How To Know When It’s Time To Shut It All Down

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hamyaw podcast title graphic for episode titled we killed our darlings.

My friend (and #HAMYAW co-host) Margo once shared a brilliant article  all about why she shut down her much-loved virtual co-working space, The Arena.

In creative work we call this “killing your darlings”, a phrase that originated (I believe?) from writers describing the excruciating experience of editing out even the most gorgeous paragraphs and sentences when we discover they don’t actually serve the larger purpose of the piece.

If you haven’t read the article, you should. It’s brutally honest, and chock full of lessons. In other words, completely #onbrand for Margo.

Saying Goodbye to a Happy Place

But what you may not know is that I was a member of The Arena myself — and I remember the moment I read her announcement, my heart sank.

What the Arena had done a fantastic job of was bringing together work-from-home entrepreneurs who were not only largely isolated by the nature of their professions (no office = very little social interaction), but by the nature of their very industries.

When I joined the Arena, I wasn’t necessarily starved for community — I’m an active member of a handful of copywriting-related Facebook groups — but what I did need was exposure to people outside of my specialty who were a few steps ahead of me who could challenge me, provide outside perspective, and generally show me ways I could grow that I’d never thought of before.

Why Shut It Down, Even When It’s “Working”?

And that’s exactly what I got. So when Margo made the call to close it down, I wanted to know exactly why.

From the outside, it can feel bizarre to watch someone shut down something that not only seems to be working, but is also something you actively use and enjoy.

However, knowing Margo as I do, I knew it was a decision that had had its pros and cons painfully weighed over the course of innumerable sleepless nights, and was the absolute best call for her business — even though it was a tough choice.

Which is why I’m so glad I managed to persuade her to talk about it on today’s episode of #HAMYAW.

Because, as someone in an era of darling-killing myself (you may remember my Wordshops shut down sale once upon a time), I think more open conversations are needed about the nature of releasing money-making, successful-on-paper stuff that has stopped serving us, and our larger vision for our businesses.

The Upside(s) of Killing Your Darlings

So catch today’s episode where we reveal what it’s like to close a chapter on where you thought your life was going, and give sales page eulogies for our discontinued products #RIPDARLINGS

Click to watch now, and here are your timestamps if you want to skip around:

2:40 Are You Going to be the Founder That Continues Through The Dip (Should You Be?)

3:58 Margo’s Arena Sales Page Euolgy

7:35 Self Awareness: What Are You Trying To Do With Your Platform – Margo Admits She Was KiiiiiindofJust Being Reactive Instead Of Deliberate

8:28 Hillary Admires Her WordShops Sales Page (Eulogy for Her Copywriting Course #RIP)

10:38 Real Talk On Fears Around How Much We Can (Reasonably) Sell

13:20 “Founder Blindness,” Building Something You Don’t Want To Manage, And Other Rookie Mistakes

14:25 Margo on Why She Didn’t Immediately Feel a Sigh of Relief After Closing The Arena

ENJOY, and let us know in the comments: do YOU have a darling (or two) that needs to die?

And if so, what’s stopping you?

Happy viewing. Happy darling-killing.

And as always: write on,


Episode Transcript

Wait, lipstick?  

Yeah, I have a navy blue lip stain, it’s awesome. I actually didn’t wear it much this winter, that’s a bummer. Yes.  

Did you look like a corpse?  

No, I looked amazing. I looked like an amazing corpse, thank you very much. (drums and claps)  

Welcome back, guys, for another episode of HAMYAW, and today, I wanna talk about something that’s causing a little bit of pain deep in my heart, and the heart of Margo, which is the creatives’ requirement of doing the very unpleasant task of killing your darlings.

The term killing your darlings is easily one of the phrases that annoys me most in the creative process, because it sometimes causes people to throw things away that shouldn’t be thrown away.

However, learning how to close down what isn’t working anymore for you and your business is one of the finest arts and most under-celebrated arts of entrepreneurship. Which brings us to today’s topic, and guys, Margo has a bit of an announcement to make.  

Oh god.  


It’s so hard. I killed my darling. Oh, that sounds morbid. (cackles)  

Someone check on Brian. No, go on.  

He’s not my darling. It was time to bring one of my products, one of my favorite products to an end, and it was a really difficult decision, I ended up closing it in February, and wanted to talk about why you choose to close something, how to be objective about that decision, because I definitely wasn’t for many, many months leading up to the decision.

So I was running a virtual coworking community for about two years, and we were built of solopreneurs, and lifestyle businesses, people who worked from home, who had a small team of contractors, and were outside of major cities and didn’t know people like them, and the idea was to connect people with people like them, because this life is really, really lonely.

And it was working, it was working, it was awesome, it was amazing, lives were changed, my members were some of the greatest people and business owners that I’ve ever come to know.  

I was one of them.  

You were one of them. (laughs) There came a point about three or four months before I actually shut it down, where a colleague of mine noticed that it was causing me more stress, and it also wasn’t growing in the direction I needed it to. Now I’m not about the hockey stick growth, I think I like the long tail, but you still are looking to hit your benchmarks, right? A

nd so things weren’t working, and I had this question that I think we all have, which is, “Is it the market? Is it me?” And how do you know?  

Ooh, yeah.  

And there were a few big lifestyle shifts for me, like I had a kid, for example. Slight adjustment in my working capacity.  

It’s a very small potato-sized human, but it caused a lot of problems.  

Really, for someone so small, yeah. So you have to take a real serious look at what your goals are, where you’re trying to go with your business, what you’re trying to do with the product, and the company and the service, and I ultimately looked at…

There were a lot of mistakes that I had made in what I was trying to build, and I can go into them if we want to, but then there was also the very honest truth, that I was distracted in building other things. I was teaching writing workshops, and those were working, by the way.

I wasn’t having to try as hard… I was still hustling, but I wasn’t pushing in the way I was for the Arena, and the margins were way better, and at a certain point I had to look at the numbers and be like, the Arena has to be three or four times the size for this to work.  


Do I want to endure… it’s the dip. You have a choice, like, are you gonna be the founder that continues through the dip? Because you can. Or, are you gonna bail, because now is the time to, before you lose too much, and go do something else. And so I ultimately decided to shut it down, and it was a really emotional decision for me, but when I got there, it turned out to be the right thing to do for my business.  

Yeah, shall we do a eulogy for the sales page? I wanna see it just one last time.  

This was one of my favorite pieces of copy. It came from a conversation I had with one of my members, who was just complaining, and she was like, “My boyfriend doesn’t wanna hear another story about my business.” And I was like, “But we do.”  

You’re gonna have to throw the whole man away. Your boyfriend should wanna listen to you about your business, but I love this headline.  

No, you know what she means, because we all feel that, where we come home, and your husband or your boyfriend or your wife is like, “Yeah, that’s great, that’s cool.”

And you’re like, hold on. I just told you all these big things, where’s the reaction, where’s the brainstorming, why is there no insight here, they’re just like, “that’s cool, babe”, and you’re like oh. So we captured that really well in this headline.

I got a lot of people sending me screenshots of this, and being like, oh my god, this is exactly right. And I think we did a good job with the navigation. What we failed to do here, and what I had a hard time with, is that we turned this into a conversion site, so this is actually a sales page, very very simple.  

Uh huh.  

Bare bones, tested a lot of different things, it turns out pictures of actual members was what people wanted to see. Ran into a problem here, because people started to think it was an only girls’ thing.  


And I was like, ah, damn it. I thought about maybe rolling it out, but that wouldn’t have worked. So, there are little things like that that I think were dissuading people, but we had a How It Works section, and as you see, very clean, kind of the opposite of Hilary’s branding, much more of that seems important branding. I took away the…  

Oh no. RIP.  

Yeah, and we have our testimonials, which was beautiful, and all the people that we love explaining all the things. I loved this sales page.  

It was a great one, I remember it.  

But I will tell you, it didn’t work that well.  

Oh no.  

And that is what bothered me, and the jury is still out on whether it was a traffic problem or a copy problem, and I think that’s where I sat for a lot of months. Trying to understand which one was the thing, and it wasn’t getting enough traffic for me to test, the only reason I know what worked is that I had a LeadPages version of this before we rolled it out into its own website, like it was still part of that seems important, and that page did really well, so I knew the copy worked.

I didn’t know if we needed to cross the chasm that we hit a certain point where in order to scale we needed to change everything, and then the other part of it is that we sort of inadvertently became… I might have taken down the blog. Started becoming like a content machine.

And that was hard to sustain.

I was meeting writers, I couldn’t do both this and my website. It was an effort to organize, so yeah. As you can see, it’s a lot of the same branding as my site.  



I love it, though, RIP, Arena. I remember getting that email, I was like, wait, no, why? But you gotta move on, and congratulations on your writing workshops and everything else coming up for you, because sometimes you just gotta let those darlings die and expire, and retire.  

Retire but make way for the new things.  

I think what a lot of people don’t get until they start selling products or offers like something like the Arena, or the darling I had to kill more recently, which we’ll talk about in a moment, but I think it is everyone sort of pictures the fact that you start and then you grow grow grow grow grow…

And then all of a sudden it never stops, it’s human nature to believe that when something is successful and working then it’s gonna continue to work forever. And I think understandably, as you say, at that point there’s always gonna be dips, there’s always gonna be peaks and valleys, but when is the juice no longer worth the squeeze.  


And it might be an issue of your margins, it might be an issue of effort, or it might just be that you’re done, and you wanna move on to something else.  


So it’s just a tough decision to make every single time.  

Yes, this is why I harp so loudly about self-awareness. Because you see people where they’ve built something they hated, and I didn’t want to resent this thing, and was starting to look at how my goals had shifted. I know this is true for you with Wordshops, which you’ll tell us about.  


What are you trying to do with your platform? And are you hitting those metrics? And if you don’t have clarity on what that is, you’re just gonna be reactive, which is kind of what I was doing. Taking like, a few green light benchmarks, I was reacting, I was way too involved in the we’s where I should have gotten out.

I wasn’t managing people right. There were a lot of hiring issues that I had that was cutting into all my revenue. Lots of lessons learned, though.  

Yeah, hey.  

I could tell you what not to do. But tell us, like, what happened to Wordshops, and how it actually isn’t dying. Explain us what that means.  

Well, I will start doing a eulogy for my sales page, because I just, this is a thing of beauty, and I just need it to be preserved somewhere. The Wordshops, a darling I most recently killed. You see it’s in the back end of my site, because it is now offline,, no longer exists.  

I still love that picture.  

It’s an amazing photo of me, thank you. This was such a labor of love. This is my copywriting courses guides that I took offline very recently, and it was again a big emotional decision. And you can see, the website is beautiful. I even did a sales video, there I am, looking very similar to where I do now, sitting at the very desk I’m at right now, and just all of this, I was really proud of the page, I was really proud of how it looked, and I was really proud of the content.

What I really wanted to do was create a course for entrepreneurs that taught them every single step of copywriting, basically pouring my brain out of my ear and into a course that would allow people not only to understand the rules of copywriting, but understand how to break them, and understand how to create not only copy that converts, but also copy that’s creative and stands out, and makes them excited to show up and make stuff every day. 

And so, you know, there was a live version, there were versions for About, Home, and Sales pages. This was the clearance sale that just ended. And it was really something that I had worked so hard on, it took me three years to build it, I beta tested it twice, and I had this image in my head that when I launched it, I was gonna be able to start changing my business.

That I was gonna be able to do less client work, that it was going to be the answer for me, that I was gonna turn it into so many things, then it would just be this really incredible experience for me, and it would help me build the next leg of my business. Unfortunately, none of that happened. 

The whole point was, basically, I was supposed to be doing less client work, and I was gonna start shifting over into launching this quarterly and all of this stuff, but by the time I had finished putting it together, it took a team of 10 people, and it took me a long time to put it together, I launched the whole thing myself.

It just took so much effort and energy that once I had finished launching, when I had run another live round of it, I was so tired I was like, I need to take a break from this. 

And then I ended up running a secret semester in the spring, doing it with more people, and that was great, because it brought me back to the creative aspect of it. I was trying to fall back in love with it again, but at the end of the day, I didn’t scale back my client work enough because, a couple of reasons…

Probably I was too, at the time, scared that I wouldn’t be able to consistently sell this enough in order to make up for my client work income, and also that I was just, the effort of launching quarterly, and putting so much effort and power in order to make it a high end launch every single time, when it was just me, would have taken it all out of me.

So I ended up just sitting on all this intellectual property for like a year. But I had a sit down with a friend, my friend Sinead Howard, and she was like “wait a minute”.  

Love Sinead.  

Yeah, exactly. We can take this and pick it apart and turn it into so many different things, and that’s exactly what I’m doing. So all the Wordshops will live on.

The last opportunity for people to get it all as it was just ended very recently, and I had old students emailing me, being like, I can’t believe you’re taking this down, it was so awesome, I’m so glad I got in when I did, getting text messages from people being like, I know how great this course was, why did you take it offline?

And the real reason was that it was built for a version of my business that no longer exists, and never came to pass. And that is really I think something that we have to remember as we set goals as business owners, as we build this vision of what’s next for our business.

Again, same thing, you assume that once things are going well they’re always gonna be going well. That once something’s selling, it’s always gonna be selling.

That things will stay as they are, but we forget our businesses and we are constantly evolving and changing into better versions of ourselves, and coming up with different ways to approach our craft. 

And I also realized that I didn’t necessarily wanna be a copywriting teacher with my upcoming rebrand Statement Piece Studio, my MO is much more about concept development, and ideation than it is just copywriting.

Copywriting’s a piece of it, copywriting is how you get your ideas out there, but it didn’t feel like a fit for me any more to constantly be teaching copywriting over and over again, so I will be teaching a copywriter’s certification course, hopefully in 2020, so keep your eyes out for that, but for now it was a matter of taking all of this thing that I’d built with so much love, and finding it a new home. And a new way to bring it to people.  

What made you pull the trigger?  

On closing the Wordshop?  

Like did you deliberate?  

Yeah, of course I deliberated, but I realized that, first of all, the branding was all wrong for my rebrand. There are no primary colors. But I just realized there was no way to fit it in to what I was doing, it just did not make any sense.

Well it made sense because I am a copywriter, but as I move into my rebrand and I move more into a consulting and speaking space, Hillary Weiss the copywriter, Hillary Weiss the copywriting teacher is a much smaller piece of that puzzle, whereas in order to make the Wordshops work, it would have had to be a much bigger piece of that equation, in my opinion.  

I get that, I felt the same way. I realized I didn’t want to be running a SASS hybrid.  


It’s so tech-heavy, and my customers didn’t even notice, by the way, like there were parts of the membership portal that were taking up all of my time, and the payment processing that was just such a nightmare, I felt like was making us look not professional, because people would get double charged, things which shouldn’t be happening, and people didn’t notice because they just wanted to talk to each other on Slack.

And I never paid attention to that, because I was like no, we are so much more than Slack, and I was really defensive about it, I remember at the time my team was like, but this is where the connections are happening, they’re happening in email, they’re happening in Slack, they’re happening in Zoom, like pay attention to where people are spending their time, and double down on those assets, and I was like, but we need a membership portal…  

To be a membership.  

In fairness, we needed to manage the memberships.  


Like for payment and for a lot of the intellectual property and things like that, but like, no one actually cared. That was one of those moments of like founder blindness, where I’m really good at this for my clients, but for me I was like ‘Uh uh, this thing is really important,’ and everyone else was like, ‘it’s really not.’  

Yes, it was very interesting shutting it down. like shutting the page down for me cause I was like wow cause it’s closing the chapter on a vision of where you thought your life was going.  

Yes, yes. A lot of people ask if, do you feel like an exhale do you feel a sigh of relief and I was like no, you have to mourn it first.  


Before I was like okay. I really don’t have all these other things on my to-do list, I actually feel good about it now. Because a part of you really loved it. It’s like breaking up with an ex that you know isn’t right for you but then as soon as you break up you only remember the good stuff.  

Yeah, yes oh my god absolutely. Absolutely.  

It takes a while for that amnesia to go away and you’re like oh right he was schmuck.  

Oh, he was the worst. Now, I remember. Yeah, the whole man you have to throw away. But it’s so true and I think it’s an emotional experience. And we don’t talk about the emotional experience of pricing yourself, of selling and of course having to kind of fold an idea that you really thought was the next thing for you.  

Yes and publicly, right?  


Be able to talk about it. I mean how many times have you wanted to film this and then like it’s too soon.  

I can’t right now! It’s an interesting experience having to shut that down. That was the first time I had to do that cause aside from rebrands and stuff like one off things I’ve never had to actually formally take something down and get rid of it.  

Same, I could discontinue things like no one knew.  

Yeah, exactly. If it didn’t sell like, oh.  

Never make it.  

Yeah, no one saw that happen. But yeah it is a totally interesting experience when it’s something that you love and that other people love that you have to close down.  

That is our kill our darling story. I hope it inspires you to kill yours in a loving way. (laughs)  

And make some money while you’re doing it if you can. But yeah.  

Thank you for watching HAMYAW. I’m Margo Aaron.  

And I’m Hillary Weiss.  

So, if you liked this episode please like it and subscribe to our channel and we’ll see you next time.  

Bye guys.

Photo by Juliet Clare Warren

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