Being Boss

Take Control of Your Work and Live Life on Your Own Terms


By Emily Thompson

By Kathleen Shannon

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$28.99 CAD


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This item is a preorder. Your payment method will be charged immediately, and the product is expected to ship on or around April 10, 2018. This date is subject to change due to shipping delays beyond our control.

From the creators of the hit podcast comes an interactive self-help guide for creative entrepreneurs, where they share their best tools and tactics on “being boss” in both business and life.

Kathleen Shannon and Emily Thompson are self-proclaimed “business besties” and hosts of the top-ranked podcast Being Boss, where they talk shop and share their combined expertise with other creative entrepreneurs. Now they take the best of their from-the- trenches advice, giving you targeted guidance on:

    The Boss Mindset: how to weed out distractions, cultivate confidence, and tackle “fraudy feelings”
  • Boss Habits: including a tested method for visually mapping out goals with magical results
  • Boss Money: how to stop freaking out about finances and sell yourself (without shame)

With worksheets, checklists, and other real tools for achieving success, here’s a guide that will truly help you “be boss” not only at growing your business, but creating a life you love.



Being boss isn’t just a way of working—it’s a way of life.

Hey, there. Emily and Kathleen here. Before we dive in we want to make a few things clear: we are successful working creatives who have bootstrapped our own businesses from the ground up (with zero debt!), but we’re not writing a textbook on entrepreneurship. We’re not going to tell you how to build a business model that works or guarantee a six-figure launch. And while we wholeheartedly believe that being boss begins with a confident mindset, this book isn’t about manifesting your way to millions.

You crave the freedom to work the way you want, when you want, and where you want (and if you’re anything like us, you want to work all over the world—from a coffee shop in New Orleans to the beach in Tulum). You want financial independence that will afford you the opportunity to make your own choices. And on the flip side of freedom, you also crave just a little bit of structure—a way to organize your day so you feel productive and efficient, but on your terms. And we know you’ve got some big ass goals; we want this book to be a guide in how to make those a reality.

Finally, the economy is changing. The landscape of how we work and who we work for is shifting. Self-employment is not just for the risk-taking bold and brave, anymore. More and more people are working for themselves out of necessity, practicality, or opportunity, but that doesn’t necessarily mean they have it all figured out. No matter how you’ve come to entrepreneurship, you may find yourself needing some direction. You’re just trying to figure it out as you go, and guess what—so is everyone else! This book is here to give you the guidance you crave and to let you know we’re in it together.

Kathleen here! Growing up, I never imagined working for myself. The word “entrepreneur” was never a part of my vocabulary and I didn’t come from a lineage of family business. In fact, my parents valued their day jobs working for the government, complete with fantastic benefits and retirement plans—a steady paycheck with a pension was the definition of “security.” Growing up, I assumed the order of things was simple: you go to school, make good grades, go to an affordable in-state college, get a job with health insurance, contribute to a 401k, and save as much as you can. Once you have job security, you buy a modest car, get married, start a family, go on vacation once a year, work nine to five, come home, and watch your shows (our family’s show of choice was the soap opera All My Children—we watched it on our VCR every day after everyone came home). Rinse and repeat.

I’m truly grateful for my pleasant suburban upbringing and what my parents provided for us, but I always felt a little bit like an outsider. My suspicions that I was different were confirmed when I was named “most nonconformist” every single year through middle and high school. While all my classmates were sporting Lucky Brand jeans and “No Fear” T-shirts, I was fearlessly rocking argyle socks, combat boots, and thrift store flannels. My style icons were Kurt Cobain and Gwen Stefani (and still are to this day, really).

I have always liked to think of myself as the rebellious youngest sister, but the truth is I’ve got a lot of Type A, rule-following, people-pleasing genetics at play. Sure, I let my freak flag fly a little when it came to personal style and creative expression, but I was still following the very safe path my parents had forged for me. I vied for gold stars from my teachers and hated getting anything less than an A on my report card (even an A- was anxiety-inducing). I graduated from college with a degree in fine arts and graphic design and got a job right away, working my way up to senior art director at a small advertising agency. Those gold stars turned into gold medals won at annual industry banquets, followed up by bonuses and high fives from my boss. In my twenties I had a mortgage and a 401k, and felt like I had made it. I was motivated to climb the ladder ahead of me… until one day I decided to build my own damn ladder.


I had been working as an art director for five years when I developed a bit of an obsession with Mount Everest. It started when I watched a reality-style TV show on the Discovery Channel about a group of adventurers attempting to summit the highest mountain in the world. Then I started reading books about Everest and watching serious documentaries about what it takes to climb the world’s highest peak and the risks involved.

At the same time I had been keeping an online blog where I shared stuff like getting married, remodeling a historical home with my husband, learning how to cook good food, and all things adulting. Capturing, shaping, and sharing my life had become my hobby—and unknowingly, I was creating a personal brand for myself. Writing about the details of life helped elevate the mundane into something interesting, and—on the flip side—I was living more life so I’d have something to write about. I was surprised when someone besides my mom began to read my blog. I managed to attract an audience that not only liked reading about my life but would one day support my entrepreneurial endeavors.

Writing about my life intersected with my crush on the world’s tallest mountain when I thought trekking to Mount Everest Basecamp would make a great story. And you have to understand, at that point in my life I had hardly been out of the country, much less to the other side of the world. Oh, and I didn’t even own hiking boots. So along with all the things I needed to figure out to make this trek happen, I wasn’t entirely clear on how I was going to take three and a half weeks off work when I got only two weeks of paid vacation time per year. But I started my plans to traipse through the foothills of the Himalayas by buying a plane ticket to Kathmandu, Nepal. I trusted that I would figure it out as I went.


I solved the problem of having limited amount of time off by quitting my job. It sounds easy enough when I say it here, and as of writing this book that was almost seven years ago. Hindsight has confirmed that it was a good decision, but at the time everyone was freaking out about who was going to pay for my health insurance. It’s hard now to remember all the angst, but trust me—there was a lot of sobbing into a pillow and questioning my self-worth that went into handing in my notice. But I made that trek through the Himalayas, and documenting the experience on my blog solidified the newfound freedom I had found in working for myself—at first by becoming an invitation designer.

Years before, when I got married, I blogged about my tiny at-home wedding and the quirky Wes Anderson–inspired wedding invitations I designed for us. The invitations were shared by a big deal blogger (thanks, Joanna Goddard!), and she also shared the wedding itself on Glamour magazine’s blog, which she was contributing to at the time. My invitations captured the attention of other offbeat brides who wanted invitations with a little more personality. I started designing custom wedding stationery and at the same time was submitting those designs to popular wedding sites, which introduced my designs to a larger market. I charged just $300 for the first custom invitations, but by the time I quit my day job I had more than doubled that fee and had hustled enough to replace my job salary within the first year of working for myself.

I had managed to carve out a name for myself—not only as a designer but, more surprisingly, as a branding resource for other people making a living being “creatives” too. Even though clients knew me for my design style, very quickly they saw that the way I directed a branding project was the same way I directed my own business—with a go-with-your-gut, unapologetic decision-making style grounded in a strategic mindset that had stuck with me from my ad agency days.

I was designing and doing business the only way I knew how, but I saw that it gave my clients a ton of confidence in return. They enjoyed our collaboration and how much I kept the big picture of their business in mind. It was as if they were getting the fierce big-vision wolf in pretty brand-design sheep’s clothing.

After about a year of freelancing, I retired from invitation design and standalone design projects and opened a branding studio with my big sister, which we called Braid Creative. My sister had been the creative director at an advertising agency and thought she’d be there for life. When she became a little disenchanted with her own day job (even the most glamorous jobs have their downsides), I saw my opportunity to convince her to join me and double down on our strategic and creative talents. Together we built our own branding agency and team.

People ask us about the name, Braid, and we describe it as weaving together all the threads of their business vision. Whether they’re a solo creative entrepreneur or a layered business, we’re integrating their personality, voice, style, and expertise into every decision we help them make. On any given day our team is consulting, coaching, visioning, writing, and designing for our dream clients and helping them go after their dream clients in return—with a clarity that helps them really share who they are and sell what they do.

Along with documenting that life-changing hike through the Himalayas, I continued to share the story of becoming my own boss on my blog. I was writing about everything from how I was feeling, which from one day to another ranged from “I got this!” confidence to “What am I doing?!” freak-outs, to the more technical aspects of working for myself, such as how I managed my time and tricky clients. In the process I had positioned myself not only as the kind of person who has the freedom and courage to go on grand hikes that end with watching the sun rise behind Mount Everest but also as an expert in being my own boss. Plus, I attracted a tribe of other creative friends who were also working for themselves and figuring it out as they went. Friends like Emily.

70 percent of American workers dislike their job.




Emily here. I spent my childhood watching my parents and grandparents do back-breaking work that they didn’t love doing so that they could put food on the table. If you were to ask them if they liked their jobs, they’d probably say “yes” out of duty, but I could tell the difference. I watched them hurt physically, emotionally, and spiritually as I grew up, and it taught me some important lessons. My parents and grandparents modeled a killer work ethic; they worked hard to provide for their family. However, I learned a subtle message about how doing work you don’t love can put a damper on your whole life. Doing work you believe in and enjoy is the difference between being happy and being ever-disgruntled.

As I grew up, this “Do the work” ethic modeled by my parents and grandparents manifested itself in my own life. In high school I worked hard to make really great grades, took advanced classes, and even took college courses. I entered college with my freshman year almost complete, like the rebellious little overachiever that I was. In college I routinely worked two jobs even as a full-time student, not necessarily because I needed to but because I liked to do new things and wanted to stay busy in the working world. I had no problem bouncing from job to job, as long as it held my interest and my boss was a good person; I loved learning about how retail chains operated, how small businesses made it work, and how they all got their customers to buy what they were selling. I was in college because I “had” to be; I was working because I liked being in business.


In my first year of college I was presented with the opportunity to buy a tanning salon. You heard me: a tanning salon. Long story short, at the age of eighteen I became the owner-operator of that tanning salon (I can still smell it sometimes), making me feel like a total boss, even though I had very little idea as to what I was getting myself into.

I was in college full-time and running my tanning salon in Mobile, Alabama, in 2005. Less than a year after buying the salon, cleaning it up, and putting forth my first-ever marketing campaigns to make it awesome, Hurricane Katrina hit the Gulf Coast and my entire world (along with the world of everyone around me) shifted. My salon sustained minimal physical damage: we lost our sign and had some water damage. The hit came in the way that matters most to a small business—economically. Our clientele had bigger fish to fry than themselves, needing to fix roofs or assist family, and some even cut their losses entirely and moved away. For months, disposable income for the entire community was cut. I was just a kid and the pressure to sustain a commodity business in that place and time was a lot to handle, so I made the decision to sell the salon almost two years after I became the owner. But I knew I’d dove into something that would thrill me forever. Being my own boss and running my own business was in me now, and it would never go away.

That tanning salon taught me a lot. It taught me that being a business owner comes with lots of paperwork. It taught me how to be responsible for things like commercial property, contracts, and customer education. I learned about managing employees and a brand. Had I found my passion in running a tanning business? No. But I experienced something at an unusually young age that has fueled me ever since: what it felt like to be my own boss and to build something bigger than myself. I had found a passion in business. But somehow, these ideas didn’t shape the rest of my formal education at all.


I ended college with a degree in geography, a certificate in geographic information systems (GIS), and a minor in art history. I loved geography because I have a deep connection to the Earth and the things that inhabit it. I envisioned myself becoming a professor who taught kids about the world we live in, or working for the National Park Service to conserve and protect land and wildlife. What grand dreams! But they were the kinds of dreams that weren’t being fulfilled much anymore; the job market was changing. I mean, aside from a higher education, a job is one of the main reasons why you go to school, right? And for me, that’s why the GIS certificate was there: that’s where I was going to get a job, except I had no desire to be what a well-meaning professor called a “GIS weenie,” which basically meant that I would spend years in a cubicle turning paper maps into digital maps, either for a private company or maybe the government! Ew. Educating children or frolicking in wild forests wasn’t in my cards. I graduated more than a little heartbroken. Looking back on it, it’s strange that getting a business degree never really crossed my mind.


Even though I finished school with a clear path in front of me, I had no desire to continue down it. I didn’t want to be a GIS weenie. I wanted to be my own boss, and I wanted to spend my life doing something creative. I wanted to do something that I would really enjoy.

While wrapping up my last year or so of school, I started my second business. I had discovered Etsy and adopted it as the platform where I would launch and grow my first online business. In addition to loving business, I have also always been a maker. All of my friends had friendship bracelets I made. I crochet and cook and sew. Etsy gave me the opportunity to turn a jewelry-making passion into a money-making endeavor.

Etsy also provided a community that showed me how to be a business of one, selling what I make online. Making for a living, no matter where I was located. What a cool way to work! This job I had created for myself gave me flexibility beyond my wildest dreams, and I had a very fruitful couple of years growing my jewelry business online and in my local community. But as college graduation neared and the reality of life began to set in, I needed more than just some extra income, and I wasn’t positive that my jewelry business was one that I wanted to scale large enough to fit our needs. My partner, David, was heading into his master’s program, which offered a very small stipend, and it was up to me to pay the bills. Over the last months of my jewelry business, I had moved my online shop off Etsy and onto its own website. In high school I had picked up some website-making skills, so I did all the work myself: designing, coding, creating, and loading up content. I had a blast doing it. Before I knew it, I was spending more time tinkering with my website than I was making jewelry, and I had Etsy friends asking me to make websites for them, too. Two weeks after graduating I posted some website design services on Etsy and sold my first project. Thus, my third business was born.

It’s important to note that by this time we also had a family, having brought a baby into our lives as well. Our daughter was almost two when I started my web design business; I wanted to stay home with her. I had already proven that running a business was something I could do and that doing it online would afford me the flexibility and freedom that I desired. But I was also responsible for financially supporting our family while David finished his education, so I had no choice other than to make this work.

In this third business of mine, I found a calling in helping creative folks start businesses online. I spoke their language and I knew what they wanted. I was one of them, and I spent the next six years creating websites for stationers, yogis, photographers, and other creatives who wanted to make their mark in the online world. But I wasn’t only launching websites, I was helping them start and grow businesses that let them do what they loved, work from wherever they wanted, and live by their own rules. I built a sustainable, profitable business that did some good for the people I worked with, made good money that supported my family, and filled me with purpose that left me energized at the end of the day. It was also a business model I could scale and grow, satisfying my need to stretch and strengthen my business muscles. I increased my revenue, expanded my team, and never had to go be a GIS weenie (even though that unused education has proven to be essential in ways that I never expected). The sacrifices I made were different from the ones that my parents and grandparents made. I gave up organized benefits for flexibility. I gave up a dependable paycheck and low-risk employment for doing work that compensated me in ways other than cash. None of it was easy, but I can promise it’s been worth it.


Everyone always asks how our paths crossed.

Kathleen here. Emily and I became online friends in a time when you still had to clarify whether you knew someone from the Internet or “in real life.” We read each other’s blogs and left encouraging comments or inquisitive questions. Emily suggested that we video chat over Skype, and one time turned into monthly sessions. We exchanged information on systems and processes that were working and how to handle difficult clients, and we even got honest about our income and how we price our offerings. Our paths crossed in real life at a blogging conference and we began hiring each other as we grew our businesses—Emily hired my company to help her with personal branding and I hired Emily to help me scale my one-on-one services into an online course. We were also sharing clients and, in general, appreciated each other’s work ethic and drive.

In 2011, we had an idea. We wanted to launch a weekend workshop in which we would teach creative entrepreneurs everything we knew about our combined expertise in branding, building an online business, and marketing it to attract the dreamiest of customers. And it totally failed. We got one signup and decided to call it quits before we sank any more effort into something that wasn’t working.

Failed project aside, we still got together over video chat regularly to talk shop. We found ourselves talking about things nobody else seemed to be discussing out loud—from how much money we were making to how we juggle work and family. We openly shared business secrets and insights with each other. We became really good friends whose favorite topic of conversation was nerding out about business.


In December 2014, Emily proposed the idea of starting a podcast together. We were already creating content on our blogs, sharing what we’d learned with our following, and having candid conversations with each other and our peers about the work and life of being a creative entrepreneur. Why not hit record and release these conversations for everyone to hear? Emily has always had her finger on the pulse of business trends, and as grandiose as it seemed when she said, “Podcasts are the future and ours is going to change the world,” I believed her.


Doing the work is what makes you look like an overnight success ten years later.

We started Being Boss as a place to bring our vulnerable conversations about work and life, our experiences as small business owners, and our expertise in branding and online business to others who were going at creative entrepreneurship, too. Together we’d chatted with thousands of clients and creative peers about the mindset, habits and routines, boundaries, and balance that go into being a working creative—and we were ready to bring those real conversations to an audience. We thought we’d reach a few listeners looking for guidance on how to go out on their own and make a living doing what they love. We were surprised by how quickly the podcast gained traction.

Within weeks of launching our first episode we hit the top of the charts on iTunes, quickly attracted a loyal following, and landed some lucrative sponsorships from like-minded brands who believed in our vision and our voice. We snagged interviews with accomplished entrepreneurs and our own personal heroes, including Brené Brown, David Heinemeier Hansson, Ramit Sethi, Chalene Johnson, and Melissa Hartwig, to talk about topics ranging from money and living a rich life to staying healthy as an entrepreneur, as well as personal stories of success and failure. We created space for our audience not only to listen but also to join the conversation and create connections—from online forums to in-real-life vacations and retreats.

To the world we looked like an overnight success, but we knew it was just the beginning of a new vision that countless hours of hard work had brought us to.


So here we are. Writing a book—something we dreamed about for years as part of our plans for world domination (mwahaha!) and a natural next step to what we’re already talking about on our podcast. We’re here to share our own experience, advice, stories, tactics, and to-dos that will help you make money doing what you love while being who you are 100 percent of the time in work and life.

Now, enough about us… who are you? Well, if we had to guess, we’d say you desire the freedom to work the way you want—on your own terms and your own schedule. But with that, you might struggle with creating structure for yourself. You’re brave and you set big goals for yourself, but sometimes you’re overwhelmed by all your ideas and what it will take to reach your dreams. You want to grab life by the horns, but sometimes you feel less than confident and too trapped in your head to get your ideas to fruition.

We know you because we are you. And we’ve worked with hundreds of creatives just like you.

Whether you are still working a day job with a creative hustle on the side, you are fresh on your path to working for yourself, or you have a few years under your belt—you can be boss. This book is for creatives and aspiring entrepreneurs (designers, photographers, artists, musicians, coaches, nutritionists, trainers, stylists, event planners, consultants, chefs, yogis, wellness professionals, athletes, performers, community organizers, etc.) who need more tools, advice, and inspiration to level up, hunker down, and do the work.

This book is going to help you dig deep, dream big, and take action. We’re not going to show you how to run or market a business (though we are pretty bomb at that). We’re not going to show you how to “get rich quick” by meditating and manifesting your way to success (though we are a little woo like that). The nitty gritty details of how to grow a team or launch a new product is another book for another time. Instead, we’re going to show you how to set up the foundation to be boss so that you have what it takes to expand your capacity for success (as you define it!), cope with inevitable failures (’cause if you’re behaving like a boss, you’re gonna fail), and take responsibility for creating the life you want to live.

We suggest you read this book from cover to cover. We’ve included some of our best stories and tactics along with quotes, excerpts, and Q&As from our favorite creative peers and industry experts. You’ll also find some worksheets in here—you can fill those out in the book—or you can download them at, print them off, and fill them out that way. If you feel challenged or stuck along the way—that’s okay! Keep reading. You can always come back to it, and we hope you do. We want this book to become one you’ll keep on your shelf, that over the years you’ll reference, highlight, tab, and wear down with love.

And if you want more of us, you can follow us on Instagram at @beingbossclub or subscribe to our podcast on iTunes.


  • "Finally, a book for entrepreneurs that honors your intuition while cultivating your inner badness...full of real-life insights and bold strategies to help you define success, take charge of your day, and create the life you've always wanted."
    -Melissa Hartwig, Whole30 co-creator and #1 New York Times bestselling author
  • "Ditch the myth that creatives and business don't mix. Being Boss is the uncomplicated guide to creating your own success."

    - Mike McDerment, co-founder and CEO, FreshBooks

  • "Kathleen and Emily are two of the hardest working and passionate hustlers around. Their care and attention to detail doesn't just show in their work, but in how they've built a tribe of raving supporters. In this book, they don't just talk about creating the business and life you want--they show you how, step by step."—-Jasmine Star, photographer, influencer, and renowned business strategist
  • "Holy crap-this book is beautifully written and laid out, helpful as only something from the trenches could be, and offers no-BS ideas for truly becoming and being the boss of your business."
    - Paul Jarvis, online brand consultant, host of the Sunday Dispatches podcast, and author of Company of One
  • Being Boss is a practical guide to inspired sovereignty in your work and in your life. This book offers a roadmap for finding agency, authenticity, and joy, and it is chock full with helpful strategies the reader can get started with right away. Want to make the most of this gift of a life you've been given? Kathleen and Emily will show you how.—- Tara Mohr, author, Playing Big: Practical Wisdom for Women Who Want to Speak Up, Create & Lead

On Sale
Apr 10, 2018
Page Count
200 pages
Running Press

Emily Thompson

About the Author

Emily Thompson founded Indie Shopography, a design and strategy studio for online entrepreneurs, in 2009. Emily has worked to help makers, coaches, and designers develop an online business model, strategize and launch websites, and grow their online business. She lives in Chattanooga, Tennessee with her life and business partner, David, and their daughter.

Kathleen Shannon is the founder of Braid Creative and Consulting, a boutique branding agency and consultancy she co-owns with her sister. Together they have helped thousands of creative entrepreneurs authentically brand and position themselves as creative experts. Kathleen also does creative coaching and is regularly invited to speak on personal branding at design conferences and retreats. She lives in Oklahoma City with her husband and son.

Learn more about this author