Bossy Pants – Confidence and Leadership

Kid, you’ll move mountains.” – Dr. Seuss

The other day my 6-year-old daughter Miss O, came home from school and told me about a conversation she had with a friend at recess.

Miss O: You are bossing me.

Friend: You’ve been bossing me since Kindergarten

There are times as a parent that I try not to laugh. This wasn’t one of them – I burst into laughter and my daughter laughed right alongside me. It sounds so dramatic that way – so much better than just last year. It also reminded me how early that word bossy is introduced for these young and precious girls.

It’s the fear of being called bossy that has made my confidence as a leader falter. I say that after 20 years of having my own business, teaching employees and subcontractors and being accountable to a bottom line for both my family and my company.

In the years that I’ve had business partners for my computer consulting business, they’ve always been male and I’ve been far more comfortable with them providing the visible leadership. Even when I’ve had better ideas, more experience and am the one calling the shots.

About a dozen years ago, I owned a small office building with two business partners that housed my consulting company offices. We’d purchased the building in 2007 at the height of the market. When things got messy because one business partner told me of my husband’s infidelities and my husband was the other business partner, our partnership in my consulting business fell apart and I bought back their shares in that company. But we still owned the building together and after the 2008 crash, the value of the building was less than its mortgage.

My partners were no longer interested in being involved, the building couldn’t make ends meet and I had to do something. So I went to the Small Business Administration and asked them to restructure the loan for the building. The advisor gave me a list of things I had to do like changing all the tenant leases and restructuring the accounting.

Five months later I scheduled an appointment with the SBA advisor, showed him the list and all that I had done to meet each point. He sat back and said, “I’m impressed.” I wondered why because all I’d done was what he’d told me. He replied, “Because not many people come back after I give the list of what needs to be done.” I burst into tears. Even through my tears, he restructured the loan for me anyway and when the market came back enough so we could sell the building, I finally sold it and ended the partnership with those guys.

And still after all that, I didn’t have the confidence to call myself a leader until about age 50 when I had children as a single person and they looked at me asking “what are we going to do today?”

Brené Brown defines a leader as “anyone who holds him or herself accountable for finding potential in people or processes.”  Fortunately that’s a definition that is broad enough for me to confidently own my leadership. Given that I’ve been leading for years, one wonders why I haven’t had the confidence to do so til now.

“Bossy” says it in one word. I don’t want to be called that word that people use for girls as early as first grade (and maybe earlier).

Brené Brown has a model of types of power as they relate to leadership (link goes to a PDF of the model). She differentiates people who lead using power overbelieve that power is finite and use fear to protect and hoard power” from those who lead using power with/to/within. Those leaders in the latter category “center connection and humanity with empathy-driven agendas, policies and values.

Those are a lot of big words for a first-grader but I think it’s worth trying to talk to my daughter about how to build confidence in leadership and power. I think any leader, male or female, who works with the power with/to/within is more effective because they believe that “getting it right is more important than being right.” And building on my daughter’s sense of empathy, she can learn the confidence to work with others to lead and not fear being called bossy.

Have you ever been called bossy? Do you think of yourself as a leader? If so, what gives you confidence as a leader?

This is my fourth post about confidence. Here are the others:

I Can

Fear and Confidence

Growth Mind-set

(featured photo from Pexels)


34 thoughts on “Bossy Pants – Confidence and Leadership

      1. Thank you, but I must warn you, it is very long. And remember what Oscar Wilde said: “There are only two tragedies in life: one is not getting what one wants, and the other is getting it.”

        Liked by 4 people

    1. Agreed! And I find it interesting the adjectives that are used to describe capable girls vs. boys… The way I look at it is, when in doubt, take whatever is said as a compliment. Makes me feel better, and confuses the person who may or may not have intended it as a compliment 🙂

      May I ask why you cried when the SBA advisor told you that you were one of the precious (literally) few who return?

      Liked by 2 people

      1. What a great strategy – take it as a compliment! I love that and I’m passing that on to my daughter.

        You truly ask the best questions, EW. Why did I cry? I think I’d been working so hard to make it happen without any appreciation or assistance at a hard time of transformation in my life so it was so much relief to know I’d done well and was going to get some help.

        Liked by 2 people

      2. It saved me from a lot of potential heartache. Still does!

        I’m so glad you did get help and that those were tears of relief, though I’m sad you had to go through that by yourself ❤


  1. Have you ever been called bossy? I’ve been called bossy, I’ve been called a bitch. I take both descriptions as external validation that I’m doing things the right way to accomplish a stated goal.

    Do you think of yourself as a leader? Yes

    If so, what gives you confidence as a leader? Experience, education, an innate sense of fairness, and a desire to leave the world a better place than when I entered it

    Liked by 4 people

    1. Ashley, I think you are exactly right. But then we don’t give them much training/help/coaching on what to do with that as they try to navigate the world. Maybe because they have moms like me which prefer to be quietly confident or even harder, they have moms who haven’t nurtured their own confidence at all. God help me do a good job with this… 🙂

      Liked by 4 people

  2. I love this post, Wynne. And the featured photo has me grinning 😁. Brown’s definition of leadership is perfect, and how lucky Miss O is to have you as her teacher, coach, and role model. All young girls need these lessons. Brava!💜

    Liked by 2 people

  3. Oh, boy, does this hit me where I live right now.

    I recently had my one-year performance assessment. One component of this was a self-assessment, which assessment included a “leadership” element. I stared at that element long and hard, a “???” thought bubble over my head.

    This word is used so many different ways by so many different people, I shut down even attempting to get at the definition. I wish I’d then remembered Brown’s definition. By that specific definition, I am indeed a leader.

    Your bursting-into-tears story reminded me of an exchange with my doctor a month or two back. I said something that made her go, “Give yourself a break!” I’d told her all the ways I felt I was missing the mark; she returned all the ways she thought I was doing an extraordinary job navigating a whole ton of stuff, any one alone of which would have been hard. I appreciated her assistance perspectiving, and feel grateful for the perspectiving opportunity you’ve provided here, too.

    Thank you. 💕

    Liked by 3 people

    1. And thank you for adding your perspective to this post, Deborah. If only we could remember the definitions and support we need at the moments we need it. I for one have a hard time coming up with this stuff on the spot and need time to reflect on it. I’m so grateful that my reflection helped add to your perspective. May both reflection and perspective guide us as we grow!

      Liked by 3 people

  4. Excellent post, Wynne! Calling the female “bossy” from a young age is one of the subtle ways in which the “dominator patriarchal society” (from Riane Eisler) keeps us in an inferior position. As women, we learn to lead from behind thereby avoiding direct conflict with men, as you did with your business partners. As we grow older in self-knowledge, self-acceptance, and self-confidence, we are better able to own the leadership positions we have always held. Being called “bossy”–to our face or behind our back–no longer holds any power over us when we are, indeed, the boss. Brené Brown’s description of leadership as “using power with/to/within” is what Eisler terms a “partnership society” in which the male and female are not ranked as superior and inferior beings but rather based on linking, a mutual connection. All the best in raising your daughter and son to take their place within a partnership society, yet to be fully realized.

    Liked by 2 people

    1. Such an interesting comment, Rosaliene. It makes me think of what Brene added to the conversation – that we are seeing the last stand of white, male, power over regimes. And last stands are often bloody before they go. So here’s to getting through that and to a partnership society for all our kids and grandkids!

      Liked by 2 people

  5. It’s always fascinating how the word leader and assertiveness is filtered differently depending on whether you’re a man or a woman.

    For a man, it’s a desired and respected trait. For women, it often has a threatening or negative connotation.

    I’m glad you embraced your inner leader. Shine that flag brightly and proudly!

    Liked by 2 people

  6. I don’t remember being called bossy to my face. I tend to work behind the scenes to make others successful enough so I get called “boss”, even by one of the CEO’s who was my boss. I believe my leadership kicked into gear when I saw someone drowning and no one was attempting rescue. In seconds I ordered people around and we rescued the man. A switch was flipped in my mind that day.

    Liked by 2 people

    1. Wow, talk about a situation in which leadership is critical. I can see why an event like that would be transformative – for both you and the man that you rescued. Amazing. But I’m also fascinated by your comment about working behind the scenes and being called “boss” – a critical role that often does hold much of the power. Interesting – thank you for adding this to the conversation, Gary!

      Liked by 2 people

  7. I spent my early adult years trying to be the opposite of my mother who was dominating and enjoyed controlling and manipulating others. She took strange pride in pushing peoples buttons so they’d lose control of their emotions and then she could gloat that she was the calm one.

    The word bitch was something I wanted to avoid being described and I felt a glow of pride at being called nice.

    Took me years to shake all that self limiting stuff off, like slowly disrobing and garment by garment finding out that people didn’t reject me. It was so empowering to finally learn to set boundaries with others and not worry about what kind of names they might call me. I learned that I actually didn’t care if someone was upset with me for setting boundaries, because those were the people who liked me best without them.

    This taught me to allow my leadership skills to just shine instead of hiding them!

    Love this post! Like so many, helps us see ourselves in your words and helps us see our own progress!


    Liked by 1 person

    1. I love how neatly you unpack that history with your mom which shows how thoroughly you’ve done the work to understand it. Sheesh, no wonder you avoided the same behavior! But I love your revelation that as you took off those layers that you put on for protection when you were young, you became freer and more empowered. So beautiful – and inspiring! The idea of boundaries also makes so much sense too. Thank you for this great comment that adds so much to the conversation, Tamara!

      Liked by 1 person

      1. Thanks Wynne! It’s always a challenge to try to be different from what we saw as kids, but unless we do the inner work we won’t be able to move the needle very much because we subconsciously repeat what we knew.

        I remember people laughing at me, telling me that as much as I hated her behavior that I’d end up exactly like her, because that’s what happens. Those pronouncements only made me want to work harder. I believe that anyone can change if they work on it. That was and is my motivating thought and I’d get so depressed when I feared that they were right. I didn’t want to be locked into a predestined set of behaviors, simply because it was what I knew as an example. I realized in my youth I had other examples around me, so I ended up modeling myself on my step mother’s sister in law, who now that I think about it is a lot like you! Your stories may end up being very helpful to others who need different role models for life! 😊


  8. What a wonderful post, and timely as I am starting to read Boundary Boss: The Essential Guide to Talk True, Be Seen, and (Finally) Live Free by Terri Cole this summer with a group of students. I personally think the word is a derogatory term toward women, when I am referred to with the “B” word. I smile and ask if you can elaborate and/or explain how my attitude is different from being a leader. That often shuts down the conversation, or often gets the individual to thinking…


  9. Even when I was a boss, I wasn’t bossy. I like to be friends with my coworkers, even when they’re subordinates. There are Type A personalities out there, but I’m more like a Type K.

    And I’m o-K with that.

    Liked by 1 person

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