Thea Kennedy

Thea Kennedy is an award-winning, multi-disciplinary art director, and designer with a primary focus on art direction, design and content creation for the digital space. She has broad online and offline experience in luxury goods, home, fashion, beauty industries, and is now breaking into the tech industry. Thea is also a member of our Creative Lady Directory!

We are absolutely loving her insights regarding the differences in work flow between full and part-time freelance work, and really appreciating the wisdom she shares around things that are important to have in place before you make a big cross country move. 

Thea Kennedy | Freelance Wisdom

Tell me about your path to becoming a freelance art director and designer.

I got my first break with a job in the Global Marketing Department at Ralph Lauren. I designed printed materials for product, presentation and training internally. These included mainly books, posters, and brochures. 
During this time people started to reach out to me with freelance projects. I would take anything on that I had time for. Annual reports, logo’s, wedding invitations, magazines, packaging and so on. I didn’t realize it at the time, but balancing freelance work with full-time corporate design work was a great education in project management. When I began to move on to more senior roles in my corporate life, it felt like a natural transition. I already knew how to manage my time, set expectations, work within tight timeframes, and manage up. I also could clearly communicate with non-creatives, thanks to all my freelance clients. 
After being solely a print designer for about five years, I decided I wanted to transition into the digital space. Mainly for practical reasons, but I also was enamored with the idea of the impermanence of digital design
A friend from grad school had just gotten an Art Director job at a start-up called One Kings Lane, and he asked me if I wanted to work for him. I thought it was the perfect opportunity to dip my toes into the waters of the online design world. And it was great to work with a friend, who would be patient with me as I learned how to design in the digital space. 
We were the first two hires in the creative department, so we built everything from the ground up. Templates, templates and more templates, along with evolving the branding look and feel. Ironically, because it was a start-up in the tech space, I was one of the only people who knew how to design for print, so I ended up doing all the print stuff too.
Thea Kennedy | Freelance Wisdom
I then went on to consult as BaubleBar’s first art director. My focus was tightening up and strengthening their existing branding, as well as working on the UX for key areas of sale on their site.
From there I went to Bumble and bumble, my first job exclusively focused on digital design. As my work experience expanded to heavily digital design, I noticed that the social space was often neglected, and it seemed like such a huge miss. Creatively, it was a place that could be taken less seriously and you could have more fun with! (A Creative’s dream!) This was in 2012, when most people in corporate leadership positions didn’t quite realize the power of social media. I made a point to always create a social component to each campaign we launched while I was there.
Around this same time, my own social presence had blown up, and I started getting paid to do partnerships and collaborations with brands I admired. I also started my blog around this time.
A few years after that, I went on to philosophy skincare, as their Digital Art Director. Things by then had really shifted, and I remember during the interview, everyone seemed more interested in asking me about social media. I realized then, that it might be perhaps possible, to be an art director just for social media….
Throughout all these jobs, I was still freelancing non-stop on the side. I was also getting pretty burned out. I decided to take a risk, quit my job at philosophy, and see if it would be possible to freelance full-time instead. The day I quit my job I got an offer to work with the Creative Director at a new fashion start-up called Spring. And I could work remotely… It seemed like the stars had aligned. My only request was that I work 4 days a week, so I could dedicate one solid day to my own work.
I did full-time freelance work for about a year and a half- working for Spring, West Elm, and Chloe + Isabel, along with a handful of entrepreneurs and small business who needed help with branding.
Then an opportunity came along that lured me back into corporate world… an offer to be Design Director at Bobbi Brown Cosmetics, focusing specifically on Social Media. It seemed like too perfect of a fit to turn down…I had to take a chance and go back into the corporate world.
Thea Kennedy | Freelance Wisdom

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

Almost all my freelance clients have been from referrals, or from people who follow me online, and are familiar with my aesthetic.

Do you have any tips for being your most productive? 

My tips for being your most productive are two-fold:
1. If you’re a freelancer who has a full-time job, I recommend really planning your time and creating a schedule for yourself that works best for your lifestyle, and acknowledging any roadblocks that could potentially happen along the way.
For example: I find it really challenging working every night after work on freelance projects, so I try to create a schedule from the start that is mindful of that. I like to work in large chunks of time, over the weekends. So, when I send a project schedule to a client, I usually note that I will have work for them to review Tuesday (giving myself a day buffer to look at the work I’ve done over the weekend with fresh eyes). Tuesdays are great, because it usually takes clients 1-3 days to respond, so then I’ll collect all feedback by the end of the week, and then can proceed with revisions over the weekend. 
For this reason, I also seldom take on rush jobs, because I can’t work on a compressed timeline for a freelance job, and work full-time during the day. I know I won’t produce good work. 
2.If you’re a full-time freelancer:
When I’m working full-time as a freelancer, I’ve found it hugely beneficial to create a very strict schedule and routine for myself. I wake up early- usually between 5:45 AM-6:30, and I hit the gym. Then I like to do Morning Pages, drink my coffee, make myself breakfast, and do a ten-minute meditation before I start my day. Usually, my workday starts around 10 AM. 
All my projects have detailed timelines broken out by day, so I know every morning what I need to focus on. I prefer to take on a few large projects at a time, instead of lots of little ones, so this helps immensely too with my day to day schedule. I only do small one-off projects for clients I’ve worked with in the past and have good relationships with.
I try to stick to an 8-hour work day, although of course that’s not always possible. When I’m working from home, I like to light candles and dim the lights about half an hour before my workday is over. If I’m not already listening to music, I’ll put on a favorite album too. This helps calm my brain a bit, and get ready to unwind. I think it’s important to leave the mental stress of work behind, especially if you’re working from home, and don’t have a physical space to leave behind. 
Thea Kennedy | Freelance Wisdom
Thea Kennedy | Freelance Wisdom

What has been your greatest struggle as a freelancer so far?

I often find myself too busy with projects to take a step back and think of big-picture goals for my business, and for myself as a designer. I need to start doing that more. 

What is your favorite thing about freelance?

My years of freelancing and balancing a full-time job have taught me so many lessons, some expected and some unexpected, and I’m really grateful for that.
Working full-time as a freelancer, I love the freedom, especially creating my own schedule and my own ways of doing things. 

After 13 years in Brooklyn you made the move back to CA. How are you feeling about that transition? Do you have any recommendations for ladies who may be feeling a similar pull?

The transition has been a lot more challenging than I could have imagined. Besides the fact that the industry in California vs. New York is like night and day, culturally, California and New York might as well be different countries. Everything is different here. The pace is different. The way people interview out here is different. The work itself is extremely different. The skill set expectations are slightly different. The hierarchy is different. In New York, creative leads. In California, tech leads. 
My general recommendation for any creative ladies who might want to make the move out west - try and line something up before you get here. The industry is much slower out here than it is in New York. I wasn’t expecting that, and I was pretty thrown off. However, if you’d like to pick up and move out here on a whim, like I did, just be prepared. Save a lot of money, and be patient. Things always have a way of working out in the end. 
Thea Kennedy | Freelance Wisdom
Thea Kennedy | Freelance Wisdom

With the recent move in mind, how do you continue to attract your ideal clients? 

When I moved from the East Coast, I also had a career pivot in mind. Less fashion and beauty work, more work focused on branding, innovation, and technology. Situating myself in the heart of Silicon Valley, I hoped the work would just come to me… and it did!
The first thing I did when I moved to California was sign up for a desk at a local WeWork. I did this mainly to keep up a routine, because at the time I was living out of a suitcase, and I hadn’t even decided what city I was going to officially relocate too! This ended up being hugely beneficial to my freelance career, which I wasn’t expecting! My first client I met at WeWork. He and his wife had just started a company together, and I did their branding. They were a dream to work with, and they will always have a special place in my heart, as my first California clients.
I also reached out to all my creative friends out here. It just so happened, that my friend’s husband, also an Art Director, had recently gone from corporate life to freelance as well, and he needed help on a large-scale branding project he was working on. He asked if I would like to help out, and I jumped at the chance. Over the years, he and I have spent countless hours’ nerd-ing out over typography and our design hero’s, and it felt so good to partner with someone who was just as passionate as I was. 
But, after I few months, I realized that I actually didn’t want to work on my own. I wanted to build up a new network, a California network. And because I was not just relocating, but also wanting to change industries, it made the most sense to me to seek out work within a large company. I felt like I needed to understand the system and the culture of the tech world. 
So, currently I’m doing contract work at Apple, as well as maintaining my own clients on the side. 
Thea Kennedy | Freelance Wisdom

Can you tell us a bit about your decision to start Design Quixotic? Additionally, how has this outlet and community informed your design work? 

I am somewhat of a reluctant blogger, I usually would rather be designing. But, after I amassed nearly 2 million followers on Pinterest through sharing my daily design inspirations, I decided to expand that into the blog format. The blog for me is very personal, and really, it’s a way to stay connected and always search out inspiring or interesting things. 
Having a large online following is an amazing way to get a pulse on what people respond to visually. While it hasn’t dictated my work, I feel confident going in specific visual directions, and it’s a great way to convince clients of definitive visual directions I’d like to explore. I can say, I’ve seen a lot of responses to X style, this is what’s on-trend currently- let’s explore it! Or, the opposite. I’ve seen this style online for a few years, it’s sort of at the end of its cycle, but X trend I’m starting to see people really respond to. I think this year it’s going to blow up. Having that kind of immediate access to what people like is incredible. 

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

Despite the scariness of things like accounting, invoicing and contracts, these are the MOST important things! Take them seriously, and don’t avoid them. If you feel overwhelmed, get help. Hire an accountant, hire a lawyer to help write up a few different variations of contracts that you foresee needing. Make sure that you are legally protected before you start any project. 
Also, don’t forget that your own branding and aesthetic should carry over to these less-glamorous facets of your business as well! Your contract, invoice, and project timeline will be the first things that your clients will see from you, so make a good first impression. Take some time with the design, and refresh it every few years, as you would with your website, media kit, and so on. 

How do you whet your creative appetite?

I go to museums, galleries, lectures, concerts, plays and miscellaneous design events as much as possible. It’s important to stay connected with your passion. I also have a weakness for art and design books.
Thea Kennedy | Freelance Wisdom

Since you are your own boss, do you have any advice for maintaining a work-life balance?

Right now, my work-life balance is pretty out of whack. Hopefully I can change that soon. I have dreams of having hobbies and free time again. I hate being a workaholic. 

Do you have any music, podcast, or book recommendations that you'd like to share?

For the past couple of years, I fell into a deep creative funk. I felt like I lost my inspiration and drive. It was really scary actually. The only way I knew how to cope with this, was through reading about creativity, (I find books really comforting). I have a short list for you!
The Artist's Way, by Julia Cameron
This book was given as a gift to me in college, I re-read it whenever I’m going through a tough time, and it always helps! I still do the Morning Pages ritual, and it really helps ground me - even if it’s just stream of consciousness ramblings. In fact - even better if it is!
The War of Art: Break Through the Blocks & Win Your Inner Creative Battles, by Steven Pressfield
The Creative Habit: Learn It and Use It for Life, by Twyla Tharp
Daily Rituals: How Artists Work, by Mason Currey 

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

Courage, Faith, Determination.
Thea Kennedy | Freelance Wisdom

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Jody Worthington

Jody Worthington is an accomplished designer and art director with 15 years of experience in print and digital design. Since 2013 Jody has been running her own one-woman studio working with national brands, PR and marketing firms, non-profits and universities, retailers, small businesses, publishers, and restaurants. The variety in her experiences over her long career has led to a depth and breadth of freelance wisdom that we are so excited to share.


Jody Worthington | Freelance Wisdom

Tell me about your path to becoming a freelance designer and art director.

My path to graphic design was a winding one! As a kid, I had a knack for turning any school assignment into a vaguely relevant art project or comic strip. We moved around a lot (a handful of US states, Holland, Australia, and England), so I was the new kid about every three years. I became weirdly fascinated with all the different cliques at each school, and would draw them in my notebooks. One day my 10th grade World History teacher caught me drawing “The Stoners” and passed my book around so everyone could see. Super embarrassing, but I think he was secretly impressed, and that led to me becoming an illustrator for our school newspaper. From there, I learned Quark (oh, the good old days!) and switched gears to editorial design. I loved it!
But in college, I decided to major in “Digital Motion Graphics.” This was back when people were really jazzed on the concept of multimedia, but no one—not even the professors—knew how to integrate it with graphic design. So, I learned a lot about Flash animation and Final Cut Pro, but had no clue what “typography” meant.
After graduation I moved to New Orleans. I had lived there for a couple years in middle school, and had always felt a deep connection to its eclectic jumble of cultures, brass bands in the street, the scent of magnolias, shrimp poboys, and the “how’s ya mom” hospitality. It was not exactly a hub for multimedia job opportunities, though. I didn’t feel qualified for anything that was available, but somehow landed a print design gig at Gambit Weekly and scrambled to learn on the job.
When hurricane Katrina hit, everything collapsed. I evacuated to Houston at the eleventh hour, and what was meant to be a quick stay turned into weeks, then months. While in Houston, I met my husband Tyler and was hired at boutique design agency, and before I knew it three years had passed. Over the next few years I jumped from editorial design, to stationery, to advertising, to branding. When I moved to San Francisco in 2008, I found myself in a corporate-y in-house design job and began taking on freelance clients as a way to stay sane. In 2009 I started working for Minted (which, at the time, was a brand-new scrappy little startup) and was able to move through a number of interesting roles, including product development and design, marketing, and merchandising.
By 2012, I had a steady roster of freelance clients and went part-time at Minted. For an entire year, I struggled with the decision to go solo. It was a slow band-aid rip. I made all sorts of excuses not to. I thought I would get lonely. I thought I didn’t have enough discipline. I wouldn’t have admitted it, but I was really afraid of disappointing myself. But—total cliché—I finally recognized that life really is short and didn’t want to regret playing it safe. My dad had recently passed away after a 9-month battle with cancer, and the world suddenly felt different.
Jody Worthington | Freelance Wisdom
Jody Worthington | Freelance Wisdom

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

My first few clients were connections made through friends and former co-workers. I was not picky and took every job that came my way, which of course led to some regrettable situations (ahem, “learning experiences”). But for the most part, things progressed steadily. One-off clients would end up coming back for more long-term partnerships, and things grew naturally from there.
For those beginning their freelance journey, I highly recommend finding one nonprofit to work with. Make sure they value good design and that you believe in their mission. Pro bono work (not to be confused with spec work!) can be so rewarding—you’re a part of something impactful, you make professional connections, and you usually have a good amount of creative freedom. I did a lot of work for 826 Valencia in San Francisco, designing books and event branding. Working with them was such a cool experience, and although it was unpaid, aligning with such a high-profile organization helped my work gain visibility, which led to new clients who found me online. Currently, I’d say 80 percent of my new business comes from referrals, and 20 percent from people finding my work online (I owe you one, Pinterest!).

Do you have any tips for being your most productive?

This one is hard. I’m always tweaking my approach. I used to force myself into a 9-5 routine, but after a couple years I realized that didn’t work for me. Nowadays, every day is different—sometimes I don’t even get started until noon. I think it’s important to work around your natural highs and lows. For instance, I definitely work best in the afternoon and evening, so I try not to schedule meetings or calls in the morning. You just can’t force productivity—at least, not if you want great results. That said, the pressure of deadlines is my number one motivator, so I’m super-duper productive the night before a due date!
Jody Worthington | Freelance Wisdom

What has been your greatest struggle as a freelancer so far?

Finding time and energy to learn new skills and maintain old ones. I’d be embarrassed to tell you how many Skillshare classes I’ve signed up for that I haven’t even started! One example: my illustration skills are so rusty these days. Whenever I try to get back into a sketching routine, I wind up frustrated because my hand won’t do what I want it to do, and I either give up or rush through it.

What is your favorite thing about freelance?

Connecting with interesting clients, flexible hours, and getting to work with my husband Tyler! I also love the variety of work that comes with each new project. Brand identity is my focus, but with that comes the opportunity to design packaging, retail interiors, residential welcome centers, maps, magazines, to name a few. I’m not sure if my nomadic background is to blame, but I have a strong compulsion to constantly switch things up, working with different aesthetics, materials, and formats.
Jody Worthington | Freelance Wisdom
Jody Worthington | Freelance Wisdom

How do you continue to attract your ideal clients?

For new clients, I definitely found that refining my website helped attract more exciting jobs with clients looking for a partnership rather than a commodity. Understandably, many potential clients can’t imagine what you’re capable of until they see it. So, rather than trying to convey “Hey! I can do a lot of things. Trust me, I’m good!” I’ve curated my portfolio to say “Hey! This is what I like to do, so holler if you like it too!”
For clients with ideal budgets—this is something I really had to work up to. I used to feel awkward talking to colleagues and other freelancers about pricing, but I strongly believe that the more we open up and share our pricing methods, the more we all can grow. Knowing your worth involves knowing what your peers and competitors are worth! I’m so thankful for resources like the Pricing & Ethical Guidelines Handbook and online communities such as the Creative Lady Collective. We’re all in it together!

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

Freshbooks is fantastic for everyday things like tracking time, invoicing, estimates, and expenses. I’ve been using them for years and only just discovered their iPhone app. It’s so convenient for keeping up with expenses. You just snap a photo of each receipt and enter the details on your phone. I can’t tell you how happy I was to get rid of my overflowing nightmare of a receipt box.
For file management, it’s Dropbox all day every day. And Creative Cloud has been blowing my mind with its new magical capabilities. I have all my devices synced—it’s thrilling to beam something from your iPad straight to Illustrator.
For estimating time, here’s a piece of advice that changed my life. Rather than thinking of small, bill-by-the-hour jobs in terms of hours/minutes, think of them in terms of half-days and full-days. In reality, it’s very rare that a project would only take 2 hours. If you spec out that work as a half-day instead, you will be allowed to slow down, be more careful, and to incorporate adequate project management.
Jody Worthington | Freelance Wisdom
Jody Worthington | Freelance Wisdom

What do you do to stay creatively inspired?

I get out and walk. If I have time, I’ll make up an errand (“Oh look, we need dog food!”) and head over to one of the many high streets here in Oakland. I just like to soak in the retail signage and storefront displays, browse in a bookstore, or just get coffee.

Since you are your own boss, do you have any advice for maintaining a work-life balance?

Be flexible but know when to switch off. For me, the balance is more like a constantly moving see-saw. My work is so intertwined with everyday life that I don’t really try to separate it. Tyler is the same way, and we don’t have kids, so it’s pretty natural. That’s not to say we are workaholics (I think that’s a dangerous aspiration)—I just mean that we don’t force ourselves into a set schedule. We skip from work to non-work pretty seamlessly. We don’t typically take long, faraway vacations, but every few weeks there will be a 2-3 day trip somewhere. Whether it’s Texas to see family, or a quick local getaway with our pup Rucci, leaving town is sometimes the only way I can truly switch off.
Jody Worthington | Freelance Wisdom

Can you tell us a bit about The Blume Saloon?

Yes! It’s a weekly podcast I started back in March with a good friend, Alison Michael. It’s a sort-of book club, with lots of tangents and comedy thrown in. Every week, we discuss a few chapters of a cherished Judy Blume novel. We’re really into dramatic readings, doing research on life and culture in the 1970s, and making up songs. We like to share our own adolescent anecdotes, to the point of TMI. We record every week, and I do the editing/producing.
It has been such a nice escape, a way to be creative that has absolutely nothing to do with design. Neither of us had any podcasting experience, but figured we had nothing to lose, so we went for it! Failure’s a lot easier to handle when you have no idea what you’re doing. The whole “fearless novice” thing was an important reminder for me not to let my expertise in graphic design be paralyzing. We now have a decent following that seems to be growing, and have received letters from some lovely listeners all over the globe. It’s so much fun. You can listen here.

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

Intuition, adaptability, curiosity.
Jody Worthington | Freelance Wisdom

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Heather Hale

After 10 years of designing for someone else Heather Hale decided to give freelance a try. Hale House is her freelance endeavor where she works as a graphic designer specializing in branding and illustration with a retro flare. She is also the Creative Director at May Designs (which recently launched a collection at Target), previously worked for Hallmark Cards, and is a mother of two. 

We found her work through our Creative Lady Directory and love how she describes design as really being all about relationships.

Thank you for sharing your wisdom Heather!

Heather Hale | Freelance Wisdom

Tell me about your path to becoming a freelance graphic designer.

Ok. The older I get, the more I appreciate how rare this story is, but I knew I wanted to be an artist in KINDERGARTEN. I dressed up for career day in a smock, beret and paint palette in hand at age 6. I come from a family of painters (mom, grandfather, aunt) so it makes sense, but as I got older I knew that I wanted my career as an artist to be lucrative and graphic design seemed like the right fit! After 10 years working for other people (Hallmark Cards and most recently May Designs) I decided to give freelance a try!

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

Whew! This was so intimidating to me! I knew I could do the work and I knew what kind of clients I wanted, but I did not know how people were going to find me. There were a couple of things I did in the beginning that really helped me to attract dreamy clients.
1. I wrote out goals on my wall calendar each month: revenue goal, marketing goal, and IN PERSON MEETING goal... ha! hello, introvert! Yes, I had to make a very conscious and calculated effort to meet people. I didn't put any pressure on the meeting and it didn't even have to be a prospective client. Working full time and being a mom had me in my car, in the office or home with kids... I just had to get connected with other humans again. This naturally led to so many opportunities. Telling your story and staying top of mind is important.
2. When I finally got brave enough to charge what I'm worth, the serious clients started finding me! Pricing my work was so uncomfortable! So many emotions wrapped up in a fee. Fear and Shame "What if this is too much?" "What if they think I'm ridiculous" ...I was lucky enough to find a business consultant who wanted to trade services and she really helped me shift my perspective. It all clicked and it totally makes sense that the clients who are willing to pay more for a branding package are the clients who are going to take the process and "you" seriously. Ah! Thank you Katie Wussow.
Heather Hale | Freelance Wisdom
Heather Hale | Freelance Wisdom

Do you have any tips for being your most productive?

The thing that has been working for me recently is to stop and work when inspiration strikes... even if it's not a convenient time. Freelancing gives me the flexibility to meet my son for lunch and be home to greet my kids when they get home, but it also means that we're ordering pizza instead of mom cooking if inspiration strikes.

What has been your greatest struggle as a freelancer so far?

I was surprised to find that I actually really enjoy setting meetings, monthly goals, accounting, invoicing. So weird. And the part that was the hardest was actually sitting down to do the work. There's something so terrifying about the beginning of the creative process for me. Staring at that blank art board is so intimidating, but I've learned to push through that initial feeling of resistance because it ALWAYS works out!

What is your favorite thing about freelance?

Relationships! All of my clients have become my friends and the community that I've created with other designers is so rich!
May Designs x Blue Sky that just launched at Target. 

May Designs x Blue Sky that just launched at Target. 

Heather Hale | Freelance Wisdom

How has becoming a mom changed how you work and/or the types of projects you take on?

When I was first starting out I felt like I needed to say yes to every project. It was that classic scarcity mentality. "I'm going to say yes now, because what if I have no clients next month?" I noticed that a friend of mine was booking her clients out. Sometimes even months in advance. After seeing her do that, I started paying closer attention to client expectations for timeline and found that most people didn't even blink an eye at having to wait a month to get started. This was a game changer! It's given me more freedom in my schedule knowing that the next couple of months are taken care of. I can relax and have a better work/life balance. 

How do you stay creatively inspired?

I believe it's important to invest in personal creative projects. No client influences or deadlines. Just fun! Earlier this year I decided it could be a good exercise to reinterpret old loteria cards (mexican bingo). So anytime I have a little bit of free time OR hit a slump, I pick another card to illustrate. 
Heather Hale | Freelance Wisdom

Since you are your own boss, and mother of two, do you have any advice for maintaining a work-life balance?

Hire a maid! The clutter and mess in the house can be such a distraction when you're working from home. And practically speaking, the hours you spend cleaning would be better spent designing. Really anything you can delegate as you grow is a step in the right direction.

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

War of Art by Steven Pressfield  I sort of referenced this book in my answer to my greatest struggle. 
"Art is a war - between ourselves and the forces of self-sabotage that would stop us from doing our work. The artist is a warrior."

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

Support system - family friends who love you
Professional community - other designers to share ideas, ask questions, talk through client frustrations
Drive passion - you have to really want it!
Heather Hale | Freelance Wisdom

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