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Becky Simpson

Becky Simpson is the founder of Chipper Things, a paper and lifestyle brand that celebrates friendship and play. Becky is also an art director, illustrator, graphic designer, author, and speaker. Her work, in all these areas, fuses her passion for connection, process and play. She believes in celebrating our wonky traits and delighting in the ordinary.

We love this interview for SO many reasons but especially because Becky embraces the dance between freelance and full-time work and celebrates what each type of work has given her. Make sure to read all the way to the end for hidden gems of wisdom on this topic!


Photo by Alex Crawford 

Photo by Alex Crawford 

Tell us about your path to becoming the illustrator and designer you are today.

I’ve always been the art kid. I’m from a small town and was pretty coddled as THE artist. Some of my earliest memories have to do with being affirmed in my creativity. I’ve always known I was going to have some sort of artsy career. I studied graphic design to be “practical” but eventually inserted my doodles into projects whenever I could. It’s just what I enjoyed doing. After doing a lot of that and developing a style (which I never sought out to do, just happened by way of drawing a lot), I became equal parts graphic designer and illustrator. Then I wrote my first book (I’d Rather Be Short) while I was at my first job and that launched me into my freelance career.

In the beginning of your freelance career, how did you attract your first good clients?

When I first started freelancing I had one main retainer client (healthcare stuff). One of my mentors told me not to put all of my eggs in that basket but I didn’t listen. Things eventually petered off with that client and I was struggling. I had no consistent work and I was terrible at quoting projects—I had zero clue as to the value of my work or the time it would take to complete. In fact, I charged $200 for my first project—album art for a friend—and I apologized for it. Facepalm. It was a long road, but I started to attract good clients the old fashioned way: creating good work, posting the kind of work I wanted to keep making and telling people that I was looking for x-type of work. It’s important to note that I had the space to be such a dodo because I had a book advance that I received right before going freelance. I wish I didn’t blow it on not being a good business owner, but that’s what carried me through those terrible months (and honestly, it was a big struggle for at least a couple of years.) Another note: That book probably gave me zero freelance work, but it did give me clout and cool opportunities, which eventually (indirectly) led to projects.
Okay, one last thing (and maybe the most important): I’ve always been involved in the design community and I’ve attended a lot of conferences. Much of the work that comes to me is word of mouth or friend of friends of friends. A lot of it traces back to folks in the industry I’ve gotten to know over the years. I showed up to my first conference not knowing ANYONE and actually left with new friends. I’m telling you, this “who you know” stuff is real and the good news is that you can meet these people by putting yourself in front of them.
Photo by Sydney Whitten

Photo by Sydney Whitten

Becky Simpson | Put Yourself Out There | Freelance Wisdom

After 4 years of freelance you switched to a full time job. How did it feel to transition back to full-time work after 4 years of working on your own?

I started working full time again about a year ago (I have since moved back to freelance and as of when this is posted—it will be my first day at my new full time job). To be honest, the process of going from freelance to full time a year ago was quite tumultuous for me personally.  I had all of my identity wrapped up into freelancing/doing it myself (I was too proud—I had spoken at conferences! Published books! Talked about business stuff!) I thought that I was failing but the reality was that at that time, freelance wasn’t serving me anymore. I wanted a remote lifestyle, but I wanted consistency and more structure. Running two businesses (freelance + Chipper Things) made everything feel heavy. I wanted it to feel light again. And the craziest, most unintuitive thing actually happened: I felt so much more freedom with a full time job than I had felt as a full time freelancer. Much of that has to do with the company I worked for, but relinquishing control does have its powers.

You mentioned that your full-time work has made you a better freelancer, can you tell us more about that?

Since I don’t need it I’m way more picky. I’m selective with my time and I charge more than I used to. I did this with a big project and quoted $12k—twice as much as I felt like I “should have charged for my time.”  And guess what? I landed it! The client said that I was clearly a pro and they were willing to pay more than they expected as long as they could have someone reliable. That happened again recently (much smaller project). The funny thing is, after both were said and done, the “high amounts” I quoted were totally appropriate prices due to all of the (underestimated) work that went into it. I wouldn't’ have found this out if I had a scarcity mindset.
Becky Simpson | Pants Notebook | Chipper Things | Freelance Wisdom

From 2015-2016 you were an inaugural Adobe Creative Resident and you launched Chipper Things during that time (congrats!). What was your biggest ah-ha moment from that experience?

I found out that chipping away at something slowly but surely (and consistently) is more powerful than big leaps. A small illustration every day for 100 days gave me a library of content that I still use. This has served me more than working hard all weekend of staying up until 2 AM grinding out work. I leaned other stuff too, but this one first came to mind.

Additionally, if you could give one piece of advice to illustrators/graphic designers thinking of opening their own shop, what would it be?

Start small. I wish I didn’t launch Chipper Things with so many products (over 80!). I didn’t even love some of them all upon launching but had it in my head (because I heard that’s how Rifle launched) that success means blowing people out of the water with quantity. What a waste of resources and energy! If you want to sell products start as small as possible, using a platform like Etsy or even printing on demand with someone like Printful. Send free stuff to people you admire (with no strings attached) and proudly, unapologetically tell the world about what you are selling. Remember, sincere enthusiasm is not bragging. Enthusiasm is contagious and gives others permission to do the same.
Becky Simpson | Good Vibes | Freelance Wisdom
Becky Simpson | Sincere Enthusiasm | Freelance Wisdom

You do all the things, freelance, run Chipper Things, manage your course on Brit &Co, work you have any tips for being your most productive?

First of all, nothing is ever done at the same time. Each big thing happens in its own season—never all at once. It’s easy to be intimidated by other peoples’ resumes, but we have to remember the most successful people focus on one thing at a time, execute it, then do the next thing. My main day-to-day productivity hack is the pomodoro technique in the Productivity Planner (I was a Bullet Journal purist until this one, though they can be used in tandem).

With all those ventures in mind, what has been your greatest struggle as a creative business owner so far?

Right now it’s getting out of the spiral of 24/7 work. Work begets work. I’m doing too much right now (but thankfully as of this week I’ll be back to a working-more-normal-hours rhythm thanks to some cool big life changes). When you’re so saturated with work/career stuff, the default mode becomes a lazy productivity: accomplishing something—anything—is easier than stepping back and evaluating the bigger picture or creating systems to eliminate much of the work in the first place. Current struggle: I want to hire help for Chipper Things in the near future but feel held back by the whole “But it’s easier if I just do it,” and “It’s not big enough to need THAT much help but it’s too big for me to keep managing it all on my own” dance.
Photo by Constance Higley

Photo by Constance Higley

Tell us about these big life changes! And how will it help your work-life balance?

In a couple of weeks my husband  and I are going to embark on a year of traveling and living in an Airstream!  And as of the publication of this interview, I’ll be working full time (remote, obviously) for Tubby Todd. These big changes forced me to 1) Get a fulfillment center for Chipper Things 2) Turn down freelance projects and 3) Greg is going to have a bigger role in Chipper Things, which means he’ll be taking over the stuff that gives me the biggest headache and takes a lot of my time. This trip is a reset that is forcing me to implement the kind of systems I’ve preached about in the past.

Do you have any tips for dealing with the nitty-gritty business details?

I wish I hired a bookkeeper day one. I thought it was so expensive but I sucked at it, which of course cost me more time and money. If you’re a small business, the bookkeeper will probably not cost very much. It’s worth looking into, so you at least know where to turn when you do feel “ready” (though you are ready right now). I love Quickbooks. It took me too long to hop on that train too. The ultimate hack though? Ask for what you want. I believe Oprah said it best: “You get in  life what you have the courage to ask for”. Oh! And I love how Kathleen and Emily (of Being Boss) say to never leave money on the table. AKA, never delay sending an invoice or cashing a check. Sounds simple and obvious enough, right?
Becky Simpson | The Roomate Book | Freelance Wisdom
Becky Simpson | Roommate Gift Ideas | Freelance Wisdom

Any music, podcast, or book recommendations that you'd like to share?

I’m due for a reread of Essentialism by Greg McKeown.  It’s all about weaning off the non-essentials in life (geared more toward business. Appropriate for both freelancers and full timers). It’s inspiring and quite freeing. Shoot, I'm going to listen to it after I’m done with this interview. I usually audiobook business books.

Anything we missed that you'd like to share?

I think a lot of times people say they want to be freelance, but maybe what they really want or need is just to work remote. The freelance lifestyle has a ton of perks (WORTH IT), but working remote and full time (for a company you love) has many of the same benefits as a freelance lifestyle. Of course, the actual company does make a big difference in the equation. And it’s likely you’ll still need and want the freedom to do personal projects. I’m a big, big fan of the freelance lifestyle (that’s what brought me so many cool opportunities). I just want to push back on the notion that freelancing is the only way to be free. There are a lot of other freedoms that come with a job: Financial security, structure/stability, energy, etc.
Becky Simpson | Everybody has a story | Freelance Wisdom

The 3 greatest attributes you need to be a freelance creative are:

Passionate, curious and accountable (I don’t think the last one is necessarily an attribute, but there needs to be some sort of accountability for there to be challenge and growth.)

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