Elizabeth Wellington

This week we are so pleased to chat with Creative Lady Directory member Elizabeth Wellington. After 10 years of practicing her craft on the side, Liz decided to go out on her own as a freelance writer. She currently splits her time collaborating with brands as a brand consultant and writing as a contributor for Travel & Leisure and Misadventures Magazine. Her work has garnered the attention of national publications and prestigious clients like Google, Fidelity, and Prudential.

Be sure to read all the way through for Liz's inspiring take on work-life balance. Enjoy!

Elizabeth Wellington | Freelance Wisdom

Tell me about your path to becoming a freelance writer.

Graduating from college, I entered the job market with few professional experiences and in the middle of a recession. I got creative and pieced together jobs that connected me to writing, mainly working at independent bookshops and teaching English abroad and on Nantucket.
My first “real” job was in academia, and again, I stayed close to writing. Our faculty included brilliant authors, and I attended their lectures on campus and read voraciously.
I’ve been writing every day since I was 18 — I got to the point when I had to call my own bluff. Why wasn’t I really going for it? I jumped into freelance writing full-time with no clear plan but a willingness to adapt. I had the advantage of ten years of practicing my craft with no pressure or expectations and a solid emergency fund.

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

I attracted my first good clients by cultivating relationships in Boston's marketing community. Ever the introvert, I'm really uncomfortable in traditional networking situations. But I continued to show up — most of the time, at least — and initiated conversations with a lot of different people.
The hardest part was introducing myself as "a writer" before I felt I could honestly own the term. I read somewhere that people who say, "I'm an [insert dream job title here]" — even if they work full-time in another capacity — are more likely to be successful at their passion in the long term. I really took that idea to heart.
Once I started to move through that imposter syndrome, I found that people were really receptive and curious. A lot of marketers needed creative help — they were so happy to offer work. I always made an effort to go above and beyond, both in process and deliverables.
Word spread fast. Before I knew it, I had a strong referral network in place locally.
Elizabeth Wellington | Freelance Wisdom

Can you tell us about your writing process?

My process varies significantly based on the project I’m tackling. Writing is a bit like cooking — some recipes are more complicated than others. Frying an egg is a two-step process, but a Thanksgiving dinner is going to require many to-do lists, pep talks, and weeks of preparation.
That said, I always try to build creative momentum. Sometimes, I can jump right in and write a draft. Other times, I need to scribble, doodle, and outline until a cohesive message starts to form.
I have some funny tricks, too. For example, when I’m nervous about getting started, I work on a project in an email to myself. Not very organized, but it feels more casual and less loaded. Essentially, I “trick” myself into making progress. Ha!

You balance working as a writer with brand consulting. Do you have any tips for being your most productive?

I read (and write) a lot about productivity. In this last few months, I decided to shift my approach. Instead of trying to change myself to be more productive, I’m trying to design each day around my natural ebb and flows. That means I'm always finding that middle ground: just enough structure and just enough spontaneity.
Within that framework, there are a few daily rituals that keep me balanced and productive. First, whenever possible, I start my day without email. I try to write for a couple of hours before I dive into my inbox.
Throughout the day, I often split tasks into quarters. For me, procrastination only hits when I'm feeling overwhelmed. Outlining a simple plan that breaks down any project into bite-size chunks helps me get a lot more done. I also reward myself for reaching deadlines or crossing something off my list. Sometimes, I'll go do something around the house, but most of the time, I'll take a short walk, drink a cup of tea, or read a chapter of a book.
Every evening, I write a list of must-complete tasks for the following day. It helps me to let go and step away from work. I also try to note what I'm grateful for because there are always moments to appreciate.
Elizabeth Wellington | Freelance Wisdom
The previous two images are from Liz's piece "Preserving Analog Tools in a Digital World" for Big Cartel. 

The previous two images are from Liz's piece "Preserving Analog Tools in a Digital World" for Big Cartel. 

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

My greatest struggle has been the imposter syndrome I mentioned earlier. Who gave me permission to be a writer? Why would anyone ever read my work? Could I ever be good enough? These kinds of questions have been my biggest struggle. They created an inertia that made it harder to trust myself creatively.
In that sense, writing every day is a huge gift. If I had another profession that felt less daunting, it may have been easier to avoid these issues. Writing requires that I overcome that sense of inadequacy every day. Just like the water wearing down a rock, my creative practice — and the joy and abundance it brings me — continues to wear on those false ideas. Soon, I don't think they'll be part of my day-to-day life anymore.
Side note: If you struggle with the same challenge, I highly recommend Julia Cameron's The Artist's Way. My copy is well-loved, filled with notes in every margin, and a bit wrinkly from reading and re-reading it in the bathtub.

What is your favorite thing about freelance?

By far, the self-determination that it requires. I love choosing my own projects, deciding which direction I want to grow in, and nurturing my creative independence. I’ve always done well when I’m in charge of my life, and the same is true for my work.
Elizabeth Wellington | Freelance Wisdom

How do you continue to attract your ideal clients?

I keep a mental tally of the traits I’m looking for in clients. There’s always going to be a contrast: things I enjoy (or don’t enjoy) about working with collaborators. I’ve had my fair share of negative experiences, but they all help me to deepen my sense of what I want moving forward.
At the moment, I’m about to realign my business toward travel, and I’m also taking on a few coaching clients. People often reach out to me to mentor them as freelancers, and I want to do that in a more formal capacity.
In the past when I’ve made a change, I’ve refocused my energy on this new goal. I’ve used every channel I have — existing networks, my own website, social media, and freelancing platforms — to pivot my messaging around what I do and open up new possibilities. I’ll let you know how that goes this time around!

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

Yes! Make the time for these pain-in-the-butt details. Get into a routine, and treat them like homework. One of my close freelancer friends, Monika Kanokova, believes that you should spend 50% of working hours actually running your business versus doing client work. I’m not there yet, but that’s a goal of mine. I think that giving yourself the time to organize and create consistent processes is key to long-term growth.
Read this article that Liz wrote for Help Scout right here. 

Read this article that Liz wrote for Help Scout right here

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

Instead of work-life balance, I aspire to work-life integration. To me, I feel balanced when I bring my whole self to my work and my whole self to my life. Ideally, my projects bring fulfillment and support me financially, and my personal life leaves me renewed and inspired to tackle my client work.
Those are lofty intentions, but really, they come down to small moments. I work from a home office, so I go for walks pretty often to clear mind and move my body. I also try to take the time for a meditation from Tara Brach during the day — it’s amazing what “comes” to me when I’m listening to her soothing voice on my iPhone.
I don’t think I’m a master at work-life integration yet, but I do love the fact that I’m not limited to a 9-5 schedule in a cubicle. I try to exercise the freedom I have every day.
Elizabeth Wellington | Freelance Wisdom
Elizabeth Wellington | Freelance Wisdom

What do you to stay creatively inspired?

On a day-to-day basis, I like a healthy mix of movement and stillness. I explore Boston and — as I mentioned before — go for a lot of walks. I’m writing this interview from a park near my apartment. There’s nothing like landing in a new environment (even if it’s just a coffee shop) to spark a new idea.
For me, travel is also important. I need to fill my tank up with beautiful experiences to feel creatively inspired. I try to do one significant trip every quarter, and I usually write about it for a publication. In 2018, my intention is to travel more. There’s just nothing like it for me.

If you could write for anyone who would it be?

As radical as this sounds, if I could write for anyone in the world, I would write for myself. I've worked with so many clients at this point, and I would love to create the space for something that’s mine. Plus, it would be cool to explore my own voice outside of the constraints of other editors.
So, stay tuned for more on that. As far as publications go, I would do just about anything to write about travel for Vogue.
Click image to read Liz's article for Misadventures.

Click image to read Liz's article for Misadventures.

A last look at Liz's workspace as shown in "Preserving Analog Tools in a Digital World"

A last look at Liz's workspace as shown in "Preserving Analog Tools in a Digital World"

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

Self-compassion, grit, and focus.

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Meg Summerfield

Meg Summerfield is a graphic designer and blogger hailing from the small state of Rhode Island. Armed with her MFA in graphic design from SCAD and loads of Squarespace knowledge, she runs her own studio Meg Summerfield Creative, as well as her food blog Summerfield Delight. She is also the founder and editor-in-chief of Squarespace Design Guild, a membership group for designers who use the Squarespace platform.

We're loving the reminders she sprinkles throughout this interview to set our own paths. Thanks for sharing your wisdom Meg!

Meg Summerfield | Freelance Wisdom

Tell me about your path to becoming a freelance designer.

My path towards freelancing started back when I was a kid, designing brands for just about everything and anyone who had an idea. A sketchbook would come out of my backpack and naming and brand values would begin. I ended up going to Rice University for Architecture as an undergrad and knew pretty quickly I never wanted to cut foam core again in my life. As soon as I realized that I wanted to be a designer, I knew I would work better independently, but knew that I had to probably get my feet wet a bit. I went directly from undergrad into my MFA at SCAD to working remotely while designing full time for a high end photography studio.
Through the insane amount of work I was doing juggling custom work for the photo studio and my MFA I had a pretty big interest in taking my career to the "next level" when I graduated. I thought that it had to be "up" the food chain, so I started working in-house for a large handbag brand here in New England. The dream of working directly with high end magazines, vendors, getting my work seen at fashion week, in hundreds of thousands of homes was all flashy and fun, but I felt creatively like I was on an island far away from where I wanted to be. So in the evenings, I started my own food blog, it became my savior and that place where I learned to be a digital designer not just print, and got to know the online freelancing world much more. After leaving my in-house job, I worked for a few other blogs including Style Me Pretty before deciding to jump into full time last June 2016.  
Meg Summerfield | Freelance Wisdom

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

By becoming involved in the community I wanted to be involved in! I originally attracted design clients for food blogs in Squarespace because I am a food blogger, and became involved with local food blogging community. I wasn't just a designer saying I could do x,y,z...I actually had a real life example that was tangible. It was better than any portfolio item I had at the time for showing clients my skills.

Do you have any tips for being your most productive?

Don't be afraid to define your own rules. When it comes to being productive, you don't have to get up early, or work late nights if it goes against the lifestyle and productivity for your creativity. Scheduling admin/data times and sticking to those is key, but allowing yourself to work at weird hours when creativity strikes is key to letting yourself really become an artist and not make your freelance career feel stuck in the mud.
Meg Summerfield | Freelance Wisdom
Meg Summerfield | Freelance Wisdom

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

Learning that others paths and methods aren't going to work for everyone! When I first started I looked up processes, methods, ideas for streamlining clients, but in the end, they never felt perfect for me. It took me a while to feel confident in "doing it my own way" - the entire reason I started this in the first place.

What is your favorite thing about freelance?

My favorite thing about freelancing is the way that your career can mold and change over time. In the corporate world my answer for "where do you want to be in 5 years" was never one my interviewers loved, but it was the truth. I want to be creative in my every day life. Freelancing allows me the opportunity to keep that as a mainstay in my career path, and let the other parts be what moves around me. 
Meg Summerfield | Freelance Wisdom

How do you continue to attract your ideal clients?

I keep my portfolio pretty limited and not show all of my projects - just the ones that fit my ideal client. This is the norm these days, but I also make sure every other piece of paper the prospective client sees is branded that way. Contracts, proposals, media kits, process documents, questionnaires are all branded so that they feel immersed in the brand experience. If a client shows their friend the proposal, I want them to see my "style" from JUST that pdf.

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

This is a common theme, but doing it YOUR way is so important! If you love your oldschool invoices than keep them, if you are terrible at email - hire someone! Don't feel like you have to use an automated invoicing software if you aren't behind it 100%. This is your business not someone else's!
Meg Summerfield | Freelance Wisdom

Just over a year ago you launched Square Design Guild, a community resource and inspiration source for designers and artists using Squarespace. Can you tell us more about this project?

A few years ago I was trying to find others like myself, designing on Squarespace for their clients, and kept looking and looking and never finding the community of people to chat to, discuss options and learn tips and tricks from. One of my friends (Jamie from Spruce Rd) asked me to join her for one of her Lunch and Learn webinars and it was then I realized maybe it was ME who had to create the forum for us to come together. I am so glad I did because now we have an incredible community of over 70 designers who are incredible friends, designers and colleagues! 

What do you do to stay creatively inspired?

Get away from all things creative! I find inspiration when I change what I'm doing 100%. Sitting on the beach, hiking, taking a long lunch (sans cell phones), and most of all cooking. I find the structure of a recipe, combined with my inability to not change a recipe allows for creativity and structure which bring me back to my "normal self". Disconnecting is the key to me being refreshed to find new inspiration.
Meg Summerfield | Freelance Wisdom
Meg Summerfield | Freelance Wisdom

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

Ask for help! Whether that's a VA, an accountant, a friend to vent, you don't need to hold the weight of your business on your shoulders by yourself. Delegating and finding emotional support will allow you to find your own path to what YOUR work-life balance looks like.

Are there any projects that you're ruminating on that you'd like to make time for someday?

Oh that makes my brain go into overdrive just asking that! I would love to really get back into food blogging one day. I put it on the back shelf for the past year or so, and wish I could dive into it with full force.

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

Independent, Fiercely Driven, and Ready to Learn at All Times.
Meg Summerfield | Freelance Wisdom

Meredith Chamberlain

We are thrilled to bring you an interview with Meredith Chamberlain, a writer whom we met through our Creative Lady Collective. Meredith creates brand voices for clients across a variety of categories, from shampoo to insurance. She is passionate about working with female entrepreneurs and collaborating with likeminded designers. We are always on the lookout for new inspiration and Meredith's suggestions definitely deliver! 

Meredith Chamberlain | Freelance Wisdom

Tell me about your path to becoming a freelance copywriter.

I started out in publishing - magazines, books, and eventually digital. I was writing a weekly email newsletter for an arts organization, interviewing emerging musicians, designers and visual artists - and eventually started getting assignments to write what is now known as “sponsored content”. One of my close friends (who is also a copywriter) pointed out that what I was doing was copywriting, and that I could be paid a lot more for it. So when my company folded mid-recession, I started seeking out clients and building a portfolio.
In the beginning, I took every opportunity that came my way. I have a vivid memory of schlepping to an interview at a HVAC factory in Long Island City. Thankfully that one didn’t pan out, but I did accept a freelance position at ConAir (oddly many of my early opportunities were air-based), which required me to reverse commute from downtown Brooklyn to Stamford, CT several days a week. That experience got me an interview at Bumble and bumble. - my first full-time copywriting position - where I made invaluable connections and friendships. The art department there was very special. Learning to collaborate and concept alongside such a talented group of designers was a real gift.
After Bb., I worked at a few small advertising agencies full time, which eventually led to a burnout. I was working crazy hours on accounts that didn’t align with my personal values, and saying yes to every freelance project that came my way. It wasn’t sustainable. It took a solid month off, several pep talks from friends and former coworkers and a move to California to get my confidence back and finally commit to freelancing.

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

I was very lucky to work at Bumble and bumble early on in my career. Their tone of voice was a natural fit for me - smart and playful with a bit of British quirk to it (I’m a major anglophile). To have the opportunity to write in a voice I was aligned with and have that work to show to future employers was huge. Many of my freelance clients came to me through people I worked with at that first job - or through other onsite jobs. I tend to connect with designers I work with, and they reach out when they’re taking on a project that needs some copy.
Meredith Chamberlain | Freelance Wisdom
Meredith Chamberlain | Freelance Wisdom

Do you have any tips for being your most productive?

I swear by The Artist’s Way, and swimming. I do Julia Cameron’s “morning pages” every morning, which clears my mind of whatever neurosis has lodged its way in overnight. Swimming laps has a similar effect; the days I’m able to get both in are definitely my most productive. The next step will be turning my phone on airplane mode, like all the great writers do, but I’m not quite there yet.

Can you tell us a bit about your writing process?

I respond very well to a structured brief. The more constraints I have the better. Once a brief is set, I’ll brainstorm rough ideas, which will lead to some fun lines, which i’ll then spin into concepts. If I’m working with a designer or art director, I’ll bounce my ideas off them, see what they respond to, and go from there. Collaborating with designers is one of the best parts of my job. Seeing my words laid out in design never ceases to delight.
There is a quote by French children’s book author Hervé Tullet that goes, “An idea is a surprise and it’s a celebration.” - that pretty much sums up why I love what I do. Many of my ideas still surprise me, and that is worth celebrating.
Full quote here for reference.
Meredith Chamberlain | Freelance Wisdom
Meredith Chamberlain | Freelance Wisdom

Name one company that you'd like to write for in the future.

More than any one brand or company, I’d like to continue to collaborate with designers I admire. And I wouldn’t mind taking on some restaurant and hotel branding projects in the future. I’m hoping to get back into editorial writing as well. I recently wrote a piece for the Madewell blog and really enjoyed the process.

How do you stay creatively inspired?

Walking, swimming, reading, and keeping up on work that I admire - especially work that combines words and images, like that of Leanne Shapton and Maira Kalman.

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

Nothing I write after 8pm is any good. I know this about myself, and I plan accordingly. I fight the urge to procrastinate during the day, because I know my brain will be useless at night. This helps create boundaries. Honor your patterns, your energy, your ebbs and flows.
Meredith Chamberlain | Freelance Wisdom
Meredith Chamberlain | Freelance Wisdom
Meredith Chamberlain | Freelance Wisdom

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

I’ve been devouring the The High Low podcast recently.
@AnnStreetStudios Instagram stories are on another level.
Gather Journal’s Spotify playlists make me very happy.
I love Ruth Reichl’s twitter vignettes.
And States of Undress is my new favorite show.

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

Confidence, drive and imagination.
Meredith Chamberlain | Freelance Wisdom

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