I think you are a detail-focused person, and a person that loves tedious activities (like organizing bookshelves, needlepoint, etc) you have a huge head start. Lettering and calligraphy is a lot less tedious than type design, but all require a love of detail. You can definitely be taught!

There have definitely been different moments where I feel like my freelance career got a boost, the first major one being when I launched Daily Drop Cap. Because the project spread everywhere on design blogs, and because I was simultaneously participating in the online design community, people started to follow my work. It feels like about once a year I have a project that really resonates with people, and makes a new "I've made it!" moment. This year's is releasing a book, last year was the Forever stamp, etc.

Big clients came slowly. When I started freelancing I was doing mostly editorial, and mostly for smaller local magazines and business mags. I would get a project here or there for a big client by way of a small design agency (smaller agencies would hire me to create art for a project they were hired to do). Still, most of my "big client" work comes from agencies not directly from the client.

For me, I feel like it's affected my career positively because everyone has been really accepting and welcoming and "yes! more ladies!" when it comes to inviting me to speak / participate in projects, etc. I know this isn't the case for everyone, and I think part of the reason why it's worked out for me is because I'm really extroverted (openly speaking your mind, being confident in your skills, cursing too much, etc are weirdly seen as "male" traits). I have always been a "dude girl" (I grew up in a neighborhood full of boys and always had a good amount of male friends). I know a lot of women that have had the total opposite experience.

Finding type foundries you like is very similar to finding musicians. You might have a library of 500,000 songs, but if you had to choose an artist off the top of your head to listen to, there's probably just a handful of go-tos you could rattle off. The mistake most designers make is memorizing FONTS instead of the designers of the fonts. If you remember the designer, you know you can look through their catalog and probably like other things they've made.

I'd look at sites that have a naturally curated list of foundries they work with (like vllg.com) or even some of the webfonts distributors (like typekit or webtype).

There are loads of good classes on Skillshare, Lynda.com, and other learning sites. When you say "typography" though, that technically means designing with type (like good ol' graphic design). I'd search for "lettering" or "type design" if you're interested in creating projects from scratch. Not to promote my own stuff too much, but I have a skillshare class up where I cover A LOT about how I create letterforms, and also have a book coming out called "in progress" where I go through as much detail as I can about how I work and what I learned from doing the type@cooper course (halfway completed it)

I just try to make sure whatever I'm doing online is a reflection of how I am in real life. I don't know how people do it when they have to develop a "persona" for their work-selves that is different from how they are at the core. It's just easy to be me all the time!

I don't spend a lot of time worrying about how to market myself, but I do get self-conscious if I feel like I'm posting too much content to twitter that my audience might not be into. When I was pregnant / first had the baby, I was doing most of my online sharing on Facebook because I didn't want to overwhelm my twitter audience (people who follow me specifically because of my work) with gross pregnancy / baby related things. I don't filter myself much, but I just try to keep a balance of life/work posts.

I haven't had a daily project in a while, but I think it's something I'd really like to consider starting back up. Right now, I've been just figuring out how to adjust to my new work schedule (now that a baby takes up all my outside of work hours). Once I get a handle on that, I'll likely be able to dive back in to for-fun side projects again. I have a lot of half-completed typefaces and want to make a goal to slowly start completing / releasing them.

Of course! One of the things I do when looking at lettering is I try to strip away all the decorative bits (which includes color, gradients, swashes, illustrative elements, drop shadows, linear ornamentation, etc) and look at the letterforms themselves. Usually someone that is early in their career focuses way too much on the decoration (because, honestly, ornamentation is exciting and fun) and less on the letterforms. If the letterforms don't hold up without the decoration hiding all their flaws, I know the person has a lot to learn.

My most embarrassing moments usually happen when a designer with an encyclopedic knowledge of design / type history asks me if I know something and am totally blank about it. While I am a nerd, I am not the level of nerd that has everyone and everything related to the design / type world memorized, so I find myself in situations a lot where I'm being introduced to THEE famous whomever and I'm like "yeah! I...definitely...know...your work..."

And what if I say, "join the queue"? :-)

I use a combo of cheapy technical pencils (like the clickable Bic ones you buy in bulk packs) and Blackwing pencils (the black kind) for refining sketches!

I try to always make sure I have a lot of projects in the works—be they client projects, personal projects, etc. I only find myself TRULY procrastinating when I don't have another project to work on. I also forgive myself if I start something and really have no desire to finish it whatsoever. Generally, as long as I make sure whatever I'm working on could be completed in under a week if it totally took over my life, I have an easier time completing it.

I definitely spend more time hanging out with people in tech here than I did in NYC. In Brooklyn, I have two main groups of friends—a group of mostly illustrators, and a group of mostly graphic designers / web leaning folks. It was great to see the world from both perspectives and to talk to A LOT of people that were in a similar situation to myself—fulltime freelance doing mostly client work. Here, I feel like the freelance design / illustration community is TINY but strong. I feel like more of an anomaly in a city where most of the people my age are working for startups / tech companies.

There are a few things about startup life that intrigue me for sure. I love working with people and think I would thrive in a busy office. I would love to know that if I wanted to go on a last minute vacation there was someone I could delegate my work to (right now, I'd just be screwing over clients if I decided to randomly skip town). But overall, I really like being the master of my own schedule and I love that every few weeks I'm working on entirely new projects. I'm terrible at working on big long term projects so the high turnaround of freelance work is best for me.

1 - tons! There is a whole crew of lady type designers that I've been in closer contact with online lately that I would love to lunch with.

2 - I'm at the office from 10-5:30 these days, and try to make sure I'm actually working the whole time I'm there. Occasionally I have to do an hour of work in the evening after the baby goes to sleep or some work on the weekend but those are my general hours. This weekend I had to migrate all of the websites on my server to new sub-accounts because everything was getting hacked so crazily, which was the first time since I've had the kiddo that I've worked a full weekend day.

3 - This is hard to pinpoint, since a lot of my "vacation" is conference travel (which is only vacation if I can take Russ with me, which I usually cannot). If I had to guess, I probably take 3 actual weeks of vacation, including the holidays, with occasional "play hooky" days here and there.

4 - Pee-my-pants excited! When I first started working on it I thought it would just be a collection of my sketches but it became soooo much more as I was working (including a 30,000 word manuscript which turned it into a semi-textbook!)

I started by incorporating lettering into my existing illustration projects—as a designer you could do this by offering to letter some headlines for a project instead of using a typeface (if that worked for the project). As far as resources, there are now loads of online classes (skillshare, lynda, etc), and the Type Directors Club is a great place to look for workshops / livestreamed events / book recommendations. I also have a Pinterest board of all design related books if you want to check that out!

The first week was tough, but I found that as long as I get my time with her in the morning, being separated from her throughout the day isn't hard. The thing that has been tough is that my work day is a lot shorter, and it has definite start and stop points (I drop her off in the morning at 9:30, which means I get to the office at around 10am, and I have to be home by 6 to feed her after Russ picks her up). What's been good is that while I'm at work I'M WORKING. Like, really working, not fucking around on the internet. Mornings and evenings are just too precious and I can't give them up to finish up a project I was procrastinating from during the day. I've had to turn down work and certain speaking gigs that require a lot of travel, but I know that I'll hate myself if I lose any time with her in this first year to a project I felt so-so about taking on.

The hardest adjustment has been the near-constant pumping at the office. I'm actually pumping right now.

I did a creative mornings talk and the biggest thing I tried to say about this subject is "you learn the tools to make the things you want to make". I wanted to make side project websites and not have to pay someone to make / maintain them (knowing they would make no money and I just wanted to do them for fun) so I learned as much as I needed to know to work with existing CMS's and make those projects real.

I think if you are a web designer, it's imperative that you at least know a bit about how to do front end development just so that you can communicate clearly with your developers. I think outright deciding you won't learn ANYTHING about HTML / CSS / JS / PHP, what-have-you, is like moving to France and saying "nope, I'm never ever going to learn even one word of French. I'll just figure out how to communicate by pointing at things".

I think certain kinds of lettering will definitely go out of style because of over-saturation (motivational-poster-style lettering, chalk-lettering, etc), but lettering and type design are REALLY diverse fields. It spans everything from really subtle logo work (which will always have a place) to the more illustrative stuff you see all over Pinterest. Good designers have to be agile and adaptable, so I think that people that find themselves caught in the middle of a trend just have to make sure that they're taking on diverse work, and working on diverse projects so that they're not only associated with something that could fall out of favor.

Definitely print out your work as you're working on it, and critique it as if you were a classmate in art school. It can be really hard to crit your own work on screen or figure out what needs to get fixed as you're working on it, so I try to print things out as much—it helps me see mistakes more clearly.

honestly, I haven't really made a proper birth announcement yet! The posts I make on instagram of her weekly photos use a half-finished typeface I made a while ago when designing something for Erik and my studio Title Case, and the secondary typeface is a new-ish but unreleased version of buttermilk I've had in the works for ages. After she was born, the last thing I wanted to do was spend any time designing (I was too busy being a human food machine). Now that I'm back at work, I could finally carve out some time to design something proper for her, but I'll probably wait until her first birthday or some next big life moment.

I'd love to do weekly posts for a year, and then maybe switch to monthly posts after that. It's been kind of difficult to stay on top of (we just ran out of blankets!) but it's really important to me that I at least keep it going for the first year of her life.

Giving back to the design community has helped my career immensely. I love being able to teach what I have learned so far to others, and by posting educational content to my site it gives people another reason to visit (and makes me really happy in the process—feeling like I'm contributing more than just "pretty pictures" to the world.)

If you want to get started giving back, know that no matter where you are in your career you have something to teach others, even if it's teaching all the mistakes you've made so that others don't have to make them. You don't have to be an expert in anything to share knowledge, you just have to be real about what kind of knowledge you're sharing.

The boardgame got back-burnered while I was working on my book, but I'd loooove to bring it back to life! I think no matter what I'll at least post it to my site this year. I'm working on making more "case-study-esque" work posts so that I can give better context to certain projects and that would be one where I'd want to walk through it a little more intensely than I do my usual work.

Yes to more alphabirds prints! There are individual letters up there now but I'll be putting a new full poster up in my shop (hopefully this week if I can get to it) that was printed before I had the baby that's in silver and gold foil!

I definitely like the direction it's taken, but there are some things about it that bug me—mostly how it feels heavily weighted toward the gle at the end because of spacing / color. I think the G they use alone (in the heavier weight) is great, but when you see the G in the new logo it seems light (generally type designers add a little weight to uppercase letters so that optically they don't appear lighter).

Most of my inspiration for projects just comes out of the constraints I'm dealing with—clients give me the words / phrases, the layout, general art direction or a moodboard, and I work from there. I make small decisions as I go rather than a giant decision up front, which lets the piece take shape naturally. That's not to say I don't look at other artists work, I just try not to do it often or while I'm actively researching a particular project because it's really hard to not accidentally rip stuff off!

Really scary! I was very very clear with Chronicle that I didn't want it to be a monograph because I feel like it's way too early in my career to make a book like that. I knew that as long as I could make it useful, and make it all about process, that I would be less intimidated to put it together (and less self-conscious having it out in the world as an unchanging snapshot of a particular time of my life).

The skillshare I have up has a lot of the content from our Letter Together workshops. I'd love to do more online workshops, but the letter together format might be difficult to carry out online (the limited class format really helps make sure I can fine tune critique everyone's work). I tried to put as much of the letter together content into the existing skillshare as I could, and much of what we teach in those workshops is also in my new book!

I would love to take a letter tour of the world, but I do feel like local designers are probably the best chroniclers of their hometowns. Erik, my studiomate, takes tons of pictures of sign painting around San Francisco—you should do the same for where you live in India and post online so we can all take a virtual tour! I think there were a few sites / instagram accounts documenting local lettering (there are definitely a few for NYC).