Calligraphy from a hobby to a home business - insight into my personal journey

Everyone’s journey is always so different and inspiring which made me share this lengthy post about how I got started with lettering and calligraphy as a hobby and how I turned it into a home based business. Sit back, pour yourself your favorite bevvie and allow me to share with you my journey along with some practical advice!

nicki traikos calligraphy.jpg

My longtime love affair with calligraphy began when I was a teenager.

Since I was a teenager, I’ve always been a fan of calligraphy and obsessed with neat and beautiful handwriting.  You see, I wasn’t ever one of those kids who had pretty penmanship but always envied those who did.  To this day, my everyday handwriting is messy.  Really messy. You would never tell by my calligraphy work that I have messy handwriting.  That’s because I learned how to draw each letter and practice calligraphy for hours at a time!

my everyday handwriting vs. lettering.jpg

Let’s go back to the beginning!

For years, I tried to teach myself calligraphy.  I played around with different nibs and fountain pens but didn’t like the blunt tip of a fountain pen. I could never control the pen well enough, and didn’t even know how to form the pretty letters I’ve envied in books etc. I would try and try again without any success.  In fact, I still have a journal from the 90s and cringe every time I look at the failed calligraphy attempts!! (see photo below)

One of my personal journals from the 90s as I attempt calligraphy. eek!

One of my personal journals from the 90s as I attempt calligraphy. eek!

The internet didn’t exist then, resources were limited and I couldn’t find any calligraphy books that spoke to me unless I wanted to learn Copic or  Spencerian calligraphy styles, which weren’t my jam.  Finding pens and nibs was the next challenge, I had no idea what to even look for, or where to find them!  So I would put away the pens that I had and forget about calligraphy for a while.

Fast forward to about 5-6 years ago.  I started seeing posts online about Modern Calligraphy and quotes that spoke to me as well as the style they were written in spoke to me! I loved how loose and informal the modern calligraphy style looked.  At that time, I was journalling often and writing was so very therapeutic for me. Not only was I pursuing my art career and wanted to include some calligraphy in my work, but I also wanted to just enjoy the art of handwriting!  So again, I bought a set of calligraphy pens from my local art supply store and went to work!

Guess what happened?!


my early attempts at calligraphy without any instruction or the proper tools.

my early attempts at calligraphy without any instruction or the proper tools.

I was just as frustrated with the fountain pens – which were advertised as “calligraphy pens” but were again, not the right tools that I need to learn how to do modern calligraphy.  I was so confused.  I wondered why I couldn’t write the same as the beautiful calligraphy I saw online!

I am a very visual person and can figure out a lot on my own.  I’ve taken an art program at college but consider myself to be mostly self taught when it comes to all things art related.  However, I just couldn’t figure out this modern calligraphy thing!

Here’s where the breakthrough happened finally!!

I became a member of Skillshare which is an amazing online platform where I’ve learned a great deal of new skills from!! I took an intro to modern calligraphy class with Molly Jacques where I learned about her favourite tools and techniques to begin learning modern calligraphy properly. 

So I went online, ordered her recommended dip pen, nib, ink and paper and I started practicing!

Guess what happened next?!

{You may be expecting me to share a miracle here.}

It wasn’t exactly a miracle, but it was progress! Finally!!

my early calligraphy practice compared to my current calligraphy practice is amazing to see now when I look back at old work!

my early calligraphy practice compared to my current calligraphy practice is amazing to see now when I look back at old work!

I finally had the right tools, and some basic instruction to help me learn modern calligraphy.  I practiced for hours at a time.  Until my hand cramped, my fingers were black with ink and my desk was covered in letters and words. 

This is what my calligraphy practice looks like

This is what my calligraphy practice looks like

That deliberate practice was where the miracle happened.

I still had lots of questions and needed more instruction, but I had trouble finding anything to help me get to the next level.  My goal was to go from a beginner hobbyist, to a full-time professional calligrapher.  So, I worked hard, I messed up a lot, and I spent more time that I needed trying to learn on my own! 

I did eventually enjoy offering calligraphy and lettering services to clients and I created a product based business mostly with my calligraphy and lettering! 

I designed lettering to go on surfaces like wall art and coffee mugs.  I invested in a printing machine where I could actually print my own mugs. It was crazy, like sweat shop crazy!

I screen printed saying on tea towels.

I hand lettered poems and versus for people in my modern calligraphy style. 

All the while, as I offered these products and services to my clients, I developed my own personal calligraphy and lettering style which I worked hard on.  I shared my work online and on my website.  I enjoyed referrals and repeat business.  I was amazed and grateful that I could build my creative business based on something that I did for years in my journals which was write pretty words that spark inspiration, but now I was getting paid to do it!!

How amazing does that sound?!

The best part of this journey really is that I got to stay home with my kids when they needed me. I walked them to school every morning, even brought them hot lunch. Every school holiday and break, I was home with them. Yes, it was challenging at times, but aren’t we all challenged regardless if we work from home or outside of the house?! I worked when I could, and fit in time for creativity when I was able.

Fast forward a few years and where I started getting asked about teaching workshops.

How I got into teaching calligraphy and lettering classes.

small brush modern calligraphy wrokshop with life i design.jpg

I didn’t know if teaching workshops was something that was ever on my radar, but I had people ask me if I could teach a class or a workshop often enough that I just started.  Calligraphy and lettering was becoming popular online and more and more people wanted to learn how to do it themselves.  So early 2016, I started teaching local workshops to small groups.  Each workshop left me feeling inspired to share more.  To teach what I knew.  To help others save time and mistakes so that they could learn faster, easier and make it affordable for them.

I saw that there was an interesting mix of people looking to learn calligraphy.  Some wanted a creative outlet to help them express themselves, others wanted to try something creative but didn’t consider themselves to be artistic.  A few wanted to learn so that they could start making money doing something fun and creative outside of their boring, stagnant jobs. I was so inspired by my students and wanted to share as much as I could so that they had a solid foundation to get started and then to grow their experience will calligraphy.  I wanted them to fall in love with calligraphy as much as I had and I wanted them to have success early on!

This is where my workbooks came in. 

I developed workbooks for people interested in learning calligraphy and wanted them to be able to practice, trace and practice some more! These workbooks have been really great and I’m constantly creating new workbooks to help with learning how to letter different words and phrases along with how to get started with calligraphy.  The workbooks are a great tool, but I wanted to offer more to my students!

After a few years of teaching calligraphy workshops I realized that people needed more support after they took a workshop with me.  Even though they had a workbook that I created for them.  I felt like they need more instruction, reminders on how to draw each letter etc. and opportunity to advance their skills and learn what they needed, to start their own calligraphy business from home too! 

So I started playing around with the idea of creating online courses that closely resemble how I teach each workshop.

I’m a huge fan of online classes. I took my very first online class in 2012 and learned how to design and create my first website for life i design. I haven’t stopped taking online classes since and believe that it’s the best way to get great instruction, from experienced instructors, for very specific interests, affordably.

During the summer of 2018, I started planning.  I decided that I wanted to create a complete series of classes to help people learn modern calligraphy and lettering, but also how to grow from there!  Something that I found hard to figure out on my own and know I could have saved myself lots of time and struggling if I only had more classes to grow with!

Recording my very first class.

Recording my very first class.

So I continued working on my class plans, and began figuring out how to best record my classes and even how to edit them.  This was a huge undertaking for me! After 2 months of solid work and focus, I published my first online class on Skillshare! I was no longer just a student on the platform, I was starting to give back to my community!  I taught a beginner dip pen modern calligraphy class and it took off! I currently have 651 students enrolled in that class at the moment.

I developed and published classes that help take students go from the beginner level to an advanced level where they felt confident developing their style and offering their calligraphy services to friends, family and even paid customers.  With each class, I stress how important practice is and with each class, I show you what you need to learn and work on in order to grow a calligraphy business - if that is your goal.  My first 7 classes are exactly the classes I wished I had access to, when I was starting.  Kind of a blueprint if you will. 

Realizing that Skillshare isn’t a platform for everyone, I decided to create life I design online.  A site dedicated to hosting online classes for my students who want to take a single class with me or multiple classes at an affordable cost and to have the classes easy to access and be able to watch from anywhere!  Currently, my classes are available on Skillshare, life I design online and Udemy. I currently am taking less design clients so that I have more time to support my students and develop classes that will help them.

This takes us to present day where I still offer calligraphy and lettering design services, I teach online and enjoy my own personal and satisfying practice!

My Advice to you

 If you are interested in calligraphy or lettering, I have some sage advice to offer!!  

  • Start with proper instruction from a teacher who has lots of experience! There’s nothing worse than learning from someone who is just starting out themselves. I’ve seen this happen and it’s frustrating, especially for the student who is trying to learn and has invested their time and money on a class. 

  • Watching videos on Instagram is fun and can be very mesmerizing (trust me, I fall down that rabbit hole often!!), but you won’t be doing yourself any favours trying to “figure it out” as you watch.  Save the videos for inspiration only when you have had instruction.

  • Learn about the right tools, and how to hold your pen properly, whether it’s a dip pen, a brush pen or a paint brush! Understand your tool, how it works and how to easily create your thin and thick strokes.  Even how you hold your tool in your hand is extremely important! These are things only instruction from an experienced teacher can help you with! 

  • Learn how to draw each and every stroke properly so that you can then work on your personal style and enjoy writing each and every letter with flair and personality!

  • Practice often and enjoy your practice! It should be slow, therapeutic and enjoyable! Practice writing words that speak to you and that spark positivity!

My advice to the hobbyist

Once you’ve read and worked through a workbook, or finished an online class, find ways to practice what you’ve learned by looking for fun projects to try.  Check out my blog posts for ideas of how to use your new calligraphy skills to impress your friends!

For the adventurists who want to explore calligraphy more

Develop your calligraphy skills by practicing daily, take an advanced class, maybe even start posting a photo or two of your practice and show your friends and family what you are doing and learning.

Perhaps you can even set a goal to two and see if you can achieve it.  Maybe you want to letter a quote to frame for a gift, or letter a poem for a loved one.  Creating a piece of your calligraphy work to give to someone is a great way to step out of your comfort zone.

For those serious about learning calligraphy to potentially start a side hustle and make some money doing calligraphy.

Get proper instruction! I can’t stress this enough.  Pick someone who is doing what you want to be doing, who resonates with you and who can offer you a variety of options to learn from.  Be disciplined with your practice.  Build that muscle memory, skill and confidence.

Start a website, grow your email list, build your social media following. Start building a portfolio of work that you can share and show potential customers. Decide what services you want to offer and what your fees will be.  Take my online class, My Top 5 Ways to Make Money from Home with your calligraphy/lettering skills to help give you a better understanding of what type of work is available out there. 

Learn how to digitize your work so you can offer clients design files.  Hone in on your creative skills but also start developing your business skills.  Make time and space in your daily life to learn, to practice and to grow. 

Don’t look at what everyone else is doing and feel discouraged.  Everyone, and I mean, everyone, starts somewhere and what you may be witnessing is their year 7 which you are comparing to year 1.  Sometimes the hardest thing to do is to start, but start you must! Look at experienced calligraphers as mentors and learn from them, be inspired by them and grow yourself!

My guarantee

What I can guarantee is that with slow and steady practice, you will grow, improve your skills and develop a nice stream of income doing something as beautiful as writing in calligraphy!

You will improve everyday with practice. You may not notice the improvement right away, but if you keep all of your early practice sheets and take photos of your work, you’ll be amazed at the difference a month can make, the difference 3 months can make and the difference a year can make!

Start with a good foundation and build from there!

I hope you enjoyed this long post but most importantly, I hope you have a clearer understanding of your own path and are more confidant of your own personal creative journey!

Happy lettering!

Nicki x