Raw and gentle

Notes on when to soften and when truth must land

The Death of Socrates by Jacques-Louis David, 1787

I’m caught between two ways of showing up for others. As an East Coast go-getter transplanted into California’s therapeutic culture, I’ve learned to alternate between the direct and the gentle. One approach creates space for healing, the other cuts to the no-bullshit truth. I’ve witnessed both change lives. They’ve both changed mine.

When I was leading teams in Silicon Valley, the number one criticism I received in feedback was that I was “too direct.” This was also the main feedback my ex-lovers had given me. What can I say? I was a partier, chance-taker, just a general all-around, fast-shuffling crazy dude. This highly agentic attitude gave me a leg up on certain aspects of California chill culture. Yet …

Being direct is a problem if you’re an asshole. During my time on the West Coast, I learned, the hard way, to soften. To let go and listen. To do my best to meet people where they are. This became the great work of my life, unlocking insanely deep connections with all sorts of people.

Over the years, I became quite skilled at this softer, more therapeutic way of being. Various trainings strengthened this evolution, from studying somatic psychotherapy to many other modalities in the healing arts. Working with psychedelic and indigenous sacraments proved especially informative in this regard. In psychedelic facilitation, the core principle is dead simple: ensure safety, then get the hell out of the way. Let the intelligence of the medicine do its work. Only amateurs feel the need to talk too much, to do too much, to be a “healer.”

A lot of my friends—therapists, coaches, dharmanauts, and psychedelic guides—are emblematic of this gentle presence. My partner Grace, a psychotherapist, naturally maintains that “you-do-you” vibe. She’s taught me volumes.

These lessons in gentleness have only deepened through my coaching. Working with everyone from brilliant founders to sensitive creatives to folks facing devastating addiction and loss has shown me human nature stripped bare. One of my favorite psychoanalyst thought leaders, Jonathan Shedler, captures something I think about at least once per week:

“Real psychotherapy has nothing to do with giving advice. If there’s one thing we’ve learned in more than a century and a quarter of treating mental and emotional suffering, it’s that giving advice doesn’t help.”

The paradox is the harder we push advice, the more people instinctively push back. It’s not just stubbornness; our brains are wired to protect our freedom to choose. The psychoanalyst Donald Winnicott, a proper Brit who wrote about mothers and babies with surprising punk rock insights, called this the “true self” fighting against compliance.

We all know the feeling: someone gives you well-meaning advice, and, suddenly, you want to do exactly the opposite, even when they’re right. It’s why good therapists learn to roll with resistance instead of fighting it, creating what Jung called a “holding environment” for the psyche to unfold at its own pace.

And here’s the other thing about advice: sometimes our urge to share comes exactly when it’s not needed, when it’s more for you than the other person. To jump in with solutions when someone just needs to be heard, to fill the silence with our brilliant insights when silence itself might be the medicine.

I’ve seen this principle play out in the highest stakes of my work. In addiction treatment, the gold standard is motivational interviewing: rather than telling someone to quit using, you help them explore their own mixed feelings about change. You listen for what’s called “change talk,” those moments when someone begins to voice their own desires for transformation. Only then do you subtly contact that part of them that earnestly wishes to change—often using their own words back at them. It’s like a gentle Jedi mind trick to help people discover what they actually want without seeming like you have an authoritative agenda.

Time and again, this approach proved its worth despite my reflex to fix, fighting against my urge to control. I gradually learned to be more like water, leveraging flow instead of force. This shift from directive to collaborative, from expert to witness, legitimately transformed how I show up for others.

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But lately, I’ve been craving something different: the unvarnished, unqualified, uncandied truth.

I’m realizing I’ve lost something in this swing toward therapy-speak and safety culture, where we’re fluent in boundaries and “holding space” for a process, but have forgotten how to just tell it like it is. Despite everything I’ve integrated about gentle presence, some of the most distinct pivots in my life came out of hardcore candor.

Take my early recovery. I was barely hanging on—sixty days sober after my fifth-or-so attempt at outpatient treatment, still wrestling with withdrawal, drowning in debt, marriage in shambles. When I casually told my sponsor I was thinking about drinking again (it was only the hard drugs that were the real problem, right?), he didn’t offer therapeutic containment.

“Al, are you out of your fucking mind?”

He listed every way drugs and alcohol had destroyed my life—the wrecked cars, the lost jobs, the Tenderloin double life, the web of lies, all of it. This would make any “certified counselor” or therapist cringe. It’s fear-based, confrontational, everything we’re taught not to do. But that direct, real-talk approach shook me awake. It’s what makes the peer-mentor model of 12 Steps so powerful. These folks are graduates of the school of life, unconstrained by institutional niceties.

These moments of radical honesty worked precisely because they weren’t gentle. They weren’t therapeutic. They were truth bombs dropped by people who cared enough to risk my comfort, and our relationship, for my growth.

It’s why I’m drawn to men’s groups—we create exercises for this kind of direct feedback precisely because it’s so rare now. In one such container, another mentor told me something that altered the course of my life: “You know what your soul’s calling is and you have the talent, you’re just too damn scared to go do it.” Even if it took me three years longer than I wanted, that fiery comment set me on the path to quit my job.

Then there was Grace. Fresh from my divorce and fancying myself “poly” (I know, I know), I’d convinced myself that love couldn’t be contained by traditional boundaries. Grace had been clear: her adventurous phase was over. She wanted commitment, not another wishy-washy ‘conscious relating’ California bro. When I crossed a line, she didn’t gentle me through it. Instead, she named exactly what I couldn’t see: I was still in my addiction, chasing states and experiences, blind to the beast still raging within me. Her words—and her decision to cut me out of her life for violating that boundary—wrecked me, launching me back into weekly therapy, genuine healing, and the shadow work I’d been avoiding. She later told me she regrets being so direct with that statement. Yet somehow… it’s exactly what changed me.

Sometimes being gentle and “holding space” is just another way to avoid the hard stuff. Especially now, when we’re drowning in mental health crises, spending much of life behind a screen, balls deep in modern addictions. We’ve gotten masterful at rationalizing, justifying, minimizing. We’re so slick with therapy-speak now that we can turn any real confrontation into a mindful exploration of our “process,” dodging the difficult conversations behind a veil of conscious communication.

There’s a whole lineage of maverick therapists who went straight to the heart of this. Fritz Perls, the gestalt guy, talked about the difference between “support” and “breakthrough”—like when he’d push anxious clients to fully inhabit their nervous habits in front of the group until something cracked open. James Hillman, one of Jung’s most rebellious students and a fierce critic of therapeutic hand-holding, went further. He said the soul sometimes needs what he called therapeutic violence—like telling a grieving client that their endless processing was just another way to hide from life. Those moments when only savage honesty can dissolve our elaborate walls of self-protection.

This is one reason I remain a coach rather than pursue licensure, despite my psychological bent. I want to be free in how I show up for another human being, not restricting myself based on some three-letter framework. I may have softened my edges so much that people who meet me now think I’m some mellow Nine or INFJ—but beneath the chill veneer, there’s still an anxious OCD junkie with you-can’t-fool-me street smarts and business instincts. I think we have enough people holding space—what we need is more people willing to say the hard thing, to name what they see, remembering that this existence is but a flash, so why hold anything back?

The wild thing is, after all this back-and-forth between tough love and gentle presence, what I’ve found is deceptively simple. These days, with softness finally in my blood, I trust my instincts more. Sure, sometimes those street smarts kick in screaming “bullshit!”But that’s just another signal to notice, more data on the person before me, not a command that must be followed. After hundreds of failed reps trying to fix Grace or anyone else’s problems, I’ve learned, more than anything, to trust other people. To trust that their life is theirs to live, not mine to direct. The timing of any gritty necessary truth arises from a place beyond my thinking mind, and when it comes, both the words and the other person’s capacity to hear them will be there. Yes, no more second-guessing that.

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I’m curious, how do you hold this tension between gentle and direct?

When was the last time someone’s raw honesty changed your life? What made you able to hear it in that moment?

And for those of you practitioners doing this work—how do you know when to gentle someone through their process versus hitting them with the unvarnished truth?