Altitude & Ego: A Series on the Paradox of Working Together

Why individual satisfaction and collective success feel like opposing forces, and what that means at every level of an organization

DISCLAIMER: views and commentary are my own. I welcome conversation and constructive disagreement. The goal: help myself and others think more clearly by expressing ideas, testing them, and refining them over time.

I’ve spent over twenty years in advertising, mostly in sales and sales support roles. I’ve been an individual contributor grinding quota. I’ve been a manager trying to develop people while hitting a team number. I’ve watched leaders above me make decisions that seemed either brilliant or baffling depending on where I was standing. I’ve had opinions about all of it, some earned and some not.

This series is an attempt to work through a question that’s followed me the whole time: How do you build something together when everyone involved is also trying to build something for themselves?

That tension shows up everywhere. The individual contributor who wants credit for the deal they closed, even though a dozen people made it possible. The manager who genuinely wants their team to succeed but also, quietly, misses being the one in the spotlight. The senior leader making tradeoffs that look callous from below but might be the least bad option given constraints nobody else can see. The chief who’s responsible for everyone and seen clearly by no one.

Most business writing frames this as a problem to solve. Find the right incentive structure, the right culture, the right leadership philosophy, and the tension dissolves. I don’t think that’s true. I think the tension is permanent. The question isn’t how to eliminate it but how to hold it well, and what kind of person thrives in that holding.

What this series covers:

I’m going to work through this question at four altitudes: the individual contributor, the manager of individual contributors, the leader of leaders, and the chief. Each level changes the shape of the paradox. What works at one altitude fails at another. The personality traits that make someone effective shift as they climb, and not everyone should climb.

Beyond the four altitudes, I’m going to explore the dynamics that cut across them. The “messy middle” where most of the actual work happens and where the rules are least clear. The legitimacy gap between levels, where each altitude looks at the ones above and draws conclusions that are partly right and partly wrong. The customer as the outside force that should cut through internal politics but often doesn’t. And finally, the question of what kind of organization might actually balance individual and collective interests rather than defaulting to capitalism with socialist slogans.

What I’m not going to do:

I’m not going to pretend I have this figured out. I’ve lived Parts 1 and 2 of this series. I’ve observed Parts 3 and 4 from a distance, with all the distortions that come from looking up. I’ll be honest about where I’m speaking from experience and where I’m speculating.

I’m also not going to land on clean answers. The deeper I’ve gotten into this topic, the more I’ve found that the honest conclusion is usually “it depends” or “both things are true” or “this is a question worth sitting with rather than resolving.” If you’re looking for a framework that makes the tension disappear, this isn’t it.

Who this is for:

If you’ve ever felt the pull between wanting to matter individually and wanting to be part of something larger, this is for you. If you’ve ever looked at leadership above you and thought “they don’t get it,” and also wondered if maybe you’re the one missing something, this is for you. If you’ve ever managed people and felt the weird guilt of wanting things for yourself while being responsible for others, this is for you.

And if you’re just trying to make sense of why organizations feel the way they do, why the incentives never quite line up, why the culture deck says one thing and the reality says another, I’m hoping this series offers some language for what you’re experiencing.

The series structure:

1. “I Closed the Deal. Did I?” — The Individual Contributor

2. “The Coach Who Also Wants to Win” — The Leader of Individual Contributors

3. “Managing Systems, Not People” — The Leader of Leaders

4. “Servant of Everyone, Seen by No One” — The Chief

5. “Where Everything Gets Done and Nothing Is Clear” — The Messy Middle

6. “What You Can See, What You Can’t, and What You Get Wrong” — The View From Below

7. “The Only Stakeholder Who Doesn’t Care About Your Org Chart” — The Customer as a Mirror

8. “Playing Without a Final Score” — The Unsolvable Game

9. “What If We Actually Tried to Balance This?” — The Hybrid Organization

A note on how this will unfold:

The structure above is a working model, not a locked outline. As I dig into each piece, the ideas will evolve. Some parts may expand, others may collapse into each other, and new questions may surface that deserve their own space. That’s part of the point. I’m working through this in public, not presenting a finished product.

I’m genuinely interested in what you think. If something resonates, or if something feels wrong, or if you’ve lived a version of this that I’m missing, I want to hear it. The commentary will shape where this goes. Consider this a conversation, not a lecture.

For now, this is the model I’m working with. Let’s see where it leads.

On to Part I: We start where most careers start, and where the myth of rugged individualism is strongest: the individual contributor. The person with their name on the deal, their number on the board, and a commission check that says this win was theirs. But was it? And what does it cost to believe the story too fully?