Over the past few months, I’ve been interviewing some of the best content marketers and freelancers in the industry to learn more about how they got started, what lessons they’ve learned, and what advice they would share with other freelancers.
In this first interview series, you’ll learn from the following experts:
Elna Cain
Adrienne Barnes
Rand Fishkin
Maria West
Kat Boogaard
Lizzie Davey
Jessica Malnik
Dana Herra
Jason Resnick
Tommy Walker
Deya Aliaga Kuhnle
Let’s dive in!
Elna Cain
1. How did you get started with freelance writing and blogging? Take us through your journey.
I started freelance writing in 2014. I had just ended my 1-year maternity leave, and at that time we moved from British Columbia to Ontario. Before I had twins, I was a Special Education teacher and primarily taught children with Autism in ABA therapy. My MIL helped me raise the twins and moving in with them was the best decision of my life.
When September 2014 came, I had enough time during my twins' nap times to dabble in something. My husband suggested VA work but I found freelance writing a better fit for me. I'm more creative, and I didn't want to manage something, I wanted to create something instead. So I read up on moms who were staff writers and talked about staying home and getting paid to write. This intrigued me. I had blocks of time, I had a laptop, maybe I could do this?
My husband helped me design a simple service-based website, and I spent my free time reading about freelance writing. I started emailing other writers, asking them what to charge and about managing clients. This was new to me. I only used the internet for Youtube, Facebook, and Amazon!
I spent the first few months writing blog content, marketing my business, and finding clients on job boards. I found my first client, and over time I changed my niche from natural health and parenthood to digital marketing. Over the years, I've worked with small businesses and big notable brands, and this has also grown my other business: blogging and product creation.
And this freedom to start new websites or work with certain brands has allowed me to volunteer at my twins' school, have family road trips and start fun renovation projects.
2. What two lessons from blogging can be applied to email marketing sequences?
Be authentic and use storytelling.
I started my brand, Twins Mommy in 2016. This was the place I shared my case study in growing that blog. I wanted to try "traditional" blogging tactics like affiliate marketing, product creation, and using platforms like Pinterest and Instagram. I found the blog posts where I shared my challenges and thoughts about my blog plan I received the most comments. People follow the blogger, not the blog. So, I didn't shy away from my failures. Instead, I used it to connect with my audience through storytelling.
The same goes for your email sequences. I get the highest open rates when my email subject lines are more internal (What I did to land a client, How I grew my pageviews to 54,000, or I've been on Twitter more...), and in my email, I share a story about what I did. This helps my subscribers trust my information and who I am as a person. I'm a mom who is a writer and blogger. Not a marketer who is a mom.
Adrienne Barnes
1. How did you start your work in marketing? What was the first job/gig you took?
I started working in marketing as a freelance content writer. My very first job came from Upwork, and I wrote blog content for a neurofibromatosis charity with a positive and upbeat tone. It was an interesting project for sure.
2. I have two sub-questions here: What is the one brilliant way you've seen data being used in content strategy, and what's one terrible example of data-driven content strategy?
A brilliant way I've seen data being used, is when a B2B SaaS company uses their own proprietary data to create content that will be interesting to their industry. It makes such a difference in the quality of the content. The worst example is when data isn't used to create a content strategy. This happens often when marketing teams aren't clear on their customers' pain points, needs, and jobs-to-be-done.
Rand Fishkin
1. Can you share your journey in the marketing industry? You've worn many hats in the past 20+ years.
I started in digital marketing doing web design, then SEO consulting in the early 2000s. In 2003, I launched a blog called SEOmoz that later became the software company, Moz, and grew that from a tiny team to 200+ people, $50M+ in revenue, and tens of millions of monthly visitors. In 2014, I stepped down from the CEO role and left the company 4 years later to start a new one: SparkToro, which makes audience research software. We're very different at SparkToro - eschewing venture capital and hypergrowth in favor of Chill Work and a tiny team of only three.
As SparkToro's CEO, I do a lot of talking to customers, helping folks use the product, and talking about the problems SparkToro helps solve. We all work remotely, but I'm on the road a good bit for conferences and events.
2. What are two things you wish (as a SaaS founder) a freelance marketer/writer should know or do?
We've used a lot of freelance and consulting talent at SparkToro, and I've been consistently impressed with folks in that world. My best advice for anyone in that role is to think like a business owner/founder/CEO -- put yourself in their shoes, think about the things they care about results-wise: branding, traffic, sales, leads, perception, etc. If you're struggling, ask! Business owners love talking about themselves, what they care about, what they're focused on, what they value and don't. Use those learnings in how you pitch projects, present results, and prioritize work.
Maria West aka DTC mom
1. How did the brand DTC mom come to be? Was it from the beginning of your marketing journey or evolved somewhere in the middle?
I started my content marketing career in an agency with complex B2B clients, then moved in-house to financial services after that (boooooring). When I started freelancing over the pandemic, I fell in love with the consumer space and wanted to lean into the clients I was getting that matched my new-parenthood life stage. I decided to niche down as DTC Mom last year (during the third trimester of my second pregnancy), and it gave me the energy to get back into things after having my son. Since "I'm not like other moms," people quickly came to know me as the parenting copywriter for DTC/ecom space, so it's helped my personal brand immensely. However, I'm about to take a career pivot with a new B2B SaaS full-time role. It'll be interesting to see what happens! Stay tuned.
2. You have a unique personality—witty, funny and unapologetic. What's the secret to developing that, and how does it help in being a kickass marketer?
LOL Well, thank you (I think!) Honestly, I'm me. Ask anyone who has met me in person, and they'll say online Maria = IRL Maria. I do a lot of my best work and most creative stuff off the cuff, so I found Twitter a natural place to connect and share thoughts. I'm also a starter and think quickly, and I love networking and hyping people up. People skills and being genuine and likable can go a long way, and using your gut to find clients, projects, etc. YOU like matters big time, too.
Kat Boogaard
1. Do you recall your first (a few firsts) writing project? What was it like, as in Freelance or in-house, what niche etc.?
I did quite a few writing projects throughout college and even in my in-house marketing job. But as a freelancer, my first paid writing gig was writing one article per month for a local women's magazine (in print!). I was paid $50 for every 500-ish-word article and was absolutely thrilled. Some of my other early projects were writing blog posts for a storage unit company (for $40 per post!) and product descriptions for fitness trackers as part of a content mill. Not exactly a glamorous start.
2. Your blogs have a theme of making freelancing topics relatable for people with traditional jobs. Is this something you aimed at, or it naturally evolved as such?
My niche as a paid writer is the "world of work," which means I write a ton of advice and content geared toward people who are employed in "traditional" full-time jobs. But on my own site, most of what I publish is aimed at fellow freelancers who are trying to start or grow their businesses. I worked in a traditional full-time job prior to freelancing, so I do try to write content for existing freelancers as well as people who are considering taking the leap.
3. On the same note, develop your voice is often an advice for freelancers to stand out. How to develop that voice/flavour when working with multiple clients?
One of the compliments I receive the most is about my writing style, which is always flattering. My own writing voice tends to be pretty casual and conversational, with a decent dose of humor and sarcasm peppered in. Obviously, when doing client work, I need to adapt to my client's tone and style guide. But honestly, most of my clients found me because of my own voice and style—they see my work in other places, enjoy it, and want to do something similar with their own content.
From reading your work aloud to taking notes about the approach of other writers you admire, there are tons of tips for finding and refining your own voice. But my go-to one is usually something along the lines of "stay patient and commit to the process." Finding your voice is a journey, and an oftentimes-long and constantly-evolving one at that. Keep experimenting to find what feels right for you. I go back and read some of my old stuff and chuckle because I don't think it sounds like me at all.
Lizzie Davey
1. How did you start freelancing?
I started freelancing in 2014 when I decided to spontaneously move to Spain with my ex-boyfriend with just one month’s notice. It was chaotic, but I had already been blogging for five years prior to that and had a successful travel blog I thought I could leverage to get clients.
My very first client was the company I’d left which hired me for a day’s work. My second was a hotel brand I found on Craigslist. I ended up working with them for 1.5 years. At the time, my roster was a mishmash of clients in pretty much every industry you could think of (so much for becoming a renowned travel writer!) that I found through content mills, job ads, and doggedly pitching.
I had set myself the goal of replacing my full-time income in a year otherwise I would go back to the UK and “proper employment”. Turns out freelancing was pretty lucrative and here I am almost 10 years later!
2. What are your 2 tips for managing personal content with client work for freelance writers?
I’m an absolute stickler for time management! Ask anyone I know, and they’ll tell you I’m predictably on time, every time. These are my best tips:
a. Bulk create content and plan ahead
I have a personal content schedule that I map out at the end of each week for the following week so everything is set up and ready to go. Bulk creation is my best friend and I will often spend a couple of hours on a Friday writing up social content, scheduling blog posts, and planning my LinkedIn content and newsletter topics for the next week.
b. Time block days based on my most productive hours
I also plan my days to maximise my productivity hours. I’m most productive between 8.30-11am and then I usually get a second wind between 2-4pm. I focus on client work for the first chunk of the day (basically I “eat the frog”) and then in the afternoons, I focus on creating content for my personal brand, taking calls, and working on future personal projects.
Jessica Malnik
1. How did you get started with freelance writing?
I started moonlighting on the side of my day job writing the occasional freelance article or two about a decade ago, and then in 2018, I started my own business.
For me, I had saved up enough money in advance to have a runway for about seven months, and my previous boss also became one of my original anchor clients. This gave me peace of mind in the first few months as I was still getting a feel for running a business.
I made a ton of sacrifices. There were many late nights and Friday nights spent in front of my computer instead of going out. In the end, I’m also building something that’s truly my own. And that’s deeply satisfying.
2. What's your advice for freelance writers in the context of finding their tribe?
I wrote an article regarding this, you can find more about it here. As a remote/asynchronous worker, I think there are a lot of chances of meeting and making internet friendships, whether that be through Twitter, LinkedIn, or even Instagram hashtags, you can always find minds that think like yours and strike up interesting and fun conversations, just for the sake of it. Put yourself out there!
But mostly, I would recommend investing in conferences that are going to make you grow! The largest investment I made last year was going to CaboPress in early October 2022, and it was so worth it. Two and half months later, it has already paid for itself 3x over.
Dana Herra
1. What's been your journey in content marketing?
I was a journalist first. That's where I learned critical skills like storytelling, interviewing, and cutting fluff without cutting flavor. After 10 years, I eased into marketing - my first full-time marketing gig was as the editor of a university's alumni magazine. So it was journalism but from a marketing angle. I learned copywriting on the job (and from Copyhackers) and while I still do a fair amount of it, found I prefer long-form written content.
Over the next few years, I held marketing director jobs for several organizations. I kept learning everything I could about content marketing, applying it on the job as I went along. When I learned an interesting concept I couldn't get approval to try, I started freelancing. The whole B2B world was a giant lab for me to experiment in and learn from.
Late in 2020, I was a victim of pandemic-related layoffs. By that time I'd been freelancing for almost six years, and taking my side hustle full-time seemed just as good a bet as getting another job. January was the start of Year 3.
2. You recently tweeted that "4 blogs per month on some keywords" is a bad content strategy. Give us a sneak peek (1-2 examples) of a good content strategy.
The problem with basing your content strategy on tactical advice like "write 4 blogs a month" or "post 5 times a week to LinkedIn" is that it's tactical. It's not strategic. If that activity is going to make an impact on your progress, you need to know what to create, not just where to put it. Otherwise, you're just spinning your wheels and making noise.
A good content strategy starts with a goal. Like "become a recognized thought leader" or "generate 10 demo requests a month." You need to know why you're even creating content in the first place.
Next, you need to figure out how to measure your progress toward that goal. I just wrote a newsletter about this. For the thought leader goal, you might track social media engagement, press opportunities, or invitations to speaking engagements.
Figure out the audience you need to reach to make those milestones happen. Who are they? What's important to them? What makes them excited or scared or mad? Where do they hang out? Who do they trust for information on your topic? And why should they listen to you?
Now you're ready to start strategizing. Your content strategy should be designed to post the kind of content your target audience likes to consume in the places they expect to find it. Your strategy tells you where to post and how often, but more importantly, it tells you what to talk about and why.
"4 blogs a month" isn't a content strategy. It's not even the beginning of a content strategy. It's the middle. Before it you have "why do this" and "who is it for," and after you have "where do I distribute this" and "how do I measure it." Then you take what you learned and start again.
Jason Resnick
1. How did you get started with a career in email automation?
I started out as a web developer, but then around 2014-2015 I saw a trend that tied in what people saw on the web with what they were taking action on in their inboxes.
As a study of human behavior (I minored in Psychology in College) and a data geek, this fascinated me and I was hooked.
My unique ability to map out complex ideas and campaigns in a simple way due to my skills as a developer, it's helped me and my clients tremendously.
2. What are your 2 tips for marketers or creators to avoid being "just another email campaign?"
The first tip I would say is the more specific you can be with your campaign, the better the results. That may sound vague, but when you use the language that your subscribers use and can anticipate their thoughts, the campaign becomes much more powerful.
The second tip is any nuance and personalization you can make will go a long way.
For example, I run a newsletter that has a tagline/ In that tagline I use the word "freelancer." Not everyone on their list calls themself a freelancer. Some identify as a consultant, virtual assistant, or a developer, etc.
If they've filled out a survey and told me what they describe themselves as, I store that information and swap "freelancer" out for it.
Tommy Walker
Q1) How did you get started with content marketing? How was the journey to The Content Studio?
I started my career after getting fired from a retail job over a pair of pants. Having never been fired before, I decided I'd never put myself in a situation where someone else had that kind of control. With zero prospects and a laptop with a crack in the screen from corner to corner, I started studying what was going on in internet marketing, which I had a small background in.
Two weeks later, I was introduced to my first client by someone I met at a random Super Bowl party. I took whatever work that'd pay, which led to running a Facebook page for a client where we grew from 0-150k followers in the first month shortly after Facebook introduced Pages to the platform.
A few years passed, and I eventually started writing for the site CXL.com where I would become the most trafficked author in my first year of writing, which I then negotiated into becoming the full-time editor. We built that blog to a pretty considerable size, and eventually, I was recruited into an unknown startup called Shopify (pre-IPO).
Within a few months of working on the core product's blog team, the CMO asked if I'd be interested in running the enterprise blog, where I had the unenviable task of:
1.) Distinguishing Shopify Plus from the rest of the enterprise ecommerce market, and
2.) Distinguishing Shopify Plus from Shopify when there were very few differences in features
Fortunately, I was able to do both and helped see Shopify Plus to their first 1,500 customers.
Eventually, I left Shopify Plus to work with Intuit where I went from running the U.S blog to running Global content spanning 16 markets with 45 contributors across multiple disciplines. This was an amazing learning experience where I learned how to build content operations that could scale quickly and efficiently. Sadly, Intuit eventually ended up laying off 7% of their entire business portfolio, of which I was one of 117.
Shortly after the announcement, deciding I never wanted to be put in a position to be laid off again, I registered my business - The Content Studio, and in the past two years have had the pleasure of working with clients like GoDaddy, Twitch, and LinkedIn.
In late 2021, The Content Studio also launched a web series called The Cutting Room, where we talk to industry-leading marketers about their content marketing philosophy, process, and pre-game before they edit an audience member's article live on the stream.
Q2) What is a lesson from The Cutting Room which is relevant in 2023 as AI tools see increased adoption?
The biggest thing my guests and I have talked about is differentiation. Having a point of view and taking a stance on whatever industry it is you're in.
A.I. has been an excellent research tool, and works well to provide inspiration and help position your thoughts, however the idea itself has to be born of market research and tap into some kind of desire, which can only be done by a person.
We've heard people recommend using A.I tools for tasks like generating headline ideas and recommended semantically related keyword clusters, which have genuinely been great use cases.
For my part, I've been experimenting with improving the specificity of my prompts to give the A.I a far clearer direction, which has, in turn, has helped me to give better feedback to the people I collaborate with the most.
Deya Aliaga Kuhnle
1. How did you get started with freelancing? What role did your internships and uni days play in that?
Never in a million years did I think I would be freelancing or end up owning my own business.
I was raised to follow a very step-by-step path: study hard, get straight A’s, get into a good college, do a few prestigious internships, get an entry level job and climb the corporate ladder for 40 years. So after graduating from university, I started a 6-month internship at a large consulting company where I was working more than 40 hours a week earning minimum wage.
That was honestly the first time I ever confronted the concept of: “THIS is what I am supposed to do for the next 40 years?”
I couldn’t make peace with it.
This brief glance into my corporate future forced me to re-evaluate a lot of things about my life. Out of pure desperation for an alternative (ANY alternative), I began freelancing in the evenings for $10/hr.
I offered absolutely everything as a freelancer because I had no clue what I was doing. I offered voice overs, admin work, design, copywriting, editing, translations, and a few other things when I first began.
All of those eventually led me to become a freelance Digital Business Manager — which was the career that stuck. :)
2. You've been in key decision-making roles as a freelancer as compared to, let's say, writing a blog for a company as a freelance writer. What's a day-to-day takeaway you have from having those roles?
So many takeaways! Though I will say that in working alongside CEOs: A CEO’s favorite freelancer is the freelancer who asks themselves: “How can I make things easier for my client?”
For example:
If you need a client to review something, include the link and specifics on what you need feedback on to move forward.
If you need a decision from your client, present them with researched options instead of just handing them your problem.
If you don’t know something, google it first. Double check the team google drive, search through your slack history, search through the project management tool. Try your best to figure it out first.
If your client seems stuck on something, offer up ideas or advice you have on the topic. You have a unique perspective on their business; most business owners would be delighted to hear your strategic feedback.
From the client’s perspective, they have a million things on their to-do list, a packed calendar and everyone (internal team members & external clients/customers) is constantly adding more problems and questions onto their plate. Do your best not to be one of those people, and you’ll be their favorite person on the team. When the CEO and I decide who to re-hire for a job, who to pay more $ to, or who to refer to others, it’s always the freelancers that make working with them a breeze.
And I know it’s easy as a freelancer to say, “that’s not really within my job description,” or “that’s out of scope,” and that’s totally within your right to say and think. But if your goal is to be indispensable, to be promoted, to increase your rates, to be referred out, to become the industry go-to — this is the easiest way to get there.