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Running an Online Business [Offline] with Kendall Cherry

Running an Online Business [Offline] with Kendall Cherry

I tweaked my creation process in an intentional, non-draining way- here's what happened- PART TWO

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My friend Allison Hardy recently interviewed, copywriter and repurposing Queen, Kendall Cherry. Their episode: Running an Online Business- in Offline Mode sent me in a (good) tizzy and inspired deeper conversation in both: Maybe I Don’t Want to Run an Empire and If You Don’t Want to Churn Out Content for Consistency’s Sake. Here’s a continuation of this content creation series.

Online business makes you think it's open 24/7 but it doesn’t have to be. As a copywriter, I'm probably writing two hours a day for clients and maybe a couple hours doing other admin stuff, but I am not setting up a 24/7 style of business, even though the internet never shuts off. I will quite literally delete Instagram daily from my phone because I know I'll sit there and scroll or compare myself or I'll think everything is so urgent when it’s not.

When I listened to Kendall share her tech boundaries on that podcast episode with Allison, I felt a sense of relief. A sense of “there is another way.” So I deleted Instagram off my phone and put up an 18 grid to support those who come across our account- only reinstalling the app to post for our Podcasting Moms Conference in April.

I even took my work email off my phone and deleted a ton of my apps. I am definitely detoxing right now. I'm putting my phone in the drawer when I’m with the kids and am noticing such a different relationship with the present and my business. Recognizing how many times I'm grabbing and crossing over during my day where it's supposed to be mom time but I'm over here like, well, let me send this “quick” Voxer because I love being in that world. But it just makes me anxious all the time.

It's the hardest part of having an online business that people don't think about. We think, Oh, it's just one email or it’s just how I’m coordinating plans but it’s more than that. It creates an urgency that’s stressful- especially when it’s pinging me all the time with notifications or that little red bubble.

Quieting Your Scarcity When Marketing

For me in this process, I've had to deschool and decondition myself in thinking that Instagram is the “only” place where I can find clients. So how have you worked through that and what have you seen change in your business? You're mostly referral based, right?

Oh girl, yes! Let's go.

I was telling my coach this morning: my number one revenue generating activity is pickleball. I play at a club in downtown Austin and there are so many people around that are business owners. They need copy, or they know somebody that needs what I do and so for me, when I am offline and around people it’s magic. Don't underestimate the power of in-person networking in unexpected places.

Platforms Kendall Focuses Her Time On

We do a lot of repurposing, so my Instagram is basically all old recycled content. It's just nurturing the people that are there. I have an email list of about 500 people and we send a repurposed email once a week. On Fridays I do something called Wallflower Fridays, which is basically me live journaling my life. And the other thing besides in-person that has been growing my business is LinkedIn.

The magic of LinkedIn

I was such a non-believer, because for me, I used to have a corporate career, and so LinkedIn was always that space. But I started finding aligned people from using hashtags and commenting with them. Literally last week, I had a virtual coffee chat with this guy and asked him about mentorship for a new idea I had and now I have an opportunity to potentially co-found a second company with him. (Which I never thought was in the bingo cards for the year or for my life.) But it just dropped in.

There are a lot of people eager to collaborate on there. They're willing to help each other out. It’s simply about being authentic there with your voice.

LinkedIn hashtags

Here are the “magic” hashtags:

  • #entrepreneur

  • #business

  • #contentmarketing

  • And depending on your business (she recommended for me):

    • #contentcreator

    • #podcastmanager

That's all I do. I don't do anything fancy. That's the secret.

What I find that’s so special about LinkedIn over the other social media channels is the way that their algorithm works.

You don’t have to push out a lot of content for people to find you. It's literally like a spider web. So, for example, if you and I are connected, and you like my post, it’s then going to show my post to everyone that you're connected to.

So, if I use #copywriter, a lot of copywriters are going to see my content. But, a lot of the copywriters on there tend to be more junior. They're not quite at the caliber that I'm at. So they tend to take notes or they find what I'm doing helpful. But anytime they're engaging on my content, it's getting pushed to their audience- the spiderweb concept.

If you struggle with the scarcity mindset of the other social media channels, I love LinkedIn because it is like literally laced in the abundance mindset.

My post just needs to find the right eyes and connect with the right people for an authentic reason and it will just catch on.

I wrote a very emotional post last month. It was a photo of me from my corporate days and I basically said, I look sick. My skin, my hair, what am I wearing? I was so unhappy and I wrote: I want to cry for the girl in the photo for two reasons. 1. I'm mourning and grieving the woman I was. 2. I'm proud of the woman that I am today who took the risk.

I thought- there's no way this’ll go anywhere. That morning I sent it to my coach and I was like, do I have to publish this? This is like vulnerability hangover territory and all my old coworkers are going to see it. But it resonated with the right people, grew my audience 15% from one post, got 70 likes and people were resharing it. They emotionally connected with it.

Even this morning I woke up and had 30 new followers because I posted something while I was cooking dinner last night. I heard this little voice say, oh, this is an important concept- you should post this. So I put it out there while I was in the middle of stirring my soup. I broke a thousand followers from content that for me feels really aligned.

Posting-wise for LinkedIn, I use a content bank for three posts a week and then I treat LinkedIn like old school Twitter by live journaling.

If you're feeling authentic and creative, there's literally no barrier. You don't need to create a graphic, you don't need to make a reel, there's no video content. You can quite literally, write two sentences, it does not have to have a lot going on to resonate with the right people. PLUS content lives for like four weeks there too. That's, why I prefer it.

Just trust me. I know it's weird. Give it three months. Comment on some people that you think are interesting. Engage if you can be consistent about it. I promise it's worth your time.

Creating Consistent Content (w/o burnout or the ick factor)

I resonate with this so much. My thing with coming on Substack was, when I have something to say, I'm just going to get behind the mic and say it. And it's been so interesting, the vulnerability that I've had here, I've seen so much good connection where we all feel seen and engaged. And I think that's the way I'm seeing the pendulum swing from the masculine to the feminine in marketing. People want the real stuff and to feel like, oh my gosh, that's me. So I love what you're saying with LinkedIn and I feel like there's an overlap there- that whatever you put on Substack you could also put on LinkedIn.

You also mentioned consistency. This is a hot topic for me. I did a post the other day and the heart of it was: creating because you have something to say versus churning out content for that consistent adage. I was debating when do we let flow happen? Like you did, when you were standing there cooking and you had an intuitive hit, and took action. You created based on that versus I have to put something out and that pressure we put on ourselves. So where have you found the intersection of that and your own creation?

It's one of my favorite topics because it is the hardest thing to attain as a business owner and as a human being.

Creator’s Constraint

My little concept, nobody steal this, is this phenomenon called the creator's constraint. And it's this idea that you as a creator, get some kind of hormonal hit when you create something fresh. It feels so magical, so you think that every single thing you publish has to be fresh. But it is literally impossible to do this. The world's best creators do not do this. If we all need an expander, Taylor Swift has literally made millions and millions and millions from rerecording her other albums from when she was 15.

What I realized last year was that waiting for this bolt of lightning to hit me also discredits the times when those lightning bolts have already hit on other pieces of content.

That’s where repurposing comes into play. Your content is evergreen. Your marketing content does not need to change that much. So I put those lightening bolt posts in a content bank to review and scrub quarterly and then use.

It's hard as creative people. We feel this need for creation and expression, which is so important, but you cannot create as an artist all the time. Regardless of it's for a business or if you are creating on behalf of clients, it is taking some of that creative battery.

So if you’re willing to say, I can't create it all and instead think: the lightning bolt struck, I bottled it up, it's in a concept that I’ve already got it, now how can I leverage this piece of content? You’ll see a difference.

This could literally look like if I have a tweet style post and the background was blue the first time, next time I'm going to repost it, nothing changes, but the background is yellow. Or if I have a 10 slide carousel slides two through 10, they're the same and the cover slide is different.

We hear from all these creators: it's gotta be fresh. It's gotta be this intricate 16 pieces of content system every week. Instead I’ve seen that your business can survive on 3 quality concepts that can be repurposed. (Plus I always love doing a newsletter because I think it’s one off and exclusive. Or if you do a podcast- that scratches the itch too. Whatever it needs to be.)

You don't need 16 pieces of content. You just need really quality content that you can also build over time. Unless you have had a massive pivot, you're probably sitting on content that can either be slightly tweaked or, if not, it’s time to get your content to a place where it's an asset.

If we were in more masculine businesses, we would think of content as an investment that's paying out dividends. It is an asset of your business.

So at first take, when I hear what you're saying of showing up consistently is important to keep putting stuff out, my mind goes to, why are we creating content? Is that consumptivitis? I find myself stuck where we want to be fresh and we don't want people to be like, I just hear you saying the same thing over and over again, but then there’s this pull of, I have to make sure I post every Tuesday, but maybe I don't have to have something to say this Tuesday.

Yeah. It's not necessarily about consumptivitis. To me, it's reinforcement. The best businesses have a consistent message and they're telling you exactly what they're selling. They're telling you exactly what services they have to offer. That's the piece that's consistent. If you have content that supports that message then you can come in when you're in your sparkly fairy girl energy and you can bottle up that fresh content- but your business doesn't have to survive.

That basically replicates old school feast and famine creativity. I see this all the time with creators (and I've been this person too) who thinks: Well, I don't feel like creating today or I don't feel like posting today so I'm just not going to. And you wait for the creator's personal creative capacity vs. the business functioning as a marketing engine.

If you have these other pieces setup then you can leave room for magic.

For me, what's coming through and resonating is this idea of our content being like solar power. I’ve found that when I have an idea, I need to get behind the mic right away and I need to get it scheduled because the further I get away from an intuitive hit- it starts to peter out. So this reminds me, instead, of a solar panel where I let it soak up the creativity when it’s there and then schedule it out to be shared in the future. And when stuff did go well, I can add those to the solar power bank too (and scoot them down the line if another creative flow hits.)

This creative flow resonates with me because I struggle with the intentionality of it. I'm very much into slow living and feminine business and so, I don't want to show up and say something unless I'm 100% in it. And there are times where it ebbs and flows, right? Like you're saying, the feast and the famine, I'll have five ideas and then I'll have nothing that I want to say right now. But those five ideas could have actually been going out and then the next wave could have come.

The ideas you have today are a gift for your future self. So just because they come in today, it does not mean they have to be posted today.

When I first started, I would get so tripped up because I’d have a month long content plan with everything in its place and scheduled. And then the posts and content would go out the week of and I'd be like, Ew, this doesn't feel good.

So now they might be pre-scheduled and then me and my artist self can go in and make it a little messy and be like, Hmm, what does the collective need to hear this week? So it's more timely and not tone deaf. While your messaging doesn’t need to be changing constantly (if it is, you might have a business or sales issue holding you back) there are real things that affect us in real time, based on world events or your industry, that can impact what people are receiving.

Distraction-Free Work

A few other things I do to run an online business [offline] is use a digital typewriter called a FreeWrite for most of my writing projects. It has the same surface as a Kindle with just a keyboard, and there's even, a slight delay when you're typing, so you get into this flow, with basic word processing.

For client work, I tend to work from my laptop, but in airplane mode. I have a perpetual out of office message on and I try to focus on one specific client at a time.

Once that project is done, I close out of those tabs and move on to the next project. My brain needs separation of church and state so I have to do one thing at a time to keep my my brain organized.

I related to this point a lot. I used to say “I work when it’s work time (aka I have childcare) and I mom when it’s mom time (aka no childcare/unschooling time.)” I can't cross over, because if I try to do ten things at once, I'm doing nothing well. I used to do this and definitely need to get back to it because I've been crossing over a lot lately, and it's chaos.

Setting Boundaries in Your Business


I have a lot of boundaries around my time too. When clients sign on with me, they get an invoice, they get a contract, and then they get a second contract around expectations and boundaries. They sign this document which shares, these are the hours I typically work (which are sometimes weird hours,) you might notice that I'm sending emails at a weird time or on the weekends- I run my business offline because as a creator, it is so important to me to be at peak creative performance.


I have all these things in place that are really important to me so that my clients get my best work and I am upfront and tell them what to expect. I even have a 2-3 day deadline expectation for flexibility, so I’m not rushing to meet a deadline and changing my work. I would rather give you 100% of my product versus 70%, but you get it on time.


There's also stuff around how you can communicate with me. I was doing Slack access with clients up until December of last year. It became this very secret energy drain where (you might notice this in your business model) as a copywriter, the line between being a fractional CMO and a copywriter was very thin. Extremely thin, especially when I was serving more small business owners that don't have the budget.

So they're like, let me just ask you my questions about marketing and I, being a people pleaser/recovering people pleaser (my coach says, I had a tendency in the past to people please) [great way to put it right?] I would want to help them because I have years of experience. It was fine to send that two minute memo for 1 client but when you have 4 of them- my brain started going down those rabbit holes and I would get so drained from it.

So now we have a pretty clean process where if clients have ideas, they can email them to me or send me a voice memo in an email, but I don't do any back and forth communication because for me to do my best work as a copywriter, I need to tune in😉. I need their voice to be extremely clear. Otherwise, if they're unclear, I feel it. If it's not clear, table it, go process it offline or however you need to do it. Not to say that there's not seasons, maybe you're mid-pivot, or you're still experimenting. That's okay.

But, especially with the kind of content that I do that can be salesy and sensitive, it requires a little bit more of a intentionality or a strategic patience to it.

Such gold. ✨

Want to run your online business [offline]? Check Out Kendall’s Workshop in our paid subscription

Here's my thought let’s put a Creating Your Content Bank Workshop in the Mompreneur Community side of this Substack. I think this three quality content concepts for marketing your business is so interesting and supportive.

Yeah, totally. There's definitely a few quick wins that I would say if you're trying to build a very modular content bank, like there's three or four posts that you can just ride home on.

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Tuning In Podcast
A newsletter + private podcast where mompreneurs connect with their inner knowing and a new way of thinking. Join our community to explore slow living, mindful mompreneurship, feminine marketing strategies on our journey to a familypreneurship lifestyle.