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Jessie Kwak: On Focus, Freelancing, and Fiction Writing

Jessie Kwak: Focus, Freelancing, and Fiction Writing

At Freedom we love our users – not just because they use our product but because they’re cool – cool people working on cool stuff. Academy Award-nominated screenwriters, best-selling authors, editors, designers, star TV actors & writers, academic researchers, and entrepreneurs – the Freedom community is packed with curious, creative, and efficient go-getters. We love to share their stories and advice, because how better to learn about productivity than from the productive?

Meet Jessie Kwak.

This week’s Freedom spotlight goes to published author, freelance copywriter, and self-declared ‘farm girl’ Jessie Kwak. Jessie has worked as a  catalog copywriter, a popcorn slinger, a carpenter, a beer monger, a tractor driver, and a house manager at a regional theater, and decided that she liked writing best. She received her BA in literature and minor in theater from Seattle Pacific University and is now fulfilling her passions of writing and travel as a freelancer.

How did you become a writer and what were some of the steps to getting where you are today?

I’ve always wanted to be a novelist, and have been writing stories since I was a kid. I actually wrote my first 60k-word novel longhand in a series of spiral notebooks when I was in middle school.

I got my BA in English literature, where I learned that serious writers submit to literary journals and teach in MFA programs to make a living. Except the literary journals didn’t want my sci-fi ghost stories, and teaching in an MFA program sounded boring. So I decided to travel and wait tables instead, all while working on a series of fantasy novels.

Waiting tables got old after a few years. One of the regulars of the bar I worked at was a copywriter, and she helped me get my first job at a catalog company. I loved the work, but hated being in an office. Eventually I took my skills and went freelance, focusing in content marketing and blogging.

It was pretty mind-blowing that I could make a great living writing, without having to take the “literary” route. The flexible schedule of freelancing also meant I could create time to work on my fiction — plus, the fast pace taught me to stop relying on the Muse, and how to run a profitable writing business.

It was a circuitous route, and I’ve always hustled to get to the next step. But I really love the life and job I’ve created.


What advice would you offer less experienced writers/freelancers – especially in regard to staying productive, motivated, and focused?

When you’re working for yourself, you often lack that external motivation that comes with a day job and a boss. Sure, deadlines can keep you accountable to others, but there are a lot of business-building tasks you have to provide your own accountability for.

My biggest advice is to create systems and habits that keep you on track, even if you’re not feeling motivated. Willpower is a very limited resource, so hack your life to reduce the amount of willpower you need to spend. That’s why I use Freedom to automatically block social media for most of the workday, and to block my email before 9 am. I’ve learned that if I rely on my own willpower to stay away from internet distractions I’m hopeless.

The other thing is to be really honest with yourself about how you’re spending your time. Yesterday I spent at least an hour on Twitter, which is ridiculous. But because I track my time each day, I can’t pretend it didn’t happen — which means I can do better today.


What is the biggest mistake you have learned from as a writer?

As a freelancer, the biggest mistake I’ve made is staying too long with bad clients. Either low-paying ones, or ones that were a pain to work with. You’re better off dropping them and using the time you save to prospect better clients.

As a fiction writer, my biggest mistake has been to not ask for help. In the last few years, I’ve joined some amazing communities of writers — both in person, and online. They’re some of the most generous, thoughtful people I’ve ever met, and I’m kicking myself for not seeking them out earlier.


What excites you most about your industry?

The ability to be self-sufficient in publishing is the thing that excites me most — both as a freelance content marketer and a novelist. I’m excited to see more brands and individual industry leaders take advantage of self-publishing tactics to tell their stories.

I think storytelling is such a powerful way to connect with your customers and build your tribe. It’s cool to see so many people embracing it.


When/where are you most/least productive, and how does this shape your daily working routine?

I tend to be most productive before noon, with another good burst from about 3-5pm. I can also fit in another hour’s worth of good creative writing time after dinner on nights when my brain isn’t too tired. I tend to burn out in the early afternoons and need a break.

On a perfect day, I get up around 6:30 and exercise, then grab breakfast and work on the most important project of the day for a few hours. This would be either fiction, or whatever client project I have due that day.

This is the best time for me to do solid writing, so I try not to scatter my brain too much with smallish tasks or research. If I wrap up my most important project, I may tackle more than one biggish project before noon.

I normally take an hour lunch break to deal with emails and housekeeping stuff, then dive into researching and rough drafting for whatever tomorrow’s most important project will be. When I get sick of staring at the computer screen, I’ll often take my outline and go for a walk around my neighborhood to dictate a rough draft.

I can sometimes get back in a deep writing groove for the last couple of hours of the day. But some days my brain’s shot, so I stay surface-level and work on admin tasks and research.


What resources or tools do you use daily and have found most beneficial to your writing process?

I use Scrivener for all my drafting — both for fiction, and for client projects. It’s just so convenient to have all my research, notes, and past drafts in one place, and I like the writing interface.

I use Freedom religiously to keep me on task, both on my phone and my laptop. I also use StayFocused for Chrome to limit the amount of time I can spend on trouble sites during the periods where my automatic Freedom block is turned off.

I use Dragon Dictation for rough drafting. Definitely while going on walks, but also while sitting/standing at my computer. I find it easier to dictate nonfiction than fiction, so I haven’t used it as much for my novels as I do for my client projects.

I use Evernote to organize my to-do lists and schedule, as well as to collect ephemera relating to client projects or novels I’m working on. Evernote is basically my exobrain.


What project are you currently most excited about?

I should say that it’s my upcoming sci-fi gangster novel, Negative Return, but I’ve been living that book for months now! So while I’m excited to see it come to life, I definitely have shiny-object syndrome and am obsessing about my next project.

The next project has come about entirely by accident, because I keep distracting myself by imagining how much fun it would be to write various client projects with zombies in them. I’ve decided to give into the urge, and am working on a short story collection titled Business as Usual: Corporate Communications From the Zombie Apocalypse.

So far I’ve written a story in the form of emails from a creative director trying to put the Fall 1 catalog to bed even as the world crumbles around her, a webinar about the world’s only zombie employee offboarding software, and a blog post titled These 12 Jaw-Dropping Facts about the Zombie Apocalypse Will Transform Your B2B Content Marketing Program. That last was just accepted by McSweeney’s Internet Tendency, and should be out any day now.

It’s ridiculous, I know. But so much fun.


What are your biggest distractors/obstacles you face daily and how do you combat them?

Besides the current urge to write zombies into all my clients’ projects, the single biggest obstacle I face is letting myself get pulled in too many directions at once. If I start the day by jumping frantically from one thing to the next, I destroy any ability to work deeply later. I just get frazzled and stressed out.

I’m constantly trying to figure out a better way to maintain focus. The biggest things I do right now is schedule out my priorities the night before, and use Freedom to block distractions when I really need to focus.

I also keep a bunch of themed to-do lists for things that need to be done eventually, but not right now. Jotting a thought there helps me get it out of my brain so I can get back to what I should be focusing on.


What are you hoping to accomplish in 2017?

In my freelance business, I’d really like to take on more ghostwriting projects for business authors and coaches. It’s work I really enjoy, and I’d like to make it a bigger part of my business.

For my fiction business, I’m hoping to publish a few more novels this year, and continue honing my craft. That’s my favorite thing about writing fiction: there’s always more to learn!


Where are you currently based?

Portland, Oregon.

Jessie Kwak is a freelance writer living in Portland, Oregon. When she’s not working on B2B marketing copy for clients, you can find her scribbling away on her latest novel, road tripping with her husband, or attempting to tailor a three-piece suit for herself. You can find her more of her writing at, or follow her on Twitter (@jkwak)