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7 Things to Know Before Having a Challenging Conversation

I have learned many things this year, but if I had to pick one thing that has been the most rewarding, I would say having “challenging conversations” wins above all else.

So what does this mean exactly? One person’s challenge could be waaaay easier for others, so let’s see if you’re anything like me.

Ingredients for a Challenging Conversation (IMO):

-a person who is recovering from codependency, perfectionism, and people pleasing... or just any human who never learned how to communicate their feelings and needs (aka ME)


-something (like an event, a conversation, or action) that has triggered / hurt / frustrated / initiated uncomfortable feelings


-the person who was the catalyst (but not necessarily the reason) for the above “something”.


-anxiety, fear, and sometimes hours of over analyzing and deliberation beforehand because I’m fully aware that sometimes I still care more about other people’s feelings than my own


-having to vulnerably, honestly, and clearly express my opinion, thoughts, feelings, and/or needs


-actually following through with the challenging convo *cringe*


Does any of this resonate with you?

If it does, I feel you! Most of my childhood and into adult life I had such a hard time expressing myself because I never learned how to do so. I did not have parents, friends, adults or relationships around me that exemplified how to effectively and safely share feelings and needs. In fact, I learned all the "what-not-to-do's". It was normal to be very obedient, people please, repress feelings, care more about other people’s opinions than your own, and of course, AVOID CHALLENGING CONVERSATIONS to keep the peace.

As I hit my late 20's, I realized I didn’t even like or know who the “real me" was because, as I avoided challenging conversations, I also avoided getting to know myself. Self abandonment, codependency, and insecure attachment were the major blocks that kept me from having a voice and kept me from having deep and meaningful relationships. Not learning to speak up for myself was really taking a chokehold on my mind, body, and spirit. I knew something had to give.

Now, in my 30s, I realize I no longer want to live in a prison (of my own doing at this point) or remain a silent victim of my history. So I did a deep investigation on the major blocks I mentioned above and started practicing communication. Sounds so funny, right? It's not like I'm a baby learning how to say "mama". I'm a full blown adult learning how to truly speak from the heart instead of my ego, perhaps for the first time?? At first I felt such shame, embarrassment, and guilt that it took so long to learn this because (duh) "communication is key" but when it comes to this subject, it really is better late than never.

So when I stepped into being a Joy Guide, I started to see that this is not a unique problem of mine. From my sessions with clients and chats with people over the years (of all ages), it seems that challenging conversations, particularly ones that involve communicating feelings and needs, are a real Achilles heel. So if you want to start facing your fears and desire to empower yourself, this post is going to support you through the initiation.

Here are tips I wish someone had told me…

7 Things to know BEFORE starting a challenging conversation:

1. At first, there may be very little to no joy throughout the process because you’re about to push yourself out of your comfort zone(s). Your brain may flip out, start catastrophizing, jump to conclusions, play the blame game, magnify the negative, or just go into a total meltdown. Your feelings may flood and send you into overwhelm. Your body may feel sick and/or you could lose sleep. Sounds enticing, right? lol. I know I felt all of these and more at the beginning, which makes sense why I spent decades avoiding challenging conversations. However, as someone who has now experienced the benefits, the rewards are SO WORTH IT.

Acknowledge that the joy and relief you want to feel will most likely come after the conversation. In hindsight, the growing pains of challenging conversations I've had have led me to some of the most mind-blowing & joyful experiences I never thought possible, despite the above initial reactions. I now feel extreme relief and happiness from sharing my true self, as well as, feeling so loved by the honest relationships that have witnessed this version of me. And most importantly to me, I accept myself for exactly who I am (at my best and worst) even when others do not.


2. If you can, it's best to stay away from challenging conversations when you're still triggered. Because you're "in training", you want to make sure to you take the time to fully feel your feels and calm down. When I was pushed to my limits in the past, I went from zero to 1000. I think it makes sense to erupt like a volcano if you've been repressed for so long. I was totally guilty of being that stereotypical fiery Aries as well as an insecure codependent (worst combo) that preferred to react immediately versus pause to respond. Not only did I fail to get my points across in the heat of those moments, but I also ended up saying things I didn't necessarily things I mean and ended up hurting the other person. I also hurt myself because I wasn't even listening to my own needs! DoUbLE WhAmmY. So if you are not ready to have the convo, CHILL and ask for space/time.

Here are things you can say to respectfully step away:

"I am not sure what I'm feeling right now, but I definitely need time to think about what you just said / did."

"Can we pause this conversation? I am starting to get [insert feeling] and I don't want to say or do anything I will regret."


3. Remember that the mission is to share your experience and your feelings / needs without having to “be right” or “win”. This is not a competition! The main goal is to practice expressing yourself honestly and without causing harm to the other person. If you are saying mean things and end it with "I'm just being honest!" or "Well, that's just my truth"- that ain't it, friend. Try again. Before you go into your challenging conversation, I would highly recommend asking yourself what you want out of this interaction. If it's to prove someone wrong or win, then you're probably out of alignment. You are not going to make a meaningful impact or deepen a relationship if your ego keeps shouting, "Don't take the L!!"

For me, reading Nonviolent Communication was a total game changer for how I started to approach conversations. This book showed me how intentional speaking is vital for addressing problems as well as creating effective solutions. Most importantly, it showed me how going in trying to win is actually a lose-lose situation for all parties involved... and frankly, that's no fun.


4. Expect the unexpected! It is possible that the outcome of your challenging conversation could be good, bad, or downright ugly. It's natural for us to "prepare for the worst". It is possible that the person may not hear you, understand you, may become defensive and may even argue with you (I can already hear the collective NOPE coming from the non confrontational crowd). But, remember that the person is allowed to think or feel whatever they may.

If you realize before you have the challenging conversation that you have expectations around how the person should react, you're already off track. The point is to NOT control or convince them of how they should think or feel. That is actually manipulative and you wouldn’t want anyone to do that to you. The intention is for you to practice communicating how you think and feel, share your heart, and best case scenario, create a more deep and intimate relationship where you can truly be yourself. Let life surprise you! What if the worst doesn't happen? What if this conversation could actually be the best thing that ever happened to your friendship, relationship, career, marriage...?


5. Have a safe support system. When it comes to challenging conversations, it's helpful to have a sounding board. Is there anyone in your life that you could talk out the situation with before you confront the other person? And, no, I don't mean recruiting someone to gossip with LOL. I mean sharing your potential feelings and needs with a trustworthy parent, friend, therapist, etc. who will listen to you without judgment and give you constructive feedback.

From my experience, it is important to choose someone you respect and you know has healthy relationships themselves. There's nothing more toxic than asking someone for advice who is already at a "Pity Party Table for One". Some people just want others to commiserate in their misery with them. These are not your peeps right now. They are not trying to support your best interest and may even use your own feelings and needs against you. So use your discernment when picking people in your inner circle.


And if your main (and only) sounding board is actually the person you're going to have the challenging conversation with, take time to...

6. Get to know yourself! This is actually your secret weapon. The more you can understand your own thoughts, opinions, feelings, and needs, the better the conversation can be. It is not up to the other person to tell you about you, although (beware) sometimes they may try. Don't let their opinion of the situation deter you from correcting their perceptions of you. And from my experience, the only way you can truly inform someone from an honest, vulnerable, and loving place is by first giving that gift to yourself.

From my years of trial and error, here are my favorite questions to ask myself before going into a challenging conversation:

  1. What are your feelings about what happened? Be specific: anger, sadness, hurt...

  2. Why do you think you feel this way?

  3. Was it really about this person (they are the source of your wound) and/or did it trigger something from your past (they are the catalyst for you to be aware of a wound)? **self awareness and context is key**

  4. What do you desire from this conversation?

  5. What do you need from this person?

When you can answer these questions (and maybe even chat with someone you trust about it), I have found that the initial trigger can disappear altogether! WHAT SORCERY IS THIS?!?! Sometimes, I realize that my trigger may not have anything to do with the person at all. It's just my own baggage coming back to be unpacked. Knowledge is power!


7. Practice makes progress so it will get easier the more you do it. So don’t give up if your first try goes horribly. In fact, most of my challenging conversations took multiple attempts. At first, this really pissed me off because I desperately wanted to get it over with versus doing it to foster deeper connections and true understanding. My inner voice just kept shouting, "Please, just make these uncomfortable feelings go away!" and yours may say that too. That's ok, but don't give up if this relationship is truly meaningful to you. And, of course, it takes two to make a thing go right... so if the other person isn’t willing to try again, then it’s ok to give them space or maybe even let them go with love.

Before going into a challenging conversation, I give myself A LOT of compassion, self love, and supportive words. I have been known to say to my inner child:

"I am safe to share my feelings and needs."

"I am loved no matter what happens."

"I am practicing how to love myself."

"I am worthy of being heard."


If you feel inspired to have a challenging conversation after this, just know YOU GOT THIS! I'd love to hear your experience.

Also, if you have any tips on what to do before having a challenging conversation, please share your thoughts in the comments!

From my heart to yours,



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