The Loneliest Job in the Agency
You built something that requires you to make decisions nobody else can make. That doesn’t mean you have to make them alone.
A few weeks ago, I had a meeting with an agency founder that was supposed to be thirty minutes. It turned into two hours.
We weren’t catching up. We weren’t brainstorming. We were untangling. There were four or five decisions that needed to be made, and on the surface, they looked separate. But every time we pulled on one thread, it moved three others. Which decision comes first? If we solve this one, does that change the calculus on that one? What happens to the team if we sequence it wrong?
This founder knew the problems. They mostly knew the options. What they needed was a sounding board. Someone to poke holes in their theories and suggest alternatives they hadn’t considered. Not someone to tell them what to do. Someone to sit in the mess with them and say, “Okay, let’s map this out.”
That meeting stuck with me, because I realized how hard these types of decisions are to make alone. You need someone to bounce ideas off, someone who can challenge your thinking and surface options you weren’t seeing.
Human Tetris on the Hardest Setting
Here’s a pattern I see constantly in agencies. You have a handful of people who are not only great at their jobs but also chameleons. They take initiative. They can flex across roles. They pick up the slack without being asked. And because of that, they end up straddling two or three roles at once.
Everyone celebrates these people. They’re the glue. They’re the ones who keep things from falling apart when someone leaves, or a project blows up.
But there is a danger to this that is hard to perceive. Because somewhere inside that straddling is a piece of the job they hate. They do it out of loyalty, out of obligation, out of the fact that nobody else is going to. And that’s where burnout starts. Not from working too hard on things they love, but from carrying work they never signed up for because they care too much about the business to say no.
The obvious answer is to move each person into a single role where they’re focused on work they’re both excellent at and enjoy. In practice, this is almost never simple. Maybe the role that needs filling isn’t full-time. Maybe shifting one person creates a vacancy in a critical role. Maybe the budget won’t stretch to bring in someone new. Maybe a key person just left unexpectedly, and the whole puzzle shifted overnight.
Getting all the right people into the right seats while keeping the work serviced and the books healthy is very challenging. It’s like playing Tetris on boss level, except the pieces have feelings and opinions about their shape and where they fit.
The Hardest Truth Nobody Talks About
The conventional wisdom here isn’t wrong. Hire for core values. Get the right people in the right seats. Build a team where everyone is doing work they’re great at. That’s all correct. It’s also incredibly difficult to execute when you care deeply about the people involved.
What do you do when you have two right people and only one room for promotion? What happens when you promote one and the other leaves because they feel unseen? What about the small agency that isn’t growing fast enough to offer growth paths, and eventually, some of those right people outgrow the place? You should be proud of them for going off to their next thing. You should help them get there. That doesn’t make it any easier to fill the void they leave behind.
And then there’s the hardest truth of all. Some of the people who got you from A to B are not the right people to get you from B to C. People you genuinely love. People who helped you build this thing. But the business has evolved, and their role in it has shifted, and the emotional tax of navigating that is enormous. It costs you in sleepless nights. It costs you in real dollars too, because every departure triggers a time-consuming hiring process, not to mention the fact that new hires often come at a higher salary than the person who was already in the seat.
Solving people problems while maintaining budgets and profitability is not a spreadsheet exercise. It’s an emotional endurance test.
The Weight You Can’t Explain
So the founder sits with all of this. The tangled decisions, the competing loyalties, the budget constraints, the knowledge that someone will be unhappy no matter what they choose.
And here’s what makes it lonely: they’re rarely choosing between a good option and a bad option. They’re choosing between a handful of options, none of which they like, trying to figure out which one is the least terrible. Which option has the lowest likelihood of something going sideways. Which one they can live with.
They do the thinking. They agonize. They weigh the options. And when they finally make the call and roll it out to the team, the team is still angry about it. Because the team doesn’t have the full picture. You can’t explain that you spent two weeks wrestling with it. You can’t share that you chose the option that protected the most people. You just absorb the frustration and move on.
Every founder I know carries decisions the team will never fully understand. Not because they’re secretive, but because the full context isn’t appropriate to share. When it comes to people decisions, it’s nobody’s damn business why you made the call you made. And that gap between what the founder knows and what the team sees is a very lonely place.
The Skill Nobody Teaches You
Agency leadership doesn’t get easier as you grow. It gets more complex. More clients, more revenue, more team members means more tricky decisions, not fewer. The puzzle pieces multiply, and so does the emotional weight of moving them around.
Every successful founder I know has figured out a version of the same survival skill. They’ve learned to decide which parts of the work they’re going to allow to emotionally exhaust them, and which parts they need to let go of just to keep moving forward.
That’s what thick skin actually is. Not being unfeeling. Not being detached. It’s emotional triage. And it’s a skill you build over years of carrying decisions that nobody else in the building fully understands.
Just because it’s difficult doesn’t mean you’re bad at it. It’s hard because you care. And the fact that it hasn’t gotten easier isn’t a sign that something is wrong. It’s a sign that you understand what’s actually at stake.
What Changes When You’re Not Alone With It
That two-hour meeting I mentioned? It didn’t change the decisions that needed to be made. The options were still imperfect. The tradeoffs were still real.
But something shifted. Instead of one person spinning through scenarios in their own head at two in the morning, there were two people mapping scenarios in real time. What are the options I’m not seeing? Is there another door? If we pull this lever first, what falls? What’s the actual risk here versus what just feels risky?
What everyone wants at the end of a hard decision is to know they’ve thought through all the available options, picked the best one, and had another smart person confirm that it’s probably the right call. Not to be told what to do. Just to not be alone with the weight of it.
That’s not a luxury. For a founder making people decisions that affect livelihoods, it might be the most practical investment they can make.
I'm Katie Bedford. I spent a decade helping agencies run better. Now I help agency leaders think better — about their business, their role, and what it all actually means. If something in this piece hit a nerve, I'd love to hear about it.