How Being An Employee Taught Me To Be A Better Boss

A woman holding a mug that reads,

It’s quite a paradigm shift, this becoming your own boss thing. One day I go from being someone’s employee, hired to fill a specific professional niche and the next day I’m in charge of everything. That’s right, EVERYTHING.

For solo practitioners, like me, that’s quite a long list of obligations. From office supplies to insurance policies, new business pitches to projects due for current clients, brewing the coffee to cleaning out the pot, there isn’t a minute of the day (or night) when I’m not at least peripherally thinking about my business and how to make it better. Throughout my career I have never encountered this degree of professional independence, nor the accompanying level of stress. There’s a lot to be said for my lifetime as an employee and how it paved the way towards my current business ownership. Good thing I paid close attention over the years!

​​Most of us don’t choose to become entrepreneurs right out of the gate. A typical professional person, assuming they’ve earned a college or graduate degree, starts their career by working for someone else and may remain as an employee their entire career. The Bureau of Labor Statistics says that around 49% of start-up companies will make it through the first five years. That’s great news! Another slightly darker interpretation could be that over half of start-ups will not find success. Those are tough odds that many workers, especially those with added domestic responsibilities (such as kids, mortgages, electric bills and groceries) may not be willing to take.

It’s not that being an employee is any easier or harder than being one’s own boss. There are challenges in both roles. Employees exist within a psychological framework revolving around a defined list of roles and responsibilities and limits. When you work for someone else, you are being guided by and seeking to achieve that person’s vision for his/her operation. And while a work model based around external forces may not feel comfortable for all employees, shouldn’t it really be that way? After all, the company belongs to the boss, right?

When I worked for other people, I was one of those employees constantly trying to push past the boundaries of my job description. I wanted to take on more responsibilities, more leadership, seek out additional projects outside of my scope of work and try new things. I always thought I could do a better job if I could just expand upon my company profile. Looking back on many years of this “pull and tug” behavior, I can see now that I was probably a tough person to have on staff. When it comes down to business, time is money and I expended a great deal of my own and others’ energy pushing up against the limits set for me. There was always this steady undercurrent of dissatisfaction because I couldn’t change my status. While I was willing to do whatever it took to make these extras happen (and there’s no doubt my work ethic was admired) I’m sure it was a bit exhausting to be my boss.

For this post, I looked up some data to find out what factors most strongly affect employee engagement on the job. The Society for Human Resource Management publishes an annual profile containing this kind of information. Based on a 2013 SHRM report, the #1 aspect of job satisfaction comes from “Compensation/Pay” as rated by 60% of study respondents. Money? That’s not surprising. I was more interested to see the second place title given to “Opportunities to use Skills/Abilities” by 59% of survey respondents. I must not be alone in the desire to engage a full portfolio of my talents on the job.

Bringing on an employee (or two) may be necessary, but the prospect feels daunting for all of the reasons I just outlined! What happens if my employee starts to feel that her role needs to expand in order for her to be happy? Should I hire someone exactly like me: a self-diagnosed perfectionist, always seeking change and wanting more? Or do I look for someone who is more laid back, less driven, and hope that we can balance each other out over time? How will it feel to be the emotional and motivational compass for my future staff?

Navigating the hiring process will surely be one of my biggest challenges and I still have a lot to think about as I pursue this next stage of my company’s growth. From where I stand today, I have gained a new perspective on and greater appreciation for my past employers’ efforts. Thanks to them, I have a clearer picture of what I aspire to be when I eventually become someone else’s boss.

Anne Richardson

Anne Richardson is the owner and media director of Richardson Media Group, an agency specializing in media planning and buying, advertising campaign management, and SEO.


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In addition to her role as owner and media director here at RMG, Anne authors the majority of our blog posts and hosts our BSuite podcast. Favorite topics for both platforms include the entrepreneurial journey, sustainability + social responsibility, media planning, media buying, and forming productive agency partnerships.