January 1st, 2014. I had always gotten a kick of out drawing letters, so I posed a challenge to myself. Any tool, any medium, simple or complex composition. The only rule: draw one piece of lettering a day.

Today is day 183, the halfway point, and this project has taken me on a journey that I did not expect. I’d forgotten what it was like to experience something for the first time and be excited by the learning potential. I have learned a lot about myself as a person and as a designer over the past 6 months and it has been immensely rewarding. I’d like to share some of what I’ve learned so far.

Don’t be afraid to get started

I had a couple friends ask me about how to get started, telling me they were afraid. I thought this was quite odd. What’s so scary about putting a pen to paper? Not only that, you don’t need any fancy tools to get started. All you need is a writing utensil and some paper.

As a designer, when was the last time you tried something new? Remember that feeling of discovering Photoshop and all those filters? In all honesty, I found that a lot more overwhelming than putting pen to paper. Branch out, try something new!

Immerse yourself

Not only is Instagram a great tool for documenting my work, it’s a great place to be inspired. I love the work of Neil Secretario, Dana Tanamachi, Molly Jacques, Jennet Liaw, Gemma O’Brien, Ben Johnston, Sergey Shapiro, Scott Biersack, Christopher Craig and so many more.

For anyone who’s interested in starting and has no clue how, here is my advice: copy the work you like.

Now don’t get me wrong, I am in no way saying you should copy someone’s work and publish it as your own. What I am saying is study the work that you like and understand why you like it. Personally, I like looking at a piece of work and trying to replicate the way it feels. A composition can be soft, elegant, edgy, or bold. That’s what I try to replicate. Paying attention to the quirks and details will help you decide what it is you like about a piece.

Spend time experimenting with different styles so you can develop your own. Practice flourishing or drawing letterforms in different ways. Watch videos of how other people draw and try different tools. Don’t be worried if you don’t develop a single style, you don’t have to narrow yourself down if you don’t want to.

Practice and commit

I have come to realize that practicing every day, no matter how short of a session it may be, has yielded improvement. Some of my dailies received more effort than others, but when I look across the span of the last 6 months, there is a progression in my work.

Akin to the way people describe exercising, I found it a little difficult to commit at first. It wasn’t part of my daily routine and I hadn’t even decided if I was going to follow through with the 365 until about day 5.

As I started numbering my pieces on Instagram, I started putting pressure on myself to keep going. I gave myself a reasonable window of not being allowed skip more than 20 days within the 365 as an out (but since then I have thrown that rule out and am committed to the full thing).

After a while, I found the commitment engrained into my daily routine. There were days where all I could think about was going home to draw. That’s not to say some days haven’t been tough. Balancing a daily commitment can be hard, especially when you have other things going on. Social life, relationships, family, and work can all take up time and cause stress that can prevent you from reaching the goal. That being said, lettering has become very therapeutic for me and doubles as a stress reliever.

Make yourself accountable

Another way that Instagram has been very helpful to me is making me accountable. As more friends paid attention to my work, I felt more accountable to not miss a day. I didn’t want to disappoint them or have them catch me being tardy.

It has also been very encouraging to see other letterers and designers on Instagram also working through 365 projects of their own. There was much congratulations in the community as many of us reached the halfway point today and it was a wonderful feeling to be a part of that. It made the commitment so much more satisfying.

Do it for you

As helpful as it is to use friends and community as a way of staying accountable, beware of the pitfalls of the Likes Trap. It is very easy to get lost in wanting more likes, more comments, and more recognition. For a while, I fell into this trap and forgot the most important thing: this project was for me. I started this because it was fun, because I wanted to learn new skills, because I craved exploration.

People will like things for reasons out of your control. Art speaks to different people in different ways and the number of likes does not determine the value of your work.

What you should do, however, is embrace the community around you. Comment on work that you like and reach out to people you admire. Be open to compliments and criticisms. That’s important! It’s far too easy to let compliments slide and let criticisms get personal.

Challenge yourself

Don’t be afraid to step out of your comfort zone and try new things. In April, I had the pleasure of attending Creative South. At the conference, I signed myself up for the inaugural Live Type Fight. I was more than nervous going into it, as were several of the other designers I met. That being said, it was such a fun experience and it really pushed my abilities.

The other thing I learned was to not be afraid to share or talk about my work. When I first started, I would doodle at home and post it on Instagram without really telling anyone. After a while, friends would ask me about it and I’d sheepishly explain to them what I was doing. Today, I’ve learned to be more comfortable talking about my work. I try to share the pieces I’m more proud of and get feedback on the compositions that challenge me.

Be open to opportunities

The beautiful thing about this project has been how it has branched out in such an organic way. People have taken note of my project and reached out to utilize my new skills in a variety of projects. I’ve been given opportunities that I would have otherwise not been able to experience.

I’ve had the honour of designing birthday gifts, tattoos, and even a wall mural. It was thrilling to step out of my comfort zone and take on projects that I had never worked on and didn’t know how to do. Amazingly, my friends have been completely okay with letting me experiment and trusting me to figure it out.

One of the best things about being a designer at Shopify is how much room you are given to grow. My coworkers started recognizing my new hobby and began incorporating my skills into projects at work. I get to combine my new skills with my day job — what more can a designer ask for?

Leaving a personal place to design for others is daunting at first, especially when it’s something new that you want to keep to yourself. But don’t be afraid to say yes to opportunities. Designing with limitations can be a challenge that will ultimately make you better at what you do.