Mastering Team Leadership

Chapter 1

Responsibility and Reward

Do you remember what you felt like on the first day of your first job? 

Many business owners learn important lessons early in life. Time management, scheduling, customer relations, profit and loss, and the life cycle of the sale—these critical skills, even if we don’t know it at the time, first become part of our understanding when we mow lawns over the summers, babysitting neighborhood children or our siblings, or even setting up the proverbial lemonade stand. 

While these are valid work experiences that teach budding businessowners and leaders valuable skills, I’m curious about the first day of your first real job. 

We all start our professional lives someplace. Many of us apply to positions, interview for them, and nervously wait to see if the words our friends or parents prepared us to say were enough to earn us the trust of a total stranger—a total stranger who will then be willing to train us, teach us, put real responsibility on our shoulders, and in exchange pay us real money. 

I have a friend whose first job was bagging groceries at her local supermarket. She was a fast learner, had great grades, and aspired to save money for college. She was motivated to do well and was thrilled at the chance to be paid for her work. She showed up early, followed the dress code, and asked, “Paper or plastic?” with a huge, sincere smile. 

But as you probably have experienced, the reality of the job came crashing down within the first couple of weeks. Retrieving carts from the parking lot in snowstorms—when she weighed under 100 pounds soaking wet—was not what she had in mind when she dreamed of ways to sock away cash in a savings account. 

The store she worked at was a union shop, so imagine her surprise when even as a sixteen-year-old, her first paycheck wasn’t at all what she expected—not after union dues, taxes, and social security were deducted. 

Maybe in your first job, you had to show up at a scheduled time wearing certain clothes or even a uniform. A trainer or manager explained how to clock in or use a software system. You were issued a badge or a password or an employee ID. You had a desk or register or station, were taught the rules, and were told what you had to do when.

If you showed up on time, dressed properly, and fulfilled the expectations of the role, you earned a paycheck at the end of the week, every two weeks, or every month. With that very first professional job, we are each immersed in a system that most of us will participate in—with varying levels of success—over the course of our entire adult lives. Whether it happens at sixteen or sixty, in a grocery store, pizza place, hospital, office, or school, work eventually defines our lives.

Most of us grew up in a family that had a system of responsibilities and rewards. Coming from a family with seven children and two parents running several small businesses, I was expected to do chores at home and contribute real work after school and on weekends. When I was young, my parents made a game of entrepreneurship. Saturday Surprise meant getting in the car, getting out of the house, and getting to do something different—we never knew what the day had in store. 

The “surprise” part of our Saturday routine was always some form of manual labor. My parents made owning a business a family affair. Rather than put us in front of the TV, they brought us to work and put us to work. Sometimes we swept parking lots or cleaned baseboards, restocked supplies or organized storage closets—all far from glamorous jobs. But I received an allowance, and sometimes even a paycheck.  

As the daughter of businessowners, I experienced my first taste of real money not by pushing carts or bagging groceries at the local grocery store, but by working within my family businesses—even if that taste of earnings was often just a nibble. I learned the value of teamwork, the discipline of commitment, and the often painful reality of failure.

By working with my family in our businesses, I received an education—the type of education most people don’t receive until long after they have entered the workforce. And, to be candid, some people never learn these lessons. They simple hold down jobs or struggle in positions that they were never suited to and have no passion for. 

My earliest memories of laughter, weekends, down time, and love are all intermingled in a beautiful stew of family life. Whether my mom was arranging flowers in our home before she opened a shop, my grandfather worked his small supermarket, or my parents ran a small business that fit the needs of the community at the time but didn’t last very long (remember the “We Buy Levi’s” era of the 2000s?), work was a defining quality of my life growing up.

Of course, every family system is different. Whether those differences come from socio-economic status, education, or opportunity, or as a result of circumstances such as illness, disability, family structure, or faith, every person is raised with a different relationship with work. 

We would never believe that every relationship in our lifetime will be happy, healthy, and permanent, right? And yet, somehow, we’re all expected to arrive at the threshold of adulthood know how to do this thing called work. Whether we access that work through employment or entrepreneurship, we’re expected to do it successfully for our entire life!

 How does that make sense when colleges do not teach job skills? When trade school prepare you for a specific skill but not all the other concerns that factor into successfully creating a career in trades? When most Americans see their job as a means to a very short-term end, such as health insurance, a paycheck to cover this month’s rent or mortgage, or a stepping stone to whatever comes next, it’s no wonder that so many people reach the age of sixteen, twenty-one, thirty, and even fifty, and they have an unworkable, unsustainable, or simply unfulfilling work life.

Work is something that we share in common as humans—whether that work is compensated through a paycheck or uncompensated as part of the essential work required to run a household. While some families pass wealth and businesses down for generations, there are far more of us with the opposite experience. Many of our parents and grandparents struggled under career options that were limited and insecure. Whether it was you personally or relatives several generations back, many of us have left behind homelands, cultures, faith systems, and everything familiar to pursue better work opportunities.