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{#TransparentTuesday} The Green-Eyed Monster: Digging Into Insecurity, Jealousy, & Envy


I’m not typically a jealous or insecure person, but I recently had an experience I want to share with you.

This is a topic that comes up a lot with my clients. I actually love helping a person understand and process her feelings around jealousy, because there is always such rich material for growth and self-actualization underneath– as you’ll see from my story. 😉

For context, “jealousy” is a three person scenario (usually a reaction to the threat of losing something/someone you care about) while “envy” is a two person scenario (a feeling of lacking something).

When it’s balanced, I consider envy to be a beautiful symbol of desire. Envy can tell us what we’re longing for, or what we’re missing. Jealousy on the other hand represents both our intuition (aka our spidey senses that something’s up) and our desire to protect what (or who) is most dear to us.

That having been said, learning what jealousy and envy has to teach us about ourselves is often hard AF, because the feelings themselves are soooo uncomfortable.

So let me tell you what happened last week.

A friend invited me out to a bar for “green beer Sundays.” I didn’t realize this was a whole “thing” and just assumed I would grab a drink with her and her friends. I finished up working from 10am-4pm and headed out.

As soon as I got there I realized I had misunderstood the situation.

Basically, “green beer Sundays” is like a multi-block local frat party in celebration of St Patrick’s Day. When I finally made it through the crowds to the actual bar, it was packed to the gills with early 20-somethings, all of whom were wearing green “kiss me I’m Irish” t-shirts and pins and necklaces, and all of whom were already wasted.

I pushed my way through the crowd to try to get to the bar to order a drink before searching for my friend. I felt extremely aware of several facts:

  1. I am way older than everyone here.

  2. I spent all day working on my business, and these people apparently spent all day drinking.

  3. Every single woman here is hotter than me.

It was that last one that felt like a dagger through my heart.

I gazed out at the green colored masses of sloppy socializing and I felt like every single woman had the same exact kind of beauty: skinny, hyper feminine, long highlighted hair, and identical makeup. I felt way out of place.

Connecting with other women is usually my secret weapon against insecurity, so as I stood there waiting for a beer, I attempted to connect with a few of the women standing around me, and got somewhat brutally iced out.

Suddenly I felt a hurricane of sadness, insecurity, envy, and even jealousy of all these beautiful, drunk, unfriendly women. The bar seemed to shift then from being filled with “drunk people” to “hostile threats,” so I fled to the outdoors (without ever getting a stupid green beer), tried to find my friend, and eventually gave up and went home.

This story is obviously a bummer.

But as I thought about what had happened later, I challenged myself to put into words exactly what had created that tornado of insecurity.

I pulled the tornado apart into it’s individual parts, using the kind of emotional processing and mental organization I would offer a coaching client in this situation.  (For an example of what a coaching session looks like, check out my recently recorded demonstration sessions here and here!)

Here’s what I came up with as I peeled back the layers:


I don’t feel super sexy lately, for a variety of reasons. (There’s plenty for me to work on there, if I want to.)


I envied these women their freedom to daydrink instead of work. (Whoa that one was a surprise since I love working, but it showed me that I’m feeling a bit trapped/resentful of my work schedule, and wish I could have more weekends off.)


I was envious that everyone there seemed to have big, messy, loud groups of friends. I desperately miss having that, and haven’t found a group of any kind since moving back to Syracuse.


I felt like maybe I “should” be putting more effort into looking hot. When I was in NYC, gorgeous women were everywhere, but the most “valued” kind of beautiful women were models. These women are like sexy gazelles; they don’t have to wear a ton of makeup or dress sexy, because their body and bone structure give them away. I never felt jealous/envious of these women, because they were so genetically unlike me that it would have been silly to ever compare. I didn’t try to be something I wasn’t, because there was no point.

This bar on Sunday was filled with normal-looking women like me, but all of them had clearly put a lot of work into looking traditionally “hot.” I felt insecure because I realized I could compare myself against these women, and therefore I suddenly felt like maybe I should be trying harder to look feminine and “hot.” (Note: I don’t actually believe that, it’s just what washed over me in the moment.)


I felt sad that everyone seemed to know “the rules” except me. Everywhere I go, I watch the fashion trends, social patterns, and demeanor of the people. I’ve traveled a lot and found that every city has it’s own vibe, style, subculture, and “rules” for how things go. I find it fun to get to know a particular city’s culture in that way.

Syracuse, like anywhere, has many different subcultures, but that bar represented a subculture I don’t vibe with and felt like I didn’t belong in. Especially when I found the women around me to be unfriendly, I imagined those women to be completely unlike me: effortlessly a part of this city’s culture in ways I’m not, because they all got some memo about how to dress and act that I never got.


I’m lonely here. Those women all seemed to fit in– with each other, with the vibe, with the rules, with the city. My biggest takeaway from processing this whole event was that I don’t feel like I fit in here. Since we’re wired to crave acceptance and belonging, at first I felt threatened, but later on I just felt heartbroken.

So there you have it. This is what can happen if you go digging deep under the surface of insecurity, jealousy, or envy.

I was able to shift my attention away from the distraction (the other women’s hotness) and onto the important information: I’m not jealous, I’m isolated and lonely. That’s super valuable information.

This is what I do for my clients as well: help them get away from distractions, see the truth, and organize the various components of what they experienced so that they can learn, grow, and create a plan that brings them closer to living the life they most desire.

Which reminds me: I have space to take on 5 new private coaching clients!!

I haven’t taken any new clients in a while, but I have a handful of clients who just “graduated,” and I’m excited to work with some fresh faces!

To hear a bit about how coaching has affected my clients, check out some of their experiences here!

Note: I’m accepting clients who want to work on body image, of course, but I’m also open to working with clients of any gender who want to gain confidence in any area of their lives. And yes, that includes sex. 😉

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