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How to Be a Lady Boss Part I: Overcoming Your Shadow

A lady boss getting work done!

As a customer, I tend towards the side of being agreeable, happy, and unimposing. Even though I don’t like drinking water with ice, I reluctantly accept it at restaurants out of not wanting to be too “fussy.” I never send back food unless the dish is profoundly flawed. (Having worked in restaurants for years, I just wouldn’t do that out of etiquette!) As a lady boss, this is not a good sign.

This is all indicative of me not taking a stand for what I really want. As benign as room temperature water may be, it’s actually symbolic of a bigger pattern that’s affected me in business and how I operate as a strong woman leader—getting lost in my own shadow.

Since I am extremely relationship oriented (I am a Libra rising after all) I have a tendency to be so sensitive to the feelings of others, sometimes at the expense of my own. I can remember bumping up against a shadow tendency in managing an important project in my business—a moment where sticking to my guns felt super awkward because I had to take a stand for an unpopular opinion. Doing so, I harshly judged myself for being a “bitch.”

This moment was tough, but it taught me this: making sure any project gets done to my liking means asking for what I want—and consequently risking being negatively perceived in the process. It’s part of being a leader, and it’s OK, cause it’s going to happen.

Now don’t get me wrong. Being compassionate and empathetic is a serious pro in my leadership style, assuming I do it with the appropriate boundaries! As a lady boss, I have to be vigilant about asking for what I need, holding my team accountable for delivering the required results, and giving thorough feedback too. I’d be lying if I said this is always easy. It’s not.

I’m sure you can relate to the idea that asking for what you want sometimes feels hard?! Sometimes I feel as women we go along to get along, since our survival, health and happiness benefit from working well with others.

Yet, this “I don’t want to ruffle any feathers” approach doesn’t allow us always to be our most authentic selves, and it’s a surefire way to sabotage our best collaborative efforts. Not good, lady bosses!

As women leaders, we need to take a stand for what we want. We can’t do all the work alone, which means outcomes are influenced by how we manage and collaborate with others.

And a core part about being a strong woman leader? Self-leadership.

I think you know where I’m going with this. Before we can be great lady bosses for others, we have to be great lady bosses for ourselves. And that means going deep and owning your shit. Time to get real!

Now is a strong time to take a look at how we are showing up as the strong lady bosses we can be—and how we might be holding ourselves back.

For the sake of total transparency, I want to share some of the most unhealthy interpersonal behaviors of my past. Take a read and see if you resonate with any of them. (I know I am not the only with these tendencies!)

3 Habits to Avoid as a Lady Boss

1. Overdoing for others so you are loveable.

Have you ever found yourself in the throws of giving, giving, giving, only in the end to feel a twinge of something ugly inside, maybe even resentment? Chances are, you may be operating from a shadow motivation to secure love. You know, the one that tells you, “If I give my all to others, I’ll finally be worthy to receive myself.” Ouch! Remember: we don’t earn our worth. It’s an inherent part of who we are.

2. Aligning with others to feel safe.

This is a real doozy that will for sure zap your voice of truth in a nano-second. You know how this goes: being agreeable to the point of dysfunction to stay loyal, friendly, keep up and belong. This behavior is the kryptonite of authenticity and bravery in interpersonal relationships. (Authenticity and bravery being key to intimacy and bonding—as well as leadership!)

3. Feeling the need to be liked.

This is systemic of the two behaviors I listed above and stems from sourcing our worth from external validation rather than internal sources. It simultaneously evolves from having a disdain for conflict.Usually when this one rears its ugly head, we have to ask ourselves where we are not being kind enough, loving enough, and sweet enough to ourselves to the extent we rely on others to do it for us. When we fully accept and love ourselves—completely—it’s easier not to care what others think

Now I’d love to hear from you in the comments. What is your biggest shadow tendency when it comes to leadership and staying authentic to you work? What steps can you take today to step out of this shadow?

Also, be sure to check out Part II and Part III of the How to Be a Lady Boss series, where I share how to get a support system in place and build on a foundation of gratitude.

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  • Anne

    Hi Jennifer, Your blog and astro posts are fantastic. I heard you in an interview with Sara Avant Stover on her podcast She Talks and have been following you ever since.

    I resonate with all the shadow traits you listed above. One other that I recently have come to understand is a powerful one. Like a lot of women raised in the western world, I elevate the masculine and denigrate the feminine. Despite being a woman who values equality and thinks women are some of the most powerful and divine creatures on the planet, this shadow tendency manifests itself quite regularly. In a group of men and women, I project authority and intelligence onto the men in the group. Even if I have a strong idea for a project, if a man (especially my partner or family member) proposes something different, their ideas automatically gain my acceptance even if my intuition and instinct tell me differently. Later on, I frequently admonish myself, saying, I knew that wasn’t the best approach, I should’ve spoken up.

    There are a lot of other qualities that I have which I project onto the men in my life and subsequently stop owning myself: being hardworking, smart, assertive, strong … negative ones too such as: demanding, needy, negative etc etc. Then I don’t allow myself to be smart, assertive, strong, hardworking, needy, demanding or negative and walk around constantly controlling myself to make sure I don’t display these tendencies. Unless I am in relationship with other women. With other women I can sometimes be strong, needy, negative, demanding, but only if I really really feel bad. Awareness is the first step and it’s been great to realise this about myself and slowly try to tip the scales towards equality.

    Another way this manifests in my life which I’ve been able to powerfully change is that I express gratitude to the men in my life automatically and verbally, with actions to match. The women I just assume know that I am grateful for them! How crazy is that. So I have started expressing gratitude verbally and actively to the amazing women and my life. No more assuming they know how I feel about them.

    Your writing is so honest and inspiring! Please keep sharing. Thank you!

    Anne Marie Basquin, New Zealand

    • jracioppi

      Hi Anne, Thank you for this thoughtful, in depth, response. I completely understand every point made here. You are right, awareness is the first step. I love that you are now verbally expressing gratitude to women too. Again, thanks for this comment. Big hugs!

  • Victoria Klein

    I adore your posts, Jennifer – incredibly intelligent 🙂 My shadow tendency is to want to conform to whatever my possible clients need. It’s taken some practice to really listening to my intuition on whether or not accepting a client (and ultimately, their time and money, and MY time) and loving turning away people that aren’t right for me. Having filled my client roster in 3 months, I’ve reached the point of having a waitlist, which I’m very grateful for, but not all of those folks are my ideal client either, so I’m working on creating a product for them 🙂

    P.S. I would LOVE to have you on my podcast! <3

  • jracioppi

    Hi Victoria, Thank you so much for your comment and compliment, I appreciate it deeply.

    Yes, contorting yourself to meet your clients needs can leave you feeling depleted. Congrats on filling your practice with the right people! And developing a product. So cool.

    And feel free to email me about the podcast:!

    So much love to you:)

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