Kaleigh Moore AMA: How to Build a Successful Freelance Career

Jimmy Daly
November 16, 2020

Kaleigh Moore is a freelance writer who also runs courses, coaches other creatives, runs a podcast and builds products for writers. She's built a successful career by defining a niche, going deep and building several revenue streams.

You can connect with Kaleigh on Twitter, subscribe to her newsletter and check out her course. We'll be doing more of these. To participate in realtime, join our free Slack group.

It seems like you’ve thrived as a freelancer. I dabbled in freelancing once and was terrible at it. What do folks get wrong about freelancing? How have you built such a successful freelance career?

Kaleigh: There's no real guidebook for freelancing, and so it's a lot of trial and error. I think what helped me a lot was that I started as an apprentice of sorts. I worked as a subcontractor to an established writer who taught me how to create good content AND run the business side of things, so it was like having training wheels. It helped me feel more confident in my abilities before going out and rounding up business on my own.

I also am super organized--and I always do what I say I'm going to do. That alone seems to make me stand out from the crowd, which still surprises me.

Also: I took and picked an area to specialize in. That was a game-changer. You can't be everything to everyone, you know?

Do you ever get asked to write content outside of your knowledge domain? And if so, how do you approach it?

Kaleigh: I used to, and I wanted that MONEY, so I'd say yes. But then I'd get SO FRUSTRATED by how much I had to learn to do a good job. It made the work take so much longer, and I resented it. So I started saying no to gigs outside my realm of expertise and referring other writers who were a better fit--which was great, because then they returned the favor!

Wondering if you follow a standard launch process for products (i.e., new courses, communities, etc.). If so, is there a step-by-step cliffs notes version you can share?

Kaleigh: I wish I had a standard launch process, but honestly I do not, lol. I'm working on doing better at this (my husband is a pro at this, so leaning into his guidance for my next iteration of launches.) This is my first year with my own digital offerings, so it's been a lot of trial and error, just like everything I do. So far TBH my efforts have been too unfocused, and because of that, I've wasted a lot of money, time, and effort. It hurts me to say this but it's true. When I get strategic, I will share my process in a blog post. 🙂

What’s your freelance pitching/proposal process like for new clients? Any tips (esp. for freelancers early in their career)?

Kaleigh: So, at this point I rarely pitch, as most of my work is referral based, therefore pre-vetted and greenlighted. BUT! I have a whole lot to say on communicating one's value proposition effectively that I've learned along the way. I actually did a live session on this last month, and you can still get access to the recording/slides:

What percentage of your time do you spend prospecting versus working on client stuff? What's your most effective source of leads?

Kaleigh: I don't prospect anymore, which I never thought I'd say! I have so many referrals coming my way now that I'm at capacity. So 99% of my time is spent doing client work. I wrote about how I got to this point re: referrals:

Do you have a team that helps you? With writing and creative work, or with stuff like accounting? Seems like some freelancers really are one-person shows and others are one-person businesses.

Kaleigh: I have a go-to roster of subcontractors for if I reach capacity and have overflow projects (or if I get sick, life happens, etc.) This has been a game-changer (and it keeps my less-busy writer friends stocked with work, too!) I also outsource my accounting and bookkeeping as of this year because I hate numbers so much. That's been lovely.

I'm curious how you navigate working with internal teams. As a freelancer who comes in not burdened by an org structure, what are the most common sticking points or challenges you see internal teams struggling with?

Kaleigh: TOO MANY COOKS IN THE KITCHEN is a huge problem. I can't deal with 5-10 editors all telling me to do different things, so I now require clients to do their internal edits on their own time and then come back to me, from a single point of contact, with a version I can iterate on from there.

At what point did you feel like it was beneficial to start marketing yourself as an expert and start building out your personal brand?

Kaleigh: About 1-2 years in. I was saying yes to all kinds of gigs and was getting so burned out. Plus: No one knew me for that "one thing." I was a generalist rather than a specialist. I pivoted from offering a lot of services to a lot of people to offering ONE service to one very specific group of people. That was scary, because I wanted work! I wanted money! And saying no to gigs felt counter-productive. But once I niched down, I started getting busier. People knew me as the content gal for ecommerce all of the sudden. It stuck. ( finally drilled the importance of picking a niche into my brain.)

How do you price your writing services? Since you don’t do copywriting (as far as I know), pitching based on value is hard, so do you have a flat fee per content length? If so, how do you justify it?

Kaleigh: I do word count-based pricing because in my experience it's the easiest way to scope blog content--but I also factor in my value-adds to those rates (like the expert sources I can get quotes from, my subject matter expertise, etc.) Pricing goes up as demand goes up, and I raise my rates once every ~6 mos on average as well by about 10-15%.

Got into this in a lot of detail here, where you can still get access to the slides/recording:

Would love to hear how you manage your team of subcontractors, how much of your time is spent managing them vs other aspects of your biz, how you keep them engaged etc.

Kaleigh: I am actually working on a new digital product that gets into ALL OF THIS. The sales page is being written now, so stay tuned, my friend! I don't want to give away the ship, but I'll be sharing my process/docs for all of that very very soon.

I'm wondering if you have any recommendations for a content production schedule for your OWN brand. Do you sit and write blogs for yourself when the mood strikes, or every Xday at Xpm?

Kaleigh: I syndicate my newsletter (sent every other week) and that's my blog content. I also have started doing some SEO content to target certain keywords, but on a very small scale.

How do you overdeliver to your customers? I’d like to be able to “wow” my customers, but I’m having a hard time finding what that factor could be and how to deliver it to them.

Kaleigh: The short answer here is: ASK. Find out what the value-adds they want/need are, and then provide them as part of your services.

I am sure you must have worked for a lot of different industries by now. Do you have a general process that you follow before embarking on content or you review each industry/product differently and then write?

Kaleigh: I only specialize in one industry now, so unless it fits into that bucket, I don't take it on. But I do have a process for writing:

I seem to be losing gigs because I don't offer SEO or content strategy or analytics. Is it impossible to be a pure "writer"?

Kaleigh: I don't think you have to offer those services, but you should have relationships with folks who do those things who can then hand them back to you when it's time for the writing to be done. This approach has helped me a lot, and the reciprocity it leverages keeps gigs coming back my way. 🙂

I'd love to hear if there's any common advice or 'best practices' that get tossed around (whether about writing or freelancing) that you disagree with.

Kaleigh: Good question. I don't think it's super important to have a schtick for your personal brand (so, like an alter-ego.) Lots of folks lean into gimmicks around their branding, and I think it's totally find to just be yourself without any extra bells and whistles.

How much time do you dedicate to building your freelance business and how much to client work? What's the break-out?

Kaleigh: I don't work on prospecting anymore because I have so many long-term engagements and inbound interest at this point (which is mind-boggling, but so great.) So the only time I do this is about once every month where I check in with past clients and say, "What can I start on for you this month?" if I haven't gotten an assignment from them yet.

What type of content do you specialize in? For what I’ve seen, you focus on educational articles, but have you ever consider offering copywriting as a service?

Kaleigh: Just long-form blog content, because it's what I enjoy and do best. I do the very rare copywriting project (usually About page revamps!) but my expertise is in SEO and storytelling, so that's where I focus. Copywriting is more technical, and 99% of those I refer out to writers with CRO expertise who can do a better job than me.

How do you build better working relationships with your clients to the point where they feel they can be comfortable coming to you with assignments and you can start planning your schedule around that stability? I'm at the stage where freelancing just feels like waiting for assignments that may or may not come from various clients. Basically, how do you go from being a one-off writer to someone on their roster?

It has a lot to do with asking questions about how you can make their lives easier. Got into detail about this in this session, which you can still get access to. It's way more in-depth than I can share here in short-form.

Where is the best place for people follow your work / connect with you

Kaleigh: Sign up for my newsletter:! I'm also on twitter a LOT

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