How to Have an Uncomfortable Conversation

Picture it. 2007. My godson’s baptism.

I am over the moon happy that I am about to be a fairy godmother to my godson (who, if you ask me, looks just like me, even though we aren’t really related by blood).

I take my commitment very seriously. I attend the fairy godmother class in Miami, as is required by the Catholic church. I buy his christening outfit. I also get him a little baptism kit, per the recommendation of the Mexican bazaar where I purchase his outfit. The Baptism kit consists of a candle, seashell, rosary and little towel. I deliver these to my comadre (Spanish for co-mother) the day before the baptism. I am so excited.

The next day, we get to the church and proceed to have the ceremony.

During the ceremony, the priest asks for the candle and the seashell to perform the baptism. In her haste to get herself and two small children (under the age of 2, I might add) ready for the ceremony and make it to the church on time (mothers everywhere feel me on this one), she forgets the baptism kit.

The priest doesn’t hide his disapproval. I can’t remember exactly what he said, but he pretty much embarrasses my comadre in front of her entire friends and family. After the ceremony, she is in tears, upset that she forgot the baptism kit, which she literally placed by the door so she wouldn’t.

I feel terrible for her.

After the ceremony, we go into a small room at the side of the altar to speak with the priest. When my comadre becomes overcome with emotion and starts crying, she can’t speak. So I step in.

Meaning, I kinda lose my shit. On a priest. In church.

I’m not really certain what all I said but I know it had to do with how this was supposed to be a happy day because we were welcoming a child into God’s family and in the scheme of things what did a shell and a candle really have to do with anything because Jesus didn’t have a shell or a candle when he was baptized by John the Baptist in the River Jordan and how Jesus was always very welcoming of little children and that a priest is God’s representative to people on earth and that for some people in attendance he was the only Jesus they would ever see and what did this say about Jesus to them.

Right when I get to the part about writing the Archdiocese about this experience, my compadre stops me. The priest is in tears along with my comadre. He mumbles something about how it upsets him when the baby doesn’t have everything he needs because the parents aren’t doing what they should.

I tell him that I understand that, but that is not the case with my comadre. She is a fantastic and very loving mother to both of her kids. I stand by this statement, even to this day. She is a wonderful mom and I admire her very much. When it comes to my loved ones, ain’t nobody gon’ treat them bad on my watch. Not yesterday. Not today. Not tomorrow.

Turns out, another family is waiting in the church to baptize another baby. When we walk out of the room, they all look up at us, wide-eyed. I guess they heard our conversation, too.


I guess you could call me the Queen of uncomfortable conversations.

I’m not really one to beat around the bush. After all, I’m a Sagittarius.

However, that’s not to say that I’m a fan of having them. I dread them just like everyone else. There is nothing fun about having an uncomfortable conversation. You have to get out of your comfort zone and bring up stuff that is sometimes embarrassing, hurtful, and/or negative.

I equate having an uncomfortable conversation with pulling weeds out of your garden. It’s necessary and not very fun. However, if you want to keep your garden healthy and growing, you gotta pull them weeds, boo.

I realize that not everybody is like me. In fact, most people shy away from uncomfortable conversations, even though they know that they need to have them.

Today I’m sharing with you my seven step process for having an uncomfortable conversation. Also, don't forget to download the FREE workbook that accompanies this blog post. 

1. Set the date and time for the conversation.

Contact the other party and request a sit-down meeting,  phone conversation, FaceTime, etc. Carve out time in your calendar and send them a calendar request with a 30 minute reminder before the event starts.

2. Create an agenda and talking points.

Include time and space for both parties to speak. Compose your thoughts and write down things that you don’t want left out during the conversation. This will guide you during the conversation, especially if you are overcome with emotion and are having a hard time thinking about everything you wanted to say.

Think about your end game -- in your opinion, what would be the best possible outcome? What changes in behavior, circumstances, or perspective would you like to see happen? Take a few minutes to write this down.

3. Make sure you’re in a good space energetically before you have the conversation.

Getting yourself into a positive energetic state is of the utmost importance. Don’t go into the conversation in a bad mood (or sad mood, negative mood, etc). It’s important to not let yourself be ruled by emotion because you may say things you don’t really mean or that aren’t really helpful to the situation. Meditate for five minutes. Work out. Rest. Eat a nourishing meal (so that you’re not hangry). Spend about five minutes visualizing the best possible outcome of the conversation. Pray for the highest good of all.

When you’ve about to have an uncomfortable conversation, remember that it’s not you against the other party. It’s both parties against the challenge or obstacle. It’s not a competition to see who wins the conversation. It’s about speaking truth, listening to truth, and working together to achieve the solution of the highest good.

I’m gonna keep it real: Steps #1 to #3 are my area of opportunity. I hate to admit the fact that I have, more than once, had an uncomfortable conversation at an inopportune time, before I have thoroughly processed my feelings.

Thinking back, I probably should have scheduled a talk with the priest instead of the stream of consciousness mouth vomit conversation that ensued.

When you know better, you do better.

I’m sharing these tips with you to help you and as a reminder to myself to interact with life from my highest self at all times.

4. Invite God to the party.

With God all things are possible, even uncomfortable conversations. Invite God into the conversation to help you speak from your highest self and to stay in your light. The Universe is always with you, wanting to help you out and to keep you in a state of love.

In Step #2, you thought about your end game. Offer this idea up to the Divine and be open to the fact that this may or may not be the outcome you receive.

Trust that whatever happens is working in your favor and that God is with you, no matter what happens.

5. Speak, even if your voice quivers and your hands shake.

You deserve to express yourself and speak your truth. You deserve to take up space. Speaking your truth is like exercising a muscle: it takes practice. Even if you get a lump in your throat or your hands start to sweat, say what you need to say.

If you find yourself stammering, speaking too quickly, or you’re at a loss for words, take a step back. Stop talking. Take a deep breath. Take two deep breaths, if you need to. When you’re ready, begin again. By breathing deeply, you are resetting your energy.

6. Listen to what the other party has to say.

Really listen (not just to reply afterward). The other party may say things that are hard to hear. When you have an uncomfortable conversation, it is just as much about listening as it is about speaking your truth. Instead of becoming defensive, look at this as an opportunity to view life from the other person’s perspective (which is just as valuable as looking at life thru your own).

I like to take notes during conversations because it helps me to process what I’m hearing and experiencing. After they make a point, repeat it back to them to make sure that you understand what they’re saying.

“So, you’re saying that it bothers you when I leave my clothes on the floor. Is this correct?”

Remember it’s you and them against the challenge, not you against them. By taking this approach, you eliminate the need for a pissing match or negative energy. You really are working with them to find a solution of the highest good for all.

7. After the conversation is over, restore your energy.

Meditate for five minutes. Sage yourself. Practice a cord cutting meditation. You can also call your power back to you. Eat a yummy, nourishing meal. Have a good cry. Call up a dear friend and have a good laugh. Journal. Write down what you learned.

Take a moment to bask in your strength. You got thru it. It probably didn’t go the way you expected AND that’s okay. It went the way it needed to.

Keep in mind that just because you got your energy right before the conversation, things can still go left during the conversation. Do your best to speak your truth with love and know that people who are on a different level sometimes can’t hear you, no matter how many different ways you try to express yourself.

That’s okay.

Send them love. For 40 days, envision them surrounded by a white, healing light for 5 minutes. When you wish someone well and keep your heart clear from resentment, anger, and blame, you keep yourself open to the Divine Source and blessings will pour into your life.

Honey Bunny, having an uncomfortable conversation never gets easier. You just get stronger. You can never predict how the conversation is going to go, how the other party will respond to your truth, or how it’s going to end.

You can only control your actions during an uncomfortable conversation. Make sure your energy is clean before you go into the conversation. Speak your truth with love. Don’t be ugly. Be firm. Listen to what they have to say. Take notes to keep track of what they’re saying and of your thoughts. Wish them well and clear your energy after the conversation.

Uncomfortable conversations have the power to move your life and your relationships forward exponentially. Every time you speak up for yourself, remember that Life is always listening. The Universe will give you want you really want. It’s waiting to hear it from your own mouth and your own vibe.

You deserve to take up space, to speak up for yourself, to create boundaries that honor your being. You deserve to be in an environment where you feel safe to express yourself.

It is by having these uncomfortable conversations that you practice loving yourself so much that others know how to love you, too.

No one can read your mind, so you’ve got speak up and let them know what is bothering you and what would make you happy. You deserve to be in relationships and situations where your needs and wants are honored. This also means taking into consideration the needs and wants of others and determining if you want them in your life.

If you are having a hard time, work with a therapist or life coach to strategize and practice how to speak powerfully and with love. If you are in an abusive relationship, get help by calling The Domestic Violence hotline at 1−800−799−7233.

Now it’s your turn. Comment below and let me know about a time when you had an uncomfortable conversation and how you handled it.

I’m cheering for you. Like you are standing up for yourself.

From the Front Row,