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Take A Shot: Give Yourself The Chance to Win

“If we do something together after this, it’s not going to be a retainer… it’s going to be another project. Things are just taking too long.”

Those are the words I heard through my phone’s speaker while standing in the frozen foods section of Aldi. Those words absolutely crushed everything I had expected – and everything I had promised to my wife.

But let’s back up for a second.

A year of frustration

It’s a bit of an understatement, but in a lot of ways, 2015 has not been very good to me and my family.

Most crucially, we’ve struggled from a financial standpoint. Clients have disappeared. “Sure things” have been anything but.

Back in August, I had capped off a yearlong effort to get in with one of the top copy publishers in the finance industry. These guys know how to make money, and so their copywriters make plenty of it.

They flew me in to visit their offices in Baltimore, where I met with the copy chief and the owner of the company. We agreed on a monthly retainer, but we didn’t jump in just yet.

They wanted to see what I could do. So we agreed to do one project together to feel each other out first. It was expected to be a quick one – shouldn’t have taken more than 6-8 weeks to finish.

By all accounts, it was a formality. Everyone, including me, was expecting to switch to a retainer agreement as soon as this project was done.

Bumps in the road

Weeks turned into months.

At the start of every month, I would tell my wife, “I don’t see any reason why this project won’t get done this month. We’ll be on retainer by the start of the next month.”

Over and over I said this, and over and over it became false: the project was taking forever. That retainer kept getting pushed farther away.

Meanwhile, our reserves were just about tapped out. I took on clients that I didn’t like to squeeze out a few more bucks. We were dipping into the Christmas money we had socked away in January just to make ends meet. Time was running out.

I started to voice my concerns with the team in November. I wanted to create some urgency.

Many of them told me this timeframe was normal – that most projects take 6 months or more to finish. They told me not to worry.

Those who were telling me this, however, were getting paid every month. I had gotten paid not even a month’s wages back in August.

Speaking up

So, at the beginning of December, I called up the copy chief and asked about whether or not I could be put on retainer. After all, everybody seemed to like working with me, things were going pretty well, and we were apparently within the normal timeframe for a project with them.

He told me that wasn’t going to happen. They were concerned by how long it was taking, and if we were to continue working together beyond this project, it would be another one-off project first, not a retainer.

So, to sum up: I called to see if I could get paid in January. I was told that I basically might not be paid until February, and then the next payment probably wouldn’t come until April or May.

My wife cried. I cried. We were at the end of our rope, and frustrated beyond belief. Despite every effort I was putting into my business, we were falling apart, sputtering on fumes to close out the year.

The client, in the interest of moving the project forward (to their credit, they knew I was anxious to get paid), flew me out to their offices again last week so I could work in-person with the team.

I decided that, while there, I would sit down with the copy chief and plead my case.

One more swing of the bat

I wasn’t sure what I was going to accomplish. I wasn’t expecting anybody to suddenly write me a check, or put me on a retainer. I just wanted him to understand my perspective on the situation.

I saw him in the first hour I arrived at the office, but he was busy. I was going to be there for two days, so we agreed to meet up the second day, in the afternoon.

I spent the entire day thinking about what I was going to say in that meeting. At night, I couldn’t sleep (despite my 3:30am wake-up call to get to the airport the previous morning). I got out of bed several times and paced back and forth in my dark hotel room, running through everything I wanted to say and exactly how I wanted to present myself to him.

The next afternoon, I discovered that he wasn’t thinking about that. He wanted to meet with everybody to discuss the project. It was a review meeting, not a chance for me to present anything.

After the meeting, he went back to being busy. I went back to my temporary desk, defeated and frustrated, thinking I was going home with nothing.

I had promised my wife I would come home with good news, though. In my realistic scenario, I’d come home with a clear timeline for when I’m getting paid again. In my best case scenario, I’d come home with a check for the few thousand dollars they owed me.

I wasn’t going to get any of that from the copy chief. He was just too busy.

I looked at the clock. It was 4:00pm. In an hour, I was going to have to leave to get dinner and head to the airport.

The owner of the company – the guy who signs the checks – saw me in passing earlier in the day and told me to stop by his office and say “hi” at some point. So I figured this was my last shot.

Nothing left to lose

I closed my eyes and took a few deep breaths to calm myself. Everything was riding on this. It sounds melodramatic, or that I’m just saying it that way to build the tension for the scene, but it’s the absolute truth.

If I succeed, I have some semblance of financial security for a couple of weeks, at least. If I fail, I’m set to spend the first half of 2016 without any reliable income – an option that we couldn’t handle anymore.

I grabbed a note pad and pen, got up, and walked down the flight of stairs to the boss’s office. He welcomed me in with a smile and invited me to sit down.

He started off with a few pleasantries, but thanks to my nerves, I couldn’t handle them. I cut right to the chase about why I was there.

I spoke passionately, but respectfully. I spoke with confidence, but tried to stay as humble as possible.

About a quarter of the way through the conversation, I recognized that he did not know that I had not been getting paid this whole time. He offered me a very generous check – multiples of what was owed me – to make up for some of the lost time.

I was flabbergasted. This was beyond what I was expecting. If I came home with that amount of money, my wife would be ecstatic. It would take the pressure off the bills for the next two full months.

What I normally would have done in that situation is thank him profusely and walk out to avoid screwing anything up. Instead, I said something to the effect of:

“That is really generous, thank you so much. I appreciate that, really. But I’m also thinking long-term here. I don’t want the check, I want the retainer.”

We went back and forth a bit on what I would want from a retainer fee. There was a lot of resistance to our original higher fee – understandably – on his part.

But we came to an agreement on a number that we both could be happy with. For them, they weren’t investing any more than they were spending on their rookie copywriters (and I am not a rookie copywriter).

For me, I’d be able to pay all the bills and still have a little bit of money left over every month.

But he wasn’t offering the retainer to me yet. He said, “Okay, so send me an invoice for that check to make up for the lost months here, and then we’ll talk about getting you on a retainer at this rate we’re agreeing on.”

Clinging to this conversation with everything I had left, I pushed it one step further: “Do you mean getting the retainer started in January right away, or…?” And I left it open.

It’s amazing he didn’t throw me out. I had to have been annoying. But he never showed any signs of being annoyed. I think he respected my perseverance a bit.

He called the copy chief into the room, who sat down next to me. This was the guy who, two weeks ago, told me I wasn’t getting a retainer any time soon. The boss told him that I really wanted to work for them and wondered what he thought about putting me on retainer starting in January for our agreed-upon fee.

I held my breath. This was everything I was pushing for all year long.

“Okay, sure. That sounds good. Let’s do it.”

After a (much more relaxed) conversation, I walked out of the office with a handshake agreement: both for a lump sum to make up for some months I wasn’t paid, and a monthly payment to be sent to me starting next month.

I don’t know who saw me, and I didn’t care: I was pumping my fist repeatedly to myself the entire walk back to my desk. I couldn’t stop smiling all the way through dinner, my trip to the airport, and my flight home.


This wasn’t just unexpected news. It was darn near impossible news. There was no logical reason to expect all of that to happen.

But it did. Because I took a chance.

How often do we not bother going after something because we think it’ll be impossible? We feel there’s no point in even attempting to do it because our brains can’t wrap around the idea.

But good things can happen. Those people who seem to always get the breaks? They’re the ones who take the most chances.

Sometimes it won’t work out. But if the stakes are high enough and there’s a possibility of it working, your best bet might just be to charge after it as hard as you can.

Every once in a while, you’ll break through and get everything you wanted – and more.