What a Year Full of Wednesdays Can’t Do
On leaving the calendar behind long enough to actually change
Can you change a person’s basic personality traits to meet the needs of higher level leadership?
I get some version of this question every year. A leader who has always been able to think her way through any problem, now being asked to feel her way through a team instead — no spreadsheet for that one. A husband who’s spent decades being the strong one, being told what his family actually needs isn’t more strength — it’s more softness, more presence, more of him just sitting on the floor with his kids instead of solving something for them. I’ve sat across from a dozen versions of the same ache: someone extremely good at going it alone, being asked, late in the game, to stop.
Was I supposed to help them become someone else?
That question doesn’t only belong to CEOs. It shows up for a spouse whose kids need more connection and more affirmation than they’re getting, and the parent giving it isn’t wired that way either. It’s the same question, just wearing a different outfit.
Leadership development, as an industry, tries to answer this mostly with more information — another 360, another assessment, another competency model. I use those tools, and they’re useful. But information is rarely the actual problem. In their heads, most of these leaders already know what they’re supposed to do differently. Set the boundary. Say the hard thing with truth and grace integrated, not as two separate moves. Stop being Jekyll and Hyde about it — sweet and accommodating right up until there’s a real disagreement, and then suddenly clipped, parental, hard to reach. Get buy-in for a decision nobody wanted to hear. Half of them could write the training themselves.
So why couldn’t they do it?
This is where I’ve come, over many years of recommending intensives to clients, to believe something that still surprises me every time I watch it happen: something opens up in a week away that a year of Wednesdays doesn’t touch. Not because the coaching or the therapy is wrong — it works, over time, and I believe in it. But there’s something about leaving the calendar behind for a solid week, no meetings pulling you back to your inbox, surrounded only by other people who are also there to grow, that accelerates things in a way one hour a week, wedged between everything else in a life, simply can’t. It isn’t a forced process. It’s a gentle opening. Sometimes not so gentle. But it’s an opening — awareness of others, and awareness of your own limitations — that starts to happen almost on its own once you stop protecting it.
I know this because it happened to me.
I went to the Ultimate Leadership Program in 2006. Rod and I had been married almost a year. I had already done a lot of healing work after my divorce, and I was genuinely thrilled — I lived with a good man, in a healthy, nurturing relationship, and I knew it. But something kept creeping up on me anyway. Some unfinished business I couldn’t quite name and couldn’t ignore. When an email crossed my desk about a program in California, I knew, somewhere underneath the knowing, that I needed to go. I sensed there was something unhealed in me that could sabotage this marriage if I let it sit there long enough. I was afraid I wouldn’t be able to fully let in the love Rod had to give me — that I’d get critical, or restless, or bored, or find some other quiet way back to the old pattern. Alone. Lonely. On my own again, the way I knew how to be.
What I found that week was exactly what I’d hoped for and hadn’t known how to ask for. Small groups, safe, facilitated by skilled counselors. We brought up loss. Trauma. Disappointment. Anger we’d been managing for years without ever actually feeling. Using psychodynamic principles, and psychodrama exercises at times — a word that, I’ll admit, makes people picture something between a soap opera and an exorcism. It isn’t that. Strip the drama out of the word and it’s simpler than it sounds: instead of talking about the thing that happened to you, you put it back in the room and move through it. Someone plays your mother. Someone stands beside you and says the sentence you’ve never once managed to say out loud yourself — that’s called doubling, and it’s somehow both the strangest and the most relieving thing that can happen to a grown adult in a room full of near-strangers. You might sit across from an empty chair and finally say the thing to the person who was never actually going to sit in it. Nobody hands you a script. Nobody’s grading your performance. You just, finally, get to finish something that got interrupted twenty or thirty years ago.
Here’s what made sense of it for me later, once I understood a little more about how the brain actually works. Talk therapy is largely a conversation with your prefrontal cortex — the part of you that reasons, reflects, narrates, writes a very tidy paragraph about your childhood. It’s essential. It’s also, on its own, incomplete. The stuff that actually runs you under stress — old fear, old shame, the flinch before you even know why you flinched — doesn’t live in the part of the brain that talks. It lives lower, older, filed away in the body before you ever had language for it. You can understand a wound with total clarity and still not be free of it, because understanding is a top-down conversation, and the wound was stored bottom-up. That’s the real case for something like psychodrama, or any body-based, experiential work: it goes and gets the material where it’s actually kept, instead of politely asking the reasoning brain to pass the message along. There’s a reason Bessel van der Kolk called his book on trauma The Body Keeps the Score. Insight is necessary. It’s just not sufficient.
I cried tears that were long, long overdue. I got angry, out loud, in a room that could hold it. That was so validating.
The program is called the Ultimate Leadership Program, offered through GrowthSkills.org, built on Dr. Henry Cloud and Dr. John Townsend’s Character Growth Model. The name makes it sound like it’s only for people running organizations. It isn’t. I’ve watched pastors go because they needed a week to actually stop and recover before they burned out completely. CEOs go for perspective, so they can take the business to the next level without taking themselves apart in the process. A young mother who felt like she was drowning went. A widow who couldn’t picture what her purpose was for the rest of her life went. It’s not really a leadership program. It’s about growth. There are real leadership skills in there — boundaries, the roots of the fears and habits that no longer serve you, how to hold truth and grace together instead of choosing one, how to give a hard critique without flipping into someone your own kids wouldn’t recognize — but those are just growth skills wearing a suit and tie. They serve anyone, not just the people with a title.
It’s built on a Christian framework, but you don’t have to be a person of faith to walk through the week. There’s no altar call, no offering plate passed around while you’re mid-sob, none of what people brace themselves for when they hear “faith-based.” Just people doing the work.
It’s also, practically speaking, one of the best programs I know of, and it’s inexpensive, because it’s a nonprofit. It started as a customized offering for Campus Crusade’s executive leadership teams, then evolved into something open to the public, and it’s been running for fifteen years now. It’s only offered in one place — Orange County — Monday through Friday, 7 a.m. to 8 p.m. Hotel and meals are included. Bring your own stamina.
It isn’t the only one, either, and I want to name a couple of others, because the point was never that one particular program is magic — it’s that this kind of immersion does something a weekly hour can’t. Onsite Workshops, in Tennessee, runs a similar week-long intensive with no faith framework attached at all, using many of the same experiential and psychodrama methods. I’ve referred a number of clients there over the years, and I think of them collectively more than individually now — a man who’d spent years in a marriage that was slowly grinding him down, who came out the other side finally able to name the guilt and the contradictory feelings he’d been carrying since before the split. A leader who went in exhausted past the point of even noticing he was exhausted, and came out remembering what rest felt like. A mother who’d been carrying a fear for her children that had less to do with her children than with her own childhood, and set it down for the first time in decades. Different weeks, different people, same thing underneath — something that had been held so long nobody could feel it being held anymore, finally set down.
And long before UL, in my own post-divorce years, I did a program called The Road Adventure. It was incredible — one of those weeks I still carry pieces of, all these years later. Partly because of a man in my small group who, by midweek, told me a truth nobody else in that circle had the nerve to say out loud: that I kept myself closed off from people while working overtime to please them — two things I didn’t know I was doing at once, let alone that they were related. I cried. I still think about how much courage that took.
Here’s the part I’m less proud of. Earlier that week, when he’d shared his own history — a young Black man, drug dealing, time in prison — some tired, self-protective part of me decided I didn’t have much to learn from him. I discounted him. Which is an embarrassing sentence to type, but there it is. And then he was the one who saw straight through to exactly what I needed to hear, said it, and changed how I show up in a room to this day.
So when someone tells me, “Oh, I don’t do group work,” or “I’m too private for that,” or “I don’t need that kind of thing” — think again. I’ve lost count of how many first-day texts I get from people I’ve referred to one of these weeks, complaining about the strange, annoying, entirely-wrong-for-them people in their small group, sometimes flat out asking if they can switch. By day three, it’s a different text. They can’t believe how right that group turned out to be, or what they learned about themselves because of exactly the person they wanted out of the room.
The people who come back from a week like this don’t necessarily look any different on the outside. But they lead differently. They bring more trust to a team that used to just get instructions from them. They come home and are actually there, not just present in the room. They stop bracing for the version of themselves they become under stress, because that version doesn’t have as much to grab onto anymore.
So — can you change a person’s basic personality trait to meet the demands of higher level leadership?
Not exactly. But you can meet what was never finished. And once that opens, the rest starts moving on its own.
A Few Questions to Sit With
Before you close this:
Where in your life are you the one everyone leans on, and who do you lean on in return?
What’s the thing you already know, intellectually, you should do differently — set a boundary, say the hard thing, ask for help — and still haven’t managed to actually do?
When was the last time you cried, really cried, about something old? If you can’t remember, that’s information too.
If a stranger in a small group told you the truth about yourself by day three, what do you think they’d say?
What would you have to leave behind — your calendar, your competence, your reputation for having it together — to let a week like this do its work on you?
You don’t have to answer any of these out loud. But if one of them stopped you for even a second, that’s probably worth listening to.
P.S. If any of this stirred something, here’s somewhere to start.
An intensive is not a meditation retreat, and it helps to know the difference before you go looking. A silent retreat — the kind of week you’d spend at a place like Spirit Rock or the Insight Meditation Society — is built around quieting the mind. You sit. You breathe. You watch your thoughts come and go without following them anywhere. Genuinely powerful, and not what I’m talking about here. An intensive is the opposite motion: instead of quieting what’s underneath, you go looking for it, usually in a small group, doing active, experiential work instead of just describing it. Neither is “better.” They’re different tools for different seasons.
A few things worth checking before you book any of them: who’s actually facilitating (licensed counselors or therapists, not just coaches, especially if real trauma is involved), how small the group is (the whole thing depends on it becoming genuinely safe, which doesn’t happen at scale), whether it’s experiential or just lecture (a week of good talks is a conference, not an intensive), what happens after the week ends, whether the faith orientation fits you one way or the other, and what the cost actually includes.
A short, non-exhaustive list to start with — programs change, so call and ask questions before you commit to any of them:
Ultimate Leadership Program (GrowthSkills.org, Orange County, CA) — the one I’ve written the most about. Built on Cloud and Townsend’s Character Growth Model. Christian-based, though you don’t have to be a person of faith to attend. Nonprofit, inexpensive, week-long, small facilitated groups.
Onsite Workshops (Cumberland Furnace, TN) — secular, experiential, similar use of psychodrama and group process. Their Living Centered Program is the closest analog to ULP without the faith framework.
The Road Adventure — a faith-based nonprofit offering weekend-format group work. Smaller commitment than a full week, if that’s what you’re weighing.
The Hoffman Process (multiple locations, including Napa Valley, CA) — secular, well-established, week-long, built around what they call the “Negative Love Syndrome” — inherited patterns from your family of origin. Runs several thousand dollars, on the higher end of this list.
Survivors, at The Meadows / Rio Retreat Center (Wickenburg, AZ) — a more clinically-oriented, trauma-specific workshop, part of a larger behavioral healthcare organization. Worth knowing about if what you’re dealing with is specifically trauma rather than a broader growth or leadership question.
Marble Retreat (Marble, CO) — Christian, and specifically for pastors and ministry leaders who need somewhere to fall apart that isn’t their own congregation.
Retrouvaille — Catholic, specifically for struggling marriages, weekend rather than week-long, run largely by volunteer couples. A different shape than the others, but the same basic instinct: you can’t always fix this alone, at home, in the cracks between everything else.
None of these are mine to sell you on. I’ve sent clients to a few of them and been to two myself, and I trust the ones I’ve named enough to put my own name next to them. But the point was never any single program. The point is knowing, when something in you finally says it’s time, that you have real places to go.
For paid subscribers
Okay — but what do you actually do with a week like this once you’re home? That’s the harder question, and it’s the one I answer in a companion piece for paid subscribers, “What Comes After the Week”: the inexpensive monthly follow-up UL itself offers to keep your same small group together, why some people come home and finally go find a therapist — and why that’s not backsliding — and the small group four friends and I built around my own dining table that lasted many years and changed all of us.