Have the tough conversations first

The first job I ever took out of college was in sales.

Everyone thought I’d be great at it. I was competitive, outspoken, and never backed down from an argument. I had a strong personality—one that could withstand getting hung up on dozens of times per day while cold calling.

I hated it.

Never once did I consider myself a timid person. At least until that job. I loved my prospects and could sneak past almost any gatekeeper on the phone. But as a lead trickled further and further down the pipeline, I struggled getting to the meat of the conversation.

Because talking on the phone is great and all, but eventually you have to cut the crap. Can you afford this? Are you going to buy? Or are we just going to shoot the shit for six months until you ghost me?

I just couldn’t go there.

Even last winter, when Meg hired me to photograph her cookbook, we did not discuss my fee until she physically moved-in to my apartment. I was a total pussy about the whole ordeal. We were actively shooting when she cornered me outside my apartment and said, “KARA. I have $xxxx that I can pay you, RIGHT NOW. Now WHAT is your Paypal?”

How pathetic is that?

I just wanted to create this awesome, creative thing with my friend. I didn’t want all the stiff, tough conversations that went into making that happen.

At some point this year, I finally grew a pair and figured out how to have the tough conversations—with clients and elsewhere.

And to paint you a picture of why you should never, ever avoid those subjects, I’m going to tell you what happens when you do.

My first, major client was a friend of mine. Half our phone conversations started with a forty-minute catch-up session talking about our lives.

I thought the absolute world of my client. The company moved at breakneck speed, never slowing down for bullshit or long emails—everything I hated while working for a marketing agency.

When the company asked for my help—and this is pretty common, with all my clients—they were desperate. They had a deadline in forty-eight hours, tried to do it themselves, and at the very last minute caved and said, “We’re fucked. Let’s call Kara.”

Again—totally common experience for me. I’m a one-woman operation, remember? People hire me because they could never afford to hire a full-fledged marketing agency. Most are small business owners or entrepreneurs, who are 200% invested in every single aspect of their company. Therefore, they will do everything themselves, until doing it themselves is simply no longer an option.

With the client on such a tight deadline, I said, “Listen, if you want me to finish this assignment in two days, there’s no way I can write you a proposal beforehand.”

Again, we were friends, we trusted one another, and they were cool with it.


Here’s what ended up happening: That proposal never got written.

I worked for two months (honestly, it’s embarrassing for me to type this) on a verbal agreement and pure faith, without being paid a dime. Whenever friends, my parents, or even my boyfriend asked me how I was being compensated, I gave a wishy-washy answer around the lines of, “They’re taking care of me.”

And because these people are some of the best people I have the privilege of knowing, when they got breathing room they said, “Crap! Kara, we haven’t paid you!”

So I sent in my hours. Almost three months of work, at a freelancer rate (a 25% premium over a full-time employee), all at once.

My client didn’t blink. These people adored me and thought my copy was some of the best the industry could buy. They forwarded my (finally!) written proposal and documented hours to their investors.

And that is when hell broke loose.

When their investors—people who never met me, had zero personal relationship with me, and honestly did not care if I dropped dead choking on my coffee, saw what they owed me, they FLIPPED.

For the first time—possibly ever—my client-slash-friend ghosted me. I sent emails, texted them on their personal cells, and eventually called them without warning; all trying to figure out what was going on.

To this day, I have no idea what happened with those investors.

I know it was bad. Like, really bad. When my client finally answered my phone call, the words “living nightmare” were thrown out. Multiple times. And what Shark Tank fails to educate you on is this: Just because you receive funding, doesn’t mean you will keep it. And when investors are involved, a founder CAN get fired from his/her own startup.

I got paid. It wasn’t the full, hourly rate I originally quoted, but it was still well worth my time. Out of anyone, I was the person who came out best in this story.

All of this, because I didn’t want to have the tough conversation with a friend.

Talking money is an ugly conversation. Freelancers, and those who fantasize about being one, don’t like to talk contracts because they think it seems greedy. It reminds them of the same corporate assholes they once left.

That’s bullshit.

The truth is, when we avoid tough conversations, one party always gets screwed.

It doesn’t have to be the money conversation. It could be a conversation you’re avoiding with your parents, or even grandparents for that matter. It could be a roommate discussion you keep putting off.

People avoid the tough subjects because they don’t want to hurt feelings or appear selfish, bitchy, or egotistic. But if you care about the other party at all—whether it be a family member, client, or business partner—you better suck it up and discuss it anyways.

And if you don’t, you better pray YOU’RE the one who gets screwed—not them.

I’m going to tell you how this story ends, not because it adds anything to the lesson I learned, but because you’re probably curious.

My client, the one I inadvertently fucked over, hired me again. [Like I said, we’re talking about really good people, here.]

And the first thing I did? Laid out the terms of our agreement. I didn’t bother with the polite phone conversations. I didn’t laugh, make jokes, or say, “No rush! Just whenever you get around to this, I totally know this is just a formality because we’re friends….


The second time we worked together, I said the tough stuff first. I treated them as I would a client with no personal relationship. Because saying the tough stuff—the shit no one else would have the guts to say to your face—is, actually, what friends do.

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For All the F Words
You have flaws. You f-up on a daily basis. And that should be ok.