What to invest in and what to get for free

How this writer makes it work

If you're serious about being a writer, there are no two ways around it: You have to invest in yourself. The good news is that some investments are free (wahoo!) while others will cost you a bit of cash (less-than-wahoo).

If you're serious about being a writer, there are no two ways around it: You have to invest in yourself. The good news is that some investments are free (wahoo!) while others will cost you a bit of cash (less-than-wahoo). Here are my favorite sites, apps and Twitter chats for learning and earning.

When I moved from the average working life to one dedicated solely to writing, I found it hugely empowering to make these investments. If I took myself seriously, others would follow, right? It turns out they did, and I've loved sharing tips and shortcuts with fellow writers. I thought it might be helpful to share this experience more widely, so below, you'll find my favorite sites, apps, Twitter chats and more I use to build a following.

A quick note: I'm not receiving any cash, props or high fives for the below. These are simply a few of my favorite things.


I really love Squarespace, which I use to build this very site. It's reliable, respected and malleable. There's an annual fee that covers hosting -- with a coupon code for the first year of service -- and that's all I've ever had to pay; the cost hasn't changed since I began with Squarespace.

Do you know any HTML or CSS? I didn't know any of the latter starting out and still don't completely understand how to read it, but I do lots of Googling for answers. In Squarespace, you can drop HTML boxes onto individual pages or add custom CSS at the master level to apply to all pages. (You don't need to know a lick of code to use Squarespace, though.) In addition to Squarespace's help docs, there's an open forum where users trade their custom code. I've tailored a lot of that code to suit my needs.

Finding clients

I've used Upwork and Thumbtack to generate 99% of my recurring client work. I like Upwork because payment is done through the site and guaranteed, though Upwork does take a percentage of each project's profit. I like Thumbtack because I can use my own invoicing without the site taking a fee, but payment isn't guaranteed that way, and some clients have disappeared (boo, hiss) once I've delivered their project. Now whenever I collaborate with a client outside of Upwork, I ask for 50% of the final project cost up front to protect me (in case they disappear) and them (so I must deliver the project to receive my full amount).

A note about Upwork

You'll hear from lots of writers who say Upwork is a joke, that it's impossible to make good money on the site, and that can be true: There are loads of Upwork job postings that totally devalue your expertise and skill. I've had great luck with Upwork at what I feel are reasonable rates at my career stage. I just did a quick calculation in my accounting software, and from February to March (when I started using Upwork to find clients), I had a 4,383% increase in profit. That's healthy, no?

It does take patience to find the right clients who fit your interests and pay grade. I only target clients who've hired many people through Upwork in the past, have verified payment methods and are looking for freelancers in the expert range (there are three levels: entry level, intermediate and expert). I took a couple lower-paying gigs early on to build up my reputation (never anything like some of these $5/blog post jobs you hear about; don't you just want to give those complying freelancers a hug?) then started to land larger jobs.

In addition:

  • I've done lots of experimenting with my profile to see which content clients respond to -- testimonials, a new tagline, specifics about past projects, etc. I also created a video, since you're more likely to be hired if a client sees and hears you, learning you're a real person. It's the same video that's on my About page.
  • I've also played with the keywords that appear along the top to see the types of job invitations I get. It's illuminating to see how clients classify their postings.
  • I display some Upwork test results down toward the bottom, so prospective clients can see how I rate against other freelancers.
  • I have a fairly full portfolio on my profile that links not only to Upwork projects but outside work as well. My thought is this may help clients see that I'm working for folks everywhere, not just Upwork. It could lend more credibility to what I do.
  • I do have my experience set to Expert, which is one of the reasons I focus on the clients searching for experts: I got some scoffing from those looking for a deal, even though there are some writers charging $150/hour, which is more than I charge right now. The fact is you get what you pay for.
  • I've saved searches to only show me projects with the following criteria: Copywriting, editing and proofreading jobs in the U.S. (to avoid a language barrier and time zone kerfuffle) that are hourly or have a fixed rate of $250+ that are no longer than six months, posted by clients who've hired 10+ freelancers and are searching for experts.


I use Square for invoicing outside of Upwork. I like its slick, modern design, and it had the lowest credit card processing rate that I've found -- though that's about to change: I've apparently been on a promotional rate of 2.75%, which expires this week. It will increase to 2.9% + 30¢ per online invoice, which is in line with other invoicing apps I've seen (including Wave Apps, which I discuss below).

I'd love to hear if you've found and love an alternative invoicing option!


If you plan to really lean into client work -- I do a good deal of content marketing -- I suggest setting up a separate bank account and credit card. You can connect that account with Wave Apps, a free online accounting software to keep track of your profits, business expenses and more. You can also invoice using Wave, but I still prefer Square's lower processing.

Katie Gonzalez of linenlaid&felt recommended Wave to me: I met with her a few months before leaving average employment to write full-time, and I'm so glad she shared her Wave experience with me. (It's yet another reason to fully dive into your creative community: We want to help one another.)

Getting advice

I've found loads of help by making connections online with other business owners and writers. I'm in a few Facebook groups: Blog + Biz BFFs, Six-Figure Freelancing and Creative Freelancers Unite. I'm also signed up for emails from Mariah CozMelyssa Griffin and Halley Gray for tips about marketing, blogging, finding clients, structuring a business and more.

Being social

When I can, I participate in Twitter chats like #bufferchat, #createlounge, #storysocial and #creativecoffeehour, using TweetDeck to manage my participation. I use Buffer (full disclosure: I used to work there) and Emma (ditto) to schedule tweets and send emails to my subscribers, which helps find and convert clients. (Click here to sign up for those emails, if you'd like!)

That's the nitty-gritty. For more of the emotional side (working solotaking care of yourself), I had a post earlier this year on earning your goals, if you'd like to read it!

Another important piece is determining what kind of writer you want to be, not in terms of fiction vs. non-fiction, but rather what your morals and ethics are. For me, I drew the line at ghostwriting.

I also don't want to take on every, single project just for a buck. I want to feel invigorated whenever working with others, since this takes away time from my own creative endeavors, and stay true to my inner moral compass.

What other questions do you have about creating a lucrative writing career? Let me know in the comments below, and I'm happy to share my experience!

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