A Boss Life

Emily Thompson, Kathleen Shannon

July 11, 2018

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"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 manifesto is here to give you the guidance you crave and to let you know we're in it together. Being boss is a constant practice, and after three years of hitting publish on our podcast (and now a book) we've learned that it's conversation that is constantly evolving. Here are some key patterns and foundational insights we've picked up along the way."


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

You see, our book Being Boss: Take Control of Your Work and Live Life on Your Own Terms was born out of almost a decade of conversations about creativity, productivity, habits, money, “fraudy” feelings, systems, processes, and balancing family and career.

We started building our own businesses in branding (that’s Kathleen’s jam) and developing websites and successful online business platforms (where Emily finds her groove) for other creative entrepreneurs, freelancers, and side-hustlers who were knocking out their passion projects outside of their 9-to-5 at a time when all of our friends and family were collecting steady paychecks and benefits from their own bosses. The world of eCommerce was still uncharted territory and we weren’t only figuring it out as we went—we were paving the way. Who you work with can make or break how satisfied you are with your job—so when you’re working for yourself, even if you’re building your dream job, it can be isolating and lonely. Without peers to show you the ropes and mentors to guide you along the way, it’s easy to get lost in the daily grind or worse: paralyzed from taking the next steps.

We were a couple of creatives who were craving connection and conversation. Every couple of weeks we would hop on a video call and talk shop. After a year or two of this we decided to hit publish on our “business bestie” conversations and release them in a podcast called Being Boss. Our show caught on quickly; we became the go-to podcast for other creatives and aspiring entrepreneurs who wanted to hear insights and real talk about what it takes to do the work. “Do the work” has become our motto—because making a living doing what you love isn’t always easy and it takes hard work. Being boss means getting in the right mindset, cultivating confidence, practicing productive habits, setting healthy boundaries, finding your tribe, and really nurturing the lifestyle you want to live beyond the work that you do.

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 wanted to be a guide in how to make those a reality.

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!

Being boss is a constant practice, and after three years of hitting publish on our podcast (and now a book) we’ve learned that it’s a conversation that is constantly evolving. Here are some key patterns and foundational insights we’ve picked up along the way:

Mindset: You can’t be boss if you aren’t in the right frame of mind. The challenges we tackle when it comes to creating a career and life that are fulfilling require the right mindset: confidence in who you are and the decisions you make, a will to seek out motivation and inspiration, committing to setting and working towards big ass goals, trusting yourself and showing up to do the work, knowing and practicing your values, remaining positive, and tackling fear and your own inner critic.

Boundaries: Boundaries are the physical, mental, and emotional “rules” that you define for yourself. These rules keep you from feeling overwhelmed and overworked. Boundaries also help you decide which opportunities you say yes to, what you say no to, what you let in, and what you let go. Boundaries are how you carve out time to do what you want, prioritize what matters, and define how you live and work.

Habits & Routines: If mindset and boundaries get you emotionally and intellectually prepared for doing the work, your habits and routines are how you get the work done. From setting goals and establishing a morning routine that sets you up for success, to taking care of yourself outside of work, habits and routines are how you behave like a boss, every day.

Your Wolfpack: It takes a village to build a boss life and work, and cultivating a pack of justthe-right people is easier now than ever before. Your wolfpack supports you, encourages you, and assists you, and includes your friends, family, mentors, peers, and collaborators. You’re never too old/shy/busy/etc to meet new people, nourish relationships that are mutually beneficial, collaborate, partner, and ultimately work with others to build something really boss. Relationships are everything, and they can help you go far.

Your Work: As a creative, your work is how you make money doing what you love while staying true to who you are 100% of the time. This work takes a dedication to your craft, unwavering focus on your goals, and reliance on your own skills to take you from dreaming and scheming about what’s next to actually doing the work.

Your Life: As much as we love our work, we don’t just define ourselves by the work we do or the bottom line in our bank account. The most admirable bosses we know prioritize connection, relationship, family, friendship, travel, and really good food (yeah, what, we like our food) over making money or being a slave to their Rolodex (if you don’t know what a Rolodex is, just Google it). Bosses are curious about life outside of work and use their resources to enthusiastically pursue what they find interesting.

It was in December, 2014, that Emily proposed the idea of starting a podcast together. We were already creating content on our blogs, sharing what we’d learned with our followers, 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?

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 goes 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.

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.

We recently learned that over the next two years, nearly 14,000 women per day will quit their traditional job and begin to work for themselves. By 2020, the population of selfemployed women in America will triple, growing from 5 million to 15 million. (Freshbooks Cloud Accounting)

That’s a pretty impressive stat and we can’t help but want to help those 14,000 women a day along the way. You see, working for yourself—being your own boss—isn’t just for folks who were born with an entrepreneurial spark or rich entrepreneurial parents. In the unfolding economy, being your own boss is available to everyone.

But that doesn’t mean it’s easy—the uncertainties, insecurities, and overwhelming to-do lists pile up. The most boss creative entrepreneurs we know have a couple of key things in common. They’re confident. They know what they want, and they know how to make it happen. They work in a way that’s smarter, not harder. They focus on impact and strategy. They have no problem seeing the big picture, or breaking it down into a plan to get it done. They work like artists, makers, and shakers, but they think like entrepreneurs. They are open-minded and see their work as an experiment. Their work is personal, but they don’t take failures personally. They value getting it done over perfectionism, and prefer community over competition. They blend who they are—their personalities—into the work they do. They feel good about the money they make doing the work they love. They reliably deliver, and they hustle like a boss.

Being boss is about knowing what you want and being unapologetic about it. It’s being who you are, nurturing your talents, and sharing them with the world. Being boss means doing the work to get you to where you want to be, even when it’s hard or when no one understands. A boss owns it all, stands up for what she believes in, is brave enough to take risks, has the courage to make mistakes along the way, and makes big, beautiful things happen, even when the process doesn’t always feel easy or fun.

Because life happens in that hot mess of a process. It’s big and beautiful there, too. But only when it’s something you believe in, when it’s something that you find joy in—day in and day out. Being boss is living what you love, every day and in every way that you can. You have to build a life you love as if it’s your job. Because it is.

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