Running an agency can make us question the whole plan, even when the business is still moving forward. A rough stretch at home, delivery friction, or a few tense client moments can make a healthy shop feel broken.

Kurt von Ahnen and Toby Cryns put that tension on the table in a way many agency owners will recognize. Their conversation lands on a simple truth: agency work is emotional work, and we need better ways to judge progress than our mood on a hard day.

Agency growth can feel like failure while it is happening

Toby opened with the kind of honesty most agency owners keep to themselves. The previous month and a half had been hard at home and hard at work. His team had held up a mirror to the business and found weak spots they had missed. That is a painful moment, especially when everyone involved has been working hard and still falls short of the standard they want.

That kind of season can push us toward the simplest fantasy in agency life. We start thinking about shrinking the whole thing back down. Maybe it would be easier if it were only us. Maybe three clients would be better than twenty. Maybe full control would hurt less than shared responsibility.

Kurt met that honesty with his own. Earlier in the year, he went months without a new sale and then got hit with the flu for weeks. Revenue was thin. Energy was low. He even caught himself thinking about applying for a local job at the YMCA. That thought did not come from laziness. It came from the same place many of us know well, the part of us that wants stability when the business feels shaky.

What pulled him back was ownership itself. A job can give us a title, a paycheck, and a structure. It cannot always give us the power to change what is broken. An agency can. Even in a bad month, we still have room to fix the offer, the process, the communication, and the team structure.

That is where perspective matters. Kurt said something that deserves to stick:

KPIs do not care how discouraged we feel this week.

A hard day can tell one story, while the numbers tell another. This contrast captures the tension well:

What we may feel	What may still be true
“We are struggling.”	The team is spotting delivery problems early enough to correct them.
“We should scale back to solo work.”	The business is showing us where delegation needs support.
“Nothing is working.”	Revenue may be delayed, not dead, because last quarter’s work often closes later.

Toby added a story that sharpens this point. In 2001, he worked at ABC Network News in Los Angeles for $13 an hour, shared a two-bedroom house with eight people, and could not afford needed dental work. During one shift, after fielding prank calls and even patching through Tony the Tiger for a story, he overheard a coworker complain that company dental coverage only paid 80 percent of her bill. The gap between those two realities says a lot. Our “bad month” might still look like progress to the version of us who had less money, less freedom, and less control.

Project managers do more than move tasks around

One of the strongest parts of the conversation is how both agency owners talk about project management. In small shops, it is easy to treat a project manager like overhead in the worst sense of the word. They are not building the site. They are not writing code. They are not designing the page. That view misses the point.

A solid project manager keeps the whole system working. In Toby’s agency, that means making sure clients know what is happening, watching the pipeline, checking project risk, and helping designers and developers get what they need. In a smaller WordPress shop, that seat may also overlap with account management or billing. The title matters less than the function.

A good project manager often handles work like this:

• They keep communication clear when the client is confused or anxious.
• They remove blockers before designers and developers lose momentum.
• They protect timing, approvals, and scope so delivery stays predictable.

That work is not decorative. It changes the business.

“A great project manager changes businesses.”

That line rings true because the best project managers protect focus. Kurt has made this same point in other contexts, too. A single interruption can cost around 15 minutes of productive time. In an agency, repeated interruptions do not only break concentration. They eat billable capacity, delay delivery, and invite more confusion.

The role also helps on the rougher human days. Toby described moments when he joined a client call angry, whether because of something at home or frustration with the project itself. In those moments, the most professional choice was to stay quiet and let the project manager run the meeting. That is one of the clearest benefits of a team. The client still gets calm communication, even when the owner should not be leading the room.

Kurt shared a version of this from the client side. Early in one e-learning project, a learning and development manager doubted his design ability because she wanted more polish, tighter spacing, and more visual detail than the early functional build showed. Once a more design-oriented teammate joined the process, the whole relationship changed. The client stopped seeing one person with a limitation and started seeing a team with range. She moved from critic to advocate and later sent referrals.

That is the quiet power of defined roles. Clients do not always need the owner on the front line. Sometimes they need the right person.

Process protects both margins and trust

Agency owners who like freedom often resist formal process. Toby said that outright. Strict sequences, approvals, and sign-offs do not always feel natural to people who like to move fast. Yet the conversation makes it clear that discipline is often what keeps the business healthy.

Project managers tend to see this first. They create order where owners might prefer instinct. They want the sign-off before the next step. They want the approval in writing. They want the revision rounds defined before the design goes out. While that structure can feel stiff, it keeps expectations from drifting.

Kurt gave one of the clearest examples. If phase one includes installing a CRM and phase two includes populating it, doing phase two work early can hurt the business. The work may feel harmless in the moment because we are already inside the system and in a productive groove. Yet once the client sees work from the next paid phase happening for free, the value of that phase drops. The problem is not effort. The problem is sequence.

That is why phased work needs clean boundaries. If the team finishes early, the right move is not to give away the next chunk of work. The right move is to tell the client phase one is complete and phase two can start early once the next invoice is approved. That keeps the schedule honest and the pricing intact.

The same logic shows up in change requests. Toby described a client who kept sending revised spreadsheets for import. The team thought version one was final. Then version two arrived. Then version three. The count kept climbing. Before the sixth version, the project manager stepped in and said the next revision would be the last free one. Anything beyond that would be billed. That boundary worked. Either the client finalized the file, or they paid for the extra handling.

We see the same value in formal revision rounds. A client may sign off on a deliverable, then come back later with “one more tweak.” When the rules are loose, that turns into endless cleanup. When the rules are written, the answer stays calm and simple: we are happy to make that change, and it is outside the approved round, so here is the invoice.

This is close to the scope discipline strong agencies use elsewhere, too. When new ideas appear, they usually change one of three things: scope, timeline, or cost. Once that happens, the request needs to be written down and tied to a decision. We swap scope, extend the timeline, or add budget. Anything softer than that creates confusion later.

For readers who want the full back-and-forth, the original Agency Action episode on The WP Minute is worth hearing in full.

A values framework keeps the owner from becoming the bottleneck

Clear process solves one problem. It does not solve the owner’s habit of becoming the final stop for every decision. That came up in the conversation, too, and it may be one of the most useful parts for agencies trying to grow past founder dependence.

Toby described creating a values document for his team. The goal was straightforward. He did not want every minor question bouncing back to him. Instead, he wanted team members to run decisions through a shared framework first. If a situation fit the company’s values and fell within a defined dollar amount, they could make the call without asking.

That kind of structure matters because agency owners often carry too much emotional history into decisions. We remember the sale, the promise, the first awkward kickoff, and the fear of losing the relationship. Therefore, we are often the worst person to judge a small exception. We think, “Let’s keep the client happy.” The team member who was not part of the original pitch can look at the same request and say, “That is extra work, so it gets billed.”

That separation helps. It removes baggage from the decision.

It also makes the agency more consistent. If a project manager knows the rules, they can charge by default and make thoughtful exceptions when the values support it. That is better than a system where every unusual request becomes a founder panic moment.

The conversation hints at another important line many agencies blur: support is not the same thing as fresh project work. Post-launch help often covers bugs, access issues, or cleanup tied to the original build. It does not automatically include new pages, new design rounds, or added feature work. Once the team knows that distinction, they stop treating every request like a favor.

This is where values and process meet. The business needs a spine. Clients do not resent boundaries as much as owners fear they will. In fact, clear boundaries often improve trust because the rules are visible. A client who knows what is included, what needs approval, and what triggers a charge has fewer reasons to feel surprised.

That same theme comes up in wider conversations about agency management. A discussion of agency operational challenges circles back to the same problems, unclear expectations, communication gaps, and the drag of vague scope. The details change, but the pattern does not.

Community makes the work feel bigger than today’s invoice

Purpose does not come only from systems. It also comes from connection. That part of the episode matters because agency work can get isolating fast. When every problem lands on our desk, it is easy to believe we are carrying something no one else understands.

Toby said the strongest reason he keeps going in rough seasons is his team. They count on him to be steady and thoughtful. That responsibility changes the math. Walking away would not only change his life. It would change theirs as well. For owners who employ even a few people, that weight is real.

Kurt described a different but related kind of support. For years, he worked inside WordPress without fully seeing how large the surrounding community was. Once those connections formed, the work changed. Podcasting with The WP Minute, doing weekly live sessions with LifterLMS, creating content with WP Tonic, and working through Mañana No Mas! gave him a stronger sense of belonging. The business was still his own, but it no longer felt isolated.

That kind of network matters in practical ways. It helps with visibility, referrals, subcontracting, and trust. It also matters in a more personal way. When we know the people behind the tools we use, such as WordPress plugins like LifterLMS, Gravity Forms, or Fluent Forms, the work feels less like anonymous software assembly and more like participation in a real craft community.

Kurt described those connections like a web that stretches beyond one client account or one sales month. That image fits. Once those relationships exist, it becomes harder to imagine cutting them off and stepping into a job that has no place for them.

There was another sharp point here about how we present ourselves in public. Toby raised the gap many owners feel between the polished conference version of themselves and the real person at home on a Friday night. Kurt’s answer was refreshingly plain. Honesty helps, but desperation hurts.

There is room to say things are rough. There is room to admit a slow quarter or a frustrating season. What does not help is showing up hat in hand and asking the market to rescue us. The sales that landed for Kurt in April did not come from desperation. They came from confidence, clarity, and the accumulated value of work done long before the invoice arrived. One of those wins was a public speaking engagement that came to him because of things he had been doing the previous year.

That long view also showed up in Kurt’s pricing story. Early on, he was begging people to let him build sites for $500 or $1,200. Years later, other professionals looked at one of those builds and told him it was $50,000 to $60,000 work sold at bargain-basement rates. That lesson stays with many of us because underpricing is not only bad for margins. It teaches clients to misread the value of the work.

Cash flow pressure and underpricing often travel together, which is why broader conversations about agency growth and cash flow pressure still sound familiar to agency owners. Slow months tempt us to discount. Mature shops learn to price with confidence instead.

Purpose gets clearer when we separate mood from reality

The strongest takeaway from this conversation is not that agency work gets easy. It is that hard seasons do not always mean we chose the wrong path. Sometimes they mean the business is forcing us to tighten roles, define boundaries, and stop confusing emotion with evidence.

When we have a team we trust, a project manager who protects focus, a process that guards scope, and a community that reminds us we belong, the work changes. It still asks a lot from us. Yet it stops feeling random.

That is where purpose starts to hold. We do not find it by pretending every month is great. We find it by seeing the weak spots clearly, fixing them in public, and staying in the work long enough for the harvest to show up.