Making S#!t Ain’t Easy

Simple tricks to ship more side projects.

I started 2015 by drawing letters in a notebook. I had no idea why I was doing it, or where I was going with it. I just needed to make things. Anything really, for my soul. Like Kurt Vonnegut once said:

“Practicing an art, no matter how well or badly, is a way to make your soul grow, for heaven’s sake. Sing in the shower. Dance to the radio. Tell stories. Write a poem to a friend, even a lousy poem. Do it as well as you possibly can. You will get an enormous reward. You will have created something.”

My love-story with fonts began in 2011 during a road trip with a my friend Rick. He ran an old-school print shop in Denver and only respected you if you owned a license to your font(s). At the time, I had a sweet-ass collection of every font under the sun — all stolen, of course.

Spend 18 hours with Rick, and you’ll find yourself doing some strange things. I deleted my stolen font library and developed an expensive taste for the finer types.

October 29th, 2011 I bought my first typeface (license): Mister Giacco. It was weirdly unique and somehow serious at the same time. I used it for a sex app (spreadsheets), that was both weird and serious.

As a college student, you have the luxury of buying type licenses at huge discounts (think 90% off), but once you graduate, everything changes. Gotham is priced at “you might as well steal this one” and if you’re not on a Mac, you can probably only afford one weight of Helvetica. C’mon, the most basic font, and it’s not even free!?

^ That’s the “ON SALE” price ^

Fuck it, I’ll use comic whatever.


Back to 2015, If you want to make something, there are two things I’ve found to be consistent:

1. You spend most of your time learning (the hard way). You spent ~1.5 years learning how to walk, and nothing really changed about learning now that you’re a grown-ass walking adult. Doing things wrong, the first time, is how we learn to make things.

2. Motivation, Drive, perseverance, grit, relentlessness (whatever you want to call it): managing your interest level is the key to “shipping”. Most projects never get through the “false peak” — the point in time when your interest has piqued, but you’re not yet finished with the project.

In mountaineering, a false peak is one that appears to be the pinnacle, but upon reaching, it turns out the summit is higher.

Some use this as motivation: “the end is so close, you can see it!” — others feel defeated; they realize the struggle isn’t over.

You need to finish.

I know how much energy and commitment it takes to wrap things up. I’ve also had many side-projects bite the dust. The goal is to find your rhythm, and to keep moving forward, but when you inevitably lose momentum, I’ve found a few tricks that’ll help keep you going.


Ask For Help

Years ago I discovered a designer named Tyler Finck. He was making incredibly useful fonts at college-student prices (read: basically free). You’ve definitely seen his work, it’s everywhere:

https://twitter.com/BarackObama/status/482193611535040512

Because of Tyler, I realized that really great type didn’t have to cost a fortune. He also inspired this wild idea that I could probably make my own type, no problem!

I wrote him an email. I reached out to a stranger from the internet, that inspired me, and he wrote me back!

In fact, I reached out to Tyler every time I was stuck. He was eager to install my font, even though we had never actually met. He always replied with enthusiasm and encouragement, often outlining things I could do to dramatically improve my work.

From my experience Tyler isn’t much different from anyone that has ever made something. He was happy to help another person embarking on the same adventure he’d mastered; I was appealing to his strengths. I let him know that his hard work inspired me to move.

Tyler helped me get past my false peak by showing me excitement, and through thoughtful, engaging feedback. The important thing to remember is that people from the internet (like Tyler) aren’t going to transport you from your false peak to the summit, they’re just going to provide oxygen tanks to help you get there.

Talk About It

Don’t hesitate to talk about your projects. When you say you’re doing something, it pressures you to be held accountable, especially when you’re saying it to someone that matters to you.

Coworkers would often ask if I had “big weekend plans” — to which my response was usually: “yeah I’m trying to wrap up this font...”

At a holiday party, after the drinks were plenty, a coworker asked me “So, like what’s the deal with this font?” And I understood he really meant, “Do you seriously enjoy the tedium of making letter shapes in your free time?

Translation: “Are you like, that boring?”

Yes. Definitely, yes. Ultimately, I wanted to make something for other designers. I wanted to create something useful and accessible to a large audience, like fonts at college-student prices. This was roughly how I explained it to him:

“Just like open-source is to developers: free fonts are to designers. I’m trying to make the best open-source library I can!”

By talking about it, you not only garner a sense of accountability, but you also get to refine how you’ll talk about the finished work.

Keep it Bite-Sized

Find something you can make that leverages something you’re already good at, but incorporates one thing you’ve never done before. Something that requires you’ll learn, but isn’t debillitating. You want your end goal to be 90% achievable. Take it from me: you really don’t want to rely on someone else to get you across the finish line. I’ve had many projects slow to a halt while “in development” — which is to say, I bit off more than I could chew.

These aren’t full-blown startups, they’re your weekend-sized ideas.


I was making a font. It seemed like a pretty simple thing when I started: you create 26 letters, 10 numbers, and a handful of special ones (-!$?%). Wham, bam, thank you ma’am — this thing was going to cost me a few weeks and i’d be on to the next project.

8 Months later…

1,440 characters (glyphs*) and 8 months later, I was very excitedly telling a friend about this side project, who introduced me to James Edmondson. James runs Oh No Type Co. and has a stellar track record for making really badass fonts. He didn’t know me — at all — but he could tell I was a lost puppy, shopping my font around, looking for help.

He quickly understood that I was very blindly going at this, and knew I’d regret releasing something that wasn’t up to my own standards. Imagine making something, as best you could, then putting it “out there” knowing that you, yourself, wouldn’t even use it. He wasn’t about to let me do that.

James’ first recommendation:

Take a break

This one can be quite dangerous, like fighting fire with gasoline… If the conviction to finish is strong enough, you’ll certainly return to finish your-side project. If you’re wavering at all, this is where it will surely rest; never re-emerging to see the light of day. But sometimes if you step back from a project, and leave it alone for a week, or a month, you’ll be able to re-engage with a renewed gusto. This works two-fold: you get to take a look at your work with semi-fresh eyes, and you get a chance to forget about the struggle.

When I returned, we basically started over. We trimmed the fat from every character:

I had designed a bunch of little quirks into the letterforms that eventually smoothed out to be cleaner, less goofy, more legible. The downside to such dramatic refinement was that I worried, deep down inside, that I might not recognize my font if I saw it in the wild. I never wanted to question if it was mine. I‘m not great at identifying fonts, which seems to be the go-to party question when you’re the only designer at a party.

I think ultimately James knew that would never happen; I still worry a lot.


I named my font: Affogato. It took me a little over 12 months to make, but ultimately turned into something that I’m really proud of. It’s named after the espresso over ice cream dessert, because it’s bold, approachable, and comes in 5 roasts: Black, Bold, Medium, Regular, and Light:

Affogato wouldn’t have been possible without the help from my internet friends (James & Tyler) and my girlfriend. And did I mention that it’s a free font?

Or that you can find it here: https://lobdell.me/affogato

I’m Eric Lobdell, a Designer and aspiring Creative Director. I’m passionate about making things for people to use, and I hope this inspires you to make more things!