For most creative people, professional and personal are impossible to separate and your grasp on one impacts the other. My work is my life, and my life is my work. The typical boundaries applied by accountants and mid-level managers use don’t work so well, and working at this pace requires us to develop some healthy self-awareness. 

For me, that means holding my career really loosely and acknowledging that most things are out of my control. I have to pay attention to make sure I’m working against my own standards for success. You might find a lot of your identity in being a graphic designer, but you are a human person first and I want you to have a really healthy relationship with your work!

My own career / story has been much less linear than I envisioned in college. I sort of fell into freelancing in Chicago when the companies I was most excited about working with brought me in for project contracts, and pretty quickly I found I loved it because I wasn’t tied to a desk or a client, so I got to choose what I worked on. It was an amazing way to try a bunch of different kinds of work and get a feel for what I wanted to learn more about.

As millennials we really romanticize these ideals because everyone’s Instagram feed looks so dang adorable and they hashtag things like "wanderlust" and "liveauthentic," but truthfully freelancing really isn't for everyone, and that is totally fine! A huge reason I was able to swing it at this point was because I was still working with teams and mentors who were contributing to my development and providing feedback. Also I was on my parents’ health insurance. It makes a difference.

At this point in my career, I’m guessing all of adulthood will be learning how to make choices, learning what’s a good fit. I’ve spent the last five professional years “gathering data” on what makes for positive work experiences I want to have more of. Sometimes I’ve agreed to work on projects with all kinds of red flags, and that’s how I learned what red flags look like. 

Today I’m going to talk mostly about the good things I’ve stumbled into, but it’s been such a learning process: 

  •  learning to trust my gut, 

  • learning when to say no, 

  • learning to leave room for happy accidents, 

  • and also learning not to let successes and failures in this department affect how I view myself. 

So you might notice this pattern of duality. There’s always something “good" about “bad" things, and “bad” things come along with great things. Work that you love is still work, but aren’t we lucky and soaked in privilege to love what we do!?

When taking on freelance work, saying YES! to any project means committing significant time and energy, I might need to turn down other opportunities in the time-being. I'm also committing to the tough weird client things that don’t present themselves initially.

A well-considered NO might mean missing out on a good thing, but I'm leaving yourself open to say yes to different, potentially wonderful things in the future.  Even if nothing else comes along, I've protected that time to work on other projects I'm really passionate about.

I’ve learned to take more time before committing to a project. Too many mistakes were made by immediately saying YES OF COURSE in an attempt to people-please whoever I was talking to. I'm much more satisfied with my schedule when I listen to my gut, weigh things out, and let the heat of the moment pass. 

It’s also worth mentioning that a lot of times I don’t get to have the final say in whether I work on something or not. The universe or client decides for me, and in those times it’s especially healthy to take all this in stride. 

This ability to wisely say Yes/No has come from learning my own priorities and values. It's come from taking myself out to breakfast, asking myself what it would mean to be successful in my work. I can't ask the internet. It’s ok and natural to be inspired by the careers of others, but no one else’s path is going to be the perfect fit for me and comparing myself wastes a LOT of unhealthy energy.

More than follower counts and job offers, it’s amazing to know with a clear mind what projects are worth passing on, and what opportunities are worth sticking your neck out for.

This reminded me of Tina Fey’s mantra, which is “Say yes, and figure it out later.” This mentality of flexibility and opportunity is why big ad agencies send their executives to take improv classes. They learn to fail quickly in front of their peers and think on their feet. A good thing about falling on your face is you probably won’t make the same mistake twice! 

As you learn what matters most to you, as you gain a sense of the room, it becomes easier to respond enthusiastically and full-heartedly to risky situations as the present themselves.

Today I want to share a few stories about teaching myself how and when to say “YES.”

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The first story is about Lost Type Co-op, a collaborative digital type foundry that scalable licensing, making it accessible to students, non-profits, and agencies alike. 

Distributing Abraham Lincoln through Lost Type was a “sure” moment all the way through. I made this font as a college project and wasn’t sure what to do with it when I finished. I had a lot of fun making a promotional piece, and a friend in Chicago suggested I reach out to Lost Type.

A huge thing I learned from this process was to ask. It seems like we’re all waiting to be invited to the cool graphic design party, but the people hosting really need you to tell them you’re interested. Offer to contribute to their project! Submit your work to their blog! Attend the drink and draw! It’s scary but it’s also not at all.

Abraham Lincoln is on Lost Type because I emailed Riley and said “what do you think?” and he said sure. The font was released in the spring of 2012, and it's still going strong. 

Since we’ve launched Abe, it’s been really incredible to see how many people find the font useful. Making a tool for other designers is humbling and amazing. It’s shown up in the craziest places, and 100% every time I see it, it is really exciting. 

Riley and I became internet friends through constant emailing about licensing, so when he invited me to attend the New York field trip in 2013, it seemed like a really great opportunity to meet some other folks who shared a very specific interest in type design, custom lettering, and graphic design.

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But I remember this moment in October of 2013, after agreeing to join the field trip. I had booked a 10-day ticket to New York City all by myself, and I was meeting up with everyone from Lost Type for the very first time. Everyone else was staying in a loft in Clinton Hill, but I actually wasn’t so sure about the whole thing and got my own AirBnB in case I ended up needing to distance myself from all these internet weirdos. I was also the only girl with 10 dudes, and I can confirm that it was definitely a bro-fest at the loft.

As I dragged my suitcase behind me on a very hot sidewalk in Brooklyn, there was this moment when I stopped and looked around and was just like “Whoa there. Who do I think I am??? Why am I doing this?? Who gave me permission to fly across the country to hang out with internet strangers for ten days?”  (it was definitely not my dad, who didn’t let me have AOL IM in middle school) (sorry dad)

At that point I was already confirmed, things were paid for, and I really did have to follow through, but I actually had that thought a few more times on the trip. I was so glad that the doubt hadn’t occurred to me until that moment, I might not have come at all.

Everyone on the trip ended up being amazing and way less creepy than my AirBnB host (come find me if you want to  talk about Furby's as home decor), and it quickly became obvious that the result was worth the effort and panic.

Together we’ve visited New York City, Amsterdam, Chicago, Vancouver, Louisville, and Philadelphia! A handful of typefaces in the collection have come from these trips, but since we’re spread all over the globe, these trips are mainly a way for us to hang out, talk about new projects, and interact with design communities in all different contexts.

As I mentioned earlier, I had a complicated relationship with working for myself. Even though everyone tells you that being your own boss is the ultimate best thing, I spent so much time feeling I had a very bad boss.

Design work took the back seat to contracts and negotiations, and I wasn’t sure how to grow beyond the work I was making. It’s really hard to learn what makes you indispensable to your clients when every month you’re trying to make sure you have the right amount of income.

After about a year and a half of working solo, I knew I was in need of some sort of larger mentorship, and I was open to whatever that might be.   

Are you ready for a sort of tedious string of “sure!”s that ended with my butt in a chair at the biggest advertising agency in Chicago?  

(this slide utilized keynote animations that made the jumble of information and storytelling slightly more enjoyable)

This crazy string of saying “yes!” despite my own natural, self-preserving fears, lead me to a job with Leo Burnett’s Dept of Design, a branding studio inside the 2,000 person global headquarters of the ad agency that created the Marlboro Man, Tony the Tiger, and more recently, Allstate's Mayhem. I don't take for granted the number of times I had to put myself out there for this experience to happen. 

Despite being the POLAR opposite of working independently, I am so incredibly grateful for this experience, and aware that it came at the perfect time. This unique team and environment gave me a place to work about 50/50 between lettering and design.

Taking space from all those details allowed me to look at what I was actually bringing to the table in a project. I found out that I was most useful focused on a specific, illustrative aspect in small sprints, not overseeing a huge project like I’d just crossed my fingers and hoped I was when I was running my own freelance branding projects.

Another great thing was being able to get really selective about which projects I took on the side. Our boss encouraged us to stay sharp in other areas of interest. Knowing my rent was covered by my day job meant I could do things that weren’t really financially wise when I was full time for myself. The majority of Lost Type contributors actually work this way - being able to let passion projects be passion projects instead of expecting it to feed your family.

I loved working with those people and riding an elevator every day,  but when I looked at what growth within this organization would mean, I wasn’t sure I was the right candidate for additional responsibility, seeing projects through from start to finish and navigating inefficient politics with an enormous ad agency. It is strange survival working in an advertising agency, and there were a number of other independent projects I wanted to learn more about before settling into a long-term full time position.

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As I considered what might be after Leo Burnett, I read more about The Cooper Union’s type design program. They offer it in two lengths: condensed and extended (a naming convention that really lands with people who love fonts), and the summer program looked like a really great adventure. I could live in NYC for a few months, and there were so many things I didn’t learn making Abraham Lincoln. I was curious to see what would happen if I learned the technically correct ways to produce a typeface.

As I was talking to my mom, I mean my business advisor, this question of “Why not?” kept coming up. I was at a specific moment of freedom in terms of personal responsibility, and the benefits of taking this risk seemed to outweigh any possible failures. (Although, for me failure would mean moving home with my family that I adore and spending more time with my niece. I’m actually thinking I might tank this whole thing.)

So I did it! I saved up my dollars, quit my cush gig at Leo Burnett, put all my stuff in storage and moved my booty out to NYC. 

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And that's as far as the story can go for now! I have no idea what's next, but if I'm going to practice what I'm preaching to you, I'll hold all of this lightly and get out of my own way.