Allie Decker is currently a content marketer at HubSpot, where she drives both content strategy and the execution of pillar content like The Ultimate Guide to Branding and The Beginner’s Guide to Structured Data (and many more epic guides).

She’s also an entrepreneur, running her own freelance writing business since college (and continuing to take freelance clients today while working full time at HubSpot).

In this interview, we cover Allie’s unique thoughts on freelancing vs. in-house content work, common mistakes freelancers make (and also tips to get and retain more clients), and writing tips to help you succeed whether you work in-house or for yourself.

You can find Allie on Twitter at @alliecdecker or on LinkedIn here.


How did you get into content marketing? What’s your origin story?

I’ve loved writing for as long as I can remember — short stories, greeting cards, even essays at school. Whenever I was asked about my dream job, “writer” was always my answer … I just never knew what that was supposed to look like.

I also loved business. I grew up in an entrepreneurial household and majored in marketing and international business. After college, I worked for a short while as a recruitment marketer. My favorite part of the job was writing job listings, social media posts, and paid ads for our open positions. I realized there was likely a need out there for full-time marketing writers who could creatively sell goods, services, or — like I was doing — careers.

I wasn’t familiar with content marketing at the time, so I started researching freelance writers and all the ways they got paid and published. I finally quit my job and have been writing ever since. HubSpot recruited me in April 2018, about 18 months after I started freelancing full-time..

How do you describe the difference between in-house employment and freelancing full-time? What are some surprising differences you’ve learned since making the switch?

Full-time employment is about being part of the bigger picture, being a cog in a machine. Everyone has a task that contributes to the grander strategy and the bottom line, and everyone’s aware of where that line is.

As a freelancer, you’re invited to contribute to the machine, but you never really become a part of it. You really never have ownership. You’re hired for a project, and once you deliver, your role is over (or you move to another project). Even as a consultant or a long-time contributor, I never fully became part of my clients’ teams or brands; I never found myself immersed in the big picture, bottom line strategy.

I didn’t mind the detachment that came with freelancing … at first. It felt more like freedom than detachment. But after 12+ months of truly working solo — no coworkers, boss, or brand loyalty — I craved a community beyond my clients.

I still freelance, but I truly enjoy being a part of something bigger than myself. I have noticed a major change in how much I can control my day-to-day: my projects are assigned, my deadlines are set, and my schedule is rigid … but I’m OK with giving up complete control to gain a community.

Do you find there are benefits to keeping a freelance writing side hustle while working full time in-house? On the flip side, what are the challenges and your experiences with doing so?

There are definitely benefits to keeping up my freelance business while working full-time.

It goes without saying that it brings in additional income, but what I find most impactful is that I’m able to continue to flex my “freelance” muscle while employed — sourcing and pitching clients, negotiating rates, delivering work, becoming a better writer, etc.

Freelancing and running a solo business are definitely learned and practiced skills, and I didn’t want to let that muscle weaken, especially since I plan to freelance for a long time.

Freelancing has also helped me become better established in our industry as a content marketer and strategist — and not just as a HubSpot employee.

With so many different projects, time management can be tough. It’s also hard not to work all the time … work/life balance is my greatest struggle. I love what I do, but that doesn’t mean I should be doing it all the time.

What’s the most effective way(s) a freelance writer can build a portfolio of clients that enjoy working with?

Here’s my best advice:

  • Pay close attention to every correspondence. You’ll learn a lot about a client and their work habits/approach from the very first email they send. When someone contacts me, I make a note of their greeting (Did they bother to say hello?), how they approach my work (Do they acknowledge that I’m a professional, or do they assume I’ll work for free?), and what time they send their email (Does it seem like they have work/life balance — and do they respect mine?) I don’t necessarily use these factors to judge or decide whether or not to work with someone, but they do influence my first impression.
  • Be confident. I’ve learned that most clients have little to no idea what they need … they expect you, the consummate professional, to figure it out for them. If you approach correspondence with confidence and assurance (about your rates, timelines, etc.), clients will most likely follow along. They expect you to “set the tone,” given that you’ve done this for many other clients before. Confidence also assures a potential client that you’ll produce great work.
  • Promote your values, not just your skills. There are lots of talented freelancers out there, and most share the same basic skill set.  While your skill set as a freelancer makes you an ample candidate for jobs, your values are what set you apart. Promote what you stand for just as much (if not more) than what you can do … doing this will attract clients who stand for the same.

What are some common mistakes freelancers make when building the “business” side of things (so operations, client acquisition, client management, etc. – all the non-writing stuff)?

I personally think some freelancers prioritize personal branding over the actual work.

I understand the value of personal branding and have even written about the topic, but I don’t think it’s the most important part about running a business.

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In my opinion, writing is the most important part. It’s the heart of my business. Not only does doing real work bring in money (which is always great), but it also proves my worth among clients, drums up valuable word-of-mouth, and establishes my skills and competency beyond than a clever logo and daily-updated blog.

Sure, personal branding is a way to establish and market yourself as a freelancer, but I’d rather let my work do that for me. You don’t have to be known as much as you need to be good at what you do.

Also, I’ve learned that if you’re not a master of one, you’re probably a master of none. A lot of freelancers talk about “niching down,” and that’s because it’s incredibly important.

When I started freelancing, I wrote about literally everything — business, productivity, travel, health … even horses. (Ha.) It was miserable, and my content wasn’t even that good. I was just desperate to make money and have clients. It wasn’t until I backed up, “niched down,” and became intentional in my client choices and pitches.

Now, my content is way better and more authentic, and it’s much easier for me to research and write my content because I choose topics I have true experience in and passion for, which brings me to my last topic …

A great content marketer is only as good as his or her true knowledge about a topic.

While being a good writer is important, it’s also crucial to have the experience and understanding to back it up. I see too many freelancers taking courses on writing mechanics and creative writing. Instead (or in addition), spend time and money digging deeper into your niche.

If you’re a health and wellness writer, try new exercise classes, forest bathing, or trending recipes.

If you’re a sales writer, ask to shadow a friend or colleague while they conduct calls.

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Get in the mind of your reader — they’ll probably care more about what you have to say more than how you’re saying it. These experiences will also help you formulate original opinions and POVs that’ll spice up your research-driven content.

How do you think about constructing a content strategy, either in-house or for any given client? Take that how you will, either at a high level (how you generally hope to get results for a client given the increasingly crowded content space) or more granular (SEO-keyword-driven vs. thought leadership driven content, or something else entirely)

My projects at HubSpot are pretty granular. While I’m involved in the overall content strategy, I mostly focus on producing the very best individual pieces as part of that strategy. I approach each piece considering a few key things: the audience, the takeaway, and my experience. I always write for the reader, and I always include at least one actionable takeaway. I also consider how my personal experience ties in, and if I don’t have any, I find someone who does.

I’m very passionate about thought leadership content and content that’s driven by a first-person perspective. There’s obviously a place for regurgitated listicles and how-to guides (heck, I write a lot of them), but I think it’s original thought and storytelling that really creates impactful content.

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Blogs like First Round Review thrive on thought leadership (Image Source)

Every brand should feature some thought leadership in their content strategy.

Is there an aspect of your personality or your background experience you attribute to your ability to write well and succeed as a content marketer?

I’m a perfectionist. I think that’s what makes me such a good writer — at both a high-level (creative concepts, well-written outlines, etc.) and at a more granular level (grammar, sentence structure and flow, formatting and aesthetic). It also drives me to deliver spotless content to my editor and clients.

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But while it’s served me well, perfectionism isn’t something I always consider an asset. I had to learn how to mess up and be OK with failure in order to discover how to succeed.

The performance of my work as a professional marketing writer hasn’t been as easy to control or expect as my performance in school, and this wasn’t always a comfortable lesson.

What would you do if you didn’t work in content marketing?

I might be working at a magazine or newspaper, telling stories and unearthing news. I might be writing copy at Ogilvy and Mather here in downtown Chicago. I might be working with a dog shelter, using content to raise awareness and funds.

I have no idea what I’d be doing if I didn’t work in SaaS and tech content marketing, but I’d definitely be writing.

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What inspires you? What kind of writing, media, personalities do you follow, and where do you get your ideas?

I like to absorb new voices, writing styles, and perspectives, so I tend to read content that’s radically different than what I write. If I read stuff too similar to what I write (unless I’m doing intentional research), I don’t learn anything new — and I fall into a comparison trap.

My friends and family are my biggest inspiration. No one in my personal life does what I do. It’s nice to get out of the marketing/entrepreneurial/content sphere and talk to teachers, nurses, bartenders, realtors, salespeople, recruiters, and others. They’re real and unedited, and spending time with them gets me in touch with the kind of audiences to whom I’m writing.

I come up with a lot of my ideas while working out. Since I work so much, exercise is when I can truly shut off the “working” part of my brain and focus all my energy on my body … and that frees up my brain to let organic, natural ideas flow. (Stay tuned for the best way to capture ideas when running, swimming, or lifting, though — I’m still working on that.)

Gimme three tips to improve my writing? Or rather, tips that anyone can use to become a better writer.

  1. Treat content development as a multi-step process. There’s a reason that high-quality freelancers don’t turnaround work in a day. Just because I can write 2,000 words in a day doesn’t mean I do. Great content takes a few days: a few for research, a couple for “brain dump,” and a couple for thorough edits. I open and close my projects a couple of times throughout the course of developing content. Not only does stepping away from a project give you new ideas and perspectives, but it also allows you to clear your head and approach your writing fresh and ready.
  2. Read more than you write. Every writer says this, but it’s so true. I’ve established my voice and approach to content development by reading content so wildly different than what I write: news, op-eds, lifestyle blogs, even horror fiction (my favorite). Some people prefer to read content within their niche; that’s fine, too — just be consuming as much or more than you’re producing.
  3. Ask for help. I’ve learned so much through edits from co-workers and mentors. It can be difficult to subject your work to criticism, but you can’t learn unless you know precisely what you’re doing wrong and how you can improve. Educate yourself through the context of your own work. Use blogging tools, too: Grammarly, Hemingway Editor, The Writer’s Diet, and Jargon Grader are great places to start.

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