The Conversations You Need to Have But Don’t Have the Courage To

Do you ever find yourself avoiding certain conversations, even though you know they're essential? Whether it's setting boundaries, expressing your deepest feelings, or seeking growth within your relationships, many of us grapple with the fear of initiating these crucial dialogues. But what if I told you that mastering these conversations could lead to profound personal and relational growth? Join me as we delve into the art of courageous communication, uncovering the transformative power of setting boundaries, sharing vulnerabilities, and fostering healthy exchanges.

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We’ve all been there – those crucial conversations that linger in the back of our minds, unspoken and unresolved. As someone who has guided thousands through the maze of interpersonal communication, I understand the weight these discussions carry. From setting boundaries to baring our vulnerabilities, these conversations can be daunting. Yet, they are the cornerstone of growth, intimacy, and healthy relationships. Join me as we delve into the conversations you’ve been avoiding but are essential for your personal evolution.

In the fabric of human relationships, there exists a tapestry of unspoken words, silent agreements, and overlooked boundaries. These are the conversations we often avoid, the ones that require vulnerability and courage. Yet, it is precisely these conversations that hold the power to transform relationships and foster growth. As a seasoned coach who has guided thousands of individuals, couples, and business owners toward more fulfilling connections and personal growth, it’s been an incredible journey to help people learn the skills to drive firsthand the transformative impact of courageous conversations in their own lives, with a little help. In this article, we’ll explore why these dialogues are vital, unpack practical strategies for initiating them, and equip you with the tools to navigate them with grace and authenticity.

Why Courageous Conversations Matter:

At the heart of every meaningful relationship lies the ability to communicate openly and honestly. However, many of us shy away from the conversations that matter most. Whether it’s fear of conflict, rejection, or vulnerability, our reluctance to engage in these dialogues can hinder personal growth and strain our connections with others. But avoiding these conversations only perpetuates misunderstandings and prevents us from fostering deeper intimacy and understanding.

The Conversations You Haven’t Had The Courage to Have Until Now

All of us have three elements interwoven into those conversations we haven’t mustered the courage up (yet, and for many of us never will unless we get out of our own way) to have. See below and as you read, reflect on which ones you’re courage has often flopped from, as a result:

1. Setting Boundaries:

Boundaries delineate where we end and others begin, safeguarding our emotional and physical well-being. Yet, articulating boundaries can be uncomfortable, especially when faced with the fear of rejection or conflict. However, failing to set boundaries often leads to resentment and erosion of self-respect. By expressing our needs clearly and assertively, we create a foundation for healthier relationships.

2. Sharing Innermost Feelings:

Vulnerability is the cornerstone of intimacy, yet many shy away from exposing their deepest thoughts and emotions. Whether it’s fear of judgment or a desire to maintain a facade of strength, withholding our true feelings hinders authentic connection. Engaging in open, honest dialogue fosters empathy, understanding, and strengthens emotional bonds. Keeping these locked up deep inside will find their way out somehow and that way might not be the most savory for you.

*Disclaimer: This should NOT be done with those people who do not know how to value emotions and feelings. Those who are emotionally immature, self-centered, narcissistic, insecure, arrogant, or apathetic will actually be the worst people to earn such a vulnerable expression of your Self. Be mindful about this. If you struggle with this one in particular, there’s good reason for it. Likely you’d done so with someone at a young age, got burned by it, and then learned to “never again” share your innermost feelings with others. You learned that your inner world wasn’t safe to share with others, and more probabilistically speaking, you learned to even sidelining your innermost feelings when you’re with others wearing the “mask” of yourself to “fit in,” “be liked or loved,” “or be accepted”.

3. Establishing Healthy Growth Exchanges:

Relationships are dynamic ecosystems that require ongoing nourishment and evolution. Yet, growth exchanges – conversations centered around personal and collective development – are often neglected. Whether it’s discussing aspirations, addressing stagnation, or navigating change, fostering growth exchanges cultivates mutual support and alignment of goals. This one sometimes looks like helping those you love to learn what’s actually new, or evolved, about you.

The 3-Step Process for Courageous Communication:

  1. Reflect and Prepare: Before initiating a courageous conversation, take time to clarify your intentions, identify your needs, and anticipate potential challenges. Reflect on your emotions and desired outcomes, and consider how you can express yourself authentically while respecting the other person’s perspective.
  2. Initiate with Empathy: Approach the conversation with empathy and understanding, acknowledging the other person’s feelings and perspective. Use “I” statements to express your own emotions and needs, and actively listen to their response without judgment or defensiveness.
  3. Navigate with Respect: Throughout the conversation, prioritize mutual respect and understanding. Stay focused on the issue at hand, avoid blame or criticism, and be open to finding collaborative solutions that honor both parties’ needs and boundaries.

Think about what “truth bubbles” you’re suppressing on your day-to-day just to keep your relationships from entering into prospective conflict or uncomfortable conversations, and as a result, the self-respect hits you’re taking every time. Refer to the image below:

Practical Strategies and Expert Insights:

Boundary-Setting with the DESO Script Model: Utilize the DESO (Describe, Express, Specify, Outcome) Script to effectively communicate your boundaries in a clear and assertive manner. By describing the behavior, expressing your feelings, specifying your needs, and outlining the desired outcome, you can establish healthy boundaries while maintaining respect and empathy.

CBT Techniques for Adaptive Coping: Cognitive Behavioral Therapy (CBT) offers valuable techniques for managing anxiety and building resilience before and after crucial conversations. Practice mindfulness, challenge negative thought patterns, and cultivate self-compassion to bolster your courage and confidence.

Non-Violent Communication (NVC) Approach: Embrace the principles of Non-Violent Communication (NVC) to navigate conflict and foster healthy communication. Focus on expressing observations, feelings, needs, and requests with clarity and empathy, fostering empathy and understanding between individuals.

A quick tribute to the “passive aggressive” conversations and to those who are constantly needing to understand the difference between and NVC approach to a conversation as opposed to one that brings aggression and thus, elements of violence into the conversational equation. See below’s image for the variances:

Boundary-Setting Script:

Now, we all could use a little help in actually setting those boundaries, right? I can’t tell you how many conversations I have helping people do this in so many areas of their lives, and would be honored to help you activate your custom boundary script. What if we had a go-to boundary script that we could use to practice setting and establishing our boundaries, or even better, leveraging while we bring up a courageous conversation with someone whom we care about. If you’re like me, and the thousands of others who doesn’t always know what to say, use the script below to gain some practice:

“Hey [Name], I wanted to talk to you about something important to me. When [describe behavior], I feel [express feelings] because [specify needs]. I value our relationship and want to ensure that we both feel respected and understood. Can we discuss how we can [outline desired outcome] moving forward?”

In closing, courage is not the absence of fear but the willingness to act despite it. The conversations we avoid are often the ones that hold the key to deeper connections, self-discovery, and fulfillment. Embrace the discomfort, lean into vulnerability, and let your voice be heard. For it is in the crucible of honest dialogue that true transformation occurs.

I hope this Evolve Article brought you some tactical, practical value and helped to encourage you to learn more into those conversations you need to have but before this article, struggled to muster the courage to have and now feel empowered to go practice the skills and methods that help us all become the more expressed versions of ourselves that this world desperately needs.

As an experienced coach who has navigated the complexities of human relationships, I invite you to embark on a journey of self-discovery and connection through courageous conversations and get the help you need immediately if you’re struggling to have courageous conversations in life. Book a FREE 30-minute coaching call with me to work through your unique situation. Together, let’s unlock the transformative power of honest dialogue and pave the way for deeper, more meaningful connections in your life. If you want customized support to the unique situation you’re experiencing, drop me an email at about the Courageous Conversation you want to have but have struggled to have yet. You can always DM me on social media (@EvolvewithEmilia), or join us, at Evolve Ventures Society.

Light to you dear reader,



1. Brown, B. (2010). The gifts of imperfection: Let go of who you think you’re supposed to be and embrace who you are. Hazelden Publishing.

2. Gottman, J. M., & Silver, N. (2015). The seven principles for making marriage work: A practical guide from the country’s foremost relationship expert. Harmony.

3. Neff, K. D. (2011). Self-compassion: Stop beating yourself up and leave insecurity behind. HarperCollins.

4. Townsend, J. W., & Cloud, H. (2017). Boundaries: When to say yes, how to say no to take control of your life. Zondervan.

5. Reis, H. T., & Shaver, P. R. (1988). Intimacy as an interpersonal process. Handbook of personal relationships, 24(3), 367-389.

6. Feeney, J. A., & Collins, N. L. (2015). A new look at social support: A theoretical perspective on thriving through relationships. Personality and Social Psychology Review, 19(2), 113-147.

7. Miller, W. R., & Rollnick, S. (2012). Motivational interviewing: Helping people change. Guilford press.

8. Johnson, S. M. (2008). Hold me tight: Seven conversations for a lifetime of love. Little, Brown Spark.

9. Lerner, H. G. (2012). The dance of anger: A woman’s guide to changing the patterns of intimate relationships. HarperCollins.

10. Deci, E. L., & Ryan, R. M. (2012). Self-determination theory. Handbook of theories of social psychology, 1, 416-433.

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