“What should I letter?”

This is by far one of the most common roadblocks to aspiring letterers.

You know you need to grow your audience so your work can reach more people and get hired to do what you love. You know you need to put work out there so you can grow your audience and get seen. You have ideas about different lettering styles you want to try, maybe even a color palette already in mind.

But when you sit down with pen to paper (or iPad)…

…you have no idea what to letter.

Sound familiar?

I’ve read countless blog posts, listened to webinars and online course videos that preach about lettering things you’re passionate about, phrases that fit your brand and your vibe. While that’s all well and good, a lot of letterers aren’t also copywriters. Coming up with quick and witty or meaningful phrases might not come naturally to us.

And often that’s the one thing that stands between you and improving your lettering skill. How can you practice doing the actual work of lettering when it takes you an hour just to manage the first step of coming up with an idea of what to letter? Or when the difficulty of that first step prevents you from taking any action at all?

That’s where lettering challenges come to the rescue.

Outsource the Copywriting (for free!)

So what can you do to get over that hump and be able to practice your lettering?

Maybe you wish you could outsource this part of the process – have someone else do it for you?

Well luckily, in the huge online community that has grown around lettering, a handful of people are doing just that.

A lot of letterers host their own lettering challenges on Instagram, coming up with prompts to help get jumpstart your lettering piece, or even flat out providing predetermined phrases and words that you can letter.

And the added bonus is that there are a lot of other letterers following these challenges. So if you use the challenge hashtags and tag the right accounts, you could be rewarded with a reshare of your work by the challenge owner’s Instagram account – which means new followers and a much wider reach for your audience than you would have managed on your own.

Wanna get started for yourself?

In this post, I’m sharing some of my favorite lettering challenges that have substantial followings and that reshare your work on their platform, along with examples of pieces I’ve created for each one:

The Challenges

1. Homwork by Lauren Hom (@homsweethom)

Lauren Hom is well known for her sassy and colorful dimensional lettering and illustration. Homwork is a weekly challenge that provides you with a prompt for a lettering piece. Sometimes you’re given exact words to letter, but more often it’s a prompt that challenges you to come up with your own words that relate to you personally within a given theme or framework.

What to tag on IG: #homwork, @homsweethom

Sign up at https://www.homsweethom.com/subscribe to get the weekly prompt emails.

2. Goodtype Tuesday (@goodtype)

This weekly challenge is curated by Goodtype, with a different guest artist providing the prompt each week. This one is also a mix between providing you verbatim words to letter or giving you a prompt to interpret on your own (but I’d say it’s mostly verbatim prompts).

What to tag on IG: #goodtypetuesday, @goodtype, the account of the guest artist, and any special hashtags for the week (they’ll tell you in the prompt email)

Sign up at https://www.goodtype.us/ to get the weekly prompt emails.

3. Art Licensing Portfolio Builder (@ilanagrifo, @katiemadethat)

This is a year-long challenge that is aimed at getting you to create full finished pieces that would work in an art licensing portfolio. That means you’ll be creating pieces that could be printed on greeting cards, gift wrap, home goods, clothing, and other retail items. Packaged within an online course, prompts are released every week and you have access to a private Facebook group where you’ll get feedback on your work from the course authors and peers in the course. This one is a great challenge for those of you looking to showcase your work in professional ways and create business savvy pieces for which there’s a real market.

What to tag on IG: @ilanagriffo, @katiemadethat, #ALPortfolioBuilder

Sign up for the Art Licensing Portfolio Builder course.

4. 36 Days of Type (@36daysoftype)

36 Days of Type is an annual challenge that invites letterers, illustrators, animators, and visual artists of all kinds to create letters A-Z and numerals 0-9, one day at a time. The challenge typically takes place in April-May of each year, but it’s a good idea to start early if you may not have a lot of time to spend on creating these pieces on a daily basis!

What to tag on IG: @36daysoftype, #36daysoftype_[letter or number of the day], #36daysoftype07 (or whatever the number of the 36 days challenge is that year!)

No sign up necessary; just follow the IG account to see the schedule of which letter you should post on which day.

5. WTF Should I Letter?

Another brainchild of Lauren Hom, this quote generator helps you decide what to letter when you’re feeling sassy and eccentric.

What to tag on IG: @wtfshouldiletter, #wtfshouldiletter

Check it out on her website.

Looking for more? You can also check out @happyletteringchallenge on Instagram for simple one-word daily lettering prompts, and @letteringchallengehq on Instagram for a continually updated list of monthly lettering challenges being hosted by various accounts. Which accounts/challenges are your favorites? Post ’em in the comments below!

Happy lettering!