Being Boss

Being Boss Plot Summary

Introduction

Imagine standing at the edge of a cliff, feeling the wind brush against your face as you contemplate taking that leap into the unknown world of creative entrepreneurship. The view below is both terrifying and exhilarating – a canvas of infinite possibilities waiting for your unique brushstrokes. This is the moment many creative souls experience before embracing their calling to be their own boss, to craft a life and career on their own terms. The journey of becoming boss is not merely about launching a business or pursuing creative freedom; it's about cultivating a mindset that empowers you to own who you are, know what you want, and make it happen. Throughout these pages, you'll discover that being boss transcends the traditional definition of entrepreneurship – it's a way of life that blends confidence with vulnerability, discipline with flexibility, and hustle with intention. Whether you're still dreaming from your cubicle, taking your first steps into self-employment, or already running a creative business that needs refinement, the principles shared here will help you navigate the beautiful mess that is creative entrepreneurship with more purpose, profitability, and joy.

Chapter 1: The Origins: Finding Your Entrepreneurial Path

Kathleen grew up in a household where job security meant everything. Her parents valued steady government positions with benefits and retirement plans. The path was clear: go to school, earn good grades, attend an affordable college, secure a stable job with health insurance, contribute to a 401k, and save diligently. Despite appreciating her pleasant suburban upbringing, Kathleen always felt somewhat like an outsider, earning the title "most nonconformist" throughout her school years. Though she expressed herself creatively through her personal style, Kathleen followed the safe career path laid out before her. She graduated with a degree in fine arts and graphic design, immediately securing a job and working her way up to senior art director at a small advertising agency. By her twenties, she had a mortgage and a 401k, climbing the career ladder with determination until she decided, in her words, "to build my own damn ladder." The catalyst for change came from an unexpected source: an obsession with Mount Everest. After watching documentaries and reading books about the world's highest peak, Kathleen developed a desire to trek to Everest Base Camp. This posed a logistical challenge since she had only two weeks of vacation per year, and the trek would require three and a half weeks. Her solution was bold – she quit her job. Though the decision involved "a lot of sobbing into a pillow and questioning my self-worth," it opened the door to new possibilities. Meanwhile, Emily's entrepreneurial journey began at just eighteen when she purchased a tanning salon while still in college. Less than a year after buying the salon and launching her first marketing campaigns, Hurricane Katrina devastated the Gulf Coast economy, severely impacting her small business. Though she eventually sold the salon, this early experience ignited something powerful in her: "Being my own boss and running my own business was in me now, and it would never go away." These distinct but parallel journeys highlight a fundamental truth about the entrepreneurial path – it rarely follows a straight line. Whether sparked by a mountain obsession or an early business venture during natural disaster recovery, the call to creative entrepreneurship often emerges from unexpected places. The desire for freedom, autonomy, and meaningful work pulls us forward, even when conventional wisdom suggests we stay put. What matters isn't how perfectly you plan your entrance into entrepreneurship, but that you remain open to the possibilities that await when you take that first courageous step toward crafting a life on your own terms.

Chapter 2: Boss Mindset: Confidence, Values, and Overcoming Fear

Carrie and Beth, both with stable day jobs, dreamed of becoming full-time photographers. They faced identical doubts: wondering if their dreams were silly, fearing wasted time on an uncertain venture, and questioning how to begin. Carrie chose to confront her insecurities head-on. She tested her skills, invested in herself, sought mentors, and committed to learning and practicing. She gradually proved to herself that she could figure things out along the way. Eventually, she reached a point where she could leave her day job, surprisingly finding herself not in wedding photography as she'd anticipated, but as a sought-after editorial photographer getting opportunities beyond her imagination. Beth, however, allowed her questions and insecurities to paralyze her. Comfort, though unfulfilling, felt less frightening than taking a leap. The weight of uncertainty – What if I make wrong decisions? What if it gets too hard? What if I can't do it? – kept her anchored to her day job until retirement, never testing her capacity for success or chasing her dream of becoming a photographer. The stark contrast between Carrie and Beth illustrates the power of a boss mindset. Carrie embodied what it means to be boss: she didn't let fear stop her from trying something new, she allowed curiosity to fuel her creative adventure, and she didn't let inner or outer critics keep her from pursuing her dreams. She faced her fears, believed in herself, and made decisions – three fundamental elements of the boss mindset. When Danielle Krysa, creator of the blog The Jealous Curator, faced her own creative crisis, she discovered similar truths. After a devastating critique in art school where her professor told her she "should never paint again," she stopped creating for years. "I didn't push forward. I hid out," she reflects. "I was terrified of making something that wasn't perfect—so I just made nothing." Her journey back to creativity taught her that "the only way for both blocks and inner critics to win is if you quit. By simply pushing forward, even on days when your pursuits feel like they're going nowhere, you are winning the battle." This resilience forms the cornerstone of a boss mindset. It's not about being fearless – even the most successful entrepreneurs feel fear regularly. The difference is they know what they want and have the courage to move through their fear. They understand that confidence isn't something you're born with; it's a muscle you develop through practice. As Chalene Johnson puts it, "Confidence is a muscle. Just like we can develop strength, we can develop confidence." At the heart of this mindset lies your values – the guiding principles that direct you through life and help you prioritize what's important. When your actions align with your values, work and life feel meaningful and purposeful. This alignment creates a compass that guides you through uncertainty, helping you make decisions that feel authentic rather than reactive. The boss mindset isn't about having all the answers; it's about trusting yourself to find them as you go, staying true to your values, and choosing positivity over negativity even when the path gets challenging.

Chapter 3: Setting Boundaries: Protecting Your Energy and Time

Most creative entrepreneurs face similar challenges: not enough time, energy, or money to accomplish everything they want. So why do some succeed while others struggle? The answer lies in boundaries – those who thrive have established healthy limits that help them allocate their most valuable resources wisely. Emily shares her experience with creating "white space" in her schedule: "For quite some time I have blocked off a single day in my week that no one can touch. This day is traditionally Thursday, and there are no meetings, no deadlines, nothing. It's a full day of white space that usually ends up being wildly productive, wonderfully rejuvenating, or somewhere in between." This deliberate boundary gives her brain freedom to wander and be playful – essential for her creative process and ongoing happiness. Without boundaries, creative entrepreneurs often find themselves scattered and depleted, leading to burnout where once-fulfilling work becomes overwhelming. You might find yourself taking client calls during family time, filling your calendar with appointments that don't align with your goals, or surrounding yourself with people who drain rather than support you. Boundaries help you determine when to say "yes" and when to say "no," allowing you to protect your time and energy for what truly matters. Sarah Von Bargen, a writer who helps people build fulfilling lives, explains how boundaries apply to money: "Most of us—myself included—have absorbed ideas about what happiness, success, and abundance 'should' look like." She notes that when we get clear on what actually makes us happy, we can fill our lives with those things regardless of income level. This means creating financial boundaries that align with our values rather than society's expectations. "When you get really clear on what makes you happy and where your money is going, it's a lot easier to point your time, money, and energy in a happy-making direction." Jenny Shih, a business coach, echoes this philosophy with her concept of "success on your terms," which she defines as "a declaration of what you want to create both personally and professionally and what you're not willing to give up to make it happen." This approach recognizes that success looks different for everyone, and true fulfillment comes from achieving your goals without sacrificing what matters most to you. When boundaries are clearly defined, they become powerful decision-making tools. For instance, if you've established that family time on weekends is non-negotiable, it becomes easier to decline professional opportunities that would encroach on that time. Your boundaries essentially become the fence around your garden – they not only help you focus your efforts in a concentrated area but also keep out unwanted distractions and energy drains. The freedom of being boss means setting your own boundaries and making your own rules. Rather than feeling restrictive, well-crafted boundaries actually create more space for creativity, productivity, and joy. They give you permission to design a life and business that honors your values, preserves your energy, and allows you to show up fully for the work that matters most to you.

Chapter 4: Daily Practices: Routines, Goals, and Healthy Habits

Emily wakes naturally at 7 a.m. without an alarm clock. She spends an hour reading or journaling before her daughter joins her at 8 a.m. After breakfast, they walk together before Emily prepares for her workday. Between 9 and 10 a.m., she enters her home office to begin her day. This intentional morning routine sets the foundation for everything that follows, creating a structure that supports both her work and personal life. How you start your morning sets the tone for your entire day, and as a creative entrepreneur, designing a morning routine that works for you is essential. When asked about their ideal mornings, most creatives describe peaceful scenarios: waking naturally in a fresh, bright space; enjoying coffee slowly; moving their bodies gently; making a nourishing breakfast; reading something inspiring; or writing to clear their minds. Nobody ever says, "I'd like to hit snooze eight times and then rush out the door with just enough time to pick up a burnt Starbucks before my 9 a.m. meeting." Beyond morning routines, Kathleen shares a powerful goal-setting system called the Chalkboard Method®. During a period when she had launched her branding business but had no clients, her executive coach taught her to "create space for what you want." She drew ten empty lines on a chalkboard wall in her office – spaces she hoped to fill with client names. She also created a mantra: "I am attracting dream customers with cash." A week later, all ten spots were filled, and shortly after, unexpected extra projects came in as well. "The Chalkboard Method will hold you accountable for setting big goals and seeing them through. You're literally making space for what you want," Kathleen explains. The system helps break down long-term dreams into achievable short-term goals, holds you accountable, keeps your intentions visible in your physical space, and even incorporates a touch of manifestation magic. Years later, she still uses this method to track clients, grow her following, and make space for new projects. Health coach Amy Kuretsky emphasizes that self-care is also an essential daily practice for creative entrepreneurs: "Health care is what keeps you alive, but self-care is what allows you to really live." She distinguishes between basic health care (nutrition, sleep, movement) and self-care (meditation, time in nature, fun), noting that both are necessary for sustainable success. "If your barrier is time and your business is based upon your creativity, then you can't afford not to make time for self-care," she advises. These daily practices – from morning routines to goal-setting methods to self-care rituals – create the structure that creative entrepreneurs crave. They bridge the gap between the artist's desire for freedom and the entrepreneur's need for discipline. By developing intentional habits that support your mindset and boundaries, you establish a foundation for consistent action that moves you toward your goals. The most successful bosses understand that these practices aren't just nice-to-haves; they're essential components of a sustainable creative business and a fulfilling life.

Chapter 5: Doing the Work: Business Strategy and Partnerships

Kathleen graduated with a fine arts degree and one clear goal: to become the best graphic designer ever. She honed her skills through daily practice and studying great designers, putting in the hours to develop expertise. But while she enjoyed the creativity of designing for prestigious clients, she craved deeper meaning. Over time, her perspective shifted – design wasn't her ultimate purpose but rather a tool in her toolbelt that supported her broader mission. Similarly, Emily picked up web design skills in high school but never intended to pursue it as a lifelong career. When she launched her web design business after college, she viewed it as "a means to some other end that I didn't even recognize yet." Years later, she no longer offers web design services, but those skills remain in her toolbelt, having served their purpose in helping her build businesses in the online space and develop new capabilities. This evolution reflects an important truth about creative entrepreneurship: your skills are tools that support your purpose, not necessarily the purpose itself. As Tara Gentile explains, "Your business model is simply the system you use to create, deliver, and exchange value. Or, in more straightforward terms, your business model is the system you use to get paid for creating something people really want." Understanding this distinction helps you focus on the expertise you want to be known for rather than trying to monetize every skill you possess. Building a successful business also requires knowing your numbers. When you're an entrepreneur, tracking metrics becomes crucial: How much money do you need to make? How much have you made? How much do you need to spend? These numbers provide boundaries within which you can make informed decisions for your business, directly impacting the life you want to live. For many creative entrepreneurs, collaboration becomes a powerful growth strategy. Kathleen and Emily's partnership began when Emily proposed starting a podcast together. They had already worked together professionally – Emily had hired Kathleen for branding, and Kathleen had hired Emily for website development – and they knew their work ethics were compatible. They clarified roles, goals, and vision, establishing regular check-ins to ensure alignment as their collaboration evolved. Their partnership eventually required formalizing their agreement, leading to what they call the "Be a Good Person/Oprah" clause in their operating agreement: "Each member promises to be a good person. 'Good person' means: if something feels funny we have a conversation about it, if we mess up we won't sue each other but we could apologize. We won't say no if Oprah calls, we'll be happy for each other. (But we'll try to get each other on the Oprah show too.)" This approach to partnership highlights key considerations for collaboration: complementary work ethics, clear boundaries and roles, efficient systems, and comfort with difficult conversations. Not everyone needs a business partner – many creatives build successful solo ventures – but finding the right collaborator can help you create something bigger than yourself. Whether you're working alone or with partners, doing the work means showing up consistently, creating value for your clients, and being strategic about how you build your business. It means developing your skills, understanding your business model, tracking your numbers, and making decisions that align with your vision. The path isn't always straight, but with each step, you gain clarity about the work you're meant to do and how to make a living doing what you love.

Chapter 6: Living Your Vision: Balance, Self-Care, and Personal Growth

In 2015, Emily embarked on a cross-country road trip with her family, calling it #indiegoeswest – a journey made possible by the business she had built. For forty days, they drove 10,000 miles across twenty-two states, visiting national parks, hiking, cooking over fires, and camping each night. "This adventure was the epitome of a life hustle," she reflects. "In forty days we drove 10,000 miles, visited twenty-two states, toured dozens of our national treasures, hiked, cooked over a fire, and slept on the ground." The trip tested Emily in unexpected ways, challenging her to provide basic needs for her family in unfamiliar settings. They adjusted their mindset, established boundaries, and created new routines throughout the journey. "When #indiegoeswest was complete, we were all different people," she writes. "That life hustle made me more boss than any work hustle ever could, and rewarded me in ways that my business never will." This story illuminates an essential truth about being boss: creative entrepreneurship isn't just about building a successful business; it's about creating a life worth living. The freedom and financial independence you gain through your work should fuel the experiences, relationships, and personal growth that bring meaning to your life outside of work. For many creative entrepreneurs, balancing work and family presents ongoing challenges. There's natural guilt when trying to be present as a parent while focusing on your career, but these roles can complement rather than compete with each other. Being a parent can make you a better boss by teaching adaptability, focus, and perspective. Meanwhile, the boundaries, habits, and time management skills you develop as an entrepreneur can help you navigate parenthood more effectively. Self-care becomes another crucial element of living your vision. From scheduling regular "treat yourself" moments to establishing "Mandatory Lazy Days" where you commit to doing absolutely nothing productive, giving yourself permission to rest and recharge is essential for sustainable success. "A regular self-care practice will help you cope with the stress and challenges that inevitably come with running a business while having a life," the authors advise. Beyond self-care, living your vision means cultivating meaningful relationships and continuing to grow as a person. The entrepreneurs we admire most aren't just dedicated to their businesses; they're committed to being students of life – exploring their curiosities, reading widely, trying new things, and remaining open to change. This approach makes them well-rounded, memorable, and fulfilled beyond their professional accomplishments. The ultimate measure of success isn't just a thriving business, but a life that reflects your values and brings you joy. Emily and Kathleen remind us: "Being boss is a lifelong commitment and an exciting ride... Being who you are 100 percent of the time, owning your shit, making money in a way that reflects your values, being creatively fulfilled, and living a good life along the way will only happen when you get intentional about what you want and making it happen."

Summary

The entrepreneurial journey begins with a simple yet profound choice – to trust yourself enough to create a life and business on your own terms. Throughout these stories, we've witnessed how ordinary people transformed their creative passions into thriving businesses by developing a boss mindset, establishing healthy boundaries, cultivating supportive daily practices, implementing strategic business approaches, and ultimately crafting lives of meaning and purpose. Each path was unique, yet all shared common elements: courage to face fears, clarity about values, consistent action toward goals, and commitment to personal growth alongside professional development. The art of being boss isn't about achieving some perfect end state but embracing the ongoing practice of aligning your work with who you truly are. Whether you're taking your first entrepreneurial steps or refining an established creative business, remember that your greatest asset is your authenticity – your unique blend of skills, experiences, and perspective that no one else can offer. By showing up fully, doing the work consistently, and remaining open to evolution, you create not just a sustainable business but a fulfilling life. The journey may be challenging, but as these stories reveal, the freedom to design your days, express your creativity, and make an impact on your own terms makes every obstacle worthwhile. This isn't just about making a living doing what you love – it's about crafting a life that loves you back.

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Emily Thompson

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