A totally incomplete guide to finding your creative-career bliss

One measure of success that I wasn't anticipating is that I now receive fairly regular emails from other creative upstarts or people wanting to switch careers who think that I might hold some keys to fulfillment and career-bliss. 

I am honored that people care what I think or that I might have something useful to say, so I take these emails seriously and spend a lot of time trying to thoughtfully respond.
Or at least - I did. You'd be surprised how many times you can write a long-ass email and not get so much as a "thank you" for it!  I have tried not to take this personally or be bitter about it but let's be honest - it's rude and it's a waste of my time, which any self-employed person knows is precious.  

And *while* we're being honest, I have done the same thing. Have you? You get all excited or inspired to get the nerve up to write someone these soul-baring questions and then you hit "send" and... you forget all about it. When the person eventually finds time to write you back or shows that they've invested in you- you've either moved on, lost the spark, or think you have to plan some kind of elaborate "thank you" gesture that never gets done and sent. I STILL do this. I have like, 3 thank-you cards sitting here waiting to be sent like a dummy.

So, in the spirit of recognizing my own failings, and wanting to pay forward the generosity that others have shared with me (but still save some time on emailing), I would like to share some of what I've learned as a creative-business-lady in the last 2.5 years right here. I will periodically come back to update this, so I hope it can serve as a kind of evergreen FAQ.  Feel free to share it. 

First, a section on calligraphy + lettering, specifically.

Q. I would like to do what you do. I used to try calligraphy when I was young but gave it up to work and raise a family. I'm old now, and a late bloomer. Is it necessary to go to art school to do what you do or are you mostly self taught. Any advice for beginners? I'm not steady of hand like a younger person might be so something easy to start and not too discouraging. I enjoy your blog very much. You are blessed with an amazing gift. Thanks for sharing it.

A: First, thanks for your kind words! That’s just about the nicest, most validating thing to hear so I appreciate you taking the time to say it.

Second, I was actually a self-taught beginner. 
I went through a pretty intense 2-year arts program at my public high school, and did a few terms at university as an Art major, but as far as lettering and calligraphy goes - I bought a friend/mentor take-out dinners for like, 7 tutoring sessions before I moved away from NYC so that he could reteach me the alphabet, and since then, I’ve just been kind of winging it + building on that knowledge.

I knew I wanted to pursue a new career in lettering and illustration and felt woefully unequipped to do so (especially having some very talented graphic design and artist friends to whom I compared myself) but I had to start somewhere. Granted, with no kids or looming debts or real responsibilities, it was easier for me - plus I would not be able to support myself without the generosity and patience from my very loving and encouraging partner. I know that, and am grateful every day.

But, I intentionally made some decisions to get to this place of freedom and took some risks and so here we are.

So that’s my confession. My caveat is that I have too much respect for the art and craft of calligraphy to call myself a calligrapher yet. I practice a form of calligraphy called “modern calligraphy” or “pointed pen” that is more freestyle, but I couldn’t write a thing in formal Spencerian or Copperplate to save my life! 

Advice, as unqualified as I am to give it:

1. Start with lettering. I mentioned that my very talented friend and mentor (despite being like 6 years younger than I am), tutored me in actually relearning the alphabet from scratch. I’d initially contacted him with some questions about calligraphy tools and he whoa-Nellied me and asked what I really knew about lettering. I said I had been told I had nice handwriting, and wanted to learn how to use that professionally, at which point he probably rolled his eyes and suggested the tutoring arrangement. We started with the basics. I mean Kindergarten BASICS. He re-taught me the Roman alphabet starting with majuscules (“upper case” letters) and then miniscules (or, “lower case”). My homework was just to write the alphabet over and over again. I’d listen to music and write bits of lyrics, I’d sit in coffee shops and transcribe snippets of overheard conversation. I practiced a lot. I still do. 

2. Practice. A lot.

The purpose of relearning the alphabet was to get a fundamental understanding of how letterforms are built, what pieces of them are essential and make them recognizable, and the proper strokes to put them together. This becomes imperative in learning calligraphy - understanding upstrokes and downstrokes, which is how you can achieve those beautiful thicks (swells) and thins (hairlines). Buy a book! Watch tutorials online! Follow great calligraphers and lettering artists on social media and absorb their work. And then practice until you start to develop Carpal Tunnel Syndrome. (Hopefully not, but, probably).

3. Know your tools.

Lettering artists argue that you can use just about anything to letter, so no excuses if you don’t have the “right tools”! But I would argue that calligraphy is a bit different and does require some specific tools. You will need:
- a clean, flat or slightly inclined, smooth work surface

- a comfortable chair or stool at the proper height

- smooth paper. I like Rhodia notebooks, but artists like Molly Jacques recommend something with guides, which makes sense. 

- a pen/nib holder (best to start with something oblique and inexpensive)

- nibs (totally depends what style you are going for. Do some research online and read product reviews or visit calligraphy forums to explore). My recommendation for beginning nibs are the Nikko G, Nikko Zebra, and Brause Rose. You can buy all of these at John Neal Bookseller.

- a flat, inexpensive paintbrush (to load the ink onto your nib. You can move towards dipping the nib into the ink, but, I feel like that takes some practice).

- ink.  Lots of options here. Walnut ink seems to be popular, but I haven’t tried it. I have tried Bombay Ink, but it’s pretty runny and finicky in my experience. I prefer to use designer’s gouache. It’s cheap, but you have to work with it and play around with adding water to get the right consistency.  The “right” consistency can vary according to nib and paper type, but, it should stay put in your nib for a few lines of text, and run off the nib smoothly without catching or blobbing on the paper. Mix in some gum Arabic if you like.

And then just play and experiment!
Be fearless in making ugly stuff for a while - it will shake out into something prettier, eventually, I promise.

Other than that, I would recommend just taking a workshop or class if you can. Something that allows you to dive in, focus on just the task of creating lovely letters, and boosts your confidence in the process.


now, some less-specific, general career switching notes

Q: How did you get started? How did you know when to leave your old job?  I assume you just jumped in?

Sort of!

You are right in that I have a background in the arts with some training, but mostly have relied on the fact that creating has always just came naturally to me and, yes, makes me happy.  After working corporate jobs for six years but always frenetically generating creative side projects, the time came for me to just listen to that voice that was screaming inside me and looking for a way out into the world.

I truly had no idea for a long time how to pursue visual arts as a career.
Especially living in NYC, with a talented graphic-designer roommate, I felt like I’d missed the boat and didn’t know how to catch up.  I was working at a fun job with amazing coworkers (including my now-husband) and making a good amount of money but I always knew it was temporary - when that situation started to get less fun, M. and I decided, essentially- "let's get out of here and build the life we want."  

I don’t remember the official declaration where I was like, “Yep, we're gonna move to Austin so I can be a calligrapher” or at what point I realized I needed to honor the creative in me beyond just hobby. 

As I mentioned above, the first step towards officially exploring it was to arrange some lettering tutoring sessions before leaving the city with Ray Masaki.

I loved doing it, had always had good handwriting, and it seemed like a more practical application of my skills than “art” in general. I had no idea how it would look as a business beyond that. But I committed to learning some basics to explore it and was grateful to have found a person willing to mentor/tutor me patiently for a few months.  

Not only did he make me relearn the alphabet from scratch, but he made sure I had a deep respect for what I was learning to do and a deep respect for everything I could not yet do! I think in this DIY YouTube/Etsy/Pinterst culture it’s easy to think “oh man, I could totally do that!” and while that spark is important to getting started, I think a firm foundation of knowledge is also useful - you gotta learn, and then at least know about the gray areas of what you don't know about yet

I still feel like I’m winging it sometimes and am insecure that it shows in some ways. If I could do it over, I probably would have taken my re-education a little more seriously rather than learn everything the harder, slower way. (Lookin' at you, Adobe Creative Suite).

I also have to admit that a big break came for me fairly immediately:

Right before I moved to Austin my best friend, who works at a creative agency said,  “Hi I need you to come in and do some illustration work for our client, Starbucks. I can pay you $x for two days of work.”  

And that was it.  I was officially a professional.

No one else in their office knew I’d never done paid work before - I showed up for the shoot, and the production schedule that day said in print “Talent: Jessica Crowell.” That confidence boost was all I needed to get started in truly believing I could do it for a living.


1. Seek out a mentor or tutor! Take someone to lunch whose work you admire, or someone who has a job that you think would make you fulfilled and challenged (also happy).  Pay them to tutor you in a specific skill set for a few weeks, or ask if you can job shadow on a project. Be an “intern” on the weekends!

2. If you have a partner, make sure you guys discuss all the possibilities and that (s)he is on board with all the outcomes, and that (s)he is excited for you! Don't be afraid to discuss the financial realities of what's about to go down. Are you still going to split rent, groceries, entertainment, etc. the same? There is zero room for resentment, here so make sure you're on the same page.

3. All it takes is one project or gig to put on a resume that says, “Yep, I can do this. I am a pro.” to get you to believe in you, and therefore, other people to hire you.

4. Focus on the work. Do it in your free time. Develop your skills, your style, your brand.  Make it good, then make it better. If the work is good and you present yourself professionally, the business will come.

Q: Did you work part-time at a stationery store or full-time? 
do you still work there?
Should I get a part-time job related to my own career pursuits?

I did! But my last shift was Christmas Eve 2015. I worked there 30+hrs/week for about a year+4 months.

I got the store job after living in Austin for about 7 months (during which I’d been freelancing willynilly - taking whatever work I could get after an abrupt career switch) and badly needed some structure. Working from home alone can be rough on a type-A gal. 

It wasn’t a financial imperative at the time, and I only was working 10-20 hours there per week at first so it was truly the perfect complement to the freelance work I was doing: I was visible in this specific community of Austin and started to be viewed as a resource. I became familiar with products, my "competitors"/peers who shopped there, and how the store's custom print department worked (and learned how to price myself competitively). I offered services (discreetly! Like "here's my business card let's chat about this later, please!") that customers needed that the store flat out didn’t offer (custom art, and calligraphy). And I got a discount. 
If you are considering a part time job, make sure it’s not vaguely related to what you want to do, but actually allows you to do what you want to be doing.

Then I got kind of pressured into taking a management role at the store and worked there at least 30 hours a week (including weekends and holidays). Then M. took a start-up job that paid no money. While we were engaged. And I was getting about 40+ hours of freelance work a week on top of that. NOT VERY FUN, GUYS.

The store job, like every job I've ever had was perfect for a while, until it wasn’t. Gotta know when to say goodbye.

It was retail, so that part sucks. You can’t just not show up one day or sleep in and “work from home” and your feet will hurt all the time.   If you do get a “shop job” keep that in mind!

Q: How did you get to a place where you could do your own thing full-time?

1) I plugged away at building my business to a point where I had more hours of freelance work coming in than I could balance with working retail. That's just simple math.

2) I have a really supportive partner -both emotionally and financially. I know this is a huge advantage and I am very lucky.

3) M. and I have designed a lifestyle that doesn’t require me to make as much money as he does, or as I used to in NYC. (We share a car. We live in a (nice) one-bedroom apartment even though I would have loved to buy a family home by now. I don’t shop for clothes or shoes as much as I did when I made a lot of money. I don’t travel home as much as I’d like to. We missed the weddings of close friends in France and Italy last year). So we’ve made some decisions about priorities that allowed for us to be flexible with our combined finances. Ideally of course, my business will end up making a berbillion dollars and he can be the stay-at-home dad eventually, but in the meantime, it’s important to consider how much money you will be making at first and making conscious lifestyle decisions to support that.

Q: How do you find clients? How should I?

At first, clients were all friends and acquaintances. Plus, one of my best friends from high school who is kind of internet famous  hired me right off the bat + was generous with crediting me publicly. That exposure got me 3-4 clients, none of whom were a great fit for me, honestly. I probably should have turned down some of them, but didn’t know how to do that at the time or why I would turn down money. 

The best thing I did, kind of accidentally, was to connect with other professionals in town who were also fledgling businesses in my field. Specifically, wedding planners, photographers, and event rental professionals. We have fostered really strong relationships amongst ourselves and I think of them as my coworkers now, even if it's a slightly different configuration of them on each wedding or styled-shoot. Many of them are also young women in their 20's and 30's who are working from home, trying to figure it out as they go.  
So find your "co-workers" for a number of reasons, but also because they can lead you to clients. These "co-workers" can even be people who do the same thing that you do (known in some circles as "competitors" but, ew. Community over competition, everyone) because maybe you can offer something they can't, or won't.

I haven't advertised yet.  I have had modest success with focusing on cultivating my work, and then positioning my brand through strategic partnerships and an intentional social media presence. 

Q: How should I price my work?

I don't know. What are you selling and to whom? How good are you? How much money do you want to make? What's your value proposition? Where's your competition priced? What are your costs of doing business?

I asked this question, got met with these questions back, and had to figure it out myself - so you do, too!
You'll lose some customers in the process when you aim too high. You'll get more work and get a lot more experience when you price low. Learn from it every time.  Her Royal Highness, Jessica Hische has great advice.

I hope you will find this encouraging and useful. I wrote and erased and came back to it over a few days and copied/pasted some parts from older emails so let me know if parts don’t make sense.


Q: Final thoughts?

The worst thing that happens is that you try and fail. So what!

We only get one life, and we’re responsible for what we make of it - make it great! 



There are people far more qualified than I with way more experience and intelligent things to say about all of this. My most precious resources on questions about pricing, contracts, and creative business have been blog posts, videos, or conversations from: Jessica Hische, Ryan Hamrick, Emily McDowell, Tim Goodman, Simon Sinek, AIGA, & fellow artists on the Flourish Forum. Do the legwork!