Own Your Shadow – Fearless Self-Awareness & Wholeness

By John Coe

I know what you're thinking before you even say it.

We're sitting in some coffee shop near Farragut Square, or maybe you've caught me between podcast recordings, and you're about to ask me about cap rates, deal velocity, how to position yourself for that VP role everyone's eyeing. Real questions. Practical questions. The kind that get you somewhere.

And then I'm going to tell you we need to talk about your shadow first.

Looking in the mirror to understand your shadow

I can see it in your face already—that slight pull-back, that mental gear-shift from "ambitious professional mode" to "wait, is this guy about to get weird on me?" You're wondering if I've gone soft, if I've traded in spreadsheets for self-help, if this is the part where I tell you to journal your feelings and meditate on mountaintops.

Fair enough. I get it.

But here's what I've learned after interviewing more than a hundred Icons across the DC real estate landscape: not one of them—not a single one—became successful by pretending they had everything figured out. Every single person who's built something lasting had a moment when the shadow showed up uninvited. Ego. Fear. Insecurity. The desperate need to prove something to someone who stopped watching years ago.

And in that moment, they had to make a choice: grow, or repeat.

Let me take you into what they taught me.

Matt Kelly didn't become CEO of JBG Smith by being the smoothest talker in the room. Early in his career, a deal went bad. Not "slightly off-target" bad. Bad bad. The kind that makes you want to update your résumé at 2 AM and start looking at opportunities in other cities. His mentors could have told him to spin it, to protect his image, to focus on confidence and forward momentum. That's what we're conditioned to do, right? Never let them see you sweat.

Instead, they told him something that probably saved his career: "When something goes wrong, you've got to own up to it real quick and lay out the options."

That's it. No corporate jargon. No strategic repositioning. Just radical accountability before the shadow—pride, defensiveness, shame—had a chance to write the script.

Matt learned what most people spend decades avoiding: deal with your shadow before your shadow deals with you.

I remember the afternoon Ethan Penner told me his billboard would simply read: "Live aware."

Two words. That's all.

Ethan helped architect the modern CMBS market. He's operated at levels most of us only read about in industry publications. And his advice wasn't about deal structures or market timing or relationship capital—though he knows all of that cold.

It was about presence. About being awake enough to notice what's actually driving you.

Because here's the trap that catches almost everyone: confidence without humility becomes delusion. Humility without confidence becomes paralysis. We swing between these poles like we're being pulled by invisible strings, never quite understanding why we keep overshooting or undershooting the moment.

The Icons I've spoken with—the ones who've sustained success over decades, not just quarters—they've figured out how to hold both at once. They walk into rooms knowing they're competent and knowing they're fallible. They make decisions with conviction and remain open to being wrong.

That's the duality you don't want to hear about because it requires actual inner work, not just tactical adjustments.

Ron Gart has been in more hairy negotiations than some of us have had cups of coffee. When I asked him what he'd learned from all those years in rooms where egos and agendas collide, he said something I think about almost weekly:

"People are just people… and we're all flawed in the same way."

Think about that for a second.

The partner who just torpedoed your proposal in the Monday meeting? Flawed, same as you. The client who keeps moving the goalposts? Flawed, same as you. The lender who's being unreasonable about terms? Flawed. Same. As. You.

Once you actually internalize that—not just nod along intellectually—everything changes. You stop moralizing the messiness of others. You stop being so shocked when people act out of fear or insecurity. You start recognizing your own patterns in their behavior.

And somehow, paradoxically, you become far more effective.

Gary Rappaport didn't mince words when I asked him why he's still one of the most respected names in our market after all these years. "Reputation is more important than anything else in this business."

A lot of young professionals worry about "building a brand." They obsess over LinkedIn posts and industry event appearances and making sure they're seen with the right people at the right conferences.

Let me save you some time: your brand is the sum of your behaviors, not your marketing.

The shadow shows up in the shortcuts we think no one notices. The deal we shade just slightly in our favor. The commitment we make when we're enthusiastic that we quietly abandon when it gets inconvenient. The colleague we take credit from in ways so subtle we can almost convince ourselves it didn't happen.

They notice.

The market has a long memory and a keen nose for character. You can't PR your way out of pattern behavior.

Jamie Weinbaum told me he doesn't chase balance anymore. He said it so matter-of-factly I almost missed how radical the statement was.

"I'm aiming for integration rather than balance… nurturing family, career, friends, and community toward wholeness."

Balance is a math equation. Work versus life. Professional versus personal. As if you're two different people depending on which calendar you're checking.

Integration is a life philosophy. It's the recognition that the same person who shows up at the closing table shows up at the dinner table. The same patterns that make you effective—or ineffective—at work make you effective or ineffective at home.

You can't segment your way to wholeness.

Jason Bonnet offered me one of my favorite micro-lessons on presence. His billboard would say: "Estoy aquí — I am here."

Just that. I am here.

It sounds simple until you realize how rarely we actually are. How often we're in meetings while mentally drafting emails. At dinner while replaying the afternoon's frustrations. In conversations while waiting for our turn to talk.

Showing up—fully, actually—is how you gain trust, read the room, sense the future before it announces itself.

Here's what the Icons never pretend: the shadow goes away.

It doesn't.

It just gets revealed, understood, and redirected.

Some of the most powerful moments on the podcast have come when leaders described their reckoning. The failed deal that forced them to examine their judgment. The partnership blow-up that revealed their blind spots. The health scare that made them question what they'd been building toward. The moment a junior colleague had the courage to tell them they were being the problem.

One Icon—who asked to stay anonymous—told me: "The hardest meeting I ever had was the one in the mirror when I realized I was the problem."

That's shadow work. Not dramatic. Not self-flagellation. Just clarity.

Another confided: "I thought I owned the deals. Then I realized the deals owned me."

If you get that lesson early, you avoid some very preventable mid-career crises.

So here's where I usually lose people, because this is where it gets uncomfortable.

If you're serious about leadership—not just promotion, not just accumulating titles—you have to start asking yourself questions you can't outsmart:

Where am I afraid to be fully seen?

What recurring behavior of mine keeps showing up at the worst times?

What conversation of repair or honesty am I avoiding?

You can't Excel-model your way out of these. You can't strategy-session them away. You have to face them. Sit with them. Let them reveal what they're trying to teach you.

But if you do—if you actually do the work—the returns compound faster than any IRR on your résumé.

Look, you joined this field because you're ambitious. Nothing wrong with that. I'm ambitious too. Everyone I've interviewed is ambitious. That's not the issue.

The issue is what happens when ambition runs without self-awareness. It becomes frenetic striving. It becomes the desperate accumulation of accomplishments that never quite feel like enough. It becomes the mid-career moment when you wake up successful and hollow, wondering how you got he

re.

Ambition with self-awareness becomes something different. It becomes mastery.

Purpose. The kind of career that doesn't just look good on paper but feels intentional in the living of it.

The Icons didn't get here through perfection. They got here through quick accountability when things went wrong. Through presence when it would have been easier to zone out. Through integrity when the shortcut was right there. Through integrated lives instead of compartmentalized ones. And through the courage to examine the parts of themselves no one claps for.

As you build your career, do the same.

Be kind. Be aware. And don't stop believing in yourself—even the shadowed parts.

That's where your real power lives.