I Was the Constraint

A lesson learned years ago that I am grateful for. I tell people this was an expensive newly-married-with-our-first-adopted-child lesson, but a pretty inexpensive real-life MBA. Enjoy.

A friend of mine started an agency. I joined a few months later. Over time I became a partner. We were doing about a million in revenue, telling brand stories for a living, doing real work for real clients with real momentum.

And it failed.

Not in a sudden way. Not because the market shifted or a key client left or some external thing came along and knocked us over. It failed slowly, the way most companies fail. Decisions that should have taken hours taking weeks. Clients who got our best work for a quarter and then, somehow, our okay work for a year. Strategy that looked good on the wall and never quite made it to the calendar.

If you are running a company right now, or leading a nonprofit at any scale of giving, you know exactly what I am describing.

You've already diagnosed it. Probably more than once. Probably in different ways depending on who you were talking to.

Here's the thing nobody told me, and it cost me a partnership in a company to figure out.

I WAS THE CONSTRAINT

Not a constraint. THE constraint.

The pricing was wrong. For every dollar we charged, we should have charged two. I did not see it until after it was too late. We were blinded by passion and excitement and grit. We priced ourselves low to win the work. We accumulated a massive amount of projects for just a few people to execute. We labored. We put everything we had into every single project. If it was a simple print design, we designed the best version the client had ever seen. It eventually led to burnout, and it was not sustainable.

I was raised lower middle class. The you-work-until-you-die program is baked into my DNA. I was an owner-operator managing the business as a laborer, with my identity wrapped up in the belief that I could not let this business fail.

I was closing new business and project managing the same business at the same time. When project management got heavy, I subconsciously stopped selling. When sales got heavy, I let project management slip. The company breathed in and out at exactly the wrong rhythm and I could not see why for a long time. The role design was a constraint, and I was the human running both halves of it badly. Not because I was bad at either one. I was good at each skill. I was just not good at both together.

The third one cost us the company.

I did not understand the difference between what the P and L told me and what the balance sheet told me. At some point we brought somebody on to manage finance and sales so I could focus on project management. That move was supposed to relieve pressure. It became the nail in the coffin. He was closing work to get cash in the door, and a lot of that work was unprofitable. The P and L showed money coming in. The balance sheet slowly accumulated vendor debt on a project-complete pay cycle, which means I did not see the full cost of a project until months after the project was already done. Compound that across several projects and the math caught up all at once. I was not paying attention to project profitability. I was not paying attention to cash flow projections. I was not reading the balance sheet, where vendor debt was growing faster than the work was coming in.

That was the slap in the face. The thing I did not understand was the thing that was killing us, and I had hired around it instead of learning it.

If any of that lands, the drop in your stomach is the data. That's the part of you that already knew. Keep reading.

EVERYONE BECOMES A DIFFERENT CONSTRAINT

Those were my constraints. Yours are yours.

A big piece of my work as a CEO coach and a workshop facilitator is sitting in a room with a group of people and making it safe for them to identify how they are the constraint. Not their team. Not their tools. Not their market. Them. And then using that knowledge to do something about it. Break it. Hire around it. Build a system around it. Sometimes all three.

That sounds simple on paper. In a room, it is the hardest thing most leadership teams ever do together. People can name the constraints in the business all day long. Naming themselves inside one of those constraints is a different kind of work. It requires safety in the room. It requires somebody at the front of the room who is not going to weaponize the answer. It requires a leader at the table who is willing to go first.

When the leader goes first, the room follows. When the leader does not, nobody else will either, and the off-site produces a list of constraints with no human names attached and nothing changes for another four quarters.

This is the work I am paid to do. Not just to identify the constraints. To make the room safe enough that the right people can name themselves inside the right ones.

EVERY PROBLEM IS A LEADERSHIP PROBLEM

I say this in every workshop I run now and people sometimes look at me like I'm being cute. I'm not being cute.

If your team can't make decisions without you, that's a leadership problem. If your best people keep leaving, that's a leadership problem. If you've had the same three constraints on your strategic plan for two years, that is also a leadership problem, and it is almost certainly running through one specific room.

I know how that sounds. I know it sounds like I'm telling you everything is your fault. I'm not. Most things in your business are your circumstance. You inherited some of them. The market handed you others. Some of them are because the right person hasn't been hired yet or the right system hasn't been built yet.

But the fact that those circumstances haven't been resolved? That's where I start asking questions about the human running the company.

I love this quote. If it is my fault, it is my circumstance. If it is your fault, it is your character. This is how our ego sees the world. We are quick to excuse our shortcomings while attacking others' character for theirs. This is our ego's default. Becoming aware of the ego's vantage point and shifting your mental energy away from a victim mentality is the work.

You can't build and blame at the same time. And then wonder why nothing changes.

This is not a character flaw. It is wiring. Everybody has it. The work is noticing it in yourself faster than the people around you can notice it for you, and pulling the levers back.

THE CONSTRAINT ISN'T THE SYSTEM

People hire me because they think they have an operations problem.

They have new software they're rolling out. They have a sales team that isn't closing. They have a director who isn't delivering. They have a department that's burning hours on the wrong things. They want me to come in and look at the system and tell them what to fix.

I do that. That's the work I'm being paid to do.

But almost every time, the actual constraint isn't the system. The constraint is the human running the system. A CFO who can't have a hard conversation with the controller. A CEO who keeps reorganizing the org chart instead of firing the person everyone knows needs to go. An ED who is so identified with the mission that any feedback feels like a personal attack. A founder who built the company through sheer force of will and now can't figure out why force-of-will isn't scaling.

The system is downstream of the person.

This is hard to hear when you're the person. I know becuas I was the person.

THE SEASON

The agency was the season I learned what it actually meant to run a company instead of just work in one. I had been an employee. I had been a freelancer. I had been a hire. This was the first time I was on the other side of the table, and it was the most generative season of my life.

It was also one of the hardest.

We closed owing thirty thousand dollars in vendor debt. I paid it off myself. It was an expensive lower-middle-class lesson and an even more expensive MBA, and I would not change any of it.

I want to say something here about my co-founder. The partnership did not end the way either of us would have written it. That is true of most partnerships that end. It is also true that I learned a tremendous amount from him. He is a brilliant creative director and a brilliant designer, and the way I think about story and craft is shaped by years of working alongside him. I do not name names in my writing and I will not start now, but I am genuinely grateful, even where the ending was hard.

This was also the season my wife and I adopted our first son. We had to stay out of state for months because of a lawyer messup that was not our fault and not ours to fix in a hurry. The agency had also just gotten hit with a cease and desist on the name we had built everything around. We rebranded the entire company. Every document. Every contract. Every piece of collateral. While running the business. While becoming parents in a hotel two states away.

I do not want to make that period sound harder than it was. It was hard. It was also one of the most generative seasons of my life. If you have ever lived through a stretch where the personal and the professional are both rewriting themselves at the same time, you know the kind of clarity that comes out of it. You learn what you are made of. You learn what your marriage is made of. You learn what your business is made of.

When I left, I had a choice. I could blame my partner. I could blame the market. I could blame the hiring landscape, the creative talent pool, the client expectations, my health, the cease and desist, the lawyer in the adoption case, anything. There was honest material in every one of those buckets. I could have built a fully consistent story where the agency failed for reasons that had nothing to do with me.

I am a systems and process thinker. Always have been. I love to look at what worked, what did not work, and what I am going to do different the next time around. The agency was rich in all three. What worked. What did not work. What I would do different. I sat with it long enough to be honest with myself, and the honest read was that I was the constraint in more places than I wanted to be.

It took me years to find the framework that gave the work a name. Theory of Constraints. I love TOC. I love that it gives a leader a way to look at the messy human and operational stuff in their business and treat it like a system worth understanding instead of a story worth defending.

The way I think about it now is not heroic. It is not "if I remove this one constraint, all my dreams will come true or all my frustrations will go away." It is more practical than that. What constraint am I looking at today. What piece of it can I chip away at. What is the next move. It is a mentality more than a milestone. A framework more than a fix.

That is the work I do for myself. It is the work I do with the leadership teams I sit with.

WHY THIS MATTERS FOR YOUR COMPANY

The work I do now, every workshop, every off-site, every CEO coaching engagement, every two-day with a director team, is downstream of building this kind of culture inside a company. A culture that names its top constraints and removes them. One at a time.

When I walk into your company and we identify forty or sixty or a hundred constraints across your departments, I am very interested in those constraints. I will track them. I will run them through Theory of Constraints frameworks. I will help you prioritize. I will help your directors put plans in writing.

And then I am going to come back in ninety days and notice which constraints moved and which didn't. The ones that didn't move are going to point me at something that has very little to do with the constraint itself and very much to do with one of the humans on your leadership team.

Sometimes that human is one of your directors. Sometimes it's the COO. Sometimes it's the CFO.

Often, it's you.

The reason you hired me is not actually because you needed someone to identify constraints. You can identify them yourself. You probably already have. The reason you hired me is because you needed someone in the room who would tell you, with care, which one is running through you.

That is the work. That is what you are paying for.

A FEW QUESTIONS, IF YOU WANT THEM

If you are still here, something in this piece landed. Sit with it for a minute before you keep scrolling.

Pick the one constraint in your company right now that you have been talking about for more than four quarters and not moved. Not the new one. Not the easy one. The one that's been there long enough to feel like furniture.

Now ask yourself, gently, what would have to change about you for that constraint to actually move.

Not your team. Not your tools. Not your market.

You.

The answer is in there. You probably know it. You've probably known it for a while. That's not a crisis. That's the beginning of the work.

This is the shits. That's the gig.

So much respect.

Frequently Asked Questions

Q: What does it mean to say "the constraint is the human running the system"? A: It means that when a business problem persists across multiple quarters despite frameworks, hires, and reorgs, the actual constraint is usually the leader who keeps moving the levers in the same direction. The system is downstream of the person. New software does not fix a CEO who avoids hard conversations. New hires do not fix a founder who cannot price the work correctly.

Q: What are the most common constraints founders create for themselves? A: Three patterns I see most often. Pricing built around fear of losing the deal instead of the cost to deliver. One human owning both new business development and project delivery, which makes the company breathe at the wrong rhythm. And running a real company without understanding the difference between the P and L and the balance sheet, which lets vendor debt accumulate faster than the work coming in.

Q: How do I know if I'm the constraint in my own company? A: Pick one constraint in your business that has been on your strategic plan for more than four quarters and has not moved. Now ask yourself, honestly, what would have to change about you for that constraint to actually move. Not your team. Not your tools. Not your market. You. If the answer is uncomfortable, you have your data.

Q: What's the difference between a circumstance and a character problem in leadership? A: A circumstance is something the world handed you. Character is what you do with what you control. The line I use is, if it is my fault, it is my circumstance. If it is your fault, it is your character. The ego defaults to reversing this. The work is noticing the reversal in yourself faster than the people around you can notice it for you.

Q: What does a CEO coach actually do in a leadership workshop? A: A CEO coach makes the room safe enough that the right people can name themselves inside the right constraints. Most leadership teams can identify the constraints in their business all day long. Naming themselves inside one is different work. It requires safety, a facilitator who will not weaponize the answer, and a leader at the table willing to go first.