AMA on Mastering Freelance Project Management with Marijana Kay

Cierra Loflin
February 9, 2023

Marijana Kay is a SaaS freelance writer of 6+ years for brands like Shopify, Hotjar, ConvertKit and the Founder of Freelance Bold. This AMA (orginally held in the Superpath Slack) covers: 

  • Creating workflows around project planning with clients and freelancers
  • Writing content briefs
  • Handover & feedback/revisions
  • Advancing a freelance career
  • ...and more! 

You can connect with Marijana on Linkedin and Twitter, plus grab her project planner for freelance writers here.

How can you avoid the feast/famine cycle as a freelancer? That was always my biggest challenge.

Oooh even though I haven’t really felt that fear of “oh shoot where will my work for next month come from” for a few years now, I feel that question in my bones as it’s usually the one that keeps people from starting or sticking with freelancing long enough to feel great about it.

Initially (the first few years in particular), the thing that helps the most is constantly focusing on two things: building your portfolio and cold pitching. These two have to work together—your portfolio isn’t enough if no one sees it, and your pitching will be without results if you show potential clients the reasons to trust you (i.e. that you know how to write). Until you have a consistent influx of work, focus on these two whenever you have spare time!

And then later on, your reputation builds up, you get bylines, people share your work, you show up on podcasts… and so on. People start trusting you and recommending you without you doing any extra work! So in this case, I recommend booking projects in advance even if you’re currently booked out for the month or something like that. This way, you’ll always feel confident about what’s coming up, and also show potential clients you’re in demand!

And finally, some months you’ll make twice as much as you want and others you’ll make less, and once you start planning your life financials around that, life and work become a lot easier and less fear-inducing 💪

Any tips for cold pitching? Is it worth the effort - and have you found clever ways to cold-relationship-build into a pitch that didn't annoy folks?

My best advice is to place yourself in the shoes of the person on the other end; I feel like many freelance writers I talk to/coach don’t think to do that.

Is what you’re saying relevant and creates a baseline for them to trust you? Have you linked to previous work? Mentioned results you’ve created? Shown in any way that you know what you’re doing and that they’re not alone in wanting to trust you?

What’s worked best for me so far when it comes to pure cold outreach (i.e. we haven’t had any contact or connections before) is keeping the email short but really researching the company, its content, the content lead I’m reaching out to (including content they’ve shared, podcasts they’ve appeared on etc.) and tailoring those few short paragraphs to the challenges they might be facing.

I could go on and on but really spending time on researching a few individual companies—rather than sending generic, identical pitches to 100 companies—is what made the difference for me in ~2017 to win high-paying clients and build my reputation of a trusted, quality writer 🙂

What are your must-haves (from a client) to get a piece of content started? (Brief, guidelines, etc.)

The absolute must-haves are a brief and at least a basic editorial guidelines document. If a company isn’t able to provide these two (the brief for each individual project, of course), I’ll usually decline working with them.

I know some writers are okay just working off of a keyword or something like that, but for me, this isn’t sufficient and I need more details to make the piece hit the goals it needs to!

On top of the must-haves, the nice-to-haves are things like a blog post template, example of a final draft (for formatting and CMS purposes), customer case studies, a database of partners or in-house experts I can reach out to, and a library of product screenshots and walkthroughs I can reference or use.

Any tips for streamlining the SME interview process to ensure things stay timely for your sake?

Most of the times, I’ll do everything I can async over email because I’m based in Europe and more often than not, we can’t even find an overlapping time to chat on a call. So that definitely helps! I write out a list of 3-5 most relevant questions to their expertise and encourage them to respond to the one(s) that are most interesting and unique to their experience, and also recommend they use voice notes or Loom if writing might take too long. This has helped massively!

For calls (which are really rare for me compared to async interviews), I try to make it clear upfront that we’re focusing on this one-two narrow areas and that I want to respect their time and wrap up within 15 minutes or so. I hope that helps! 😊

I think I have good enough people skills to do well during a 30 minute intro, but I'm by no means a salesperson. Do you have any recommendations for turning these "chats" into more formal, higher converting "demos"?

Do you mean during discovery calls with potential clients? Or something else? I honestly rarely do those anymore because the companies that reach out to me have an established process in place and they usually choose to hire me without even talking with me over a call (Shopify and Hotjar would be some examples of those companies). We end up going on a call to get to know each other more so than for me to sell my services, if that makes sense 🙂

For those calls that I do have, I aim to focus on understanding what they need (e.g. some companies need someone who will help them direct their content efforts, others just struggle to find the time or hire the in-house writers with enough expertise so they rely on freelance writers), so I then share how I can help and what my process entails. I position myself confidently, as the pro that knows what she’s doing, and how I can help rather than skirting around the idea of them hiring me. I talk about previous clients who have had similar issues and how I managed to jump in and create results.

Is this what you meant? Is that helpful? Let me know, happy to elaborate more if you need me to!

How do you handle clients that use different project management tools? I have clients using Asana, Clickup, Trello, and Notion. And I'm losing my mind trying to stay on top of them. I've tried automating with Zapier, but it didn't work for me because of the way my clients structure their PM tool. Any advice to keep me from losing my marbles? 😁

Ohhhh the project management tool conundrum!! 😅

Honestly, I have a little folder in my Bookmarks bar in Chrome called Clients, and inside of it I have all the bookmarks to my clients’ project management tool. Asana, Monday, ClickUp, Welcome… It’s a lot🙂 I name every one after the client so that I know what I’m clicking on (instead of just naming them after the tool).

I then check each one as needed, when I’m working on a project with that specific client.

And when it comes to email notifications, I use Superhuman and I’ve created a split (like a separate email tab) with rules for all emails from those tools to go to. The rules for it go something like: OR OR OR OR and that helps massively as it keeps my main inbox clean.

I’m sure you could set something similar up in Gmail, Outlook and anything else that has the option of filters and rules! I hope that helps 💪

Other than increasing writing prices, are there any other ways you've scaled up your income as a freelancer?

Nope, not really! I’ve increased my rates every year and sometimes twice a year since I started freelance writing full-time in 2017.

I haven’t hired subcontractors and I only choose to work with clients and on projects I really like, and that’s about the best thing a job can be for me. The idea of running an agency-style service business isn’t attractive to me, at least at this stage of my career.

I do run Freelance Bold, which is a library of resources aimed at freelance writers, but that isn’t really about scaling as a freelancer but expanding what I do into new venues—so not sure if that would apply there. :)

What's your take on the freelance industry right now? are you seeing more companies rely on freelancers? or less?

I feel like the need for good freelancers is increasing, so the bar for writers has likely increased—that’s my impression as of recent. The layoffs and all the turmoil in the software/tech world makes it hard to understand where exactly we’re heading, but I think that companies see freelancers (not just writers, but also designers, SEOs, etc.) as a way to get things done and create results without long-term commitments and risks that come from huge hiring sprees. So freelancers who know how to showcase the value they bring to the table will always be valuable and in demand, I believe 👌

What are some of your go-to research sources or processes to find stats/data in the SaaS world?

I unfortunately don’t have the shortcut for this, no matter how much I wish I did! A big part of the process of finding good data is just spending enough time digging deep enough to find the original source. A lot of the “20 stats you need to know about [topic] in 2023” reference data that’s a decade old and it’s one my biggest pet peeves 😅

Some ways I try to find recent, relevant data:

  • using the PDF filter on Google search
  • using the timeframe filter on Google search
  • using a tool like Waldo that lets you sort through results
  • searching for “state of [industry]” reports because they’re usually an original report rather than the curation of many reports

I’ll add more if I think of some other ways!

What are your best tips for retainers/retainer clients? Good ways to structure a retainer, when to turn an ongoing client into a retainer, raising rates with long-term clients, etc.

I have clients that I’ve worked with on a recurring basis for 2+ years, but the relationship we have was never defined as a strict retainer, i.e. I don’t promise them X articles for $X each month.

Instead, after the initial couple of projects, we talk about whether we’ve enjoyed that process and want to keep working together. If so, my recommended process is to define a rough scope for an average month (for example, two 2,000-word pieces per month) and then, say, mid-February chat about March and confirm projects for March (along with briefs).

This allows me to plan ahead of time for any vacations and other interruptions to my capacity so I can say “hey, I won’t have full capacity in March, can we only do one piece and go back to two in April?”

9 out of 10 clients agree to this type of a deal, because it’s flexible on both ends, as long as there’s transparent communication. It also makes raising rates easier because there’s no fixed retainer in place and they can tweak scope if they need to based on their budget.

I hope that helps, let me know if you want me to elaborate on any of this 🙂

How to manage continually marketing / “keeping the pipeline full” while you currently have a full/mostly full client roster?

For me, after all these years building my name and reputation, new work comes my way from referrals and people finding me on Twitter or through an existing byline. So when they do reach out, and I already have the next month or two booked, I just slot them into the next available month (this is exactly why I’ve developed the project planner and what it helps me with the most)!

So any marketing you do that includes ‘passive’ activities like sharing your work, testimonials etc. online can follow this same approach.

And if you’re actively reaching out to potential clients, I’d recommend adding a line that’s along the lines of “I’m currently booked out for the next [e.g. 2 months], but if this sounds like something you need, I’d love to chat about a project in [the month you have your next opening].”

This shows them not only that you respect their time (and expect them to respect yours) but that you’re in demand! Which helps with the mental barrier they need to cross when hiring a new person. I hope that helps! 🙂

Do you have an example of something a client did to be exceptionally easy to work with?

Yes, I have a few!

  • Removing the process step of me sending them an outline to approve before I start writing (they said “you already do a stellar job with outlines” as the reasoning. Reviewing outlines can be a useful step but with this particular client it helped to remove it!)
  • Removing the task of writing social copy for the blog post
  • Providing a table full of customer testimonials, results, case studies etc. that I could freely use in my drafts
  • Providing connections with partners (like the apps they integrate with) for contributions to my drafts
  • Asking “what else can we do to make this process easier for you/to help you do what you do best?”

What did the journey look like to start writing for big names in SaaS like Convertkit or Spotify? Was there a 'breaking in' moment or article to working with bigger brands?

Honestly, it’s always a little bit of a “holy sh*t” moment! The big names almost always come through as a referral because a kind former client or another freelance writer mentioned I’d be a good fit for a project—and it’s always a bit terrifying.

After a little bit of initial imposter-syndroming, it always comes down to realizing that the people on the other end of that relationship are also just folks who want to do right by their boss and customers and who want to learn how they can help me do my best work while they do theirs. Some of my dearest people to work with come from these big names.

As for the ‘breaking in’ moment, honestly, my first ones (CoSchedule may have been the first big one, back in 2019ish) probably came after my name showed up in dozens of bylines of smaller SaaS companies and in various conversations on Twitter about writers. Doing great work repeatedly tends to create great things much later down the line!

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