365 Days: Learning to letter

My 365 day (of hand lettering) project is finally over. I’m relieved to say the least but it’s been so fulfilling. I’ve connect with so many people and made friends just by putting my this out there and I am truly humbled by all of the people that have cared enough to reach out or even comment along the way.

The entire 365 day process has been documented on Instagram (although there are many pieces that I would just like to blast into oblivion) and you can see the progression throughout the year (and a bit 😀).

My experience with this project was awesome so I just wanted to close it out with some food for thought and some things I learned along the way. Hopefully I can inspire you to start your own 365 day project. Or if you’re already doing one, talk through some pain points that we can share. It doesn’t even have to pertain to lettering, it can be any skill you’d like to improve — photography, playing guitar, baking, stand up comedy, anything.

From my experience with learning lettering, it helps even more if you start something completely new. You don’t have to take my word for it,

Sucking at something is the first step to get becoming sorta good at something.

- Jake the dog

So, why did I start?

I think it was just a creative itch. Things felt kind of stagnant with my day-to-day design work so I just wanted some other creative outlet. At the very core I wanted to improve my skills as a designer just simply be good at something.

The idea to start this challenge actually came from seeing a piece that Veronica Wong wrote when she was half way through her 365 day challenge. It helped me visualize what’s possible and seeing her progress really inspired me to do my own (Thanks Veronica! :D). I started with very little knowledge of what lettering really was; I didn’t even know that there was a difference between lettering and calligraphy. Oh boy.

Challenge accepted

The challenge was simple, draw or write a piece of lettering and post it to Instagram for a full year. I would have loved to do this 365 days straight but unfortunately it is exactly as hard as it sounds. I wasn’t that disciplined, so I think in total I took about 3 months worth of days off (crap!).

I think what I’m trying to say is that you shouldn’t let the fear of completing deter you from starting. The goal at the end of the day is to get better at a skill and if you feel like you need a break then take the day off and try again tomorrow. No big deal.

Making time

The most common question that I’ve received has got to be: “How much time does it take for you to do a piece everyday?”. To this day I’m still not quite sure how to answer this, the reason being that it ranges from a quick 5 minutes to a whopping 3 hours+. But I think the principle I came up with is to set aside at least 2 hours of time dedicated to the process (brainstorming, sketching and drawing). This was the sweet spot, enough time to get a rhythm and think things through, but not so much time that I would overdo it and ruin a piece (this still happens a lot).

I’d usually try to pair this time in with listening to podcasts, watching random videos or just downtime where I laze around with music in the background.

Finding that 2–3 hours for every night is a huge challenge to anyone like me trying to balance work, life, family and a relationship. But this step is so important if you want to turn any hobby into a habit. I found that the same thing helps for ‘finding time to read’, you have to make time. So what I had to do was religiously block off time where I could focus solely on lettering. It really helped me mentally to treat this like a job in order to take it seriously.

I can recall nights where my excuse to not go out was that I had to do lettering, which was always followed with a “really?”. Yes, really. This is something that I really care about, and if I wasn’t going to take it seriously why would anyone else?

Learning to give a shit

I’ve very slowly learned to love the craft of lettering. Before I even started this I made sure that this was something that I cared enough about to commit to it every day. It was all fun and relaxed at first but as I started to see progression and the sight of a plateau over the horizon, it was very tempting to just say good enough and call it quits. I don’t think it was a lack of drive or passion, but just laziness and complacency taking over.

The best motivation for me was to look to successful people, analyze what they do or how they work, and let that influence your work. It doesn’t even have to be directly related. There were many times where I would just watch interviews with musicians or montages of athletes and it would help drive my will and creativity, seriously. As long as you can find the right inspiration and you have a goal in mind, it’s just a matter of putting in the hard work and hours to create a strong habit.

Putting it all out there

The great thing about the uploading portion of this challenge is that you’re kept accountable to keep it going. There were a couple times where people would point out that I hadn’t posted something in a few weeks, and that really helped get me on my toes. When I first started, I didn’t think that I would even finish let alone have anyone noticing my project.

The weirdest encounter was one time meeting a friend of a friend for the first time and them telling me they’re a fan of my lettering. Like what? Let that sink in for a moment, they were practically a stranger and they said that, I was gobsmacked, what a weird and crazy feeling.

You’ll never know who picks up your work. I had the pleasure of seeing my work get picked up on Good Type and Type Gang, two of my favourite curation accounts. To me, these were huge accolades seeing my work along side some of the best in the world. Sometimes when things get stagnant, I can kind of look back at these for inspiration and use that drive to chase the same feeling again.

My biggest piece of advice for those starting

Just fucking start.

The worst thing you can do is sit around thinking about starting or even starting behind the scenes. This challenge is a challenge for you to improve your skills and it’s a long process, so don’t cheat yourself. Just let yourself be vulnerable and try something new.

Don’t overthink it, your first 100 of anything is going to suck and you’re going to hate it anyway. There are so many nuances and skills that you can only learn by doing and failing. Don’t discount yourself from these lessons by refusing to fail.

It’s finally over

The last couple weeks have been surreal, who would have thought I could really finish a full year of this? Now the big question is, what now?

• Keep lettering — I’m still going to be lettering (as it’s become a big part of my life) but at a smaller frequency. This way I can focus more time and energy to larger pieces without the pressure of drawing dailies. There are other aspects of lettering that I still have not tried that I would love dabble into, like quilling, sign painting and glass gilding. This is really only the beginning so stay tuned!
• Freelance — during this process, people have asked me to letter for their weddings, brands or just personal projects. With the little time I already had to do dailies, I never really got around to commit time to it but with that out of the way, I can finally get to it.
• Hit the gym — This may seem odd but working on dailies really messed up my sleep schedule which in turn messed up my morning gym rituals. I end up staying late to work out little details and end up sleeping in. Considering how indulgent of a year 2015 was, I’m sure my body will really appreciate if I get up and moving this year.

And of course

I’d really like to thank everyone for the continued love and support, I really could not have done it without you. Thanks to my girlfriend Cindy for always cheering me on and continually putting up with the random ink and scribbled piles of paper that pops up around the house.

Thanks for reading! For those who didn’t follow me along this project…

Hi I’m Kevin, I’m a designer born and raised in Toronto and I’m just getting into this writing thing (this is my first). I would actually appreciate any feedback you have or feel free to just reach out and say hi. You can reach out to me here:

Instagram — http://instagram.com/neueyork
Twitter — http://twitter.com/duongkevin
Email — kevin@neueyork.ca

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