Jennifer and Maddy discuss her transition from freelance content creator to agency owner, building a team, and writing a book during the pandemic.
Maddy Osman is a respected content strategist, content creator, and content marketer. In just a few years, she went from solo freelancer to agency owner with a team of nearly 30 that includes researchers, writers, editors, account managers, projects managers, and administrative support.
Her agency, The Blogsmith, has worked with brands like Kinsta, Scribe, Nexcess, Goodcover, Trello, Mosaic, HubSpot, Klaviyo, Search Engine Journal, GoDaddy, Wix, AirOps, Elementor, Paid Memberships Pro, Bluehost, Cirrus Insight, CodeinWP, MarketerHire, BigCommerce, Hotjar, Pagely, Envato, Sprout Social, 99designs, Freelancers Union, and more.
Maddy has enrolled in a few of my programs over the years, including Content Camp: Website Copy and Profitable Project Plan — and it’s always fun to see where her name is going to pop up next and what brand she’s working with to create high-value content that earns clicks, drives traffic, captures attention, and inspires readers to act.
And that’s exactly what we talk about on the podcast.
In this episode, I ask Maddy about her journey from freelancer to content agency owner, and we talk about what role she hired for first, how she grew her team, and the one tool she created with her team that was a complete game-changer in terms of quality control and revisions reduction.
We also get into things like:
- How Maddy got through the pandemic and stayed sane by embracing hobbies and seeking greater work/life balance.
- The story of deciding to write a book during the pandemic and actually doing it. Her book is already published and we learned how she got it done and why she wrote it.
- Why every piece of content should start with a brief and detailed outline.
- The one tool that has revolutionized the way Maddy does business and manages systems for The Blogsmith.
And yes, we get her story of getting married during the pandemic!
I can’t wait for you to listen!
Mentioned Sites, Resources, And Tools:
Get To Know Maddy Osman
Maddy Osman is a digital native with a decade-long devotion to creating engaging, accessible, and relevant content. After teaching herself web design at age 11, she found her true passion in content creation—learning the intricacies while transitioning from technical to creative SEO marketer. Maddy’s journey from freelance writer to founder and CEO of The Blogsmith yielded numerous insights to share about content creation for enterprise B2B technology brands. Her efforts earned her a spot in BuzzSumo’s Top 100 Content Marketers and The Write Life’s 100 Best Websites for Writers. She has spoken for audiences at WordCamp US, SearchCon, and Denver Startup Week.
Extra Minutes Training With Maddy Osman
To hear more from Maddy and learn how a content style guide — a system for documenting your brand voice and how you approach written communications in your business — can help you improve your content, check out the Seeking Satisfaction Extra Minutes Membership.
Members receive Extra Minutes bonus training from Jennifer and podcast guests like Maddy that provide valuable insights and lessons to help you build a better business for only $15/month.
Maddy’s Extra Minutes training continues the conversation from the podcast, diving deeper into the topic of her new book: content style. We talk about why every business should have a content style guide, what content guidelines should go in a style guide, how to use a content style guide in your business to improve your writing, and how often it should get updated.
We also talk about:
- How the best practices for creating digital content and writing for the web are similar to those for news journalism.
- What copywriters and content creators need from clients to produce quality, on-brand content that doesn’t need several revisions — and what to be prepared for if you don’t have these items defined and ready to go.
- How her team at The Blogsmith onboard new content clients to ensure they understand the clients’ content preferences and brand communications styles.
I lost my dad a lot earlier than I thought I was going to. It was unexpected and it made me question everything. And so going into the pandemic where stuff just felt so bleak. I just realized if I don’t create that balance now between my work life and who I am outside of work, it’s kind of like now or never because tomorrow’s not guaranteed.
I think I just realized partially down to my dad and like the legacy that he left, I wanna like live for myself. I wanna like have some fun, you know, I wanna, live this life to the fullest.
Welcome to Seeking Satisfaction, a podcast that inspires you to live inspired, embrace imperfection, and seek satisfaction. I’m your host, Jennifer Bourn, freelance business mentor, course creator, and agency owner.
Today, I get to work with clients I love, do fulfilling work, and have the freedom to live the life of my choosing. But things weren’t always this rosy, which is why this podcast looks at the systems that power successful businesses and fulfilled lives, going behind the scenes with freelancers entrepreneurs and professionals to discover how they juggle work and life, manage clients and kids, handle stress, and tackle unexpected challenges.
If you are seeking greater satisfaction in your work and life, you are in the right place.
Today, I’m here with Maddy Osman, a digital native with a decade-long devotion to creating, engaging, accessible, and relevant content. Thanks for joining me, Maddy.
Thanks for reaching out. I was really excited to hear from you.
So, you are the founder and CEO of The Blogsmith, you’ve been named one of BuzzSumo’s top 100 content marketers and The Right Life’s 100 best websites for writers.
You started as a freelancer though, I would love to hear a little bit more about your journey from being a freelancer to being a content agency owner.
Totally. Yeah. So, many who freelance, you know, you maybe have like a nine to five job. That’s what it was for me and I think I just realized, maybe it’s just hard for me to take direction from other people or something…
I don’t think you’re alone there.
Probably a lot of people listening are feeling the same way.
So I decided to quit that job and luckily had a client who had a bunch of work for me to make that shift easy. And, I still needed to look for other things to do too, but it gave me the confidence, to know that I could do it and to know that I would be able to pay my rent every month.
From there, I guess even before that I had taken on freelance projects on the side of another job and so luckily every step I was just easing my way in. And so I freelanced for myself. I did probably too many different types of things. I would make websites for people, I would do social media, and I would do the content writing, which I decided is like my true love of all those things.
They all play in the same ballpark, but ultimately involve many different processes, many different, you know, industries to keep up with. And so I think I just realized in order to be really good at one thing, and to become a go to for something, that I needed to focus in on the content writing side of things.
What a great Ah-ha. I think so many people do the same thing. You start your business and you’re like, I could do that. I could do that. I could do that. I need to get paid. I’ve got a mortgage. And it’s not until you start getting that experience and doing that work that you figure out, “I like this a little bit more than this.”
And I love that you just said, “If I want to really become known as the expert at something, that’s what you’ve gotta focus on.” So that’s what you did and focused on becoming a writer. What next.
From there, I had the realization. most of my projects were writing anyway but it was really just then cutting away the rest. I redid my website and it’s interesting, it was actually at Word Camp US 2019 — I don’t know what it was about that event but there was something about it that made me make that decision to go all in on content and to think about it from more of an agency model versus me as a freelancer — and just being around people. Maybe it was like, just talking about what I do and hearing myself and hearing that like the content stuff was what I was most excited about.
Yeah, so redid the website, thinking of it from that agency perspective. Started building out my processes around working with other people. And then, started making hires — more writers, some editors, a project manager, an account manager, someone to help me with the keyword research side of things.
And so, you know, it just started small and then ballooned out as I found roles that I didn’t want to do anymore and that weren’t going to add value for me to do them specifically.
Wow. So this is all fairly new then, in the last few years, your growth.
Yeah, it’s happened fast. It’s been exponential. I’m grateful for it. I think the pandemic did not hurt my business at all. If anything, it made it more important for people to have online communications. I mean, I’m sure that it’s the same for you.
Like, more people are going online, more people need to be able to communicate with their customers in an accessible way — you know, in a way that they can get that information when they need it — and so business exploded. More people needed more content and so it was just a matter of, matching that demand and continuing to grow with it.
It’s so true. The pandemic, while it was so hard for so many people, it did give this push for folks that hadn’t yet all the way embraced digital communications that kick in the butt they needed to say, “All right, let’s make this a priority. Let’s invest in our website, let’s launch that course, let’s create that membership, let’s create that store, let’s invest in our content. Maybe I’ll start a podcast, maybe I’ll start a blog, I need content. And so there is this push toward really looking at the message that people are putting out into the world.
And now how big is your team at this point?
We are approaching 30 contractors. So, they’re not full-time. I would say it’s closer to part-time and then I’m an employee of the business. And then, I recently in the past, year I hired, a second full-time employee.
Wonderful. So, this transition from freelancing to agency is fairly new for you. There is this point when you’re freelancing — when you have too much work for one person but you haven’t gotten help yet and you know you need to, and there’s kind of this Catch 22: Do I? Don’t I? Do I have enough? What did that look like for you?
So, the person, like, my first full-time freelance client who helped me make that leap, he, had started to explore the idea of working with virtual assistants. And you could say to some extent, I was kind of a virtual assistant to him, just more focused on like content marketing. And so part of what was really great about that relationship was that I was able to ask him questions. Like he was willing to be a mentor to me. That was kind of part of the deal.
That’s step one, get a mentor — somebody who knows more than you do — somebody who’s a level above you who can kind of help you navigate that path so that it’s not uncharted territory.
But he planted the idea in my head. He had started to see success so he gave me ideas for how I could do it. And so I just kind of dipped my toes into that. Hiring first, somebody to help me with some, like, admin-related stuff, some graphic design stuff, and some research.
So, my first virtual assistant would help me create outlines or they would help me do some aspect of research that I needed to complete client work. And then from there, that’s when I started to add writers who were a little bit more specialized in writing and creating content, and then the editors.
And what made it possible, I think, to grow bigger more quickly and to be effective in hiring editors to work with the writers — because, if we’re gonna grow, if it’s gonna be an agency model, I can’t be the one who edits everything and grow the business and worry about all this other stuff — we created a style guide.
And so it started with me going through what the writers created and being like, “Well, you know, I don’t like how this heading is written because of this, like, here’s a reason, here’s an example. Document it.” Or, um, “There’s something about this that feels inconsistent. What is it? Write that down.”
Once I started that style guide with the first editor I hired, and then expanded it, we were then able to grow much larger than that.
I really like that progression of things — that you started with someone that could help you get the research and the outlines done. They’re helping you get that job done faster, taking some of the things that don’t necessarily require the highest level skills that you have. And then when you were ready to take that next step, looking at writers and then looking at editors.
And I think what you said about documentation is so brilliant because we’re so busy rushing through and it’s easy to just make edits and say, “Not that, not that, change this, let’s not say it this way,” and we put all the comments in our Google doc. But taking the time to think about, “Why am I making this change? What is it about this? How do we want to do that?” And then documenting that in a style guide that people can then reference on the next project is smart.
How has that changed the dynamic and the quality or consistency through the projects for you?
I mean, it’s, completely changed it because when I was in that rat race of, everything’s new, you know, every time I approach a draft it’s a fresh approach, it’s draining. And you get frustrated too. Where you’re like, “Why are they continuing to do this?” But it’s like, “It’s because I haven’t told them not to.” Like, maybe I just made the edit and, like, never actually communicated why or even that it was an edit.
So yeah, I mean, the style guide just made it so everybody’s on the same page. People don’t have to take it personally, you know? Sometimes with edits, it’s hard to tow that line of giving the feedback and doing it in a respectful way, especially if you feel a certain way about it. But if you’re just like, we do this because of this style guide rule, there’s nothing personal about it. It’s just, that’s what it is.
Oh, that’s really, really good. Because it can be hard when you work really hard on creating something and then someone comes in to edit it and they just rip it apart and there’s no communication, there’s no reasoning for things, there’s no acknowledgment or validation — and you can really take that personally.
A lot of people get really emotionally tied to the work they produce and that’s tough. So having a style guide and saying, “Look, thank you for getting this done. You did a great job. This is the style guide. These are the rules. This is where we’re not adhering to those rules.” It’s not personal, so I love that idea.
And like, I don’t expect anyone to memorize it. It’s a reference for a reason, like, we are constantly referencing it, even the editors who use it every day. I don’t expect people to memorize it, especially if this isn’t their full-time job. it’s just a reminder.
It’s just they’re, like, “I don’t know what to do. What does the style guide say? How do we handle this?” So it’s, nice because it’s just something to refer to and it helps answer those questions so that we’re not having like a back forth constantly.
That’s awesome. So, during the pandemic, your business didn’t see any kind of slow down. If anything, it was even better.
During that time though, you took on a lot of hobbies.
I think it was my most hobby-filled time. Because probably before the pandemic, my business was my hobby, which like, I don’t recommend.
I can so relate to that. There was an early part of my career when I had first started freelancing, my business was pretty new and somebody was like, ” Oh, what do you do?” And I’m like, ” I’m a designer.” And they’re like, “No, no. Outside of that?”
Well, yeah, nothing.
What are you talking about outside of that? My business is my hobby!
And I walked away from that conversation thinking, oh my gosh, how sad. But it was true at the time. Like, it was all-consuming.
So this gave you the opportunity or the space to explore some of that. How did you kind of juggle the demands of work, still being busy full time, and then finding time for things that are fun? Was this partly because you expanded your team or how did that all work together?
Yeah. I don’t know what the moment of clarity was for me.
I’ve answered that same question, what do you do? “Oh, just work, you know?” And I didn’t see, like, a problem with it. I have a weird pride, like, “Oh, I’m just such a hard worker.”
At some point I had a realization. Honestly, it was probably before the pandemic. I lost my dad a lot earlier than I thought I was going to. It was unexpected and it made me question everything. I mean, honestly, the whole idea of death and dying grief, my own mortality is something that I’m still trying to make sense of.
And so going into the pandemic where stuff just felt so bleak. It was scary. There was so much uncertainty about what tomorrow looks like. I just realized if I don’t create that balance now between my work life and who I am outside of work, like, it’s kind of like now or never because tomorrow’s not guaranteed. You know?
And so I think I just realized partially down to my dad and like the legacy that he left, I wanna like live for myself. I wanna like have some fun, you know, I wanna, I wanna like live this life to the fullest.
I think that’s what it was.
It’s so important and those moments. Either of loss or of facing mortality, Are such powerful game changers in terms of mindset. when Brian and I were younger. I had my business. I had no hobbies.
I just worked all the time. and it was all about saving for the future and planning for the future and putting away for the future. And Brian was diagnosed with gallbladder cancer and they’re doing all these tests and the reality that you might not live to see your kids grow up changed everything for us.
And then it was like, “No, we’re taking every vacation. We’re doing everything. We’re going all the places.” We’ll still be responsible and save for retirement and do all the things we’re supposed to do but you’ve gotta live and enjoy life along the way while you’re doing all of those things.
It’s so important. So, along with discovering new hobbies in the pandemic, you also found time to write a book.
That is a huge undertaking. And for many people, the idea of writing a book feels like another full-time job.
Yeah. Not to like ruin that perception, but it is.
Yeah. That’s kind of what I figured. So how did you do this? Tell me a little bit about when you decided that you were gonna write a book.
So I do think it’s, achievable with the right approach without becoming totally overwhelming. And so I think I just knew, like, I wanna write a book at some point. Now is kind of a good time because the pandemic, like can’t go outside, so I happened to have a little bit more free time after work.
And so what I decided to do was to start the writing process in tandem with NaNoWriMo, which is National Novel Writing Month. It happens every year in November, so 30 days, and basically people just kind of come together with this shared goal of writing 50,000 words within that month.
And the good news is the way that people in this group typically approach it is the really ugly first draft. We are not self-editing at all. It’s just like word vomit, basically. Like you’re just getting the idea down. And so, what I did was just dedicate maybe like, two hours a day, but there were some days that I didn’t do anything, you know, that I gave myself a break.
And so it was manageable in that I just planned that month accordingly and I knew that, like, this was where my free time was gonna go and like, none of the other hobbies like were going to happen, you know, like it was just this.
I just tried to stay consistent with that or as consistent as I could and by the end of that month, I had my 50,000 words. And to be quite honest, not all of those went towards the book. I’d used it to, like, write some blog posts. So, even if you don’t wanna write a book NaNoWriMo is a great, accountability mechanism for just doing some content.
From there, obviously, it wasn’t done. So a couple of months later they do what’s called Camp NaNoWriMo — it’s just another iteration, I guess you could say. And a lot of people use it for editing, so that’s what I did. so I gave it some space,
I love that there was that gap because you write and get all of that out of your head and then let it sit for a little bit. But you’ve gone through the process of thinking through everything so it’s percolating and getting kicked around in your head and clarity comes from letting it sit. So I absolutely love that approach.
You used something — kind of a mechanism — that was already in place: NaNoWriMo. Was it also a kind of accountability to sit down and get that done?
A hundred percent. And like, they have a discord channel. During non-pandemic times, they have library, like you could go there and like be with a group. I didn’t really participate in those but I did share my progress on Twitter with a NaNoWriMo hashtag. So like, there was still that level of interaction with other people who were doing it just on a different platform.
Well, it’s kind of like working out. If you say you’re going to do it and you’re just all by yourself, it’s easy to not follow through. It’s easy to just say, “Ah tomorrow. Oh I’ll start next week.” But when you’re a part of a community all doing something together, it’s way easier to stick with it.
Right. Like, you don’t wanna like embarrass yourself by being like, “Well, I just halfway through quit.” I’m gonna see it through because I know that other people are watching.
It’s good for anything you want to accomplish in life. Just tell one other person about it. Even my husband. You know, maybe I’ll have a plan for the day and if I like don’t want to be held accountable to it, then I won’t tell him. But if I really do want to be held accountable for it, I’m like, “This is what I’m gonna work on today.”
Nice. I love that. Sometimes it’s just a matter of saying it out loud and I love that you said just say it to one other person. And it is that notion of saying, “This is important to me. This is going to be my priority and I’m going to stick with it for this time period.
So, tell us about the topic. What is this book about?
So this book exists to help make my life easier but hopefully to make other people’s life easier too and I think the best resources come from somebody’s own need. Like, they’re not inventing a need. It’s like the need exists.
So the topic of the book, it’s called Writing for Humans and Robots: The New Rules Of Content Style. You can think of it as the modern approach to like the Elements Of Style, which still all rings true today. The only issue with that book is that it was written in like 1917 or something like that, and so they did not know about the internet.
Things have changed. Not the foundational rules. But when it comes to writing for an online audience, there is nuance.
Obviously, there are formatting things to consider. There are grammar rules that you can break because we speak in maybe a more, or we write in a more conversational style online. And then there’s also the fact that you’re not just writing for the people in your community or your country, it’s a global audience. And so there are sort of different rules to consider so that you’re being inclusive and that you’re not unintentionally alienating someone who really is a part of your audience, regardless of what language you write in.
So yeah, the book is essentially our style guide. But fleshed out with a lot of useful examples, because I think the style guide is the rule, but it doesn’t necessarily share all the context. Otherwise it would be as long as a book.
So yeah, the book is something I wrote for my team, but I wrote it in a way that it’s for anybody who writes online,
What a fantastic idea.
Even if nobody buys it, it’s still useful.
Well, fundamentally you recognized that there was a need because your own writers, your own editors had that need. So creating this for them to have as a reference, and then putting it in a format that is shareable for anybody else having similar challenges, is such a brilliant approach because it’s immediately going to help your own business improve.
Right. If nothing else I got that covered. So I’m happy with that. And I think the other thing that I thought about when writing this book is just, like, people have questions. I want to answer them but I can’t. Like, the whole reason I scaled up my business with writers, editors, whatever is because I can’t answer all the questions all the time.
You know, I need them to work with autonomy and so this book will help them to do that:
- “I have a question about writing listicals.”
- “Okay. Well, turn to the chapter about listicals.”
- You know, “I have a question about using images.”
- “Well, we have two chapters about that you can check out and then if things are still unclear, then definitely let me know.”
One of the most consistent things that I’ve heard from person to person to person, in all of my conversations so far for this podcast, when it comes to systems and processes, it’s about removing yourself from being the bottleneck.
A hundred percent.
And I think this is such a fantastic example of that. You are only one person, right, with a finite amount of time…
Okay. Yes. Amen to that.
But you cannot be in a growing company responsible for all of the things that are happening or to be that decision point for all of those things. So, this idea of creating this book as a resource first and foremost for your team really is acting as one of the ways to remove you as that bottleneck and to protect your time.
Absolutely. And that’s why I hired all those people when I did — the account manager, the project manager, a billing specialist — it’s because I was getting in the way of the company growing. And it’s also just, like, I just don’t like doing that stuff. So, you know, that’s gonna make me procrastinate.
So, it forced me to really think about how I do it, document it, teach it to somebody else. I’m here if you need me but otherwise, you have the reigns. You know, like, you got this
I really appreciate that everything you’ve said is rooted in documentation.
Mm-hmm, that’s the writer in me.
Yeah. It is so hard to pass the reins without documentation, especially with writing. There are so many little nuances that go into things.
I have a question about voice. When you are running an agency like yours, you work with a lot of different clients and each one of those clients will have a different brand voice, a different way that they speak in the style and the feel of their brand. How do you capture that for your clients or for your writers?
Yeah, no, that’s super important to capture the nuance of each client. They’re all different. Even if they look the same, there are some slight variations. So Nielsen. Norman group has this spectrum of voice and tone across four different dimensions. It’s like funny, serious, uh, respectful versus irreverent and so on.
And so when our clients first start working with us, they fill out our intake form that asks a lot of different questions about how they want to approach different things — kind of introducing our systems and asking if there are exceptions that need to be made — voice obviously being something that we have to define.
And so they will fill out the voice and tone spectrum and then we also have some additional questions, like, you know, are there words you’d use to describe your brand from like the personality perspective? Maybe funny versus serious isn’t even the right scale. Are you sarcastic? That doesn’t really fall on the scale. I mean, it’s kind of funny, but it doesn’t capture the nuance completely to only have the scale.
So we’re asking high level, we’re drilling down, and then from there, it’s really just a matter of working with the client over time and figuring out the edits that they make and kind of making our own style guide for them.
And I will say that another thing that has become bigger and bigger lately is a lot of clients want to write in a conversational tone, which is something that is hard to capture in that voice and tone spectrum. It’s something that we ask an additional question about like, “Is that something you want to do?
Conversational is definitely harder to capture in that regard.
It’s very nuanced. Because even within conversational, it’s like, how do you converse? Like, as a brand? Like how familiar are we getting with the client or with the reader here? It’s an interesting thing. We’re definitely continuing to develop our guidelines around that.
So we put these guidelines in place. You have your style guide for reference — the book — but as much as we put guidelines and things in place, sometimes they just don’t go according to plan.
Sometimes it’s just a mess. When things blow up in your business, how do you handle those situations?
Yeah. I mean, I think it just makes me to some extent question everything. You know, like what did I do wrong? Or how could I have made this better? Why did this happen? That’s the first reaction. And then, you know, I think about it and I realize that we’re all only human.
And I think it’s really important when you have a team, when you’re working with different people who work for your company, to never play the blame game. To never default to like, “You did this wrong,” because probably what happened is I wasn’t clear enough about what I wanted. Or I didn’t communicate a concept very well. And I shouldn’t expect people to read my mind.
I wish some clients would also realize that sometimes.
But you know, we use all these different tools and processes and things to try to bridge that gap. I guess my response to a situation like that is to do some fact-finding. To present the issue to relevant members of the team, to say, “This happened. Where do we think this went wrong? What can we do better in the future? How can we rectify this issue in the meantime?” And then document it in some way.
Usually for us, that involves a tool called Process Street — it’s kind of like a project management tool but also it has some other bells and whistles. So it’s like revisiting our Process Street workflow for creating content or whatever the issue is related to and being like:
- Could we make stuff more clear?
- Do we need to add an extra step?
- Do we need to add, like, an approval step?
- Maybe there needs to be another control on this step where somebody else is reviewing the work?
So for me, that’s usually what the process is. I think that I work with pretty competent people so I’m not necessarily concerned that they messed something up. It’s more like let’s just figure out how to fix it. That’s all I really care about.
Well, I love that you said you go back and evaluate your systems.
One of the things that I found to be the most important when I was rolling out the different systems and processes, as I created them in my own business: It’s not a create it, do it, and then forget about it. It’s a create it and then gather data and make little tweaks, and gather feedback and make little tweaks, and to ask:
- The client got stuck right here. The process didn’t work right here.
- Why didn’t it work? How can we make this better?
- How can we change the system, adapt the system so it doesn’t happen again?
- So many times people think systems are set it and forget it and it’s not. It’s set it and tweak it and tweak it and tweak it and dial it in and refine it.
But I think that’s a really important point, which is like, you’re not gonna get it right the first time, no matter like how brilliant you think you are or like how well you think you understand your clients, there’s always gonna be something that’s gonna throw it off. And so everything’s, like, in beta.
I mean, we just moved our client onboarding process to Process Street to just try to be more sophisticated about it — to make sure that we’re checking all the boxes, everybody relevant knows what’s expected of them, and we’re testing it. We’re finding all the issues with it right now. And like, that’s what I wanted. I wanted to figure out how to use it. The only way I could do that was to try it.
I like that you just said, “The only way I could do it was to try it.”
We have these ideas, we talk about it, and a lot of people will pontificate without actually doing it. It’s not until you get into the doing, and the making, and the setting it up, and the using of these items that you start to realize what questions you have or where something needs to be thought through a little bit more.
The magic and the clarity of all of that comes from actually doing it and using it.
Right. And I think a lot of people are caught in the idea of perfection or, “I want to get it right from the beginning.” And it’s like, you can get it as right as you can. Like, you could certainly start off on a good foot but it’s the same thing with the style guide.
I never thought it was done. When I started it, I knew that that was just the beginning. You know, I went in with the mindset that this is going to change a lot. And I think for any process, that is probably the mindset you should have.
That’s so good. Let me ask you this: You mentioned earlier that one of the first people you hired was a research person who would go in and do some research and put together an outline. I’d love to hear how important that is in copywriting, in creating content, whether it’s blog posts, webinars, training, whatever it is. Why research?
Yeah. Or even creating a brief just having that high-level view of what you’re eventually gonna do.
I would say the majority of the process is creating the outline. For us, it happens after we do keyword research because that informs the structure, some of the topics we wanna cover, and we want to share that data with the client too.
Like, what are the keywords we’re going after to make sure that we’re all on the same page? That’s what the outline is. It’s getting everybody on the same page. It’s doing a little bit of work upfront to set yourself up for success.
You actually do most of the work during the outline if you take the time to track down statistics, you want to use if you take the time to sort of flesh out those subheadings and the points that you wanna cover within them. So, I think we’re realizing at The Blogsmith that the step before the brief is probably even more important than the outline.
We do follow briefs. We do propose topics and give some level of direction. But I think what we’re learning is it’s better to spend a lot of time on the front end, and then each next step becomes that much easier.
Less wasted time. Less back and forth.
Oh, my gosh. Yes, There’s this idea. that people that are really good at creating content just have all these great ideas in their head and…
Right? And it’s perfect.
And that is definitely not the case. Great content does come from getting that clarity — putting together that brief about:
- What we’re going to be communicating?
- What we’re talking about?
- What’s the purpose of this piece?
- What do we want people to do after they read it or when they’re engaging with it?
What’s the goal. What does it add to your business?
Well, and then that brief is going to tell you what research you need to do and what facts you wanna gather and what statistics you might wanna lean into. And if you follow that process, you have a clear brief, you do the research, you put together the outline, the keywords are in there already. By the time you get to the point of writing copy…
Half of it’s done. Yeah. I mean, it changes the game.
And I think having an outline or a brief — having agreement and approval — that’s so necessary because otherwise, everybody’s just wasting each other’s time.
So, you also got married not that long ago.
It’s been a wild pandemic — a busy one.
Tell me a little bit about how life has changed for you,
Yeah. Obviously, making a commitment with your partner it’s a beautiful thing. I kind gave him an ultimatum, like a year before he proposed. Like, “You need to make up your mind, we’re either doing this or we’re not,” and he followed through, he, was like, right on time.
With the timing of the original date being March 2020, may that date rest in peace, the whole wedding thing, like really, forced us to understand how important we were to each other. And the fact that like, when it came down to it, we didn’t really care about the party and the pomp and circumstance. It’s like, I will just sign this marriage license.
He ultimately wanted to like, make sure like his parents were here and like his brothers, and we ended up inviting — our whole wedding party showed up. So the groomsman, the bridesmaids, and then our families, and that was really special. I didn’t necessarily need that in order to like, make the commitment, but I’m glad that it worked out the way it did because that was really important to my husband. And it did make for an amazing pandemic ceremony.
Going through that during the pandemic, it’s like, we just wanna be married. Nothing else matters. We just want to be together.
For how awful the beginning of the pandemic was because that’s when we were supposed to get married. You know what? It all worked out. We’re happy.
Well, it was fun seeing some of your posts and things on social as well.
Brian and I got engaged and got married really fast. My parents wanted us to get married in our church and I called and they were like, “We’re booked solid” for like a year, and I’m like, “All I wanna do is be married.” And they had called with a cancellation I’m like, “I’ll take it. I don’t care when it is. I’ll take it. All we wanna do is be married.”
It was the day after my birthday. I have regret.
There’s something to it.
To have that, I think at one of the toughest times in our recent history, to have that bright light along with, seeing your business grow is really something I think to be proud of.
It was a light in the tunnel. And the way this whole saga ends is that we did have our bigger reception and we held out for our dream wedding of having it at Red Rocks in Colorado, which for those who don’t know is a big concert venue. I mean, it’s just like incredible. The pictures turned out amazing.
But the funny thing is we booked what we thought was outside of concert season, but then the city of Denver who owns the venue booked a concert and they didn’t cancel our wedding.
Typically, they ticket your guests if it works out that way — if you did it on purpose — so then you have to factor in like the cost of admission. But because it was their mistake, we got to have our wedding at red rocks while a concert was going on, so it was worth holding out for that. And that would not have happened if it was the first date.
Oh my gosh, what a cool experience.
And then they let us watch a little bit of the concert at the end. We just kinda like snuck in and it was November, it was cold, some girl handed me some hand warmers. It was just, you know, it was like warm fuzzy.
The story that you’ll be able to keep forever is gonna be so cool.
So, let me ask you this: What can’t live without tool do you have that you wish you discovered earlier?
We’ve already talked about it but Process Street has revolutionized the way that I do business
Process Street lets you build your own processes. It has all these different fields and ways that you can customize it and ultimately, it really reduces the complexity of what we do
For people who are just getting started, I started with Todoist. When I first started working with other writers, I would just make assignments in Todoist. Very simple. Just give it a title, give it some details, you could add attachments or comments, you can assign it to someone, give it a due date, but that’s it.
As your business grows, that’s when you want to start thinking “How can I make these tools work for me, you know, like help make my life easier?” And it’s worth investing in one that’s going to save you a lot of time and mental energy.
100%. When things are frustrating, when you’re feeling overwhelmed, what do you do to get back on track, and keep on moving forward.
Sure. One thing is to switch up your perspective, like taking a walk, getting up from the computer. For me, like doing one of my hobbies, maybe baking or even like tidying up the house. Do something else. Something different.
Sometimes I just give myself the permission to take the rest of the day off. That’ll give me time to like ruminate on the issue and then I can come to tomorrow with more energy. I think that’s something I learned throughout the pandemic don’t always force yourself through a hard day because it’s probably going to cause more issues than it solves.
Do you also find that when you give yourself that permission to walk away when you’re not feeling it, when you come back, it’s almost like you’re getting things done even faster? It’s even easier to jump back into that creative space because you’ve had a break?
I think so. Sometimes it’s just listen to your body. I think that’s what it comes down to. Just do what feels right. Don’t force something that’s not gonna help you.
That’s a great piece of advice.
Writing for Humans and Robots is available on Amazon. If someone asked you: “Writing for humans and robots? Why do I need to care about robots or do they even want the same thing?” What would you say to them?
Ultimately, the human is the most important user because they are the ones that could actually buy from you. They’re the ones that want to learn something.
That being said, I think there is a balance that can be attained without sacrifice and comes down to like, being descriptive, making it easy for robots to index your content to then serve it up to the ideal human reader.
So robots are kind of like the medium that connects you to the reader. That’s how you should think of them.
That’s ultimately what the book is about. It’s just considering from both perspectives and how you can create a process around that too so that you’re not overdoing it. You’re not keyword stuffing. You’re not creating something for the sake of Google. You’re creating something for a human that could stand to benefit from it.
Fantastic. So really what someone could learn if they go grab it off Amazon is how to create content that connects with human buyers and inspires and motivates human buyers to take action. And also to create content that is search engine friendly, and that will help your content get discovered and found more often by the people that need what you’re talking about.
Exactly. And while I mostly talk about search engine spiders as those robots, I think there are implications too, for social networks that have some aspect of indexation or algorithms that prioritize different types of content. So lot of those same rules will still apply to those types of things.
So Maddy, tell us where we can find you online. If people want to learn more about The Blogsmith, where can they go?
Sure. So TheBlogsmith.com is everything about the business side of things. clients we’ve worked with all those details. And then, Twitter is where I’m most active if you have any questions. So @maddyosman. And then, if you want to learn more about the book WritingForHumansAndRobots.com.
Well, thank you so much for sharing your journey of seeking satisfaction and some of the behind-the-scenes things that you’ve been up to in the pandemic.
Absolutely. Thank you for having me.
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