36 Days on the Side

A guide to surviving a daily side project challenge

Unsplash. Trello. Product Hunt. AppSumo. All these successful products started as a side project. Clearly, dabbling and experimenting at work can do wonders financially—but even if your side project doesn't end up being a multi-million dollar company, this kind of experimentation offers other lovely advantages.

As the Head of Design at Kite, I’ve happily transformed into a financial product nerd. I love my typical work day — in-depth user flow discussion with my Product Manager, working with my design protégé on a constantly-evolving design system, promising to write more Medium articles to the Head of Communications (*cough*), and brainstorming with Kite’s boss-lady.

However—as anyone does in any job—I found myself in need of some variation in my day-to-day, so that I can keep doing my best. I’ve been lucky enough to switch things up by indulging in something called the “Daily Side Project Challenge”.

As a design nerd, a fun casual fling for me means taking part in 36 Days of Type. It’s a global collaboration among designers to create all 36 characters (A-Z and 0–9); designers are challenged to design a letter or number each day, resulting in the same symbol being represented from many different perspectives. It’s an awesome way to connect with other designers—but it also means taking out at least 2 hours every day for 36 days (you do the math, it’s a lot of time).

The makings of a perfect fling

There are a couple of things you should keep in mind before starting a daily challenge. You don’t have to follow all of these tips, but they will definitely help in your journey.

Define what you will do and for how long you will do it.

Pick what kind of project you will be doing. It can be absolutely anything, like design, art, coding, filming, music or cooking.

Have a timeline, since it’s always a good idea to define for how long you will work on the project, and what you will deliver each day. Anything near 36 days is a good start.

Find a channel to share your work.

Its important to share the outcome of your daily challenge every day. It can be online or in person. It could be with your best friend or your Instagram followers. Pick one person or a thousand people. It’s all up to you, but do pick someone. This helps you establish accountability when you know someone is waiting for you the next day.

Don’t stress, and have fun!

Remember you are doing this for fun, so pick something which will make you happy. When you look forward to every daily challenge, then you’re more likely to do your best and keep the stress away.

Why do it?

For my personal side project, I decided to do 36 Days of Type because I absolutely love 3D design and I don’t do it on a daily basis otherwise. Plus, I knew 3D stuff would sizzle up my Instagram account.

For others, a daily side project might help you learn new skills or tools, take a break from your daily life, make an online portfolio or simply see if you can commit to a challenge. Committing to do something each day for a period of time is not easy, and you learn a lot about yourself.

My experience and struggles with 36 Days of Type

The best part was the community effect, as there were many other designers doing the same challenge. I ended up meeting several other very talented people by sticking out until the end. Plus, I got my Cinema4D mojo back, as I mainly use Sketch and Illustrator at work.

To save time, I started doing the letters during my commute (side note: Delhi has awful traffic). I would open up my MacBook in the car or the cab and just start designing until I reached back home.

I wanted to try different color palettes for each letter, and that got really hard, since I ran out of color combinations I personally liked by the end. It opened up room for some combinations I would have never tried.

Near the end, I was happy that I followed through and didn’t miss a day. I came very close to skipping a day, but just pushed through and ended up making something I’m proud of.

It also felt nice to feel some appreciation from the community, like getting my letters featured on @36daysoftype and other cool Instagram handles.

Some crazy ideas for your first daily challenge

• Make a portrait of a stranger each day (it will be more fun if you don’t know how to draw)
• Make a map of a city or a town each day
• Write a haiku or poem each day (or even a rap)
• Try a new dessert each day
• Teach your skills to someone for an hour each day
• Photograph a new dog (or a cat) each day
• Learn a phrase in a different language and say it out loud to someone (yes, each day)

I think you get the idea—there’s tons of stuff you can do.

Projects I love

Windows of New York by José Guízar (a co-worker at Fueled)

Daily Drop Cap by Jessica Hische (she is the best and I love her)

Daily Dishonesty by Lauren Hom

The Day’s Color by Nigel Evan Dennis (Colorgasm!)

Tiny PMS Match by Inka Matthew (Pantone Matching System!)