Taking Your Conversations from Uncomfortable to Conscious

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I’m gonna go ahead and guess that the picture above is an accurate depiction of how you feel about the topic of this journal. I get it, man. UGH pretty much sums it up in regards to how we feel about uncomfortable conversations. If not, you’re a Unicorn and I would very much like to talk to you. But anyway…

In my desire to connect more consistently with my community and to write more (because I genuinely do love writing), I took to the newly super popular Instagram Questions to ask people what they’d want me to write about in this space. No one gives a shit when I tell them to "ask me anything". Usually my friends just respond with explicit inquiries they already know the answer to that include eggplant emojis. Eye roll. But also - high five guys.

Much to my total excitement, people responded with really, really thoughtful prompts. The ONE “BS” response I got from a friend of mine is actually something I could totally spin. Hot Air Balloons. Stay tuned for that sexy metaphor. Every single one of them resonated with something I’ve reflected on in some capacity as of late. So, I’ll write about them all. But today, I’ll start with one by a friend I’ve never actually met (but totally feel like I know) named Elliot Slinn.

His request was this (obv the title of this post gave it away already but pretend you didn’t already know): Uncomfortable Conversations. 

This is really perfect because I have had a SHIT load of them recently. Messy, confusing, some I’ve been prepared for ahead of time and some that knocked me square in the gut with surprise. Actually I’ve already written a couple of things in the past related to the topic and I’ll list those little ditties at the bottom. But for this particular Journal, I asked myself WHY we perceive conversations as being uncomfortable. When you know you have to say something to someone that won’t be easy, or when things start to get hairy without warning, what causes the discomfort in the first place? I have a few theories. 

  • We subconsciously believe that the other persons comfort, feelings and peace are more important than ours.

  • We are speaking two different languages and aren’t actually able to hear and understand one another through our separate lenses of reality.

  • We are reacting out of fear-based programs vs. responding from personal truth

  • We afraid of being misunderstood and from there, isolated and/or abandoned.

  • All of the above can be combined in any number of ways and are more often than not, connected.

I could write an article on each one of those but in the interest of something you can actually take and use in your next uncomfortable  encounter, I’m going to put it all in one big pot of reflection soup so I can move on to the part where you can actually have more conscious and free conversations. K? K.

Communicating consciously is an art but it’s not just for Unicorns. What it requires is a willingness to bring what is unconscious within you, into your awareness, and to have conversations that are informed. I’m not even asking you to have conversations that always result in resolution. Truthfully I no longer believe in walking away from every conversation feeling peaceful. I do believe in telling the truth and honoring what I have the capacity to show up for, and to the best of my ability, honoring what the other person might need -knowing I might now always meet that need.


What I find is that things are uncomfortable because we don’t totally understand the stuff we’re coming to the table with. It’s actually so much less about the other person and much more about us, because we are the ones we can take responsibility for. It doesn’t really matter what the nature of the relationship is - familial, friendly, romantic, professional - same same, really. I come to each relationship with the same cocktail of my own shit. If you’re paying attention, the things that trigger you are commonly themed no matter what area of relationship you’re in. 

I’m gonna tell ya something in the interest of keeping it 💯 with ya. My partner and I have been fighting a lot lately. We are both empathic, highly sensitive, and are pretty damn emotionally intelligent. I am much more fiery and often react from my trigger points. I need way more space and I am unattached to resolution in the moment. His nature is more forgiving but he still has plenty of shit. He too, can be reactionary and speak out of fear. AND, he is first to apologize, always, and definitely wants to feel resolution in each conversation. Each of us being aware of ourselves, our strengths, opportunities and triggers, and our needs, allows us to learn each time and to hopefully do better the next time. Our conversations are ALWAYS intense and uncomfortable - ha! But what I find helps us to evolve is being able to tell the truth about ourselves, to each other. It means we’ve gotta tell it to ourselves first and that shit doesn’t always happen overnight.

I suppose the short version of that is that things are uncomfortable for a lot of reasons but at the root of all of those reasons are our own perceptions, beliefs and unhealed stories. Healing that paradigm looks like, first and foremost, cultivating extraordinary self-awareness. 

Now what? Well, now I give ya a few key points to reflect on for your next uncomfortable conversation and then I close my laptop and snuggle up to Apollo and listen to Harry Potter on Audible.

  1. Tune in and ask yourself why it’s uncomfortable for you

    Worried about how they’ll feel? About not being heard or validated? In fear of being rejected for speaking your truth? Calculating the risk? Know where you’re projecting a fear or your own perceived unworthiness. Just know. Don’t know the answer? Sit with it. Seriously, ask. Close your eyes and breath. Feel it out. It’ll come.

  2. Know what you have the capacity for and what you are asking for.

    Tough conversations ask something of us mentally, emotionally, energetically and even physically. Get to know what your boundaries and limits are and when you have given and received all that you have the capacity to within that conversation. If you can give the other person a heads up, awesome: “Hey, I’m gonna give a signal when I’m at my capacity for this particular session and I’d love for you to do the same and that we honor that for one another.” If you only know your limit when you’re in it, well sometimes its stickier to step away but know that it’s okay to honor how you feel and set boundaries up for yourself (its nas-tay when you don’t). Likewise, if you have a particular point or need that you want to be heard loud and clear - know what it is and communicate it to the other person (I often skip this part so I’m glad I’m writing it down). Ask them to repeat it back to you as they understood it and be as open as you can to helping them understand.

  3. Ask questions with a willingness to be impacted by what you hear (and to have to translate it)

    Curiosity is your ally in communication. Asking questions that illuminate what kind of experience the other person is having, and that help them to feel safe in speaking their truth - is such a gift. You might not love the answers, but showing up willing to hear them - and to ask for clarification when your languages are different - is a step in the direction of understanding. Compassion begets compassion, I find.

  4. Embrace your humanity - mess and all

    Sometimes it’s just gonna be hard. Sometimes you will miss each other. Sometimes you will raise your voices and lose your patience. Sometimes one or both of you will cry. Sometimes you won’t hug or kiss at the end. Sometimes you’ll need to talk again tomorrow. Or not tomorrow. Sometimes you need to press pause and take deep breaths. All of that is okay. Being human isn’t the tidiest of experiences. You deserve grace in stepping into truth. You deserve grace, period. Put on The Office and grab a PB&J and feel the feels. That’s mostly what I do TBH.

I find that all of life’s challenges are just asking us to know ourselves more authentically and truthfully, and then to step into that truth with both feet.

Whether you’re stepping in mud, or glitter - both feet, fam.

Both feet.

** See that button right there? 👇 If you click it, you’ll get to download a free guide to taking your conversations from Uncomfortable to Conscious to use as a tool for figuring out where you’re at and what you need. Do it - I dare ya.


Throwback Journals:

But First, Compassion (here)

The Art of Listening (here)