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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Elle Drouin

Elle Drouin is the founder of the Styled Stock Society and the human behind @mochiandthecity. After several years working as the Director of Marketing & Digital Strategy for e-commerce businesses, Elle launched her own business to focus on helping other women build brands that are as profitable as they are pretty. 

Elle currently runs the Styled Stock Society, a stylish stock photography membership for female entrepreneurs, as well as works as a commercial photographer for beauty and lifestyle brands. 

Elle Drouin | Freelance Wisdom

Tell us about your path to becoming a freelance product stylist, photographer, and marketing strategist.

I studied business in college and started my career in finance before pivoting to work in marketing for a few years. When I first started my business wonderfelle MEDIA in 2015, I offered marketing consulting services, launched online courses, and created other digital products. In 2016 I created the Styled Stock Society because I wanted to create a subscription based business with recurring income to smooth the ups and downs in between course launches, but I quickly realized that I enjoyed styling and photography more than constantly launching courses or working with clients one on one.
I never planned to be a full time stylist and photographer but at the end of 2016 I felt like I was being pulled in too many different directions, so I decided to focus on the parts of my business that brought me the most joy. Since then, the Styled Stock Society has grown to over 1,000 members and I’ve worked with dozens of lifestyle and beauty brands to create custom imagery for their marketing channels. I also started an Instagram account for my dog @mochiandthecity around the same time as I started my business - and while it started as a fun creative outlet, it has grown to the point where I’ve had the opportunity to shoot ads for brands like American Express and The Ritz-Carlton.
Elle Drouin | Mochi Mondrian Park Ave | Freelance Wisdom
Elle Drouin | Mochi Mondrian Park Ave Leopard Lounge | Freelance Wisdom

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

Knowing that I wanted to start my own business, I actually started a blog sharing marketing tips while I was still working a 9-5(ish) job. I built up a couple months worth of content before I ever launched a services page so when I was ready to take on clients, I already had an audience that I could offer my services to. For the first couple of months, most of my clients found me via Pinterest - they would come across one of my blog posts and end up hiring me after learning more about my services.

You run three different businesses, how do you balance the needs of each business and/or do you have any tips for being your most productive?

While I have 3 different businesses, there are many things they have in common. I batch all of my tasks so that I can focus on one type of thing at a time across all businesses. So for example, I have one week every month that’s my “content creation week” - so this is when I’ll style, shoot, edit, and upload all of the images for my clients, for the Styled Stock Society, and many of Mochi’s images as well. I’m much more productive when I can get in the zone and STAY in the zone so it makes the most sense for me to spend a few days focused on a task rather than do a little bit each day or week.
I couldn’t live without Asana - I use it to manage all of my projects! I map out everything at the beginning of each month so that I always know exactly what I need to do when I wake up and I don’t have to waste time figuring out what my priorities for each day are.
Elle Drouin | Styled Stock-Society | Freelance Wisdom

What has been your greatest struggle as a creative business owner so far?

My greatest struggle has been accepting that there isn’t usually a clear next step. When I had a corporate job, there was a hierarchy to things so I started as an assistant and worked my way up over the years with regular promotions. There was always a next step or next level to strive for that made it easy to figure out “what’s next”... but when you own your own business, there are no promotions. There’s no one to tell you what the next step is so you have to figure out what that is for yourself. It’s liberating in a way, but I’m the type of person who likes to feel like I’m progressing towards something specific so I’ve struggled with not always knowing what’s next!

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

As much as possible, I try to automate or outsource the things that I hate doing! I’ve found that I’m a much happier person when I don’t waste time worrying about things like bookkeeping or failed transactions. I’m lucky that I have a great support team to help with a lot of the nitty-gritty business details, but with that said, there are also going to be some things I have to handle myself. I have “CEO week” every month where I address any of the business issues that need my attention so that the rest of the month I can focus on creating content, marketing, and serving my clients and customers.
Elle Drouin | Blush Office | Freelance Wisdom

What are your favorite ways to stay creatively inspired?

I travel (almost) every month which always helps to fuel my inspiration but in general living in NYC keeps me creatively inspired. There are so many different people doing really amazing things in this city and I find myself constantly inspired by all of the other business owners around me!

If you could give one piece of advice to your "just starting out self," what would it be?

Don’t be afraid to get REALLY specific. I think a lot of newer business owners (my former self included) are afraid to really niche down and get really specific about who their target audience is - but my experience has really proved that the more specific I am in targeting a specific group, the better I can understand their needs, and the better I can attract and serve them.
Elle Drouin | Fall Fashion 16 | Freelance Wisdom
Elle Drouin | Creative Entrepreneur | Freelance Wisdom

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

Discipline, perseverance, and courage.
Elle Drouin | Styled Stock Society Images | Freelance Wisdom

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Olimpia Zagnoli

Olimpia Zagnoli is a freelance illustrator and artist from Milan known for her super fresh shapes, voluptuous forms, and clean palette of brights and darks. Her work has been featured in The New York Times, The New Yorker, Apartamento Magazine, and she's also collaborated with the likes of Fendi and the Guggenheim Museum. If you're based in Los Angeles, head over to HVW8 to catch her solo show, “Cuore di Panna,” up until July 16th.

Olimpia Zagnoli | Freelance Wisdom

Tell us about your path to becoming a freelance illustrator and artist.

My path is probably very similar to that of many illustrators. You love to draw, you graduate from some sort of art school, you’re out and terrified, you’re desperate to find your own language, you sorta find it, you begin to work, your first works are terrible, you get better, you work more, one day you’re like “this is not too bad” and you feel kind of happy for what you’ve done, then you’re lost again, two days later you’re happy again, you struggle to get paid, you finally get paid and you buy a nice pair of shoes. 

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

One of the hardest parts was looking for a visual language. I wasn’t looking for anything COOL back then but I was looking for something “me”. A set of subjects, shapes and colors that reflected who I was on the inside and made me feel comfortable. It wasn’t automatic but as soon as that started to take shape, more clients started to connect with my world and understand it. 
Olimpia Zagnoli | CINZANO | Freelance Wisdom

As a freelance illustrator, artist, collaborator, designer, and shop owner you are balancing a lot of roles and projects, do you have any tips for being your most productive?

I am terribly lazy. I only like to do things I like, that’s the one thing that makes me go go go. I don’t follow routines, I don’t have particular discipline, I just approach whatever feels good at the moment very seriously but with an open spirit. 

Clodomiro is a shop that you opened with your father. What do you love about this collaboration and what have you found to be challenging? 

My dad came up with the idea of opening an online shop which theme had to be “erotism” but approached in a light way. When we opened we only sold a set of china plates with my illustrations and then we slowly made t-shirts, panties, scarves and pillows. It takes us so long because we work on this side project in our spare time which is very limited and we also want to make sure the quality of everything is really good. Sometimes we work on a product for years before it sees the light. The most interesting part of the job is the relationship with the artisans that we involve in the project, especially the face they make when they realize they have to prints 50 plates with a pink penis at the center. The job is literally just me and my dad. We are the only ones who reply to emails, ship packages, drive to visit factories, update our Instagram page and take care of business in front of a plate of spaghetti. 
Olimpia Zagnoli | Spaghetti 4 | Freelance Wisdom

Do you have any advice for fellow designers looking to enter into a familial collaboration whether it be with a family member, a spouse, or a close friend? 

I think it’s a great idea, but it can lead to some stress. Defining roles like in any other relationship could be of help. I do all the drawing, communication and social stuff, my dad keeps the storage, ships items and make invoices. 

We love your surface pattern designs for fashion brand Marella and shoe company Arrels. Are there other physical products you hope to illustrate for one day?

I’ve never worked on an umbrella and I think it could be fun, but my dream at the moment is to work on some public art, like illustrating the bottom of a public pool, designing a fountain in front of a hospital, make a monument dedicated to moms or soup. 
Olimpia Zagnoli | NYSTAMPA | Freelance Wisdom

What has been your greatest struggle as a freelance creative so far?

As mentioned before, I struggle with organizing my time. I work pretty well on a tight deadline and it seems like the more time I have the worse it is. I like to improvise and enjoy the freshness of the moment. 

How do you continue to attract your ideal clients?

I try to make a good selection among the proposals I get based on how I feel instinctively about them. I try to not associate my name with brands or causes I don’t support or don’t love. I’m still learning how to say “no” more often, but the more I do it, the more I think it shapes the opportunities I get for good. 
Olimpia Zagnoli | FANTA | Freelance Wisdom

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

I couldn’t survive in this business without an accountant and a lawyer. Filing taxes and reading a 20 page contract by myself would kill my soul and send my creativity to Mars. Unless you enjoy that kind of thing, I’d say hire someone good to do it. 
I quite recently started working with an assistant and as much as it’s difficult to delegate, I’m enjoying it very much. She takes care of emails, shipping and she's of great help when I work on workshops and exhibitions. 

If you could give your just starting out self a piece of advice what would it be?

Work on the quality of what you do, less on the quantity. 
Olimpia Zagnoli | MTA STAMPA ITALIA | Freelance Wisdom
Olimpia Zagnoli | Quality over Quantity | Freelance Wisdom

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

Be critical, be radical, be you. 
Olimpia Zagnoli | Spaghetti 2 | Freelance Wisdom

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