How to Set and Keep Business Boundaries

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Once when I was naught but a wee babe of a copywriter, a client was complaining to me about another writer she once worked with.

“She was great,” she acknowledged, a sprinkle of salt seasoning her tone. “But she just wasn’t around when I needed her. She didn’t work certain days, I had to wait 48 hours to get her on the phone… ugh! Sometimes life happens and you need to get some small stuff done on a weekend, you know?”

I nodded, wide eyed, as I thought to myself: Wow, those are a looot of rules. This other writer must not be very serious about the job.

Now, for the context:

Rookie Copywriter Mistake

It was a Saturday afternoon and we were on another ’emergency call’ that was not quite an emergency — much to my boyfriend’s chagrin.

He twiddled on his phone just out of sight in his Summer whites, waiting for me to slam down my laptop, grab my purse, and hop the train with him to our delayed-by-several-hours-now brunch. For the millionth time.

“You’re so much better,” the client assured me affectionately. “It’s so nice to have someone around when I need them. I love how dedicated you are.”

I smiled back, an eager pup chomping down my treat of praise.

See? I’m working hard. I’m earning my way through this industry. I am a Very Good Girl.

Not Hard to Cross a Boundary That Isn’t There

But oh, eight years on, how my present self wants to smack my past self upside the head.

See, I was 22 and still in the stage of total entrepreneurial culture shock that someone actually wanted to pay me actual money for the work I enjoyed doing.

And so, after years of mind-numbingly boring unpaid internships and horrifically paid agency jobs, I was determined to make sure that kept happening — which meant doing basically anything any client asked me to do.

However, while I thought of myself as a “hustler” with a work ethic equivalent to a steamroller…

… What I really was was a young Hillary with 0 boundaries, 0 inclination to prioritize taking care of herself over the client, and 0 realization about the role rest plays in creativity.

Here’s the thing though:

Boundaries: Set Them Early and Often

did start learning about boundaries eventually (the word made it into enough newsletters from my digital heroes that I figured I should take it seriously) but the damage was already done.

Because the thing no one tells you about boundaries is this: if you don’t set them up from the very beginning it is a very long, very hard slog to course-correct.

If setting boundaries were as simple as turning around and telling a client “Sorry, I don’t do calls on Saturdays anymore” (which it technically is — but is it?) everyone would have them and overwork/low boundaries wouldn’t be an industry-wide epidemic.

But you train clients, and people in general, how to treat you. And you train yourself to be treated a certain way too. And it’s very hard to reverse those expectations once they’re set.

And so, the Setting of Boundaries becomes a massively messy task, combining a brutal level of un-learning on a personal level with past and present clients testing those boundaries again and again on a professional level.

So, what if you don’t start early enough?

As you might imagine – we’re talking about all this and more on today’s episode of #HAMYAW.

And this ain’t yo mamma’s “Two nice ladies calmly talk about why you should close your laptop at 5 PM” boundaries episode.

In ever on-brand #HAMYAW style, this is the real ish.

We swap our garbahge boundary stories, and talk about why that’s become the norm, what to do when you catch yourself, and what our More Traditional Job Having Very Annoyed Partners pointed out that made us either escalate our hyperbole or stop in our tracks. Sometimes simultaneously.

Better Boundaries — How do you even?

So go soak up today’s episode — which Margo let me entitle “Bro, do you even boundaries” because she RESPECTS MY ART, DAMNIT — where we discuss:

  • 5:31 How the corporate world rewards trash boundaries (“team building” anyone? more like “work-weekends-but-don’t-get-paid-extra-because-HOW-DARE-YOU” building)
  • 6:18 Why do we feel like if someone is paying us money we can’t say no??
  • 8:40 If you don’t have boundaries in your job, you probs don’t have boundaries in your life (inside look at how Margo has bad boundaries with Hillary)
  • 9:56 Why people steamroll your boundaries and how to make it stop
  • 15:22 Our advice for how to set better boundaries, but really just listen for the Tweetables, like Margo’s very astute “You stop inconveniencing yourself when you put the work on a pedestal” and my slightly less astute “Shit ain’t that serious.”

Watch. Laugh at us. Learn something new, maybe.

Then go put up some much-needed walls about your work.

We’ll be cheering you on every step of the way. From a respectful distance.

Write on,

Episode Transcript


It’s such a huge one, where it’s like, you have to train yourself how long to respond. Like, do not, if you can resist, don’t respond to the email immediately. Oh shit, you froze. Fuck! 

[upbeat music]

Welcome back everyone, it is time for another episode of your favorite internet marketing talk show, Hillary and Margo Yell at Websites! And today, we are talking about boundaries.

Boundaries, what the fuck are they? Do you need them? Do you have them? Why don’t you? Are they too high, are they too low?

I think boundaries are an essential tipping point for every single business owner. Because historically, in my experience, and in Margo’s experience too, we’re gonna share some stories with you guys about the first moment we realized we had effectively no boundaries.

They are as important to business as your admin, as your employees, as your, you know, pricing structure and offers. Having clear boundaries is the bedrock of any successful business. 

I was never really great in school, I learned how to be a hard worker.

And it was, and for a while, that actually really worked. Because when you’re starting and you’re scrappy, and you’re just trying to get people in the door, projects in the door, it doesn’t even occur to you to set boundaries, because you’re so grateful for the work coming in. 

So what did I do, Margo, what do you think I did?  

You dropped everything, you rewrote it.  

Yep, I dropped everything on my birthday.  

Did you charge them?  

Three hours later, like hating my life. So that was when I realized I needed boundaries, but it was not a simple fix from there, because when you discover that you need boundaries, then you have to create them and stick to them, which is horrible.  

I was like, all right, if I can’t get 100 on the test, I probably won’t, because I’m not the smartest one in the class, I will get 100 on my participation grade, I’ll show up on time, like, I found all the other things to be good at, and what that translated to in business was the same thing.

Like, I might not be the cleverest, most interesting copywriter, or marketing strategist or whatever it is. I’m not the most brilliant person in the room.

But I will show up every day, I will answer every text message, every email, when you say jump, I say how high, and then I go higher. I will do all the things. 

I was validating all of the drama. 

Like that was a big one for me. I don’t know what it is about Gen… Like anyone above 47 likes to call. Like, call.  

Ah, hate it.  

All the time!  

Hate it. Don’t call me, ever.  

I have 23 voicemails right now. I’m never listening to them. If you left me a voicemail, I don’t know what you said.  

This is through and through a millennial thing. My father-in-law makes so much fun of me for this. He’s picked up my phone.


And been like, how many voicemails do you have? From what time?  

My father-in-law leaves me voicemails just to make me angry. He’s like, hey! And then hangs up.  

Answering emails on weekends, being a team player, having an entrepreneurial mindset, doing more work than you’re supposed to or set out to for the good of the company…

Beyond your job description.  

Without getting compensated for it. Exactly.  

Attending every meeting that you don’t even need.

So when we go into business, we’re like, oh, you know, I just don’t think, if somebody’s giving me money, that I should tell them that they can’t do something. Or that I should tell them that I can’t do something

I don’t have the right.  

Like reply to an email on Saturday. It’ll just take a second. It’ll just take a second.  

It’ll make me feel better. I just don’t want it on my to-do list. I don’t want to be thinking about it ’til Monday.  

It is –

That’s the harder one.  

Yeah, 150%. Because again, it’ll just take a second. Like that was my tagline for my ages 22-27. Like, it’ll just take a second.  

I would say, every Friday, you’re going to get a status email. So we don’t get any of those panicked, what have you been doing today… 

It wasn’t actually helpful for me to know what you were doing. There’s more efficient ways of doing this…

Email, for example.  

This meeting should be an email! D’you know Betches is trolling me with that ad?  

I survived another meeting that should’ve been an email.  

Yeah, no not I survived, just this meeting should’ve been an email.  

Betches trolls me frequently. I do love their ads.  

I do love them too.  

As I began building boundaries in my business, and started to see how that shifted things, specifically boundaries around my relationships. 

I know I can technically do those last minute edits. I can do anything. I can punch out things quickly. I have that training and that ability. But if you do it, you are going to be expected to do it again.  

I had to have my husband point it out and yell at me, he was like, you said this to this client, but look at what you’ve done for the last three days. You’ve only worked on their stuff. And I’m like, oh, I did do that.  

God bless husbands, mine does the same thing, yeah.  

Let’s talk about this for a second, because I think that everything you just described about what a junior executive kind of looks like, being at every meeting, working at all hours, all those things that we thought meant I’m hustling, actually mean you are the worst at…

You are the worst at what?  

At productivity. Not the worst as a human, I’m sure you’re lovely.  

No, I’m the worst.  

Even during pregnancy, when I was barfing my brains out, I was still like, I will take all the phone calls! (Hillary mimics throwing up) Hold on, I’ll put you on mute! Like, it was really, really healthy. 

But I was so self-conscious about it, of saying no to events. Of saying no to client demands. Of what I felt like, under-delivering was. To say no, I’m not gonna go to that meeting. Can this be in an email? 

So I had to change. I’m not sure you can train those kinds of people to shift their expectations. You can just stop having those types of relationships.  

That’s the problem with retainers too.  

Yes, huge problem.  

God bless ’em, I had some great retainer clients, but when it’s…they get used to it. They get used to you being on call.  

That’s what they’re paying for.  

Exactly, and regardless of how much they’re paying. I think that’s so important to note too.  

And what you said about seeing that email in your inbox until Monday, that is not…

And once you know that about people, you come to expect it. And this is also why it’s bad in girl world. If someone doesn’t do that, like if Hillary takes longer than 30 seconds, I’m like, are you mad at me? (laughs) And it becomes a whole thing! And then it’s drama!  

No, this is actually really funny, and this is a side note into Margo’s private life. She apologizes to me constantly for not answering texts, and it always goes like this…

But I’m just sitting there like, no, no, no, I’m just here to load you up. And then you get to it whenever. It’s like having a little treasure trove of notes from me. But it’s so interesting, and we’ve had this conversation fifteen times.  

A hundred times.  

I don’t do calls Mondays and Fridays. I try, again, it’s a boundary I’m working on. I don’t do calls Mondays and Fridays. You need to give me at least 48 hours before booking a call with me.  

Oh, I like that one.  

Whatever. Send me video, whatever you need to do. But I cannot talk to you today, because all my days are scheduled really carefully in order to make room for both my client work and my personal work and my life.  

Mine is, I don’t make any meetings until afternoon. Like, I am really religious about that. With rare exceptions. I will occasionally break that rule, but it screws up my whole day because I need long blocks of uninterrupted time.

Like now, people know that I’m not gonna answer. Like, you will not hear from me for that chunk of time.  

So you would expect them to give you 24 hours, because again, you teach people how to treat you. So teaching people how to predict your level of responsiveness, and of giving them kind of a container for when they can expect to hear from you and flip things around is huge.  

Brene Brown’s book Dare to Lead has some really good examples in there. But if you learn, like clear is kind, is what they say. Be really clear, don’t dance around the politics, and just say what you mean, and do something that moves the conversation forward, it becomes a lot easier to be like, that’s not an emergency, I can deal with that later.  

Yes, that’s the other thing. Deciding what an emergency is. Like the most helpful thing anybody ever told me, I think it was probably Zach, I was like, oh, this is happening, blah blah blah, and he was like, I’m sorry, are you a brain surgeon? Like, is somebody gonna die if you don’t answer this email?  

Elliot says that to me, he’s like, are children dying? That’s the bar? Do you know, one day, Hillary, I answered yes. One day, it was like midnight, and he was like, are children gonna die? And I was like, they are gonna die, they’re gonna die all over the world. And he just slowly closed the computer and picked me up.  

And their blood will be on my hands! Yeah. ‘Cause that’s how it feels sometimes. And that’s another thing too. Setting clear boundaries reminds you that shit ain’t that serious. Like, of course it matters if you wanna do great work, you wanna make your deadlines, you wanna get those results, and clients who are always last minute and always panicking and it’s always a rush, rush, rush, are always like that.  

Not you.  

Which is again, just as important as having a clear process about getting great results, about doing your research, all of that matters just as much as the components that create great performance in your results. These are the components that create great performance for you as a human being.  

Yes, yes. Well that is a perfect note to wrap up on. You guys, this has been an awesome episode on boundaries in HAMYAW. I am Margo Aaron.  

And I am Hillary Weiss.  

We will back with you in two weeks. If you liked this episode, please like it below, share it with all your friends. Comment, there are awesome conversations going on there. We love your comments.  

We do.  

People have been saying really smart things and giving us something to think about, so keep it coming and we’ll see you in two weeks.  

Bye guys, ’til soon! 

Photo by Juliet Clare Warren

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