Entrepreneur Mom

with Aliza Sherman

If you own a business - home-based or otherwise - this is the blog where you'll find practical tips and smart ideas about entrepreneurship. I've started and run 4 different businesses so "been there, done that." I'll also invite successful entrepreneurs to share their best advice with you.

To learn more about Aliza, check out her profile on Work It, Mom! and her website, www.mediaegg.com.

I was the boss from hell

Categories: Business Essentials, Human Resources


bitchy bossBeing the boss can be gratifying and at the same time fraught with emotions that aren’t always on the positive side of the spectrum. Don’t get me wrong: I would not change owning my own business and being my own boss for anything else in the work world. However, now that we’re looking to bring on full- and part-time employees, I’m realizing just how challenging being a boss can be.

One thing I know is that I’m a kind and fair boss. Which is saying a lot given that 10 years ago, I was the Boss From Hell.

Ten years ago, I was running my first company, and I was in a bad place in my life despite being in an excellent place with my company, at least on the surface. Although I still don’t have a full picture of how my employees at the time saw me, I get bits and pieces as I reconnect with some of them over time, and the picture is not pretty.

Some suitable words to describe me as a boss at that time would be:

  • impatient
  • paranoid
  • angry
  • frustrated
  • bitchy
  • demanding
  • irrational
  • emotional
  • disempowering
  • unpredictable
  • insensitive

All of these qualities were probably how I came across to the 20 plus women and men in my employ, however, the truth was far more complicated. I share this now not just for my own catharsis and to apologize yet again to my former staff: I am truly sorry for the way I behaved. But I also reveal the following to let anyone know - boss, future boss, or someone with a boss - that the reason bosses can seem like they are from hell could be because they are going through their own hell themselves.

Behind the Scenes of Being the Boss

Here’s what was actually going on with me a decade ago while I struggled to be boss.

1. Fearful. I didn’t know what I was doing. I had never run a business before. I would have been better suited as the Director of Communications or Marketing Director than be expected to run a fast-growing company with no experience at all. I know other people do it all the time and succeed at it. But I didn’t WANT to do it. I was so afraid of failure that I tried to control everything and couldn’t delegate without feeling terrified.

2. Lacking in Self Esteem. Despite all of the successes I was experiencing, especially “on paper” in the press, I was certain I was a loser, a farce, a failure. The only thing that made me feel good about myself was when I truly influenced other women and girls to use technology, and I cherished every one of thousands of emails I received from people around the world saying how much I’d encouraged them, inspired them. Those missives helped me believe for a moment that I could do something good in the world.

3. Disempowered. I was in a very weak place when I owned my first company. I had a boyfriend who controlled my every move including what I wore, what I could and couldn’t say to others, who I could associate with, everything. He also controlled my business. On many occasions, major companies expressed interest in partnering with my company or buying it outright, however, they would take me aside every time and say “but only if you get rid of your business partner.” I couldn’t do it. I never did.

4. Embarrassed. Knowing that I stood on podiums around the world talking about women’s empowerment and women on the Internet was embarrassing knowing how I didn’t have control over my own life or company. On the rare moments that I reached out for help - and in some cases had people rally around me to kick my business partner out of my company - I couldn’t go through with it and shrunk back into myself, mortified that I couldn’t be stronger.

Those are just a few of the dynamics of my tenure as boss of my first company. I am not trying to make any excuses for my behavior. We all have to take responsibility for our choices and our actions.

But I just think it is important for anyone struggling with things that have a negative affect on their ability to be a good, fair and kind boss to rethink being in a position where they are the boss of others. Being a boss, like it or not, is kind of like being a parent. If you can’t do your absolute best when managing other people, just don’t do it. Find another job. Put someone else in charge. Because bosses can have such deep impacts on the people in their employ, and no one should take that responsibility lightly.

These days, I’m in a good relationship with a loving husband. I have an excellent business partner who is the perfect complement to me and also a long-term, trusted friend. We have several people we are working with who we want to hire as our core team and they are amazing and talented individuals. I work hard to listen to them, to be fair with them, and to empower them.

I want to be the kind of boss that I would want to have if I ever took a regular job again. And I swear I’ll never be the Boss from Hell again. If so, please call me on it.

Have you ever had or have you ever been The Boss From Hell? How did you handle the situation?

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4 comments so far...

  • I think it is amazing how the women we admire most seem to suffer and struggle with self-confidence. Every woman I look up to as an inspiration or mentor has a similar story about hardship, low self-esteem, stress, and heartache. This is encouraging to me when I am going through particularly rough times. Thanks Aliza!

    Shelli Martineau  |  December 28th, 2009 at 9:05 pm

  • Very astute Aliza and wonderful that you were able to recognize these negatives and vow not to repeat them. That’s the hardest part! I only wish other bosses from hell could do the same!

    Marla  |  December 28th, 2009 at 10:17 pm

  • I don’t think I’ve ever been the Boss from Hell, but I have allowed my performance in many work & life aspects be undermined by (a) poor self-esteem and (b) a complete jerk “boyfriend,” which is really another symptom of (a). Looking back, it is hard to believe that I allowed myself to descend to such depths. At the same time, since I never have quite understood it, I wonder if I could let it happen again. I sure hope not.

    It’s great that you have received the feedback of your former employees and taken it to heart, and come back feeling more confident than before. Sounds like things will go a lot better this time around.

    SKL  |  December 29th, 2009 at 1:38 am

  • It’s nice to see that someone I consider willing to take like by the horns has the same demons within as the rest of us.

    I agree that being a boss is like being a parent. In fact, I think I became a better employee when I became a parent. I now supervise interns and I feel like I am able to do a much better job now than before I was a parent.

    Thanks for sharing!

    Dana  |  December 31st, 2009 at 9:25 pm