Carissa Galloway

Carissa Galloway is captivating. As a multi-disciplinary designer and thinker living in Portland, Oregon, she is always on the go, moving, ideating, and challenging herself in new ways. 

Currently, you can find Carissa working on Stranger Fiction, a self-publishing resource she founded with her novelist partner. She's also helping women around the world as the brand lead at Voxapod. In past lives, Carissa co-founded an indie wedding collective, trained her way to professional running sponsorships, and designed wedding invitations for the Ford family.

Enjoy her wisdom!


Tell me about your path to becoming a freelance designer.

I’ve always struggled with any full-time position I’ve been in. I work quickly and grow bored easily without fresh challenges. I’ve also always struggled to sit for long periods of time. I’m a ball of energy and I need a release every few hours. So when I was first starting out as a designer, that meant my free time was always occupied by something that kept my interest. Right out of school, that looked like starting RockSugar Detroit. And when I moved to Portland, I dabbled with running professionally for a bit with Sketchers Performance (now I’m with the Portland Roses for New Balance). Side focuses allowed me to feel like I was moving forward on my own terms while I was still gathering experiences in design. Then, when I found myself under yet another creative director I couldn’t stand (and looking for a quick exit,) I jumped at the opportunity to work with friends as they were starting their own agency here in Portland. Ever since then, I’ve been full time freelancing—and I love it. It’s a really good fit for my personality. I need spontaneity in my work and I thrive on keeping my options open. To me, there’s nothing worse than feeling like I’m backed into a corner and going nowhere.

Do you have any tips for being your most productive?

I’m most productive when I’m balanced in my life. I workout 1–2 times a day. It’s really important for me to change my physical environment on my breaks from work. I need to move through real space and not just digital space. Sitting behind a computer all day is painful for the body. I start my days with a run, where I’m able to be physically productive but mentally relaxed. I let my mind be free and unfocused. Then when it comes time to focus my mind, I’m much more powerful and present.
I also try to organize my day by the different types of thinking I’ll be doing. I can be both left and right brained, as long as I can find a sort of balance. For example, if I have 10 emails to respond to, a client presentation to lay out, and logo concepts to explore, I give my best “thinking energy” to the concepting. I don’t open my inbox. I don’t even touch my phone. I just let myself dive deep into the concept work for 3–4 hours, and then when I come out of that, I’ll take a break. Go for a walk. Do some handstands in my apartment. Then I’ll come back and start tackling the more tedious stuff (like emails) because my brain is tired after thinking so abstractly, and it craves the structure of accomplishing something measured.
Carissa Galloway | Freelance Wisdom

I like that you make the distinction of calling yourself a "creative thinker." What inspired that word choice? Has it helped expand the variety of projects that come your way?

I actually really struggle with titles. I feel like we live in a society that says “just call yourself [insert whatever you want to be good at] and act ‘confidently’ and people will hire you for it.” I can see the benefits of “fake it til you make it,” but I don’t believe it’s as effective as it sounds. It’s all about “faking it” to the crowd you want approval from. Approval and judgement from just anyone other than you doesn’t actually say much at all. It all depends on who those “others” are, and where their standards and ideals lie.
So when I was trying to figure out what to call myself, I was having the hardest time with titles like “designer” or “creative director” because they always left me feeling… off. I thought, “I’m a complex, diverse, and curious individual, but is there a word that encapsulates that?” And then I thought “I’m all of those things, because I have honed and developed my thinking. It shows up in everything I do. It’s my foundation. Design is just the current medium through which I realize that thinking, and bring it to life.”
As with any title, it’s doesn’t encompass all of me, but it’s my best description for right now. I’m sure it will change as I change. I like to hold things loosely.
Has it helped with the projects that I get? I think so, though no one has ever mentioned that. I tend to work with pretty brainy people. They have smart products with complex features and they need my help to communicate concisely, along with that human touch.
Carissa Galloway | Freelance Wisdom
Carissa Galloway | Freelance Wisdom

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

Solitary confinement, ha! No, but really, I’m a pretty social person—though I actually don’t love co-working spaces. I’ve been to a couple of places like WeWork, but I didn’t like the vibe. It’s just too… There needs to be a better solve for that. Meeting people online is great, but it definitely leaves me wanting. I haven’t found exactly what I’m looking for yet, but I do meet friends out at coffee shops quite a bit.
I also struggle with self-promotion (as many of us do). It feels so gross to me, and I have a hard time with social media because of it. I know I’m good at what I do, but I don’t want to have to convince you that I’m good. And yet, culture rewards those who ask, so I know there’s a necessity. It’s not my favorite thing.

What is your favorite thing about freelance?

The autonomy it brings to my life. I love being in the driver’s seat. If I’m not going in a direction I like, I have the ability to course correct. I love the spontaneity in my days, and the ability to make more time for the things that matter to me. I can choose to work on a “weekend” so that I can drive to the coast midweek for some solitude and rest. It’s magical.
Carissa Galloway | Freelance Wisdom

How do you continue to attract your ideal clients?

It’s always been about working with good, smart people who have big visions. As a result, I tend to work with people for longer term contracts, expanding my team to meet the needs of the project. Since my ideal client isn’t a mom-and-pop shop or an individual per se, I take a more direct approach. If your product isn’t smart enough, or you don’t have a striking value proposition, I’m not very interested. And if you do, then I’m definitely reaching out, because we should at least know each other. I work for what I believe in, and if you have a truly innovative idea, you’ll be hearing from me.

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

I am very ambitious, so that marries well with my tendency toward workaholism. But I’ve learned the work will always be there. Other things/people/experiences will not. There are a few things I’ve put in place to get better at putting my work away.
  1. Self-validate. Every morning I tell myself five things I’m proud of myself for that aren’t based on achievement. It’s usually something like “I’m proud of myself for not getting into work until 10:30 am yesterday. I’m proud of myself for not taking that extra gig. I’m proud of myself for going out of town last weekend and leaving my computer behind.” Reinforcing the things that truly matter with my self-dialog is powerful.
  2. Forest bathe. I often run to the forest here from my place. (Again, changing my physical environment is important.)
  3. Become a beginner at something. I’m typically drawn to really challenging things in my free time (right now I’m trying to get my handstand press). Knowing that ambition is something I’m hungry for, I try to choose some challenges that are leisurely and playful for me.
  4. Meditate at night. If I do this in the morning, I’ll just fall asleep. I’ve been loving my Headspace app because I can just do 10 minutes a day before bed to check in with myself. It works with any schedule.
  5. Read out loud. My partner and I read out loud to each other at night. It’s a fun experience together, and we both have to be intentional about making time for it. It keeps us off the screen and thinking about stories and dreams.
Carissa Galloway | Freelance Wisdom
Carissa Galloway | Freelance Wisdom

Can you tell us a bit more about your project Stranger Fiction?

I’ve always valued the ability to be independent and self-sustaining. It’s a gift I’ve worked hard to give to myself —and it’s a gift that I want to see others have access to as well.
When my partner and I decided to self-publish his debut novel (Biome) in 2016 (rather than going the traditional route), we dove into the publishing industry and found that it’s more-or-less a nightmare to navigate. My partner is an author with the benefit of being raised by an author, so we had quite a bit of insight into the traditional industry; but things are changing, and rapidly. We saw firsthand how the traditional method wasn’t quite working for everyone, and since we’ve both spent our early careers in advertising and marketing, we understand how to sponge information and identify the good stuff.
So, when we set out on this journey, we said “Hey, let’s do this our way. Let’s use our skills to research across markets and think outside the box.” And in the process, we found so. many. problems. Bad information, misinformation, marketing bullshit, salesy “techniques” that promise you the moon, unqualified “professionals,” sloppy cover designs, vanity awards… you get the picture. We were exhausted by it. There were so many wonderful reasons we wanted to self-publish—creative control, retainment of rights, etc. But we found that because this information was so disorganized and off-base, authors are wasting most of their energy playing marketing roulette, rather than improving their craft.
Which led us to Stranger Fiction: A platform that will house quality, vetted information and resources to help authors do what they’re best at—writing good books.
From a design perspective, it’s been a really fun and fulfilling challenge to recognize a problem, solve for it smartly, form a plan, and then execute that plan from start to finish. We were able to take our thinking and bring it to life in brand form. I’m excited to learn along the way, and see how we can make sharing creative work better for everyone! It’s been humbling to learn so much already, and to learn to be more fluid in my thinking.
Carissa Galloway | Freelance Wisdom
Carissa Galloway | Freelance Wisdom
Carissa Galloway | Freelance Wisdom

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

In terms of music, I do a lot of instrumental. Right now, I’m also digging The Japanese House. As for books, I tend to gravitate towards nonfiction or philosophical works. The last one I finished was Fail, Fail Again, Fail Better by Pema Chodron. I’ve read it like six times. And I’m in the middle of reading Steve Jobs. He was one erratic human…

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

Self-belief, perseverance, and vision.
Carissa Galloway | Freelance Wisdom

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