Hard Conversations Take Bravery, Here's How to Have Them with Courage

Be brave enough to start a conversation that matters.
— Margaret Wheatley
Freezing my booty off in Bratislava, Slovakia

Freezing my booty off in Bratislava, Slovakia

In Eminem’s famous song, “Lose Yourself,” the opening lines are “his palms are sweaty, knees weak, arms are heavy, there’s vomit on his sweater already, mom’s spaghetti.” While this song is about going into a rap battle, he may as well have been talking about having a hard conversation.

Hard conversations are tough. So tough in fact that many of us avoid them all together. They can make the strongest of us feel weak in the knees, choked up, and full of fear. If these conversations are with loved ones, the harder they are, and the more we want to put them off. Depending on the subject of the conversation, this fear might come from a variety of places. It could be fear of rejection, fear of misunderstanding, fear of hurting someone, fear of being vulnerable, fear of creating separation, or fear of an unknown outcome.

In my life, I have discovered the hardest conversations to be the ones where I have to stand up for myself, set boundaries, or voice my needs, wants, and feelings. It’s only been in the last two years that I’ve had the courage to speak my voice, and bring up some hard conversations that I put off for years. I got to a point where I physically, mentally, and emotionally could not avoid them any longer. Everything I was holding inside was manifesting as anxiety, frequent cold sores, stomach issues, insomnia, headaches, lethargy, a constricted throat, and depression. I realized that the cost of not bringing up difficult conversations was causing me tremendous harm. If I continued on in silence I would not be able to live healthily and happily.

Much to my surprise, many of these conversations did not end catastrophically. Instead, they built more trust between myself and my loved ones and brought us closer. I also gained more respect and confidence in myself because I listened to my needs and acted on them. This wasn’t all by chance though. I didn’t just decide to call my loved ones out of the blue one random day and drop an emotional bomb. I prepared immensely for the hard conversations I was going to have and I believe this made all the difference.

I want to share my practice of preparing for hard conversations with you because let’s face it – we all need to have them whether we want to or not. They’re not fun and they’re not easy, but they may save you from years of pain. They require bravery, and they require self-trust. Luckily these are characteristics that take practice and that you can develop at any point in your life. If you are an Empath or Highly Sensitive Person, this practice will be especially useful for you.

It was snowing! But how beautiful is this?

It was snowing! But how beautiful is this?

Here is my 12-Step Practice for Having Hard Conversations with Courage


1.    Write out all of your emotionally charged feelings.

Subjects of hard conversations are never surface oriented. There is usually a story behind them and a lot of pent up feelings. I suggest writing or typing out all of your emotions and feelings surrounding the subject matter. Don’t hold back and don’t judge yourself for what comes out. This process can be extremely healing and cathartic. It will help provide you more clarity for your conversation and help release some pent up emotions. This step is crucial if you want to minimize the chance of emotionally erupting during your conversation.

2.    Let it simmer.

After writing everything out, take at least one night to sleep on it. You are probably still high from the emotional surge and its best to let those feelings settle down a bit. Take as long as you need so that you can best approach the conversation from a place of love and self-trust rather than blame, self-doubt, or fear.

3.    Get clear about your intention.

Once you’ve taken sufficient time to let your fire of emotions cool, get clear about your intention. If you’ve been holding off a certain conversation for years, you might want to bring up all your frustrations surrounding the matter at once. Try not to do this. That approach will likely be too overwhelming for you and the other party involved to be productive. I have been in conversations like these more than once as the recipient and it never ends well. The message gets lost, feelings are hurt, and it’s easy to go into defense mode rather than listen. Ask yourself what exactly you need to communicate and what could be saved for another conversation.

4.    Let an outside party know what’s happening and ask for support.

I find it really helpful to let someone I am close, or that I know supports me, know that I’m about to have a hard conversation and that I am really nervous. This practice can provide great comfort especially if one of your fears is creating distance with you and your loved one. Being reminded that there are other people in your life that have your back and support you no matter what can provide you the extra strength you need. Once talk it out with my chosen person I ask them to send me encouragement, strength to get through the conversation and to check in on me afterwards. Not only does this provide extra emotional security, but it also holds me accountable to having the conversation.

Trying to catch some snowflakes!

Trying to catch some snowflakes!

5.    Choose best method of communication.

Take time to choose what method of communication you want to use for your conversation. Will it be through the phone? Email? Or in person? If the person you’re having the conversation with tends to impact your emotions on a higher level, you might want to opt for the phone to protect your energy. If you feel like giving yourself time to write a well thought out letter will get your message across better and will allow the person time to process and respond, then perhaps email is the better option. If you feel like too much will get lost in translation and you want provide extra reassurance to the person as you speak to them, then in person communication might be best. Weigh your options wisely, and remember to be respectful to both yourself and the receiving party.

6.    Set aside a day and time to have the conversation.

Speaking of having respect for all parties involved, this step is crucial. I absolutely hate when people spring unexpected, difficult conversations on me with no warning. It leaves me feeling like my time is not valuable and that the conversation was a monologue instead of a dialogue. If you want to set yourself up in a positive way, please set aside a day and a time to have the conversation. Check your calendar for a day and time where you will have no distractions and ask the person you are talking with to do the same. Let them know there is something important you want to discuss with them and that you would appreciate if they set aside dedicated time with zero distractions to have the conversation. Even if you don’t tell them exactly what the conversation is about, this will at least allow them to clear their mind and be open to what you are going to bring up instead of being caught completely off guard.  


7.    Protect your energy.

Where my fellow empaths and HSPs at?!!! This one is for you! If you are someone who easily absorbs other people’s emotions and energy, at the cost of losing your own, take time to protect your energy. Set aside at least ten minutes before the conversation to connect with yourself and create an energy shield. I like to use guided meditations like this "Personal Shielding Meditation". This will help you stay true to yourself and not lose sight of your intention throughout the conversation.

One of the main squares in Bratislava, Slovakia

One of the main squares in Bratislava, Slovakia

8.    Create the space.

 Equally important is to set up your space for your conversation. Make sure that you are in a nice calm atmosphere. Boil some hot water for tea, light a candle, turn on an essential oil diffuser, tidy up – do whatever makes you feel at ease and peaceful. This is obviously much easier if you are having the conversation in your home, but you can still do it if you are going somewhere else by creating the space internally. You can set aside time to stretch your body, go on a walk or meditate to help make you feel safe in your body no matter where you go.

9.    Detach yourself from the outcome.

Now, I know earlier that I said most of my conversations ended positively, but not all of them did. Some of them ended with misunderstanding, confusion, or defensiveness, and that’s ok too. I know that I did the best I could, and speaking my truth in and of itself was healing and nourishing. As much as you want the conversation to go positively, it’s best to detach yourself from the outcome. Remind yourself that you are first and foremost responsible for yourself, and that’s what you can control. You can’t control how someone will respond to you, and how they respond is not a reflection of your worth or you as a person. People often bring their entire past, cultural upbringing, and beliefs to every conversation they have so in the words of Don Miguel Ruiz – don’t take it personally. This is much easier said than done, so just do your best.

10.    Remember to come from a place of love.

Too often hard conversations turn sour because people go into blame mode, raise their voice, or get defensive. Throughout your conversation always remember to come from a place of love. A good rule of thumb for this is to speak in “I” statements as much as possible instead of “you” statements. Connect with your intention again and again to stay grounded in your place of love. If it helps, you could even place one hand over your heart to physically connect to the love inside you. Additionally, remember that this is a dialogue. One of the most loving acts anyone can do is to listen. Be open and listen to the other person full heartedly. Even if you don’t agree with what they say, make sure they know they are heard and acknowledged. This will make them more likely to do the same for you and help lead the conversation in a more positive way.


11.    Release and shake it out.

Whatever the outcome is, take a minute to release and shake it out. I have noticed that even if a conversation goes better than I thought, all my built-up anxiety surrounding the conversation and the issue still lives within me if I don’t do something about it. So when I say shake it out, literally shake it out. Move your body. Jump up and down. Wiggle your arms. Shimmy your shoulders. Just shake it baby and let that shit go – you did it!

12.    Practice self-love.

After a hard conversation, you absolutely must set aside time to practice self-love. Acknowledge yourself for your bravery and for taking a tremendous step forward in speaking your truth. If I know I am going to have a hard conversation, I like to plan ahead for a self-love activity. I’ll schedule in time to go workout, get a massage, paint my nails, or watch a guilty pleasure show. Ask yourself what makes you feel most relaxed, and make sure you add it in to your day!

How you'll feel about yourself after a hard conversation :) 

How you'll feel about yourself after a hard conversation :) 

If there is a hard conversation that you’ve been putting off, I encourage you to take the first step. I know starting a challenging conversation can feel risky, but the greater risk is not doing it. Remember having a hard conversation can be an enormous act of self-love. The more you learn to stick up for yourself, speak your truth, and practice bravery the more you will deepen your self-trust and inner strength. The more you are your own advocate, the more you can be an advocate for others. So be brave and have courage. You got this. 

Now I want to hear from you! What scares you the most about having hard conversations? What will you do to overcome that fear in the future? Share in the comments below!

P.S. If you know someone who could really benefit from this post, please share! You could really help them out!