You're Making $300K+ and Still Asking "Is This It?"

Why Your "Successful" Executive Career Feels Like Expensive Emptiness

Here's a story that'll hit way too close to home for some of you:

Two doctors walk into a counselor's office. (No, this isn't a joke.)

One's a radiologist. One's an anesthesiologist. They don't know each other. Both making $300K+ annually. Both "successful" by every external metric.

Both asking the same existential question: "Is this it?"

I sat down with Greg Stewart—counselor, executive coach, and author of the AI³ trilogy on leveraging negative emotions—and he dropped a truth bomb that should make every "climbing the corporate ladder" executive stop and reevaluate their entire life:

You picked your career path when your brain was literally still developing. At 17. Based on a high school guidance counselor's assessment and whatever major seemed "practical."

And now you're 40, successful on paper, and feeling a void you can't quite name.

Welcome to the dark side of the traditional career path. Let's unpack why this keeps happening and what the hell you're actually missing.

The Two Tracks: Corporate Climbers vs. Entrepreneurs (And Why One Has Soul)

Greg breaks down the fundamental difference in how people enter leadership:

Track 1: Corporate Climbers

• Pick a major at 17-18 (brain still developing)

• Graduate at 21-22 (brain barely finished developing)

• Start as supervisor → manager → leader

• Vision and purpose come later (if ever)

• Progression based on skill set and personality, not heart

Track 2: Entrepreneurs

• Start with vision and mission ("I want to change THIS about the world")

• Move to leadership (influencing and gathering people)

• Then management (once organization is established)

• Heart and purpose drive everything from day one

See the problem? One path starts with "what am I good at" and the other starts with "what do I care about."

One optimizes for competence. The other optimizes for meaning.

And we wonder why so many "successful" executives feel empty inside.

This is where authentic client connections actually begin—with leaders who've done the internal work to understand what they actually care about, not just what they're capable of.

The "Is This It?" Epidemic Nobody Talks About

Greg says he can't count how many successful people in their late 30s and 40s come to him with this exact burden.

Directors. VPs. High-level executives. Making great money. Checking all the boxes. Living the "dream."

Except the dream feels hollow.

Because here's the brutal truth about the traditional career path: You were never asked what you actually cared about.

Not when you picked your major. Not when you accepted your first job. Not when you got promoted. Not when you became an executive.

You were asked:

• "What are you good at?"

• "What can you do?"

• "What skills do you have?"

• "What's your five-year plan?"

But never: "What would you change about the world if you could?"

And now you're sitting in a corner office, making six figures, managing teams, hitting KPIs... and wondering why it all feels meaningless.

Spoiler: It's because you never connected your work to your actual purpose.

This is the missing piece in sustainable business expansion strategies—leaders who know why they're doing what they're doing, not just how to do it effectively.

The Iron Man Core: Your Mission as an Inexhaustible Energy Source

Greg has this incredible metaphor that made my brain explode:

Think about Iron Man's arc reactor. Tony Stark puts it in his chest not just for power—it's there to keep the shrapnel (embedded from the explosion) from working its way to his heart and killing him.

Your mission statement is your Iron Man core.

The shrapnel? Life's endless annoyances:

• Traffic

• Weather

• Grocery prices

• Difficult clients

• Corporate politics

• Emails that could've been Slacks

• Meetings that should've been emails

Without that core—without that clear sense of purpose—all that shrapnel slowly works its way to your heart. Death by a thousand cuts. Burnout by a million minor frustrations.

But when you have that core? When you know WHY you're here?

The small stuff doesn't bother you as much. Because you're focused on that energy source. On that bigger vision.

Greg says: "You see it in people who have that. It's like, I know I'm here. And the small stuff just doesn't matter."

This is what separates managers from leaders. Managers get derailed by the shrapnel. Leaders have an energy source that transcends it.

Everything You Do Is Chasing an Emotional Goal (Whether You Know It or Not)

Here's where Greg's framework gets really interesting:

Literally everything you do is trying to achieve an emotional goal. You want to feel something.

Micro emotional goals:

• Feel thirsty → drink water → don't feel thirsty

• Feel tired → sleep → feel rested

• Feel hungry → eat → feel satisfied

But then there are macro emotional goals:

• Quality of life

• Living your values

• Fulfilling your destiny/calling/purpose

And we spend our entire lives unconsciously pursuing these macro goals through our work, our relationships, our choices.

The problem? Most people are chasing macro emotional goals they've never actually articulated.

They want to "feel successful" but don't know what success actually means to them.

They want to "feel fulfilled" but have no idea what fulfillment looks like.

They want to "make a difference" but haven't defined what difference they want to make.

So they default to external markers: salary, title, corner office, nice car, vacation home.

And then they hit those markers and realize... it doesn't feel how they thought it would.

Because we're not thinking beings that feel. We're feeling beings that think.

And if you haven't done the emotional work to understand what you're actually pursuing, you'll spend your whole life hitting targets that don't matter.

This is the foundation of relationship-driven revenue growth—understanding that business decisions are fundamentally emotional, not just rational.

The Leadership Gap That's Destroying Your Teams

Greg's dissertation was on the relationship between emotional intelligence and job satisfaction/organizational commitment.

Translation: People don't leave organizations. They leave supervisors who lack emotional intelligence.

Your best people aren't bailing because of the work. They're bailing because of YOU.

Specifically, because of how you handle your negative emotions.

Greg's insight: Your personality strengths, taken too far, become your weaknesses.

Too dominant → aggressive and alienating Too expressive → overwhelming and chaotic Too avoidant → absent and unreliable Too critical → toxic and demoralizing

High-retention client relationships start with high-retention employee relationships. And those require leaders who've mastered their own emotional experience.

Because leadership isn't about metrics and output (that's management). Leadership is about relationships, heart, vision, and creating energy from the human side of your organization.

If you can't manage your own emotional experience, you sure as hell can't create a culture where other people thrive.

Why This Matters More Than Your Q4 Strategy

Look, you can be a fantastic executor. You can hit every KPI. You can run an efficient machine.

But if you're disconnected from your own purpose, three things happen:

1. You eventually burn out. Because there's no energy source protecting you from the shrapnel. Every annoyance compounds. Every setback feels personal. Every challenge drains you.

2. You can't inspire anyone. Because leadership requires vision. And vision comes from knowing what you care about changing in the world. You can't manufacture that from a mission statement written by a committee.

3. You create transactional relationships instead of transformational ones. With your team. With your clients. With your partners. Because you're operating from skill set, not heart.

Building business relationships in the digital age requires leaders who've done the internal work. Who know their "why." Who can tap into the emotional drivers that actually motivate human beings.

This isn't soft skills bullshaet. This is the difference between companies that scale sustainably and companies that burn through people on their way to "growth."

The Question You Should've Been Asked at 17 (But Weren't)

Here's what Greg recommends instead of "what's your passion?"

"What is it about the world that you would love to change?"

Even young people can answer that. Even people who haven't figured out their "calling" yet.

Because every mission, purpose, destiny, vision, and calling comes from our life experiences.

It's not about some mystical discovery process. It's about:

• What problems do you see that piss you off?

• What human experiences do you want to enhance?

• What injustices do you want to address?

• What gaps do you want to fill?

Howard Schultz didn't start Starbucks to solve a problem. He wanted to enhance the human experience—create a "third place" between home and work.

Cruise lines aren't solving problems either. They're enhancing experiences.

Every job, every technological advancement, every business is either solving a human problem or enhancing the human experience.

So which one are you doing? And why do YOU specifically care about that?

If you can't answer that, you're just executing. You're managing. You're not leading.

This is what trusted advisor relationships look like—advisors who've connected their work to their purpose and can help others do the same.

What This Actually Means for Your Leadership

If you're sitting in that director/VP/executive chair asking "is this it," here's your path forward:

1. Do the emotional work. Figure out what you actually care about. Not what you're good at. Not what's practical. What you CARE about.

2. Connect your current work to that purpose. You might not need to quit your job. You might just need to reframe how your work serves your deeper mission.

3. Stop optimizing for skill set and start leading from heart. Your team doesn't need another efficient manager. They need a leader who gives a damn about something bigger than quarterly targets.

4. Develop your emotional intelligence. Especially around negative emotions. Because that's where you'll either level up as a leader or destroy your team morale.

5. Build your Iron Man core. Create that inexhaustible energy source so the shrapnel of daily annoyances doesn't kill your proverbial heart.

Want the full conversation with Greg's specific frameworks for discovering purpose and developing emotional intelligence? Watch the complete episode here where he breaks down the AI³ methodology and how to leverage negative emotions for growth.

Because company culture transformation strategies don't start with ping pong tables and free snacks. They start with leaders who've done the internal work to know who they are, what they care about, and how to create vision from the heart instead of just metrics from the spreadsheet.

P.S. If you're reading this and thinking "but I don't have time for all this purpose and vision stuff, I have a business to run," I have some uncomfortable news:

That's exactly why you're going to burn out. Or already have.

That's exactly why your best people keep leaving for "better opportunities" (which really means "leaders who seem to give a damn about something").

That's exactly why you're successful on paper but empty on the inside.

Greg has seen it over and over: Successful executives in their late 30s and 40s, making great money, hitting their goals, and feeling absolutely nothing.

Because they optimized for competence without connecting to purpose.

They became great executors without ever becoming true leaders.

They built careers on what they could do instead of what they cared about.

And now they're sitting in that success, surrounded by the shrapnel of daily annoyances, without an energy source to protect their hearts.

The good news? It's never too late to build that Iron Man core. It's never too late to ask "what would I change about the world?" It's never too late to connect your work to your purpose.

But it does require doing the emotional work that nobody asked you to do at 17 when you picked your major.

Time to start. Just a thought. 🦾

Karl Pontau hosts The Human Connection Podcast, where we talk about the stuff that actually matters in business: the humans running it. Because whether you're B2B or B2C, it's really H2H—human to human. Subscribe so you don't miss the next episode where we probably say something that'll make your HR department uncomfortable.