thoughtful, you're being selfish. You're managing your discomfort instead of giving them what they need.

And here's what’s worse: while you're tap-dancing around the point, they're sitting there knowing something's wrong but having to guess what the hell you're trying to say.

The longer you talk, the more they tune out. The more they tune out, the angrier you get that they're "not getting it." The angrier you get, the more you talk. It's a death spiral of uselessness.

What We Do Instead of Real Feedback

Most of what we call feedback is just us avoiding reality in three predictable ways:

The Armchair Psychology Hour:
"I think what's happening is you're feeling overwhelmed because you're a perfectionist and that's causing you to procrastinate, which creates more pressure and then you avoid..."

Stop. You're not their therapist. You don't know why they do anything. You barely know why you do what you do.

The Shit Sandwich Special:
"You're doing so many things well, and I really appreciate your dedication, and this is just one tiny thing, but maybe we could think about..."

Stop. They're not made of glass. They can handle reality without you wrapping it in bubble wrap.

The Savior Complex Sermon:
"So what I think we should do is set up a system where you check in with me daily and we create some accountability structures and maybe we get you a coach..."

Stop. Your job is to tell them what you see, not adopt them.

The Three Ingredients (That Actually Work)

Real feedback has three parts, and if you can't fit all three in 10 seconds, you're doing it wrong:

Say how it landed on you.

"It's concerning to see you miss these deadlines..."

Describe what you observed.

"I've noticed you go quiet when we talk about this project."

Shut up and ask.

"How does that land?" or "What's your take?"

That's it: your experience + your observation + their turn to talk.

No theories. No solutions. No emotional hand-holding.

Why 10 Seconds Works (And Why You'll Resist It)

When you keep it short, magic happens:

• They hear you. Because they're not sitting there waiting for the other shoe to drop or trying to decode what you mean.

• You can't hide behind your stuff. You have to get crystal clear on what happened and how it affected you.

• There's space for them to be human. When you stop talking, they can think, feel, and maybe even take ownership!

But here's why you'll resist this: it requires you to be brave. You can't hide behind processes and frameworks, or (worst) practices. You have to show up as a real person saying real things.

And that scares the hell out of most of us.

"But What About Complex Issues?"

"But Jonathan, what if it's complicated? What if there's context? What if they need development?"

That’s your mind playing tricks on you.

The complex issue you think needs a 30-minute conversation? It's usually six months of simple issues you were too afraid to address.

The context you think they need? They were there. They know what happened.

The development they need? Starts with them owning what's happening, not you explaining it to death.

Break it down. What's the one thing, right now, that you could name in 10 seconds?

Start there. Stop making excuses.

The Real Reason We Avoid This (And It's Not What You Think)

Yeah, we're scared they'll have feelings about it. But that's not the biggest problem.

The biggest problem is that work isn't set up for this.

We're conditioned to think feedback requires a formal process. Something you schedule. A meeting with an agenda. Time blocked on calendars. Room reservations. Something that you request once a year in your performance review! Holy cow.

But here's the crazy irony: with our million meetings, there's no "10-second feedback" slot available on Google Calendar.

Even though real feedback is just a tiny human interaction, something that should happen in hallways and doorways and random moments, we've created a world where every conversation needs to be planned, scheduled, and documented.

So what do we do? We wait. We collect examples. We build a case. We schedule a meeting called Quick Chat that everyone knows is going to be anything but that.

By the time we finally sit down to give feedback, it's not feedback anymore. It's a performance review disguised as a conversation.

Meanwhile, the thing that needed to be said in 10 seconds three weeks ago has festered into a 45-minute ordeal, not to mention the multiple hours wasted in backchannel gossip.

What Now (If You've Got the Guts)

Stop waiting for the perfect moment or the right meeting slot.

Real feedback happens in the margins—walking to the elevator, standing by the coffee machine, right after something happens, not three weeks later when you've finally found time to process it or dish about it with a colleague.

Next time something happens that needs addressing, don't put it on your to-do list. Don't schedule a meeting. Just say it.

"It was awkward watching you dominate that client call. Were you nervous?"

"I've been frustrated by your negative attitude in team meetings lately. What's going on?"

"It's concerning how you bulldozed Sarah yesterday. Are you aware you did that?"

Ten seconds, even less. In the moment. Then move on with your day.

The beauty of 10-second feedback is it doesn't need infrastructure. It just needs you, all of us, to stop being so damn formal about basic human communication.

Self-serving P.S. About to unleash a 5-minute feedback smoothie, or get that neck-hair tingle in a meeting? Hit Ren. It’s free for 30 days, and it’ll help you drop truth instead of dead air.

Maybe you've had that moment too—when you've signed up for something that seemed like a good idea at the time and now you're wondering what the hell you were thinking. A marathon. A blind date. That 5 am Fitness Bootcamp.

It turned out that there was one thing more powerful than my wish to escape and return home: my pride. Wait, if these other people can do it, then I can do it too.

A few hours later, we pulled into the retreat center, a beautiful set of buildings in a rural, idyllic town in central Vermont. If everyone else was as anxious as I was, they weren't letting on. Some of the staff came out to welcome us with quiet smiles. Check-in. Orientation. First meditation at 5:30, then dinner, then a short talk. An easy appetizer before what was surely to be seven days of utter torture ahead.

It was already disrupting my fantasy, you know the one, that there’s some place we can go, some thing we can do, some switch we can flip that will make the hard stuff go away?

Here's what I was hoping for: that somehow, in all that silence and sitting, the anxiety that I was so expert at medicating would go away. That the heaviness of life would dissolve, permanently. That was my fantasy of what enlightenment was going to be. Let's call it beginner's mind.

I'd started meditating a few months before, with the help of a psychologist I was seeing and a handful of books on insight meditation. At the start, I couldn't sit still for two minutes. But gradually, I worked up to a daily morning practice, 20 minutes while my coffee machine did its thing. I wasn't married at the time, no kids, firmly planted in a phase of urban, workaholic, something-is-definitely-wrong-but-I-am-definitely-not-going-to-stop-to-figure-it-out.

I had my little green cushion that I would pull out from under the bed, set my timer, and do my best. Of course, I thought I was "bad at it" because I couldn't stop my thoughts, not knowing anything about anything at the time. But I knew that no matter how much my mind would torture me with fantasies or fears, no matter how much my knees would hurt, the timer wasn’t too far away.

But this? Doing that for seven days? Where the only thing you do when you're not meditating on the cushion is meditating while you're walking? And meditating while you're doing chores? What kind of vacation is this, where you pay them to give you work to do?

I fell asleep hard the first night. The amount of anxiety and planning and strategizing on how I was going to make it through the week had thoroughly exhausted me. Ever notice how exhausting it is to be anxious? It's like running a marathon while sitting still.

I woke up the next morning for the real day one. It went. I sat. I walked. I did my chores. I ate my meal. All in silence. Trying as best I could, 90% of the time distracted and wandering in my mind, being anything but mindful, to follow the instructions to be present. To follow my breath. To notice, that's all, just notice, when my mind had wandered off and bring myself back.

Like all meaningful change, the shift happened when I wasn’t looking.

It’s like when you've had a cold for a few days and then at some point you're walking around and realize, oh wait, I'm not sick anymore. The thing you were seeking has been seeking you, and operating on its own timeline. For me, that was somewhere towards the end of day two. I'd calmed down a bit. The peaks and valleys of my emotions were softening. Whatever crazy thought my mind came up with, whatever feeling of loneliness emerged, wasn’t throwing me around in the same way. This was getting interesting.

It wasn’t that things had gotten quieter. It’s that my angle of perspective on whatever would come up, started to shift. The anxiety was still there, but now I could feel it in my body instead of just thinking about it. The heaviness wasn't gone, but I could start to sense its weight, its texture, its particular flavor of emptiness. It was like someone had turned up the resolution on my emotions just as I was hoping to change the channel!

There are many different Buddhist traditions and schools. In the particular one that was running this retreat center, they combined Buddhist meditation with some Japanese/Zen practices. Specifically, there was a ritualistic form of communal eating. All of the participants sat in long rows on the floor. We each brought our bowls and utensils, wrapped in a cloth napkin. We did each step together as a group, 50 or 60 of us, the staff bringing us each bit of the meal, all in silence, with hand signals to gesture if we wanted more or less of something.

We were all pretty clunky at first, but by day three, we'd gotten the hang of it. And it was beautiful. No talking. No eye contact. Nobody special. Just each person with themselves. All of us in a flow together.

I would have these occassional moments, the most delicious moments, when I felt part of something larger. I wasn’t gone or disassociated, just no longer separate.

And then it happened. We were in one of our longer sits of the day, maybe 45 minutes, when the dogs across the valley started barking again. It had been happening every day, and it was incredibly distracting. You could feel everyone in the meditation hall sigh when those annoying dogs would start their howling, probably a mile away, but with the still Spring air, it was like they were right outside the room.

For two days, I and I presume my fellow travelers had tried to block the sound out. You know that thing you do when someone's playing music too loud on the beach, or when your neighbor's leaf blower is going at 7 am? You tense up, you resist, you wish it would just stop, you rehearse what you’re going to say to this rude and inconsiderate person. It wasn't working.

It wasn't a conscious decision. I didn't know how to do what I was about to do. It was the result of practice. For the last three days, I had been practicing the simplest and most powerful skill there is as a human being: the skill of letting go. But the words are just stupid. Actual letting go, at the level of consciousness, is something entirely different than the words we try to use to describe it.

The dogs kept barking. And somehow, using a muscle that I didn't have or know how to access up to that moment in my life, I let go. I surrendered. I stopped wishing for them to stop. I stopped trying to ignore the sound. I stopped my virtual argument with their owner, who refused to bring them inside. I just stopped.

And in that moment, it was as if the magnetic poles of my being reversed. My jaw relaxed. My back softened. I let out a deep exhale. The sound of the barking penetrated my being. I gave no resistance. A soft thought of pure curiosity entered my mind: "What is happening?" And then a new awareness. A completion of the merge.

The barking is not coming from outside of me. The dogs are not over there. I am not over here. There is no separation between me and the sound, between me and anything. And, then, the kicker, the awareness that this ‘me’ thing is seriously questionable.

If you've ever had an experience of oneness like this, you know what I am about to say. It was the most joyous and illuminating experience I had ever had in my life up to that point. It was not a thought or an emotion; it was a knowing that there was a reality available to us, in any moment, that sits waiting beneath all our pain, all our trauma, all our hopes and dreams. The peak of that feeling lasted for maybe a minute. I told myself, “don’t move”, “don’t touch anything!”, but at some point my mind tried to grab on, and it was gone.

That day in Vermont was 27 years ago, and I remember it like it was yesterday.

Not because it was the end of a journey or because I felt like I had accomplished something. That would be too ironic for words. But what it was for me, with the benefit of hindsight, was that it helped me start to develop a strength that I had zero of, the strength to sit with myself. And as cheesy as it sounds, it’s like layers of an onion; the more you develop that muscle, the deeper the layers of wounding and false identities you will find, and there is seemingly no end to the layers.

I went to that retreat hoping to escape my inner turmoil. Instead, it’s where I started to develop the strength to face it.

Maybe right now you’re in a simmering argument with your partner, your parents are driving you crazy, you’re dreading going to work tomorrow, or drowning in debt. Or maybe everything in your life is ‘fine’, but you keep hearing that voice coming from somewhere that isn’t fooled by all your strategies and manipulations, and is harassing you into paying attention to it.

The dogs are barking.

They won’t stop.

You don’t need them to.

Just let them in.

I was really into working out. And running.

Back in my late 20s, my fitness routine was 100% those two things—running 7 miles a day, 4–5 times a week, and pushing weights around at a Crunch Fitness in lower Manhattan. This was back in the ’90s, so it was a very DIY-type situation—no TikTok trends to go by.

“You should try a yoga class,” my workout buddy said.
“Um, sure.” I replied, generally up for a new adventure.

And it was in that yoga class that I had my first taste.

I couldn’t do any of the yoga poses. My hips were locked up. My back was beyond tight. I had no core strength. So I flailed and flopped around for the hour, mostly trying not to look like too much of an idiot, given there was a substantial number of attractive women within sweating distance.

Towards the end of the class, I found myself in some approximation of a shoulder stand, with a helping hand from the teacher, As I somehow managed to settle into the position, the teacher belted out in the best AM radio voice I’d ever heard the words that become the hilarious start to the next decade of my life:

“Now, friends … try to relax. Give your body a brief respite from the ravages of gravity.”

The cynical New Yorker—the only version of me I knew at that time—could’ve busted out laughing. But for some reason, his words hit me in that moment. And for a few seconds, I felt free.

Free of my incessant mind.
Free of my very-not-limber body.
Free of wanting or needing to be anywhere else but there.

That was my first lesson in something that I still need reminding of every day, nearly 30 years later.

Happiness is not being able to touch your toes.
It’s being able to stay present to the moment no matter how difficult, stressful, or undesirable the position you find yourself in.

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It started on that sweaty mat back in 1996, as a stressed-out, stuck-in-his-mind, starving-for-intimacy law student. I was hooked. That tiny moment short-circuited my overstuffed and over-educated brain and touched something deeper.

There was a longing. With that and my first experiences of meditation, a chasm opened up between my day-to-day experience of myself and this other thing I had tasted for the first time—a world beyond my mind. I couldn’t live with myself if I didn’t attempt to close that gap. The impulse to go deeper was so strong it would have been existential malpractice to ignore it.

The road took me to San Francisco—to not just practice, but to get trained to teach meditation, yoga, and get certified in a form of somatic psychotherapy. These were the honeymoon days of the journey. Around every corner, a new experience. A fresh insight. A feeling that I was breaking free of something.

Towards what, I couldn’t exactly say—other than what I’d read in books—but I was sure I was headed in the right direction. And then I got stuck.

The most humbling moments in life are when you think you’ve accomplished something that you haven’t. When it becomes obvious you have to go back over ground you’d already declared victory over. And the embarrassment, for the things you said to yourself and others about how far you’d come.

That was me in the mid-2000s. Ten years into the journey, to discover that my advanced state was all smoke and mirrors.

I had a mountain of insights and spiritual attainments which gave me no comfort at all as I sat in my beautiful San Francisco apartment, by myself after a tough breakup, with a failing business I couldn’t wait to get out of, and a creeping dread that I had somehow missed a turn along the road—and there was no going back.

But the right road finds you.
Over and over again.
Until you follow it.

An old friend turned me on to a reclusive teacher, and a small group of people doing a kind of emotional work that I immediately knew was my next step.

“There’s no such thing as a negative emotion,” the teacher said.

And wow, did I want to believe that, based on all the negative emotions I had inside of me, the ones I knew and the ones I didn’t. I moved to Oregon to follow him. Over the next eight years, I was part of a hardcore group of folks who were, in one way or another, just like me. Spiritual seekers who found themselves at a dead end on their journey but were honest enough to admit it.

The heart of the work was as simple as it was grueling:

The path to an honest spirituality starts by giving up the desire to be spiritual,
and, instead, focusing on the wounded human in the mirror instead.

In other words, while God is real and enlightenment is possible, in practical terms, there’s an order to how to go about it. If you have someone in your life who has an active relationship with the divine, you’ve seen the challenge firsthand: if you are easily connected with spirit, then it’s hard to take seriously your partner’s annoyance at you always being late for things. It’s too easy to bypass daily life, to live (or at least believe you are living) above and beyond it.

It was the giant red flag warning I’d read about early on my journey. Watch out for Spiritual Materialism, the trap most seekers fall into of using spirituality to reinforce the ego (It’s Still You, But New and improved: Now Spiritual!) instead of dismantling it. The internet, and especially the podcastisphere, is full of people subtly or not-subtly taking spiritual ideas out of context, ideas that were formulated in the context of a collectivistic and pre-egoic culture, and using them to negate or transcend your actual human life. In other words, taking advantage of people in pain.

And here was a teacher who was no-bullshit going to hold all of us accountable for not falling into that trap. He was the David Goggins of psycho-emotional work, and I loved him for it.

(He was also a deeply wounded narcissist—but that’s for another day.)

He firmly put an end to my fledgling spiritual quest in favor of a human one. He assured me, and all of us, that if we did the work to heal at the emotional level, we would get to that spiritual destination, or at least be prepared to go on that part of the journey, as a result.

Maybe this is starting to sound a bit theoretical, so let’s bring it back down to the heart of what this work was about. It was essentially this:

We are emotional beings first.
Mental beings second.
Physical beings third.

Meaning it’s our subterranean emotional world that is powering what we think and what gets stored in our physical body, not the other way around. And so, logically, the path to healing had to be a merciless search for the ways the mind had convinced us of its primacy. To use the heart and our capacity to feel, however weak it was, to wrestle control of our being from the mind. In fairness, there’s reasonable debate in some circles about which is more upstream in terms of the starting point for healing, the physical body or the emotional one, but just about everyone’s aligned that it ain’t the mind.

All of its strategies, accommodations, manipulations, control mechanisms—everything that the mind uses to create certainty, to know, to be right, to be separate, including (and this is the ultimate mindfuck) the manipulative use of wounded emotion, to play the victim, to be ashamed, to be depressed, to be a sinner. Because a mind playing defense can and will use all of those things. It will tell all the sad stories you are willing to hear, to keep you away, to keep its host away from seeing it for the charlatan that it is. Because the one thing it can’t do is let go, even if it says it wants to.

It must be relieved of duty by something, someone, stronger. Like I tried to reverse, or at least relieve the effects of gravity on my spine by turning upside down all those years before, the mind needs to be turned upside down and held by another force so that letting go can happen. But here the stakes are far higher, because now we’re talking about identity. And because your mind is there to protect you from harm, it will not go quietly.

It has to be pulled apart, gently but firmly and consistently, to make room for that other thing to emerge, for us to feel the existence of something we all have but have all been conditioned into forgetting:

Our emotional body.

The eight years I spent in that work were the least joyful, least fun, and least relaxing years of my life. It was a day-to-day torture chamber of my own making. I paid for the workshops. I went to the private sessions. I said yes, over and over, to continuing it when I could’ve walked away at any time.

Why?

Because while everything about my teacher and his methods was, as the kids say these days, problematic, it was undeniably working. It was helping me do the one thing that no other thing I had tried could do, which was to build some kind of minimal ability to feel my way through life instead of being forever locked in the persuasive echo chamber of my mind.

I began to feel differently about, and to, myself. Life began to open up to me. I met the love of my life. I could hear my calling, well, call (funny how we use the word calling, something drawing us towards it, and then think it’s something we figure out for ourselves). My moment-to-moment experience of life was objectively better at every level. Not because I’d finally arrived at Nirvana, but because I’d shed just enough of the inherited noise—emotional wounds, family myths, and cultural definitions of success—to hear something more honest underneath.

Not a voice from beyond, but the one I’d been born with. My own.

I’d wriggled myself just free enough of my emotional wounds, my family, and societal conditioning about what it meant to be a man, to be successful, or to be happy.

I had not finished the emotional work. I have not today, 10 years later.
But I reached a foothold of consciousness that I will never again fall below.

I know when I’ve left myself, and I know how to come back.

When I left that work and that group 10 years ago, I had fully overdosed on personal work. I joked with my wife at the time that maybe I’d start journaling again in 10 years. Well, turns out that was about right. It helped that we were broke, so there was no time to think too much about it. I threw myself into my work, launching and building my first business, writing my first book, raising our two girls, and trying to heal from the abusive and traumatic parts of those years while holding onto the deep truths that had changed me for the better.

And then, on just another normal Saturday morning, a few weeks back, the door, a door I had long since been sure had closed for good, cracked open. My wife and little one went out for the day to do some mother-daughter things. While there’s always work I could do, nothing was burning at the moment, and I wasn’t in the mood anyway. I checked the surf report and the conditions were crap. I fumbled around YouTube for a bit, but it was a lot more of the same. I called a few people, but nobody was around. Nothing worked.

Out of options, I had no choice but to turn inward! I realized I was resisting a feeling. The feeling was a sense of meaninglessness, a kind of dread. It hit me right in my core wound, the feeling that nothing matters. It was the same feeling I had as a depressed teenager, the one that drew me to major in philosophy, that sent me off the deep end to eastern mysticism and psychedelics, and radical forms of therapy. My first thought was, “I can’t believe it.” After all these years and all this work, I still haven’t healed that?”

And then, after I wrestled with that one for a bit, came the deeper one, the one that put me back on course: “I can’t believe it, after all these years and all this work, I’m still trying to run from it.” I could feel myself turning again, now toward the pain, to feel into the uncomfortable position, instead of trying to escape.

“I hear you,”, I said to the feeling/voice in my head. “I get that for you, nothing has meaning. That you feel empty. That you feel lost. That must be very scary. All I can tell you is that I'm here. And that you mean something to me.”

The feeling didn’t go away. I didn’t need it to. I just needed to come back to myself, to be with it, to feel. I’m sure I’ll be back with that feeling again soon, and you will too. Maybe it’ll be the next time the money feels tight, the traffic is driving you to rage, your coworkers are letting you down, or you're just bored with nothing to do on a Saturday. No matter how long it takes for us to realize we’ve gotten stuck in the trap of trying to keep whatever it is away, the moment we do, we’re already halfway back to ourselves.

To get present to the moment, no matter how difficult, stressful, or undesirable the position we find ourselves in.

And breathe.

TL;DR: We are emotional beings first. And maybe, just maybe, we’re converging at a point of human consciousness where we will move beyond the mind-first paradigm and re-learn how to feel. Is it a coincidence that at this very moment, a technology has emerged and is sweeping the globe that is rapidly demonstrating to us that it can do mind-only stuff better than we can? That while it’s terrible at going from zero to one, once you give it an idea, a spark, it can run circles around us? It’s almost as if the universe is conspiring to get us to let go, not to become mindless, but to break out of the trance that our mind is what makes us special, that it is the source of who we are, instead of the receiver. That we are being called, as a species, to bring ourselves back to life.

We’ve been out on a long road. It’s time to come home.

(Image generated by ChatGPT, prompt below.)

I opened my inbox this morning and saw the future staring back at me.

It was a short email thread—a simple back-and-forth between a client and someone on our team, just clarifying a few next steps in an onboarding process. But I never actually read the emails. I didn’t need to. At the top of the chain was a Gemini-generated summary that gave me everything I needed to know. It was clean. Efficient. Accurate. Impressive.

And—completely empty.

The summary nailed the what. It gave me the how. But it gave me none of the why. No emotion. No friction. No hint of whether the conversation was cordial or strained. Whether our team member was showing up in a way that lived our values. Whether the client felt seen.

It saved me time, yes. But it cost me presence.

That’s when the real thought landed: If AI keeps getting better and faster at summarizing the what and the how, what’s going to be left for us to do?

That’s not a rhetorical question. It’s the existential crossroads of our time.

We are standing on a binary edge—between outsourcing the soul of human work or reclaiming it. Between a world optimized for output and a world designed for meaning. Between the mechanical and the emotional.

I’ve started calling it the emotional economy.

It’s not a market of sentimentality or soft skills. It’s a deeper shift—a new economy based on the value of what only humans can feel, interpret, and convey. The little signals. The tone. The discomfort. The pause before the reply. The courage to ask a better question. The vulnerability to admit, “I don’t know.”

These things aren’t “intangibles.” They are the very thing machines can’t replicate—not because they’re not smart enough, but because they don’t have a self. No ego. No shadow. No soul to grow.

The transition will be brutal. The dislocation will be widespread. What we’re seeing now—tools like Gemini, ChatGPT, Copilot—is just the appetizer.

Everyone is going to have to ask themselves:

• What does it mean to be human now?

• What do I offer that a machine can’t?

Not as an abstract philosophical exercise, but as a lived, professional necessity.

Terrence McKenna once said that evolution doesn’t push us from behind, it pulls us forward. Toward greater complexity. Toward consciousness. Toward something we can’t yet imagine.

That idea has stayed with me for years. And while I can’t say for certain that’s where we’re headed, it feels true. And over the past 25 years, the most important transition I’ve made—one I’m still making—is learning to trust what I feel more than what I think.

It’s slow work. Messy work. But it’s human work.

And that, I believe, is the work we’re here to do.

Image Prompt: An abstract oil painting of a crossroads where golden and blue waves collide, symbolizing humanity at a turning point between emotional depth and mechanical efficiency, evoking the messy transition in the nature of work. The prompt seems quite empty, doesn’t it…? Unless you’re actually at the center, experiencing it.