Biz diaries

10 Things Nobody Told Me About Hand Lettering Professionally

I’ve talked about misconceptions about working from home before, but today I’m taking it a step further and peeling back the curtain on what it’s like to work as a professional hand letterer/calligrapher.

So pour a fresh cup of coffee, sit tight, and enjoy the ride…


Finding your own style is necessary (and hard).

If you want to become known for your own hand lettering, it helps to have your own hand lettering. Developing a personal style that’s recognizably you is a must, but it’s also really freaking hard. Without a clear plan (like the free Signature Style Challenge, which you should totes join), it takes a long time to try on different styles and piece together the parts that you love.

Comparison is a ruthless bitch.

There are a butt load of letterers and calligraphers out there in the world. There are probably even a bunch that do work very similar to you. While I try not to get bit by the comparison bug to often, I’m still only human, and when that sucker bites he bites hard. It’s all too easy to go from appreciating someone’s awesome talent, to resenting that talent, to appreciating it all over again.



Time management is your new best friend.

Whether you’re lettering on the side, working for yourself, or going through an agent, time management all falls on you. Balancing creating work for clients or customers, promoting your work, and business aspects like invoices and bookkeeping, are all part of the job description. Not falling down the rabbit hole of Pinterest at 2 in the afternoon is also part of the job description (and if you know Pinterest, you know how hard that can be).

It’s not always fun.

Ok, so it’s almost always fun. But when your passion becomes your work, it’s hard not to get bogged down in the work part after awhile. You’re not always creating for yourself (and sometimes it feels like you’re never creating for yourself), so it’s easy to fall into creative ruts and start to feel burned out.



Explaining what you do for a living can get really old.

Don’t get me wrong, I LOVE telling people that I’m a hand letterer. I get to do what I love for living, and that’s freaking awesome. But when you’ve explained what it is you actually do for the millionth time, it starts to lose some of the fun (especially to older men – they almost exclusively never understand my spiel). Even the best elevator pitch can get tiresome when you’ve repeated it over and over again (my default: “I write pretty things,” and show them my phone case. Done.).

You’re a business, and businesses require business shit.

Invoicing. Bookkeeping. Customer service. Marketing. The dreaded taxes. If it’s part of your business, it’s probably part of your day (unless you hire people to do it for you, in which case, you go girl). This goes back to #4 – being a hand letterer isn’t always fun, because it’s not always the fun stuff. Sometimes you have to roll up your sleeves and get those taxes in on time.



Regular paychecks are a thing of the past.

What’s the one thing I miss about the 9 to 5 life? A regular paycheck. Money management has never been my strong-suite, and with a profession that makes it completely critical, my stress levels aren’t always exactly low. Much like managing your time, managing your money well is a huge part of any freelancing gig and one that can take some getting used to.

You’ll get asked to letter stuff for free – a lot.

From total strangers to your closest friends and family, people will ask you to letter stuff for free. I found the same to be true when I ran my product-based business, but with lettering it seems to be even more prevalent. Maybe it’s because I make it seem effortless, or they assume I’m not spending any money on a physical product so it must not be as valuable. But I spent years (and a LOT of money) getting my skills to where they are now, and should be paid as such.



It’s one helluva rollercoaster.

Working for yourself and doing what you love is freaking awesome (see #9). But from day to day, or even hour to hour, you can go from feeling on top of the world to a total slug.

Your work is the greatest you’ve ever done. Your work is absolute garbage. You’ll never be as good as So And So. You’re almost there. You’re killing it. And on and on it goes.

Being paid to do what you love is amazing.

It’s all too easy to get bogged down in all the negative or annoying or frustrating things that come along with hand lettering professionally. But then sometimes it hits you – someone out there loves your work so much that they want to give you money for it. Real-world, tangible money. Throw in an EIN (like your social security #, but for businesses!) and you feel like a total boss.


If you’ve been thinking about starting a career in hand lettering, (1) a million high fives, and (2) I hope this list helps you with that decision. While it’s not always pretty Instagram pictures and rainbows, it is a career I love and am proud of (even when I explain what I do for the tenth time to that one old guy at the bar).

Are you a professional hand letterer?! What do you think I should add to the list? Let me know in the comments below…