I have been full time freelancing since 2014 working on all kinds of fantastic lettering projects for lifestyle brands, small businesses, and creative agencies. It’s been a whirlwind of ups and downs, but after five years working for myself I feel like I finally have an organized process and work-life balance so I can do my best work.

In this article, I’m going to share with you all the tools and apps that I use that are a part of my everyday life as a freelancer. These resources have helped me gained a faster workflow and a seamless onboarding process to take on new freelance clients.


When I first started getting into lettering, I was all about working traditionally with a good old fashion pencil and paper. But as I got more experience, I quickly updated to digital because I needed to do more work in less time. With a quicker workflow, I could produce more content and deliver client work in record time. What used to take me two weeks to finish one piece, now takes only a few hours with the help of a few of my favorite tools.

Creative Cloud lettering in Photoshop

Creative Cloud: $50/mo

Apps like Photoshop, Illustrator, and InDesign are a must for any designer. You should take the time to learn them all to see which one suits your style the most. So I highly recommend starting out with the $50 a month subscription of Creative Cloud for access to all of Adobe’s programs till you can narrow down to which is your favorite.

My go-to app is Photoshop because it retains the look of the handmade more, so my work looks like a person made it, not a computer. You can even see my process for creating a hand-lettered phrase from scratch with from this live stream workshop I had back in January.

lettering using astropad

Astropad Standard: $30

This is the program I get asked about a lot because I post so many photos of my in-progress work on my iPad. Astropad is a screen sharing program that allows me to have Photoshop on my iPad just as if I was using a much more expensive Cintiq.

This program has single-handedly made my lettering career allowing me to complete type pieces in more than half the time of making them traditionally. By being able to mix the powerhouse of tools from Photoshop with the handmade quality from drawing on the iPad, I’m ready to create more projects than I ever have before.

lettering on a ipad pro

iPad Pro and Accessories:

I’m in love with my large 12.9 inch iPad Pro! It took a lot of thought and research before I bought this device with its $799 price tag. But when compared to that of an expensive Cintiq, not only can I draw on it with the same amount of latency, but I also have an entire computer at my fingertips.

When using my iPad, I also use a few accessories to make my workflow easier. This includes a special Ztylus case on my Apple Pencil that not only protects my tool but adds a bit more weight with a holder on edge to prevent the pencil from rolling right off the table. I also use a special drawing glove that allows me to have smoother lines as I run my hand across the screen without smudging it.


Hand Lettering Toolkit of Digital Brushes: $39

This Hand Lettering Toolkit was gifted to me by Dustin Lee of Retro Supply Co in 2017 and has been my go-to Photoshop brush set ever since. With over 98 brushes carefully designed by lettering artist Shauna Parmesan, I have a ton of natural looking options with an array of pencils, microns, and markers to get that handmade feel without the mess.


Your expenses as a freelancer can quickly get out of hand because there are just so many apps out there claiming to revolutionize your productivity. You have to be careful not to pay for things that may be more of a commodity rather than an investment where it can save you time doing things like admin and social media so you can focus more on the drawing side of the business.

buliding a illustration portfolio on squarespace

Squarespace: $12/mo - $40/mo

This platform won me over from Wordpress in 2016 when I was ready to update my website with a more focused portfolio and detailed landing pages.

Squarespace is not only super easy to use, but everything is in one place. So if you have an issue or question, just contact customer support, and they usually respond within minutes not weeks. Plus they have a ton of video tutorials covering each step of building your website from everything from adding e-commerce, to incorporating video backgrounds.

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ANDCO - Free Baby

ANDCO is an all in one solution for all your admin needs that includes time tracking, invoicing, to do lists, proposals, and even an automatic accounting of your expenses and income. Just sync up your bank and PayPal account and boom, you automatically have an updated report of your income to see if you're in the red, breaking even, or killing it consistently on your margins.

This app is crazy impressive and has allowed me to delete several other apps since this one does it all. The best part, it’s entirely fucking free since they got bought by Fivver! I’m not a big fan of Fivver and how the hurt the industry for artists and designers, but maybe they are trying to make it right by offering this free software.

Using buffer for social media

Buffer: $10/mo

I’ve been using Buffer for years now to help schedule all my social media posts across all my platforms. It’s hard enough to focus on posting consistently on one platform, let alone 5 or 10 like what I do for my business. Using this app, I can post to Facebook, Instagram, Twitter, and Linkedin all from the same screen without having to do it all natively.

The only hiccup here is on Instagram. Due to Instagram’s strict use of their API, Buffer can only remind you to post on Instagram where it copies and pastes your image and content. You still have to go into the application to hit the post for it to show up on your feed.

USing typeform for client questionaires for freelancers

Typeform: $30/mo

Typeform is a great form building app where it allows me to create a landing page for the forms that I use as an onboarding questionnaire for taking on new clients. Its’ super easy to use and allows me to include images in questions and conditional logic, so my clients feel like I’m talking directly to them.

Not only can Typeform use customers answers in future questions, like personalizing a question with their first name it can also use something called conditional logic to ask them better questions about their needs.

shipstation for illustrated products

Shipstation: $29/mo

If you are offering up your own products and want to take care of the filament and shipping yourself, Shipstation is what you need to stop pulling your hair out. It automatically syncs up with your store whether it’s on Etsy, Wordpress, Squarespace, or Amazon so you can print out your shipping labels all at the same time. Without this program, you have to print them out each individually which is a huge pain once you start to get more than five orders per week.

What used to take me 3 hours to ship out products now only takes me 30 mins. All that freed up time helps me create more lettering work leaving my competitors wondering how the hell I do it all.

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  Dropbox Business: $20/mo

I’ve been using Dropbox ever since I was in college at Full Sail University back in 2010. It allows me to always have a backup of all my work while freeing up space on my hard drive.

Especially nowadays where I have multiple devices and interns coming in, it’s so much easier to have a dedicated server for us to share files without the wait to access the documents we need.

Altogether I spend about $250 a month on my hand lettering business which pales in comparison to the 4-6k I make on average. So for me, my margin on these tools allows me to make quite a lot of bang for my buck, not to mention it saves me time so I can do more with my 5-hour workdays.

It’s important to keep in mind, that if you can’t afford $250 a month, then don't spend it! Start with free programs and work your up as your income increases, so you still are making at least 70-100%+ profit from your expenses. Here's to working smarter, not harder my friends.