Flying Solo:  Pros and Cons of Being Self-Employed

Flying Solo

I am self-employed.  Notwithstanding a part-time hourly gig, I am entirely responsible for my work product, time management, working conditions, clientele and income.  In the past, I spent years working in a corporate environment; a place I learned is not for me.  But being my own boss is not without challenges, either.  Thankfully, I have my supportive HerSavvy friends to help me over the rough spots and to celebrate my victories big and small.  In fact many of us are self-employed, leading one Savvy gal to refer to us as her “advisory board.”  I LOVE IT!!!!  Indeed there is a veritable font of knowledge flowing through this group so I decided to ask the question: What are the pros and cons of being your own boss?  And being the generous women they are, they gladly opened up and shared some of their lessons learned.  So, in no particular order, here are some answers from our HerSavvy Advisory Board:

“For what it’s worth, I love being self-employed because I have complete and utter creative and aesthetic control over my products and how they are presented, marketed and packaged. There’s no group that has to sign off on my new collection or the colors of my logo. I also enjoy being able to accept challenges and quickly modify offerings/policy based on client feedback. What I often struggle with is switching between the creative (right brained) responsibilities and the business/analytical (left brained) tasks. I find that to be most effective, I often need a bit of space between the two.”

“What I like – no issues with changing schedules as needed.  What I don’t like – being all things – custodian, bookkeeper, office manager, marketer etc…until and unless you have funds to outsource all this, it is a lot of work to wear all these hats.”

“Practically, my biggest hurdle to overcome was technical support.  I had resources to address all the legal consulting issues specific to my profession.  It was having/maintaining the technical tools that was tough. In a broader sense, I had to critically analyze my greatest weakness(es) and find outside resources to bolster my practice.  It takes a critical, objective eye and the willingness to admit that ‘you can’t do it all.’  That can be very difficult for some people. For me the biggest pros were not bowing to bureaucratic requirements that got in the way of serving my clients and freedom to set my own hours, focus on the type of law I wanted to practice, etc.  I also had greater freedom about setting my rates and even accepting consideration other than money.”

“Pro: You are your own boss.  Con: You are your own boss.  But expanding on the Pro side, you have flexibility with your time.  Even though all of us that are self-employed put in many hours each week we can take the time to go to that special family event or take our vacations on our schedule and not someone else’s.   And on the Con side being your own boss means you wear many different hats and that can be stressful and very tiresome at time.”

“Pro: Flexible schedule.  Con: Having to keep a watch on every piece of the business (i.e., billing, scheduling, business filings, etc.); not having anyone else to help manage those things.”

“Pro: I absolutely love the ‘Flexibility’ of being self-employed!  Con: The need to continuously look for the next job!”

“I thrive on the accountability of it. You do good work for a client you get rewarded; there are not as many variables between you and the work you do, unlike in a large corporate firm where the performance or needs of partners. etc., may affect you. I like control so this allows me maximum control over my work and reward. On the other side it is occasionally lonely. While your employees may be friends with each other, as their boss I could not have the same level of camaraderie. This is especially true in a small environment when you have 2/3 people working for you.”

So, there you have it, straight from the mouths of the most successful, motivated, intelligent, passionate, creative and amazing women I have ever known.  If you are self-employed, let us know your pros and cons and how you keep it all together.  Stay Savvy, my friends!

About Barbara Dab:

Barbara Dab is a journalist, broadcast radio personality, producer and award-winning public relations consultant. She currently hosts two radio shows locally in Nashville, TN. Check out her website at

Barbara is also creator of The Peretz Project: Stories from the Shoah: Next Generation. Check it out at If you, or someone you know, is the child of survivors of the Shoah, The Holocaust, and would like to tell your story please leave a comment and Barbara will contact you.

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