Chapter One: What My First Agency Job Taught Me

Janie Windmiller
November 10, 2026 · 5 min read

What my first agency job taught me about honest billing, boundaries, and the kind of business I chose to build.
On November 10, 2011, I was let go from a small marketing agency. At the time it felt like an ending. Fifteen years later, I can see it was the first chapter.
To say I learned a lot at that agency would be an understatement. Some of it was about marketing. Most of it was about the kind of business I would build one day, and the kind of business I never would.
What I'm grateful for
I want to start with the good, because there was plenty of it.
The owner drilled one lesson into me I'll quote forever. Marketing can be pretty. It can be creative and flowery and add real value. But when you're talking to a client, flowery language has no place. Business communication needs to be clear and concise, every time. I've carried that into every role since, and it's the backbone of how I write for clients now. (Hence, "clear, concise communication" written all over my site.)
I also got to work alongside talented graphic designers, wonderful people, and one of them I still hold in very high regard. Watching good creative people work up close taught me more than any class could. I learned you can take a concept, written or spoken, and turn it into something beautiful with the right elements. I didn't know such things could be designed in Adobe InDesign.
Suddenly, I looked at everything differently. Every ad, every printed publication, every website. I saw the hours behind it, because I'd been in the room for them: the hours spent laying out textbooks and magazine spreads, the attention to every detail. Good layout is complex, painstaking work. It gave me an admiration and respect for designers that's never left.
I valued the experience, I appreciated the opportunity at the time, and it shaped the professional I am.
The fee with no name
We had a client the owner found difficult. Picky, demanding, whatever word you want to use. One day they told me the client had earned a "PIA fee." A pain-in-the-ass fee.
They wanted me to get creative with the client's billing. Add hours. Stretch time frames. Make money off the inconvenience of working with them. They justified it the way people justify most things they know are off: agencies do this all the time. Call it a service fee. Call it consulting. Call it whatever makes it go down easy.
I remember my chest going tight. My stomach turned. I was only 22/23, still a kid, and too timid to speak my mind to someone in authority. But I knew in my body it was wrong, and I still feel it to this day.
I made myself a promise in that moment, even if I didn't put words to it until years later. I would never do this. If a client relationship isn't working, I say so. I name the problem, I suggest a better way to work together, or we part ways.
The discount I didn't give
Recently a client asked for a discount for paying upfront. My first instinct was to find a way to say yes. Old habits.
Chris, my right hand and life partner, asked me a better question: what does a discount tell someone who's been burned by agencies before? It tells them the first price had room in it. Mine doesn't. My estimates come from the real time the work takes, and when a project runs over, I eat the cost.
So I held the price. I took out work a collaborator was already covering, so he wouldn't pay twice for the same thing. The truth is simple: I can't offer a discount because I don't have anything to discount.
What became normal
This was a small agency, and some were relatives, or interns who left and came back, or interns who stayed on full time. Closeness can be a gift. Here it opened the door to comments and questions nobody should have to field at work.
For me, it was family. The owner, my coworkers, their spouses and kids all felt like an extension of my own. I cared about the people I worked with. We went to lunches and dinners together. I watched them get married. I was part of their lives and celebrated their big moments, and I valued it deeply at the time.
So when the questions and comments came, the ones I can now look back on and call inappropriate, they didn't feel like crossing a line. They felt like talking to family. Like talking to a friend.
Crude things were said about the people doing the creative work, none of it helpful or constructive. Creative opinions were brushed aside. Clients were mocked to other clients. Questions about my relationships and private life crossed lines.
The hardest part to admit: I thought this was normal. I believed bosses weighed in on your family, your relationships, your private matters. I believed this was how professional relationships worked.
It took me years to unlearn it.
Impact over intent
I don't think everyone at the agency set out to hurt anyone; to be clear, not everyone at the agency was hurtful to others. I didn't have the words for it at the time, but now I know: "intent and impact are two different things," and impact is what people carry home.
Today I care about my clients as people. I want to know what's going on in their world and what's at stake for them. I don't need the private details of why something happened or who it involved. I need to understand the impact, so I know how to show up, how to communicate, and how to make the work feel good for everyone involved.
I also keep my opinions about other clients to myself. When someone talks badly about another person, I always wonder what they say about me when I'm not in the room. If I have a concern about how a client does business, I bring it to them directly.
The same goes for how I bill. If a client has five hours a month with me and only sends two hours of work, I either bill two or I bother them until they give me five. Every charge I send ties back to something we agreed on.
Full circle
A client asked me recently how my business is sustainable. Don't I want to grow? What happens if I get more clients? What happens if they sign with me and a bigger company comes along?
My answer came without thinking: of course, I'd honor our commitment. Of course, I'd honor the relationship we've built and are still building.
He seemed surprised. I was surprised he was surprised. Then I remembered November 10, 2011, and it made sense. Not every agency works this way. Mine does, and it's because of what I saw in chapter one.
If you're looking for a partner who bills honestly, respects your boundaries, keeps their word, and sets clear expectations, let's talk.
