Last week I had the pleasure of chatting with Becky Simpson all the way from Austin, Texas. Becky has worked as a freelance illustrator, and as of yesterday has published two books, AND through a creative residency with Adobe now runs her own store called Chipper Things. We talked about what she learned from her year-long residency, finding structure and routine in a role that is always changing and some of the nitty gritty that makes up her daily work life. She is honest, fun, optimistic and overall a great person to talk to. Enjoy!

You’re a self-employed illustrator, author and you just launched your own online store. With a million different things on the go, what are your main focuses right now?

I’m super focused on my new book at the moment. It’s coming out June 28th and it’s called “The Roommate Book.” I’m so excited about it. It’s 150 pages of illustrations, really short essays, flowcharts, hypotheticals and a bucket list. It’s for all the young adult women who want to celebrate roommate life. That’s currently taking up the majority of my focus. I’ve been working on it for over 18 months. To finally have it in my hands and not just be a project that I’m talking about is awesome. I'm also focused on Chipper Things - my new online store.

Tell me a bit more about what your role looks like between those two things?

I’m trying to relearn a bit of a routine because I’ve been used to working on my own for years. Previously, I did a lot of freelance illustration work, which is a much different workflow than producing a product line and launching a book. It can also shift every few months. For example, I’m not going to have the same tasks with the book in three months as I do now. I’m still figuring that out, but I’m trying to focus. One thing I like to do is batch things to help me get into a flow. If I can do a lot of something in one sitting, versus peppering it throughout the week, that’s ideal for me.

Currently, my role involves a lot of emails and researching stores that I want to get into. That’s been a fun process, because I get to find my spirit stores, and be like, “I love you and I think we’d be a great team.” That kind of outreach is a big part of my day.

Everything I do right now feels so new. I have this friend and we get together every week to talk business and accountability. We're running partners in that way. I was just texting her and saying, "This feels like amateur hour... I need to figure out how to schedule my days." It's really easy to just be reactive when you have so much to do.

You recently finished up your year-long creative residency with Adobe. I’d love to know what some of the biggest lessons you took away from that were?

My initial gut feeling when someone asks, “The year is over. How do you feel?” is that I have this sense that I graduated from something really big. I really pushed myself, and I may have put in one year technically, but it feels like I came out with several years of experience. Everything was so focused. It was challenging in all the right ways. I have a lot more confidence and direction in my work. It was a really refining time.

The residency provided me with some solid accountability. To me, accountability is kind of like running with the wind. You might not feel the direct impact of it at the time, but it’s always there making it a little bit easier to run uphill or just keep going. Of course, it’s easier to notice when it’s gone (like when you have to run towards the wind). Adobe was really supportive of my endeavors throughout the year. Because they were doing so much to help me, it made it easier to help myself. I wanted to give them my best year too. It made it bigger than just being about me.

What do you find the most challenging about the work you're doing right now?

It’s a lot to manage. It’s not that each piece is too unmanageable, or too hard on its own, but when you’re juggling all these components, added up they can feel heavy. It’s not that each piece is too hard on its own… it’s when you juggle a lot of things that it gets tricky. It’s like you’re holding a few kittens and then you add more and more to the pile (how you found yourself in this situation, I do not know), but what I do know is that eventually those cuddly kittens just become very heavy. [laughs] Decision-making can be a lot of work too. I’m learning that having limited willpower in a day is a very real thing. It feels a lot like cooking and having a dinner party. You’re figuring out how to time things so that they’re all ready at the right time, and the potatoes aren’t cold when the main course is finally ready.

For example, if I need to restock a product, there’s this whole chain of events that need to happen, it’s not just one decision. It’s contingent on all these other decisions I need to make. Similarly, with the book, I need to reach out to this person in order to get this feature, before this date. We all have our own versions of that, but I’m learning what these new systems are and how to work with them the best way.

How do you know when it's time to either start something new, or when it's time to take on a new challenge, or just make a change?

I enjoy staying busy, but right now I’m practicing the art of saying “no” more. There’s always more ideas than there is time to do them. Sometimes there’s something that in my heart of hearts I’d love to do, if I did have all the time to do it, but the reality is I don’t. You don’t want to overcommit, then have to apologize for not meeting a deadline, or turning in sloppy work. I’m learning to reel things back a little. With that said, there’s never a perfect time to start something. For me, it’s usually that I’m just too excited that I can’t not do it.

The book was an idea that came out of nowhere, but the ideas that ended making up the book came from eight years of living with roommates. Once I had the idea, I couldn’t stop thinking about it. I’d find myself thinking about the jokes that I’d include in it, then I had the idea for the bucket list, then an idea about non-serious crafts and on and on. I think that when the idea sustains itself (AKA I can’t stop thinking about it), that’s when it’s worth pursuing.

On top of that, sometimes things just evolve and work themselves out naturally. The store, Chipper Things, didn’t really come out of nowhere, I didn’t just decide one day that I’d do a product line. It was several years of little victories here and little defeats there, that made me realize it was something I could do and wanted to do.

Over the course of your career so far, have you developed any particular routines or habits that make you the most efficient?

It’s definitely ideal to do the most important task first. In the mornings I generally try to not schedule meetings or calls. As soon as that happens, it can eat up the whole day. I read this post by Tim Ferriss, about getting things done. He basically said he gets distracted and lazy or unmotivated like everyone else but he’ll pick one thing he has to do that gives him the most anxiety and just carves out the time and space to do it. I try to follow that. You really do feel the most accomplished. I always feel proud of myself when I work that way because not only did I do something that I was afraid of, but I actually followed through with my agenda.

I’m also a big fan of the bullet journal.

What are the main tools that make up your workflow right now?

Illustrator and Photoshop - For design-y stuff on the computer it’s mostly these programs.

Wacom Intuos - I use it for editing all the time. I don’t usually draw directly with it, (unless I’m redrawing wonky arms) [laughs].

Capture - I use some of the Adobe mobile apps like Capture, which is really nice for vectorizing art from your phone.

Printer paper, sharpies & watercolor - Everything’s pretty analog, it’s a pretty simple system.

Any favourite phone apps at the moment?

Google Keep - I've been using it for things like making lists. I want to be better at gift giving, so I have a note for that. If someone I know mentions they love something random, I write it down so that I hopefully someday will have this whole stash of ideas. I like it because it's laid out like Post-Its.

MileIQ - For keeping track of my mileage. It's so easy. If you're a freelancer, you have to download it. I regret not doing that before this year. It makes life a lot easier and saves more money on my taxes.

Do you ever have periods where you feel a little bit disconnected from your work, or where you burn out? How do you deal with those?

It comes down to taking care of myself. I’m always better off when I go to bed and wake up a little earlier and go to the gym before I work. It’s stuff that we know to be true, but it's not until we do it that we remember why. It makes such a difference.

It’s also important to take a step back. Sometimes that feels unintuitive because the whole point of working so hard is that you think all of this work just can’t wait. But if you had a sports injury, you wouldn't be able to heal without resting. I’m trying to schedule more rest and play to make my work better and avoid burning out. I have a lot of energy and I love what I do. It takes more disciple to pump the breaks than keep on working.

I like asking that question because there's this myth that if you were your own boss, or if you were doing what you wanted to be doing, you wouldn't get tired of it, or you wouldn't burn out.

I think working for yourself sounds very romantic in a lot of circles, especially the design world. It’s not better or worse, or right or wrong. It’s neutral. It doesn't mean, if you work for yourself, that you've graduated from working for the man. It's incredible getting to do what I love every day, have my own schedule, ownership of my work, and all these other things that I wouldn't trade for the world… but it does come with a certain cost (or tax, and not in the IRS kind of way). There isn’t the same security month after month and I have to manage my energy. But on the other hand, I can’t imagine going back. Like everything else, it gets easier with practice. I love this lifestyle but I’d be lying if I said it was easy. Totally worth it? Absolutely.

What's a major aspect of what you do that you don't think most people know?

The first thing I can think of is not a sexy answer: admin work, but everyone knows that. The other thing is, with the store, Chipper Things, I know that nobody will notice the 99 things I do right. They’re bound to see the one thing that's not done right. I can't yell from the rooftops, "But I did these 99 things that you didn't get to see! I called like 10 different vendors to see who would do this thing the best, but you only see what’s on the site!" You can't do that. That’s everyone’s plight and I just have to shoot for 100/100.

Overall, why do you do what you do, and why do you love it?

I love what I do, and that's why I do what I do. I can't not do what I do. Not only do I get to work for myself, but I get to enjoy the process of creating that work. Sometimes I wonder how I can give it a bigger purpose than just being about me, but at the end of the day, I think that we should all be running towards what's already running towards us. For me, that's illustrating, it's connecting people, sharing process, creating work that's uplifting and positive and celebrates imperfection, it's real-life. Those are the things that, right now, I feel I can contribute.

Who would you want to see on Ways We Work?

Jen Moulton - My friend Jen does ceramics, jewelry, and leather. She does it all. Her process is really inspiring to me and she’s the first person that comes to mind.

Shay Spanolia – Shay is the founder and illustrator of Bunglo. Her work is beautiful and she’s a whip-smart business person.

Kathleen Shannon – Among other things, she’s the co-host of Being Boss, a podcast for creative entrepreneurs. She’s honest and wise and fun.