Escaping The ‘Yes’ Cycle

Have you ever been bullied into taking a project?

A few years ago, after a pretty tough few months, I took a project with a design agency.

The agency had offered me a full-time position a few months earlier, but I stuck to my freelance guns. When they couldn’t find someone they liked as much to join their team, they called and asked if they could be a client.

Super flattering, right?

Well, not really. When I came in to discuss the contract, in their eyes, it wasn’t so much a freelance project as a part-time job. They told me that their project was the basis of my schedule and my work; that I should think about them in the shower, because that’s when people tend to have their best ideas.

This would usually be a sign to run far, far away, but I liked their clients and thought with time we would establish boundaries — and I was too scared to say no.

After the colossal failures with clients I’d experienced a few months earlier, I was totally wiped out, and just wanted some projects that would give me financial security and peace of mind.

As we started getting into our first project, the client became more and more demanding. They wanted everything to be on their schedule: meetings scheduled the same day, phone calls at all hours, and deadlines popping up like groundhogs.

And then they disappeared. For two weeks, everyone on the team went MIA. No one answered emails, calls, or texts.

Turns out one guy was sick, one was on vacation, and everyone else — well, you know. Shit happens. But they wanted their two weeks back, and they wanted them STAT.

The bully I thought I could avoid was there waiting for me.

I explained that I had called, texted, and emailed, but all I got was radio silence. What was I supposed to do?

And that was it. My agency email was cut off, and the project was over. Unceremonious, and certainly not glamorous. I was paid, but only after yelling and threats.

Why did I take the project? I knew what kind of people they were — but I thought I could change them. I thought it made more sense to take a long-term “secure” project than to look around for something else. What if there was nothing else? What if I would turn down this project and then never find work again?

Now I know better; I know it’s better to turn down nightmare people before they turn into nightmare clients. But I learned that on my own skin.

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Being great at freelancing goes way beyond being great at what you do.

Of course, you have to be good at what you do; that goes without saying.

But, while you’re busy being good – and becoming better – at that creative thing, you also have to be an accounting master, a super networker, and some kind of project manager.

And a self-sufficient human being.

You, my freelancer friend, are wearing a lot of hats. And I know that is exhausting.

And what kind of decisions do exhausted people make?

Avoiding the monkey fight

When I was a kid, one of my favorite books was Caps for Sale by Esphyr Slobodkina.

As the story goes, a lovely cap salesman would spend his days wandering about town selling caps off of his head. One day, after a long lifetime of cap selling, he sat down to take a nap under a tree — and when he woke up, his caps were gone.

Stolen by monkeys.

The salesman begged and pleaded, pleaded and begged, but monkeys are assholes and they wouldn’t give his caps back.

After a long fight, the salesman got his caps back. But he almost didn’t: and that’s the lesson.

It’s better to avoid the monkey fight.

There’s a price to pay for spending your days carrying around a headful of caps; first and foremost being, an entire book is written about you without ever mentioning your name. You’re known as the cap salesman.

But just as important: even the most astute salesmen make bad decisions when they’re tired.

It’s pretty easy to lose what you’ve spent your whole career building because you chose to take a quick snooze under a tree.

Decision fatigue

The paradox of being overworked is that the less brainspace you have left to make decisions and do stuff, the more likely you are to just say yes to everything.

Saying no takes a lot of energy. As a freelancer, the anxiety of turning down projects can be more daunting than the project itself. The fear of needing the money or not wanting to hurt someone’s feelings can make sleepless nights seem like small potatoes.

But then the cycle continues.

And maybe at the beginning you’ll be able to handle it all. Maybe you can carry all the caps.

But that doesn’t last forever, and eventually the exhaustion turns into bad decisions — and that nap under a tree is, in your case, missed deadlines, unanswered emails, or simply enough, bad work.

So, like we learned from Caps for Sale, it’s easier to avoid the fight than to convince the monkeys to give your caps back.

Here’s how:

1. Stay rested

Sometimes, you’ll find a really good reason to stay up all night. Maybe you’re right before a vacation, or the client you’ve been chasing finally came through with something urgent.

It’s your call. And I’m not arguing against it.

What I can say, though, is figure out a way to stay rested while you’re going crazy.

Even if that means sneaking in a nap or two, or skipping a night out with your significant other. Because sleep is incomprehensibly important.

As you get more stressed, you’re going to need more time to let your brain process what’s going on. Sleeping more seems counterintuitive, but it works. The time off is what your brain needs to function better while you’re deep in the shit — and you’ll find your clients thanking you for it.

PS. Any client who wants you to stay up late for them is probably a jerk anyway.

2. Stay organized

When it feels like the whole world wants your brain, the absolute worst thing in the world is to have your brain scattered in a million pieces.

This is my biggest struggle. Lior will ask me something, and in that moment, I’m 100% there with him! And I can do the thing! And I can even do three more things!

But as soon as I’ve walked out of his office, I’ve forgotten all of those things, because my brain is in twelve different places and I’m probably hungry.

This, I have learned, is not charming, and when you are this way for long enough, people start to notice. And it starts to piss them off.

In order to avoid clients who hate me, these are the three organization tools that keep my brain working:

• Google Calendar

My life and brain live in Google Calendar. After spending three years fighting the work-life balance fight, I realized that the only way I’ll have a life is if I value my life as much as my work — so all of my important things, from birthdays to calling friends to client deadlines, go into my Google Calendar.

I use Calendar for general to-dos and things that have an actual time, so I can see what I need to do on a certain day and if my day is planned out well enough to make those things possible.

• Google Sheets

After Google Calendar, the most important part of my brain lives in Google Sheets.

Deep in my Google Drive, I have a spreadsheet called Projects with three very important sections:

Projects Where I list clients, projects, and payments on a per-month basis.

Pipeline How I keep track of who I talk to when, and just as importantly, how they found me — because I have some friends who have earned themselves a few rounds of drinks.

Partners When a client asks me if I have a designer/developer/project manager/unicorn to bring to a project, I usually do, and I don’t like to make them wait. My partners sheet keeps track of all of my freelance buddies, what they specialize in, and how available they are, so I know who to refer when.

• Inbox bundles

As much as I love Google Suite, Gmail itself is the bane of my existence.

It’s not the software itself; it’s the fact that email exists.

My inbox looks like what I imagine a salad would look like I invited all of my friends to a dinner party and told them to bring one ingredient for *something* and to show up whenever. My clients are currently spread across three continents, meaning that I’m getting client emails at all hours — plus Forever21’s neverending sales and my mom’s BarkPost forwards.

My mom refuses to stop sending me coupons for dog treats and I don’t want to quit online shopping, so the only solution is Inbox Bundles. In Gmail’s Inbox, you can designate bundles where emails from addresses you specify, or including certain keywords, automatically go.

So, every time I start working on a new project, I set up a bundle for the contact person’s email address — that way, I can be fairly certain they’re not stuck in email purgatory between Poem-a-day and Another Way To Green Smoothie!!

3. Figure out if what you’re doing works

It might be that you’re so overworked because you’re fighting a losing battle.

I don’t mean that freelancing is a losing battle; you’re here, which means you’re trying.

I mean that maybe you could do it better.

If you’re worried about money, chances are you’re not charging enough. It’s a mistake that every single freelancer has made, and some of us continue to make. And it has a really simple solution:

Charge more.

Okay, it’s not simple. That’s why we put together a class about how to do it. And wrote a book. But the principle is simple: learn how to ask for what you’re worth.

Money stress is the most exhausting kind of stress that a business owner can deal with, and it’s the kind of pressure that keeps you from doing your best work.

So if you find that you’re constantly freaking out about how to pay next month’s rent — it’s worth a shot.

What I learned from the last person who kissed me

I have a friend who has a crush on me. It’s cute and sweet and I’m very thankful that I’m finally not the friend with the unrequited feelings.

This friend came to my house the other night for coffee and a dog playdate, and as he was leaving, he tried to turn our goodnight hug into a goodnight kiss. And I was pretty surprised.

There was probably a graceful way to handle the situation, but because I’m me, I shouted,

That was weird!!!!

and sent him off into the night.

In the moment, I had two options: to tell him to back off, or to lean in and say yes.

And I’m really happy I chose to be a weird freakazoid, because now I know with 100% certainty where my, and our, boundaries are.

I live in constant fear that whoever wants to kiss me is going to be the last person to ever want to kiss me, so I’m usually inclined to just go with it — but that feels shitty, and I usually end up feeling gross in the morning.

Now I know, even if the last person I kissed is the last person I’ll kiss ever, at least it went the way I wanted it to — and I didn’t just say yes because I was scared to say no.

Post by Shayna Hodkin

Shayna is the Head of Friendship at The nuSchool, doing many things blog/community/biz dev/happy. She's a freelance copywriter working in art and design, and has two dogs named Chuck and Alma.

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