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About the Author
Jessie Kwak is a freelance writer, ghostwriter, and the author of productivity guide From Chaos to Creativity. When she’s not writing B2B marketing copy or scribbling away on her latest novel, you can find her riding her bike to the brewpub, road tripping with her husband, or juggling various sewing projects. You can learn more about her at, or follow her on Twitter (@jkwak).

Creative Approaches to Managing Entrepreneur Overwhelm

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Whether you’re a full-time entrepreneur or a nine-to-fiver with a side hustle, you know what it’s like to feel overwhelmed by the mental churn of work and life. To be more effective – and actually enjoy building your business – you need a system to wrangle the chaos, clear your head, and unleash your creative energy.


Jessie L. Kwak is a freelance writer, novelist, creative entrepreneur, and the author of From Chaos to Creativity: Building a Productivity System for Artists and Writers. I spoke with her about how entrepreneurs can learn to wrangle mental chatter, harness their creativity when building a business, and make time for the work that matters.


It seems like the build-your-own-system approach can apply to a lot of people, but did you have a particular audience in mind when you started writing this book?


At first, I had in mind people who are managing their own time, who own their own creative business or are small business owners in general – anybody whose time isn't dictated by a “standard” day job. But even though I didn't really write it for people working 9-to-5 and trying to find time to do their art or start up their side hustle, so many people in that situation have said it was super helpful.


As I was researching, one of the questions I asked people was, what is your art? At first I heard things like “knitting” or “photography.” But then I started getting really interesting answers like “developing teachers” or “raising foster kids” or “starting a business.” People were trying to make time for what they're passionate about, whether it was a creative pursuit, a cause or a business idea. That really broadened my perspective.


You mentioned business ideas. What specific lessons can entrepreneurs and would-be entrepreneurs learn from this book?


As you’re growing your business, you can get so caught up in the chaos of running things that you're not making time for the important work that only you as the entrepreneur can do – strategizing, networking, growing the business, and that sort of thing. That’s the first big reason it’s so important for entrepreneurs to find a way to wrangle the mental chatter.


It’s also crucial to come up with a system to help you manage your overwhelm so you can be more effective in everything you're doing, whether it’s life stuff or business stuff.


Starting and running your own business is an inherently creative pursuit. You’re a business person, sure, but you’re also an artist. You need to wrangle the chaos in your brain and daily life in order to make space time for your best work, and you need a system to help you keep things running smoothly.


This book was partly the product of burning out after spending years looking for ways to cram all your creative work into your free time. Was there a moment of realization that you needed to find a better system?


I don't know that it was a moment of realization. It was kind of a slow exhaustion.


My biggest passion is writing fiction. When I was working as an in-house catalog copywriter, I loved the work, but I hated that all of my most creative hours were taken up with somebody else's schedule. I knew if I wanted to build a business around fiction, I needed to reclaim that time. That was my impetus for going freelance.


But as a freelancer or entrepreneur, you’re your own boss. You can pile as much work as you want on your plate and overwhelm yourself easily, so then I was struggling with a different problem.


I’m still figuring out that balance – and not just in the sense of finding the hours to do the creative work. When you're stressed out, it's hard to clear your brain and do work that requires thoughtfulness. So I was trying to find not just more hours but also the mental clarity that comes with having a system that keeps everything organized for me.


Did you know what the book would be about when you started writing, or did it take form during the writing process? What emerged for you?


I wrote and edited the book over the course of a year, and I was definitely learning new things in the process.

I did a lot of interviews with other creative professionals: writers, artists, and small business owners. In the course of those interviews, I kept realizing, “Wow, I hadn't even thought about this aspect of it. I should include something about that.”

It was definitely an evolving process, with lots of revising.


I think the biggest change was no longer thinking that my system – using Evernote folders and files to organize things – would work well for everybody. The more I talked to other people and heard what works for them, the more I realized that wasn’t true. So I went from this idea of writing a book that will solve everyone's problems to one that is more about how to figure out what works for you and come up with your own system.


What would you suggest to an entrepreneur who’s looking for a quick way to wrangle the chaos? Something they could implement quickly and see results almost immediately.


If you’re feeling overwhelmed or like you're spinning your wheels, a great first exercise is to get your priorities in the right order. Often, we say yes to one thing, then another, and pretty soon we're scattered and aren't sure how we got there or how to get back.


Set a timer for five minutes and make a list of the top three things you want to accomplish in the next six months if time or resources were no object. Then write down 10 things you don't want to do anymore. Maybe it’s working with a particular client, or spending a lot of time on accounting when you could hire someone to help you.


Next, make an action plan for how to get one item off your “no” list and replace it with something from your priorities list. Once you can see what you do and don’t want to be doing, you can start to find a path from where you are to where you want to be.